LipidBank - Fatty acid

No	Structure	COMMON NAME	NAME	DATA No	INFORMANT	SYMBOL	FORMULA	MOL.WT(ave)	Download	BIOOGICAL ACTIVITY	PHYSICAL AND CHEMICAL PROPERTIES						SPECTRAL DATA					CHROMATOGRAM DATA	SOURCE	CHEMICAL SYNTHESIS	METABOLISM	GENETIC INFORMATION	NOTE	REFERENCES
No	Structure	COMMON NAME	NAME	DATA No	INFORMANT	SYMBOL	FORMULA	MOL.WT(ave)	Download	BIOOGICAL ACTIVITY	MELTING POINT	BOILING POINT	DENSITY	REFRACTIVE INDEX	OPTICAL ROTATION	SOLUBILITY	UV SPECTRA	IR SPECTRA	NMR SPECTRA	MASS SPECTRA	OTHER SPECTRA	CHROMATOGRAM DATA	SOURCE	CHEMICAL SYNTHESIS	METABOLISM	GENETIC INFORMATION	NOTE	REFERENCES
1		Formic acid	Methanoic acid	DFA0001	Tetsuyuki Kobayashi	Fo	CH₂O₂	46.025		Dangerously caustic to skin. Chronic absorption is reported to cause albuminuria, hematuria. LD₅₀ in mice 1100 mg/kg orally, 145 mg/kg i.v.. (Ref. 2013) Therapeutic category; counterirritant, astringent.	8.4C	100.5C	d 1.220	1.3714 at 20C		miscible with water, alcohol, ether and glycerol.(Ref. 0347)(Ref. 0481)							Formica rufa (red ant).	Made by carbon monoxide and NaOH under pressure and decompose the resulting sodium formate with H₂SO₄. (Ref. 0002)				[0002] / [0347] / [0481] / [2013]
2		Acetic acid	Ethanoic acid	DFA0002	Tetsuyuki Kobayashi	Ac	C₂H₄O₂	60.052			16.7C	118.2C	d 1.049	1.3718 at 20C		miscible with water, alcohol, ether, glycerol and carbon tetrachloride;practically insoluble in carbon disulfide. (Ref. 0168)(Ref. 0347)							Vinegar	Obtained in the destructive distillation of wood; from acetylene and water via acetaldehyde by oxidation with air. Manufacture process. (Ref. 1001)(Ref. 1002)(Ref. 1003)(Ref. 1004)(Ref. 1005)(Ref. 1006)(Ref. 1007)				[0168] / [0347] / [1001] / [1002] / [1003] / [1004] / [1005] / [1006] / [1007]
3		Propioic acid	Propanoic acid	DFA0003	Tetsuyuki Kobayashi	Pp	C₃H₆O₂	74.079			-22.0C	141.1C	d 0.992	1.3874 at 20C		soluble in alcohol, ether and chloroform. (Ref. 0347)							Milk and milk products. Can be obtained from wood pulp waste liquor by a fermentation process using bacteria of the genus Propionibacterium.(Ref. 1008) From natural gas by the Fischer-Tropsch process;as a byproduct in the pyrolysis of wood; by the action of microorganisms on a variety of materials in small yields. Very pure propionic acid can be obtained from propionitrile.	Preparation from ethylene,carbon monoxide and steam.(Ref. 1009)(Ref. 1010)From ethanol and carbon monoxide using a boron trifluoride catalyst.(Ref. 1011)By oxidation of propionaldehyde(Ref. 1012)				[0347] / [1008] / [1009] / [1010] / [1011] / [1012]
4		Butyric acid	Butanoic acid	DFA0004	Tetsuyuki Kobayashi	Bt/C4:0	C₄H₈O₂	88.105			-7.9C	163.5C	d 0.9587	1.33906 at 20C		miscible with water, alcohol, ether.(Ref. 0347)							Butterfat	Obtained by suitable fermentation of carbohydrates;preparation from n-propanol + CO at 200 atm in the presense of Ni(CO)₄ and NiI₂.(Ref. 1012); lab preparation from ethylmalonic acid.				[0347] / [1012]
5		Valeric acid	Pentanoic acid	DFA0005	Tetsuyuki Kobayashi	Vl/C5:0	C₅H₁₀O₂	102.132			-34.5C	187.0C	d 0.942	1.4086 at 20C		soluble in 30 parts water; freely soluble in alcohol, ether.(Ref. 0007/0201/0288/0334/0347)							Essential oils	Obtained by decomposition of n-propylmalonic acid.				[0007] / [0201] / [0288] / [0334] / [0347]
6		Caproic acid	Hexanoic acid	DFA0006	Tetsuyuki Kobayashi	Hxo/C6:0	C₆H₁₂O₂	116.158			-3.4C	205.8C	d 0.929	1.41635 at 20C		slightly soluble in water (1.082g/100g); readily soluble in ethanol,ether.(Ref. 0347)(Ref. 0408)(Ref. 0449)							Butterfat;palm oils	Manufactured by catalytic reduction of corresponding b-lactone.				[0347] / [0408] / [0449]
7		Heptylic acid / Enanthic acid / Enanthylic acid / Heptoic acid	Heptanoic acid	DFA0007	Tetsuyuki Kobayashi	Hpo / C7:0	C₇H₁₄O₂	130.185			-10.5C	223.0C	d 0.92215	1.4230 at 20C		soluble in ethanol, ether, DMF and DMSO.(Ref. 0347)(Ref. 0408)(Ref. 0424)							Violet-leaf oil.	Prepared by the oxidation of heptaldehyde with potassium permanganate in dilute sulfuric acid.				[0347] / [0408] / [0424]
8		Caprylic acid / Octylic acid	Octanoic acid	DFA0008	Tetsuyuki Kobayashi	Oco / C8:0	C₈H₁₆O₂	144.211			16.7C	239.7C	d 0.910	1.4285 at 20C		very slightly soluble in water (0.068g/100g at 20C); freely soluble in alcohol, chloroform, ether, carbon disulfide, petroleum ether and glacial acetic acid.(Ref. 0347)							Butterfat;palm-kernel oils					[0347]
9		Pelargonic acid / Nonylic acid	Nonanoic acid	DFA0009	Tetsuyuki Kobayashi	Nno / C9:0	C₉H₁₈O₂	158.238			12.5C	255.6C	d 0.907	1.4322 at 20C		practically insoluble in water; soluble in alcohol, chloroform and ether.(Ref. 0021)(Ref. 0022)(Ref. 0523)							Butterfat;hair fat					[0021] / [0022] / [0523]
10		Capric acid	Decanoic acid	DFA0010	Tetsuyuki Kobayashi	Dec / Dco / C10:0	C₁₀H₂₀O₂	172.265			31.6C	270.0C	d⁴⁰₄ 0.8858	1.42855 at 40C		practically insoluble in water (0.015g/100g at 20C); also soluble in ethanol, ether, chloroform, benzene and carbon disulfide.(Ref. 0353)(Ref. 0380)(Ref. 0449)							Butterfat;palm-kernel oils					[0353] / [0380] / [0449]
11		Undecylic acid / Hendecanoic acid	Undecanoic acid	DFA0011	Tetsuyuki Kobayashi	Udo / C11:0	C₁₁H₂₂O₂	186.291			29.3C	284.0C	d 0.9905	1.4202 at 70C		soluble in alcohol, chloroform and ether.(Ref. 0219)(Ref. 0523)							Human-hair fat.					[0219] / [0523]
12		Lauric acid	Dodecanoic acid	DFA0012	Tetsuyuki Kobayashi	Lau / C12:0	C₁₂H₂₄O₂	200.318			44.2C	225C at 100 mmHg	d⁵⁰₄ 0.8690	1.4261 at 60C		insoluble in water; 1g dissolves in 1 ml alcohol, 2.5 ml propyl alcohol; freely soluble in benzene, ether. (Ref. 0055)(Ref. 0226)(Ref. 0236)							Lauraceae oils;Arecaceae					[0055] / [0226] / [0236]
13		Tridecylic acid	Tridecanoic acid	DFA0013	Tetsuyuki Kobayashi	C13:0	C₁₃H₂₆O₂	214.344			41.5C	236C at 100 mm Hg	d 0.8458	1.4286 at 60C		soluble in acetone, alcohol, ether and petroleum ether.<0219>>(Ref. 0305)(Ref. 0445)(Ref. 0523)							Human-hair fat					[0305] / [0445] / [0523]
14		Myristic acid	Tetradecanoic acid	DFA0014	Tetsuyuki Kobayashi	Myr / C14:0	C₁₄H₂₈O₂	228.371			53.9C	250C at 100 mmHg	d⁵⁴₄ 0.8622	1.4273 at 70C		soluble in absolute alcohol, methanol, ether, petroleum ether, benzene and chloroform. (Ref. 0165)(Ref. 0237)(Ref. 0391)(Ref. 0461)				[Spectrum 0001] (provided by Dr. Takeshi Kasama)		Gas liquid chromatogram [Chromatogram 0001] [Chromatogram 0002] (provided by Dr. Akiko Horiuchi).	Myristicaceae fats					[0165] / [0237] / [0391] / [0461]
15		Pentadecylic acid	Pentadecanoic acid	DFA0015	Tetsuyuki Kobayashi	C15:0	C₁₅H₃₀O₂	242.398			52.3C	202.5C at 10 mmHg	d 0.8423	1.4292 at 70C		soluble in acetone, alcohol, ether and petroleum ether.(Ref. 0305)(Ref. 0362)(Ref. 0523)				[Spectrum 0001] (provided by Dr. Takeshi Kasama).			Sheep,hair and milk fats					[0305] / [0362] / [0523]
16		Palmitic acid	Hexadecanoic acid	DFA0016	Tetsuyuki Kobayashi	Pam / C16:0	C₁₆H₃₂O₂	256.424			63.1C	268C at 100 mmHg	d 0.8487	1.4309 at 70C		insoluble in water; sparingly soluble in cold alcohol or in petroleum ether; freely soluble in hot alcohol, ether, propyl alcohol and chloroform.(Ref. 0056)(Ref. 0237)(Ref. 0306)(Ref. 0317)(Ref. 0329)(Ref. 0388)(Ref. 0435)				[Spectrum 0001] (provided by Dr. Takeshi Kasama).		Gas liquid chromatogram [Chromatogram 0001] [Chromatogram 0002] (provided by Dr. Akiko Horiuchi).	Palm-pulp oils					[0056] / [0237] / [0306] / [0317] / [0329] / [0388] / [0435]
17		Margaric acid / Heptadecylic acid	Heptadecanoic acid	DFA0017	Tetsuyuki Kobayashi	C17:0	C₁₇H₃₄O₂	270.451			61.3C	220C at 10 mmHg	d⁶⁰₄ 0.853	1.4324 at 70C		insoluble in water; freely soluble in ether; slightly soluble in alcohol.(Ref. 0182)(Ref. 0220)(Ref. 0329)				[Spectrum 0001] (provided by Dr. Takeshi Kasama).		Gas liquid chromatogram [Chromatogram 0001] [Chromatogram 0002] (provided by Dr. Akiko Horiuchi).	Hair and sheep fats					[0182] / [0220] / [0329]
18		Stearic acid	Octadecanoic acid	DFA0018	Tetsuyuki Kobayashi	Ste / C18:0	C₁₈H₃₆O₂	284.477			69.6C	213C at 5 mmHg	d 0.8390	1.4337 at 70C		insoluble in water;soluble in alcohol and ether.(Ref. 0305) (Ref. 0368) (Ref. 0369) (Ref. 0445) (Ref. 0522) (Ref. 0523)				[Spectrum 0001] (provided by Dr. Takeshi Kasama).		Gas liquid chromatogram [Chromatogram 0001] [Chromatogram 0002] (provided by Dr. Akiko Horiuchi).	Animal fats(generally)					[0305] / [0368] / [0369] / [0445] / [0522] / [0523]
19		Nonadecylic acid	Nonadecanoic acid	DFA0019	Tetsuyuki Kobayashi	C19:0	C₁₉H₃₈O₂	298.504			68.6C	299C at 10 mmHg	d 0.8771	1.4512 at 25C		soluble in acetone, hot alcohol, ether and petroleum ether.(Ref. 0182)(Ref. 0277)(Ref. 0319)(Ref. 0329)(Ref. 0360)(Ref. 0527)							Ox fat					[0182] / [0277] / [0319] / [0329] / [0360] / [0527]
20		Arachidic acid	Icosanoic acid / Eicosanoic acid	DFA0020	Tetsuyuki Kobayashi	Ach / C20:0	C₂₀H₄₀O₂	312.530			76.5-77.0C	204C at 1 mmHg	d¹⁰⁰₄ 0.8240	1.4250 at 100C		practically insoluble in water; sparingly soluble in cold water; freely in hot absolute alcohol, benzene, chloroform, ether and petroleum ether.(Ref. 0182)(Ref. 0220)(Ref. 0368)(Ref. 0369)(Ref. 0523)(Ref. 0527)				[Spectrum 0001] (provided by Dr. Takeshi Kasama).		Gas liquid chromatogram [Chromatogram 0001] [Chromatogram 0002] (provided by Dr. Akiko Horiuchi).	Peanut oil;rambutan fat					[0182] / [0220] / [0368] / [0369] / [0523] / [0527]
21			Heneicosanoic acid / Henicosanoic acid	DFA0021	Tetsuyuki Kobayashi	C21:0	C₂₁H₄₂O₂	326.557			74.3C					infinitely soluble in ether, chloroform; very soluble in alcohol.(Ref. 0079)(Ref. 0361)(Ref. 0516)							Japanwax(?);peanut oil(?);synthetic					[0079] / [0361] / [0516]
22		Behenic acid	Docosanoic acid	DFA0022	Tetsuyuki Kobayashi	Beh / C22:0	C₂₂H₄₄O₂	340.584			81.5C	306C at 60 mmHg	d¹⁰⁰₄ 0.8221	1.4270 at 100C		slightry soluble in aocohol and ether.(Ref. 0181)(Ref. 0477)				[Spectrum 0001] (provided by Dr. Takeshi Kasama).		Gas liquid chromatogram [Chromatogram 0001] [Chromatogram 0002] (provided by Dr. Akiko Horiuchi).	Brassicaceae;wool grease;waxes					[0181] / [0477]
23			Tricosanoic acid	DFA0023	Tetsuyuki Kobayashi	C23:0	C₂₃H₄₆O₂	354.610			79.1C	203-205C at 1 mmHg		1.4252 at 70C		very soluble in ether; slightly soluble in alcohol.(Ref. 0079)(Ref. 0181)(Ref. 0230)(Ref. 0361)(Ref. 0477)(Ref. 0516)				[Spectrum 0001] (provided by Dr. Takeshi Kasama).		Gas liquid chromatogram [Chromatogram 0001] (provided by Dr. Akiko Horiuchi).	Peanut oil;olive-leaf wax					[0079] / [0181] / [0230] / [0361] / [0477] / [0516]
24		Lignoceric acid	Tetracosanoic acid	DFA0024	Tetsuyuki Kobayashi	Lig / C24:0	C₂₄H₄₈O₂	368.637			87.5-88.0C	272C at 10 mmHg	d¹⁰⁰₄ 0.8207	1.4373 at 70C		soluble in 91.53% ethanol: 0.182 g/100 ml.(Ref. 0061)(Ref. 0079)(Ref. 0180)(Ref. 0230)(Ref. 0361)(Ref. 0516)(Ref. 0521)				[Spectrum 0001] (provided by Dr. Takeshi Kasama).		Gas liquid chromatogram [Chromatogram 0001] [Chromatogram 0002] (provided by Dr. Akiko Horiuchi).	Practically pure in beechwood tar					[0061] / [0079] / [0180] / [0230] / [0361] / [0516] / [0521]
25			Pentacosanoic acid	DFA0025	Tetsuyuki Kobayashi	C25:0	C₂₅H₅₀O₂	382.663			84-85.0C			1.4292 at 70C		soluble in hot acetone, hot chloroform and hot methyl alcohol.(Ref. 0056)(Ref. 0182)(Ref. 0317)(Ref. 0329)				[Spectrum 0001] (provided by Dr. Takeshi Kasama).			Mycobacterium tuberculosis;synthetic wax					[0056] / [0182] / [0317] / [0329]
26		Cerotic acid	Hexacosanoic acid	DFA0026	Tetsuyuki Kobayashi	C26:0 / Crt	C₂₆H₅₂O₂	396.690			87.7-88.5C		d¹⁰⁰₄ 0.8198	1.4313 at 100C		soluble in hot acetone, hot chloroform and hot methyl alcohol.(Ref. 0102)(Ref. 0305)(Ref. 0445)(Ref. 0497)(Ref. 0522)(Ref. 0523)				[Spectrum 0001] (provided by Dr. Takeshi Kasama).			Plant and insect waxes;synthetic					[0102] / [0305] / [0445] / [0497] / [0522] / [0523]
27		Carboceric acid	Heptacosanoic acid	DFA0027	Tetsuyuki Kobayashi	C27:0	C₂₇H₅₄O₂	410.716			87.6C			1.4324at 70C		(Ref. 0390)(Ref. 0420)							Synthetic,from 1-hexacosanol					[0390] / [0420]
28		Montanic acid	Octacosanoic acid	DFA0028	Tetsuyuki Kobayashi	C28:0 / Mon	C₂₈H₅₆O₂	424.743			90.0-90.9C		d¹⁰⁰₄ 0.8191	1.4313at 100C		soluble in hot acetic acid, hot benzene and hot methyl alcohol.(Ref. 0368)(Ref. 0369)(Ref. 0522)(Ref. 0523)							Insect,leaf and montan waxes					[0368] / [0369] / [0522] / [0523]
29			Nonacosanoic acid	DFA0029	Tetsuyuki Kobayashi	C29:0	C₂₉H₅₈O₂	438.770			90.3-90.5C					(Ref. 0184)(Ref. 0472)							Montan wax;bitumen from peat					[0184] / [0472]
30		Melissic acid	Triacontanoic acid	DFA0030	Tetsuyuki Kobayashi	C30:0	C₃₀H₆₀O₂	452.796			93.6C			1.4323 at 100C		soluble in chloroform, CS₂ and hot methyl alcohol.(Ref. 0061)(Ref. 0079)(Ref. 0180)(Ref. 0230)(Ref. 0331)(Ref. 0417)(Ref. 0521)							Plant and insect waxes(almost exclusively);mineral waxes					[0061] / [0079] / [0180] / [0230] / [0417] / [0521]
31			Hentriacontanoic acid	DFA0031	Tetsuyuki Kobayashi	C31:0	C₃₁H₆₂O₂	466.823								soluble in chloroform and hot methanol.(Ref. 0390/0420)							Peat wax and montan wax (?).	synthetic.				[0390] / [0420]
32		Lacceroic acid	Dotriacontanoic acid	DFA0032	Tetsuyuki Kobayashi	C32:0	C₃₂H₆₄O₂	480.849			96.2C					Soluble in hot acetone, hot benzene and chloroform.(Ref. 0180/0183/0191/0390/0420/0472)							Stick-lac wax.					[0180] / [0183] / [0191] / [0390] / [0420] / [0472]
33		Psyllic acid / Ceromelissic cid	Tritriacontanoic acid	DFA0033	Tetsuyuki Kobayashi	C33:0	C₃₃H₆₆O₂	494.876															Ceroplastes ceriferous and C. rubens.(Ref. 0300/0302/0471)					[0300] / [0302] / [0471]
34		Gheddic acid / Geddic acid	Tetoratriacontanoic acid	DFA0034	Tetsuyuki Kobayashi	C34:0	C₃₄H₆₈O₂	508.903			98.4C					Soluble in hot acetone, hot benzene and chloroform.(Ref. 0184/0472)							Ghedda wax.	Synthesized by oxidation of 1-tetratriacontanol with the nitrile method.				[0184] / [0472]
35		Ceroplastic acid	Pentatriacontanoic acid	DFA0035	Tetsuyuki Kobayashi	C35:0	C₃₅H₇₀O₂	522.929			98.4C					Soluble in hot acetone, hot benzene and chloroform.(Ref. 0079/0183/0230/0302/0404/0471)							Ceroplasters rubens wax.					[0079] / [0183] / [0230] / [0302] / [0404] / [0471]
36			Hexatriacontanoic acid	DFA0036	Tetsuyuki Kobayashi	C36:0	C₃₆H₇₂O₂	536.956		(Ref. 0003)													Milk and milk products.	Synthetic wax; melting point, 99.9C.(Ref. 0302/0390/0404)				[0003] / [0302] / [0390] / [0404]
37			Heptariacontanoic acid	DFA0037	Tetsuyuki Kobayashi	C37:0	C₃₇H₇₄O₂	550.982		(Ref. 0003)														Synthetic wax.(Ref. 0183/0300/0302/0404/0471)				[0003] / [0183] / [0300] / [0302] / [0404] / [0471]
38			Octatriacontanoic acid	DFA0038	Tetsuyuki Kobayashi	C38:0	C₃₈H₇₆O₂	565.009																Synthetic wax; melting point, 101.6C.(Ref. 0180/0184/0191/0390/0417)				[0180] / [0184] / [0191] / [0390] / [0417]
39			Hexatetracontanoic acid	DFA0039	Tetsuyuki Kobayashi	C46:0	C₄₆H₉₂O₂	677.221																Synthetic wax; melting point, 106.8C.(Ref. 0061/0180/0184/0390/0472/0521)				[0061] / [0180] / [0184] / [0390] / [0472] / [0521]
40		Acrylic acid	2-Propenoic acid	DFA0040	Tetsuyuki Kobayashi	C3:1	C₃H₄O₂	72.063			12.3C/13C	141.9C(Ref. 0001)	d 1.0621	1.4224 at 20C		Soluble in acetone, alcohol, toluene and water.(Ref. 0184/0472)								Synthesized by oxidation of acrolein.				[0184] / [0472]
41		Isocrotonic acid	cis-2-Butenoic acid	DFA0041	Tetsuyuki Kobayashi	C4:1	C₄H₆O₂	86.089			14.4-14.6C	171.9C/169.3C (decomposes)	d¹⁵^.⁵₄ 1.0312	1.4457 at 20C		Soluble in alcohol, CS2, ether, petroleum ether. Slightly soluble in water.(Ref. 0286/0447/0451)							Reported in the seed oil of Croton tiglium.					[0286] / [0447] / [0451]
42		Crotonic acid	trans-2-Butenoic acid	DFA0042	Tetsuyuki Kobayashi	C4:1	C₄H₆O₂	86.089			72.0C	189C	d 1.018	1.4228 at 79.7C		Soluble in acetone, alcohol, petroleum ether, toluene and water.(Ref. 0286/0447/0451)							Reported in the seed oil of Croton tiglium.	Synthetic.				[0286] / [0447] / [0451]
43		Vinylacetic acid	3-Butenoic acid	DFA0043	Tetsuyuki Kobayashi	C4:1	C₄H₆O₂	86.089			-39C	163C	d 1.013	1.4257 at 15C		Soluble in alcohol, benzene, ether. Slightly soluble in water.(Ref. 0300/0302/0347/0471)								Synthetic.				[0300] / [0302] / [0347] / [0471]
44		bEthylacrylic acid	2-Pentenoic acid	DFA0044	Tetsuyuki Kobayashi	C5:1	C₅H₈O₂	100.116			8C	200C at 17mmHg	d 0.9921	1.450 at 15C		Soluble in alcohol and ether. (Ref. 0347)								Synthesized by reaction of 2-bromovaleic acid with quinoline.				[0347]
45		bPenteic acid / bPentenoic acid	3-Pentenoic acid	DFA0045	Tetsuyuki Kobayashi	C5:1	C₅H₈O₂	100.116				193C at 760mmHg				Soluble in benzene, chloroform and ether. (Ref. 0347)								Synthesized by decarboxylation of the reaction product of propionaldehyde and malonic acid.				[0347]
46		Allylacetic acid	4-Pentenoic acid	DFA0046	Tetsuyuki Kobayashi	C5:1	C₅H₈O₂	100.116			-18C	189C at 760mmHg	d 0.9843	1.4341 at 7.5C		Soluble in benzene, chloroform and ether. (Ref. 0347)								Synthetic.				[0347]
47		Isohydrosorbic acid / b-propylacrylic acid	2-Hexenoic acid	DFA0047	Tetsuyuki Kobayashi	C6:1	C₆H₁₀O₂	114.142			32C	217C at 760mmHg	d 0.965	1.4460 at 40C		Soluble in alcohol, benzene, chloroform, CS2 and ether. Slightly soluble in water.(Ref. 0347)							Japanese peppermint oil.	Synthesized from n-capronic acid.				[0347]
48		Hydrosorbic acid	3-Hexenoic acid	DFA0048	Tetsuyuki Kobayashi	C6:1	C₆H₁₀O₂	114.142			12C	208C at 760mmHg	d 0.9610	1.4355		Soluble in benzene and petroleum ether. (Ref. 0347)								Synthetic.				[0347]
49		g -Hexenoic acid	4-Hexenoic acid	DFA0049	Tetsuyuki Kobayashi	C6:1	C₆H₁₀O₂	114.142			10C	206.5C at 760mmHg	d 0.9658	1.4367		Soluble in benzene, ether and petroleum ether. (Ref. 0347)								Synthesized by the action of 1-bromo-2-butene on ethyl sodiomalonate.				[0347]
50		d -Hexenoic acid	5-Hexenoic acid	DFA0050	Tetsuyuki Kobayashi	C6:1	C₆H₁₀O₂	114.142				203C at 121mmHg	d¹⁹₄ 0.9639	1.4343 at 20C		Soluble in benzene, ether and petroleum ether. (Ref. 0347)								Synthesized by (i) treatment of 6-aminocaproic acid with HNO2, and (ii) reaction of 1-bromo-3-butene with ethyl sodiomalonate.				[0347]
51		a -Heptenoic acid	2-Heptenoic acid	DFA0051	Tetsuyuki Kobayashi	C7:1	C₇H₁₂O₂	128.169				120-121C at 11mmHg	d 0.9575	1.4488 at 20C		Soluble in benzene, ether and petroleum ether. (Ref. 0347)							Marine oils and milk fats.	Synthesized by (i) the malonic ester method, and (ii) reaction of 7-aminoheptanoic acid and HNO2.				[0347]
52		b -Heptenoic acid	3-Heptenoic acid	DFA0052	Tetsuyuki Kobayashi	C7:1	C₇H₁₂O₂	128.169			-12C	226-228C at 760mmHg				Soluble in alcohol, ether and petroleum ether. (Ref. 0347)								Synthesized from n-valeraldehyde by the malonic acid method.				[0347]
53		g -Heptenoic acid	4-Heptenoic acid	DFA0053	Tetsuyuki Kobayashi	C7:1	C₇H₁₂O₂	128.169				98-100C at 5mmHg	d 0.949	1.4418 at 15C		Soluble in acetone, ether, and methanol. (Ref. 0263)								Synthetic.				[0263]
54		d -Heptenoic acid	5-Heptenoic acid	DFA0054	Tetsuyuki Kobayashi	C7:1	C₇H₁₂O₂	128.169				117C at 11mmHg	d 0.9496	1.4444 at 20C		Soluble in alcohol, chloroform, ether, and petroleum ether. (Ref. 0098/0398)								Synthesized by the reaction of 4-chlorobutiric acid and K or Na acetoacetate.				[0098] / [0398]
55		e -Heptenoic acid	6-Heptenoic acid	DFA0055	Tetsuyuki Kobayashi	C7:1	C₇H₁₂O₂	128.169			-6.5C	125C at 15mmHg	d¹⁴^.⁹₄ 0.9515	1.4404 at 14.9C		Soluble in acetone and methanol. (Ref. 0192)								Synthesized by the reaction of 7-aminoheptanoic acid and HNO2.				[0192]
56		3-n-Amylacrylic acid / cis-a-octenoic acid	cis-2-Octenoic acid	DFA0056	Tetsuyuki Kobayashi	C8:1	C₈H₁₄O₂	142.196				154C at 22mmHg	d 0.9807	1.4587 at 20C		(Ref. 0035/0157/0297)								Synthesized by condensation of caprylic aldehyde with malonic acid in the presence of pyridine.				[0035] / [0157] / [0297]
57		trans-a-Octenoic acid	trans-2-Octenoic acid	DFA0057	Tetsuyuki Kobayashi	C8:1	C₈H₁₄O₂	142.196				143C at 15mmHg	d 0.945	1.462		(Ref. 0035/0156/0289/0297)								Synthetic.				[0035] / [0156] / [0289] / [0297]
58		cis-b-Octenoic acid	cis-3-Octenoic acid	DFA0058	Tetsuyuki Kobayashi	C8:1	C₈H₁₄O₂	142.196			-25C	150C at 19mmHg	d 0.9352	1.4433 at 20 C		(Ref. 0157/0260/0297)								Synthetic.				[0157] / [0260] / [0297]
59		trans-b-Octenoic acid	trans-3-Octenoic acid	DFA0059	Tetsuyuki Kobayashi	C8:1	C₈H₁₄O₂	142.196			1C	142C at 19mmHg	d 0.942	1.4456 at 20 C		(Ref. 0157/0297)								Synthetic.				[0157] / [0297]
60		g-Octenoic acid	cis-4-Octenoic acid	DFA0060	Tetsuyuki Kobayashi	C8:1	C₈H₁₄O₂	142.196			-35C	96C at 0.8mmHg	d 0.9301	1.4417 at 20 C		(Ref. 0428)								Synthetic.				[0428]
61		cis-d-Octenoic acid	cis-5-Octenoic acid	DFA0061	Tetsuyuki Kobayashi	C8:1	C₈H₁₄O₂	142.196								(Ref. 0367)								Synthetic				[0367]
62		trans-d-Octenoic acid	trans-5-Octenoic acid	DFA0062	Tetsuyuki Kobayashi	C8:1	C₈H₁₄O₂	142.196								(Ref. 0260)								Synthetic				[0260]
63		cis-e-Octenoic acid	cis-6-Octenoic acid	DFA0063	Tetsuyuki Kobayashi	C8:1	C₈H₁₄O₂	142.196			-17C	88C at 0.8 mmHg	d₄ 0.9378	1.4441 at 20C		(Ref. 0260)								Synthetic				[0260]
64		trans-e-Octenoic acid	trans-6-Octenoic acid	DFA0064	Tetsuyuki Kobayashi	C8:1	C₈H₁₄O₂	142.196			6C	90C at 1.2 mm Hg	d₄ 0.9422	1.4454 at 20C		(Ref. 0297)								Synthetic				[0297]
65		a-Nonylenic acid	cis-2-Nonenoic acid	DFA0065	Tetsuyuki Kobayashi	C9:1	C₉H₁₆O₂	156.222			4C	90C at 20 mmHg	d 0.9316	1.4587 at 20C		(Ref. 0175)(Ref. 0367)(Ref. 0422)(Ref. 0428)								Synthetic				[0175] / [0367] / [0422] / [0428]
66		b-Nonylenic acid / 3-nonylenic acid	3-Nonenoic acid	DFA0066	Tetsuyuki Kobayashi	C9:1						106C at 1 mmHg	d 0.9290	1.4484 at 20C		(Ref. 0367)								Synthetic				[0367]
67		8-Nonylenic acid	8-Nonenoic acid	DFA0067	Tetsuyuki Kobayashi	C9:1	C₉H₁₆O₂	156.222			5C	116-118C at 1 mmHg	d 0.9146	1.4492		(Ref. 0192)(Ref. 0367)												[0192] / [0367]
68		2-Decylenic acid	2-Decenoic acid	DFA0068	Tetsuyuki Kobayashi	C10:1	C₁₀H₁₈O₂	170.249			12C	165C at 15 mmHg	d 0.9280	1.46161 at 20C		(Ref. 0013)(Ref. 0017)(Ref. 0069)(Ref. 0478)								Synthetic by condensation of caprylic aldehyde with malonic acid in presence of pyridene.				[0013] / [0017] / [0069] / [0478]
69		3-Decylenic acid	3-Decenoic acid	DFA0069	Tetsuyuki Kobayashi	C10:1	C₁₀H₁₈O₂	170.249			18C	154-163C at 11 mmHg	d 0.914	1.4510 at 18C		(Ref. 0175)								Synthetic by distillation of hexyl paraconic acid.				[0175]
70		Obtusilic acid	4-Decenoic acid	DFA0070	Tetsuyuki Kobayashi	C10:1	C₁₀H₁₈O₂	170.249				148-150C at 13 mmHg	d 0.9197	1.4497 at 20C		soluble in benzene and ether.(Ref. 0298)(Ref. 0484)							Seed oil of Lindera obtusiloba(Japanese spicebush).	Made by carbon monoxide and NaOH under pressure and decompose the resulting sodium formate with H₂SO₄. (Ref. 0002)				[0002] / [0298] / [0484]
71		Isodecenoic acid	8-Decenoic acid	DFA0071	Tetsuyuki Kobayashi	C10:1	C₁₀H₁₈O₂	170.249				155-157C at 14 mmHg	d 0.930			(Ref. 0136)							Butterfat and milk of man, goat, and Indian buffalo.					[0136]
72		9-Decylenic acid / caproleic acid	9-Decenoic acid	DFA0072	Tetsuyuki Kobayashi	C10:1	C₁₀H₁₈O₂	170.249				158-163C at 21 mmHg	d 0.9238	1.4485 at 21C		soluble in ethanol and ether.(Ref. 0493)							Mild fats of most animals.					[0493]
73		2-Hendecenoic acid	2-Undecenoic acid	DFA0073	Tetsuyuki Kobayashi	C11:1	C₁₁H₂₀O₂	184.275								(Ref. 0013)(Ref. 0017)(Ref. 0069)(Ref. 0478)												[0013] / [0017] / [0069] / [0478]
74		9-Hendecenoic acid / 9-undecylenic acid	9-Undecenoic acid	DFA0074	Tetsuyuki Kobayashi	C11:1	C₁₁H₂₀O₂	184.275			11.4C	129C at 1 mmHg				(Ref. 0013)(Ref. 0017)(Ref. 0069>								Synthetic by debromination of 9-bromo-9undecenoic acid with (i)Na in ethanol,or (ii)Zn and propionic acid.				[0013] / [0017] / [0069]
75		10-Hendecenoic acid / 10-undecylenic acid	10-Undecenoic acid	DFA0075	Tetsuyuki Kobayashi	C11:1	C₁₁H₂₀O₂	184.275			24.5C	275C at 25 mmHg	d 0.9075	1.4464 at 20C		soluble in ethanol and ether. slightly soluble in chloroform. insoluble in water.(Ref. 0192)(Ref. 0381)								Occurs in sweat. Obtained by pyrolysis of ricinoleic acid. Preparation by bacuum distillation of castor oil:(Ref. 3001)/(Ref. 3002) Found that distillation at 400 under a pressure of 50 mm produced a distillate composed of about 40% heptaldehyde and 20% undecylenic acid.				[0192] / [0381] / [3001] / [3002]
76		2-Lauroleic acid	2-Dodecenoic acid	DFA0076	Tetsuyuki Kobayashi	C12:1	C₁₂H₂₂O₂	198.302			17C	172-174C at 8 mmHg	d 0.9130	1.4639 at 20C		(Ref. 0509)								Synthetic by reation of decanaldehyde with malonic acid in presence of pyridene.				[0509]
77		Linderic acid	4-Dodecenoic acid	DFA0077	Tetsuyuki Kobayashi	C12:1	C₁₂H₂₂O₂	198.302			1-1.3C	170-172C at 13 mmHg	d 0.9106	1.4545 at 15C		soluble in benzene,chloroform and ether.(Ref. 0298)(Ref. 0492)							Seed oils or Lindera obtusiloba and various Formosan plants.					[0298] / [0492]
78		6-Lauroleic acid	6-Dodecenoic acid	DFA0078	Tetsuyuki Kobayashi	C12:1	C₁₂H₂₂O₂	198.302								(Ref. 0052)												[0052]
79		7-Lauroleic acid	7-Dodecenoic acid	DFA0079	Tetsuyuki Kobayashi	C12:1	C₁₂H₂₂O₂	198.302			Oil			1.4486 at 27.5C		(Ref. 0478)												[0478]
80		9-Lauroleic acid	9-Dodecenoic acid	DFA0080	Tetsuyuki Kobayashi	C12:1	C₁₂H₂₂O₂	198.302				142C at 4 mmHg				soluble in benzene, chloroform and ether.(Ref. 0301)							Milk fats;cochineal wax;wax of Tachardina theae.					[0301]
81		10-Lauroleic acid	10-Dodecenoic acid	DFA0081	Tetsuyuki Kobayashi	C12:1	C₁₂H₂₂O₂	198.302			18C	166-168C at 9 mmHg				(Ref. 0134)												[0134]
82		11-Lauroleic acid	11-Dodecenoic acid	DFA0082	Tetsuyuki Kobayashi	C12:1	C₁₂H₂₂O₂	198.302			20C	171-172C at 13 mmHg	d 0.9030	1.4510 at 20C		(Ref. 0478)								Synthetic by conversion (i) from 10-undecenoic acid and (ii) of 1-bromo-10-decene to 11-dodecenenitrile, followed by hydrolysis.				[0478]
83		3-n-Decylacrylic acid	2-Tridecenoic acid	DFA0083	Tetsuyuki Kobayashi	C13:1	C₁₃H₂₄O₂	212.328			38-39C	167-171C at 2 mmHg	d³⁰₄ 0.8995	1.46121 at 20C		(Ref. 0421)(Ref. 0531)								Synthetic by rection of undecanaldehyde with malonic acid in presence of pyrideine.				[0421] / [0531]
84		Isotridecenoic acid	11-Tridecenoic acid	DFA0084	Tetsuyuki Kobayashi	C13:1	C₁₃H₂₄O₂	212.328			28-29C	183-185C at 13.5 mm Hg				(Ref. 0106)(Ref. 0135)								Synthetic by reaction of undecanaodehyde with malonic acid in presence of pyridine.				[0106] / [0135]
85			12-Tridecenoic acid	DFA0085	Tetsuyuki Kobayashi	C13:1	C₁₃H₂₄O₂	212.328			38-39C	192C at 20 mmHg				(Ref. 0013)(Ref. 0017)(Ref. 0069)(Ref. 0134)								Synthetic by (i) reaction of 1-bromo-10-undecene ethyl malonate and Na and (ii) conversion of 10-undecenoic acid to 11-dodecenoic acid.				[0013] / [0017] / [0069] / [0134]
86			2-Tetradecenoic acid	DFA0086	Tetsuyuki Kobayashi	C14:1	C₁₄H₂₆O₂	226.355			33C/50-53C	186-188C at 8 mmHg				(Ref. 0421)(Ref. 0531)								Synthetic by rection of lauric aldehyde with malonic acid in presence of pyridine.				[0421] / [0531]
87		Tsuzuic acid	4-Tetradecenoic acid	DFA0087	Tetsuyuki Kobayashi	C14:1	C₁₄H₂₆O₂	226.355			18-18.5C	185C at 13 mmHg	d 0.9024	1.4559 at 20C		soluble in benzene,petroleum and ether.(Ref. 0298)							Seed oils of Lindera obtusiloba Litsea sp.,Tetradenia glauca and related plants.					[0298]
88		Physeteric acid / 5-myristoleic acid	5-Tetradecenoic acid	DFA0088	Tetsuyuki Kobayashi	C14:1	C₁₄H₂₆O₂	226.355			20C	190-195C at 15 mmHg	d 0.9046	1.4552 at 20C		soluble in benzene, ether and petroleum ether.(Ref. 0490)(Ref. 0491)(Ref. 0492)							Sperm whale and dolphin oils;whale head and blubber oil;sardine oil;pilot-whale oil;sperm whale-blubber oil;human-hair fat.					[0490] / [0491] / [0492]
89			cis-8-Tetradecenoic acid	DFA0089	Tetsuyuki Kobayashi	C14:1	C₁₄H₂₆O₂	226.355			Oil			1.4569 at 17C		soluble in benzene, ether and petroleum ether.(Ref. 0023)(Ref. 0033)(Ref. 0429)							Lipids of all eubacteria investigated.					[0023] / [0033] / [0429]
90		Myristoleic acid	cis-9-Tetradecenoic acid	DFA0090	Tetsuyuki Kobayashi	C14:1	C₁₄H₂₆O₂	226.355			-4C		d₄ 0.9018	1.4519 at 20C		soluble in benzene, ether and petroleum ether.(Ref. 0023)(Ref. 0033)							Oils of whale blubber,shark liver,Antarctic whale and turtle;eel;milk fats;Japanese coccid wax;seed fat of Pycnanthus kombo.					[0023] / [0033]
91			2-Pentadecenoic acid	DFA0091	Tetsuyuki Kobayashi	C15:1	C₁₅H₂₈O₂	240.382			4.5C					(Ref. 0137)								Synthetic, by conversion of myristic acid, to a-hydroxymyristic acid, then, by the action of Pb tetraacetate, to tridecanoldehyde which is then condensed with malonic acid in presence of pyridine.				[0137]
92			14-Pentadecenoic acid	DFA0092	Tetsuyuki Kobayashi	C15:1	C₁₅H₂₈O₂	240.382				198C at 8 mmHg				(Ref. 0137)								Synthetic, by the malonic acid method form 1-bromo-12-tridecene and ethyl malonate in presence of sodium ethoxide.				[0137]
93		Gaidic acid / 2-Palmitoleic acid	2-Hexadecenoic acid	DFA0093	Tetsuyuki Kobayashi	C16:1	C₁₆H₃₀O₂	254.408			39C/45C					soluble in alcohol and ether(Ref. 0396)(Ref. 0434)								Synthetic, by the action of alcoholic KOH on 2-iodopalmitic acid.				[0396] / [0434]
94		7-Palmitoleic acid	7-Hexadecenoic acid	DFA0094	Tetsuyuki Kobayashi	C16:1n-9	C₁₆H₃₀O₂	254.408			21C/33C/32-33C [a-form]/40-41C[b-form]	236C at 15 mmHg value for a-form/180-183C at 1 mmHg value for b-form		1.4583 at 20C value for the b-form		very soluble in alcohol/soluble in ether/insoluble water(Ref. 0081)(Ref. 0346)								Synthetic, by the action of fused KOH on atearolic acid.				[0081] / [0346]
95		cis-9-Palmitoleic acid	cis-9-Hexadecenoic acid	DFA0095	Tetsuyuki Kobayashi	DPam / C16:1n-7	C₁₆H₃₀O₂	254.408			-0.5 to +0.5C	140-141C at 5mmHg				(Ref. 0347)							Widely distrobuted in animal, vegetable and marine oils					[0347]
96		trans-9-Palmitoleic acid	trans-9-Hexadecenoic acid	DFA0096	Tetsuyuki Kobayashi	C16:1n-7	C₁₆H₃₀O₂	254.408			31C					(Ref. 0053)(Ref. 0088)(Ref. 0437)							snade fish , human-hair(Ref. 4001)	Synthetic, by treatment of the cis-form with Se or N oxides.				[0053] / [0088] / [0437] / [4001]
97		cis-10-Palmitoleic acid	cis-10-Hexadecenoic acid	DFA0097	Tetsuyuki Kobayashi	C16:1	C₁₆H₃₀O₂	254.408			15-16C			1.4593 at 20C		(Ref. 0042)						Gas liquid chromatogram [Chromatogram 0001] [Chromatogram 0002] (provided by Dr. Akiko Horiuchi).						[0042]
98		2-Heptadecylenic acid	2-Heptadecenoic acid	DFA0098	Tetsuyuki Kobayashi	C17:1	C₁₇H₃₂O₂	268.435			57.5C					soluble in ether / crystals from acetone(Ref. 0310)(Ref. 0371)(Ref. 0372)								Synthetic, by the malonic acid method from pentadecanoldehyde and malonic acid in presence of pyridine.				[0310] / [0371] / [0372]
99		9-Heptadecylenic acid	cis-9-Heptadecenoic acid	DFA0099	Tetsuyuki Kobayashi	C17:1	C₁₇H₃₂O₂	268.435			11.4-12.2C / 14.5C	175C at 0.5 mmHg		1.4598 at 20C		crystals from light petroleum / Li solt crystals from alcohol (Ref. 0120)(Ref. 0221)(Ref. 0443)							Butterfat ; bogy fat Ovibos moschatus subsp.(Canadian musk ox)					[0120] / [0221] / [0443]
100			cis-2-Octadecenoic acid	DFA0100	Tetsuyuki Kobayashi	C18:1	C₁₈H₃₄O₂	282.461			50.5C					soluble in benzene, chloroform and ether(Ref. 0371)(Ref. 0372)												[0371] / [0372]
101		trans-2-Oleic acid	trans-2-Octadecenoic acid	DFA0101	Tetsuyuki Kobayashi	C18:1	C₁₈H₃₄O₂	282.461			58.5C		d⁹⁰₄ 0.8484			(Ref. 0093)(Ref. 0094)							No natural source					[0093] / [0094]
102		3-Octadecylenic acid	3-Octadecenoic acid	DFA0102	Tetsuyuki Kobayashi	C18:1	C₁₈H₃₄O₂	282.461			56-57C			1.4466 at 65C		(Ref. 0028)(Ref. 0164)							No natural source					[0028] / [0164]
103		4-Octadecylenic acid	4-Octadecenoic acid	DFA0103	Tetsuyuki Kobayashi	C18:1	C₁₈H₃₄O₂	282.461			52-53C					(Ref. 0164)(Ref. 0267)							Only natural source, seed oil of Thalictrum polycarpum	Synthetic in trans-form.				[0164] / [0267]
104		5-Octadecylenic acid	trans-5-Octadecenoic acid	DFA0104	Tetsuyuki Kobayashi	C18:1	C₁₈H₃₄O₂	282.461			43-44C/47.5C					(Ref. 0039)(Ref. 0398)								Synthetic, by the addition of HI to 5-stearolic acid followed by reduction of the addition product with Zn plus acetic acid.				[0039] / [0398]
105		6-Octadecylenic acid / petroselinic acid / petroselic acid / 5-heptadecylene-1-carboxylic acid / D⁵-octadecylenic acid	cis-6-Octadecenoic acid	DFA0105	Tetsuyuki Kobayashi	C18:1	C₁₈H₃₄O₂	282.461			33C	215-217C at 2-3 mmHg	d³⁵₄ 0.8824	1.4536 at 65C		soluble in methanol ,ether , petroleum ether and aqueous alcohol(Ref. 0039)(Ref. 0138)(Ref. 0341)(Ref. 0398)							Various fruit and seed oils including those of various umbellates including ivy and coriander seeds, Angelica polyclada and Petroselinum crispum (parsley)					[0039] / [0138] / [0341] / [0398]
106		Petroselaidic acid	trans-6-Octadecenoic acid	DFA0106	Tetsuyuki Kobayashi	C18:1	C₁₈H₃₄O₂	282.461			54-59C			1.4408 at 70C		(Ref. 0041)								Synthetic, by partial reduction of natural 6-octadecynoic (tariric) acid which has been synthesized by 2 different method.				[0041]
107			cis-7-Octadecenoic acid	DFA0107	Tetsuyuki Kobayashi	C18:1	C₁₈H₃₄O₂	282.461			12.5-13.1C					(Ref. 0189)								synthetic, by the alkyl-acetylene method (also true for other positional isomers up to the 12-cis-isomer).				[0189]
108			trans-7-Octadecenoic acid	DFA0108	Tetsuyuki Kobayashi	C18:1	C₁₈H₃₄O₂	282.461			44.2-44.5C					(Ref. 0189)								Synthetic, by addition of HI to 7-stearolic acid, followed by reduction of the addition product with Zn plus acetic acid.				[0189]
109		cis-8-Oleic acid	cis-8-Octadecenoic acid	DFA0109	Tetsuyuki Kobayashi	C18:1	C₁₈H₃₄O₂	282.461			13.4C [a-]/16.3C [b-]	234C at 15 mmHg	d 0.898	1.45823 at 20C		(Ref. 0189)							Reported in human-hair fat and olive oil; presence in other fats suspected	Synthetic, by the alkylacetylene method.				[0189]
110		trans-8-Elaidic acid	trans-8-Octadecenoic acid	DFA0110	Tetsuyuki Kobayashi	C18:1	C₁₈H₃₄O₂	282.461			52-52.6C					(Ref. 0189)								Synthetic, by isomerization of the cis-isomer with Se.				[0189]
111		9-Octadecylenic acid / Oleic acid	cis-9-Octadecenoic acid	DFA0111	Tetsuyuki Kobayashi	Ole / C18:1n-9	C₁₈H₃₄O₂	282.461			12C [labile] / 16C [stable]	234C at 15 mmHg	d 0.898	1.45823 at 20C		soluble in acetone , alcohol, chloroform, ether and petroleum ether				[Spectrum 0001] (provided by Dr. Takeshi Kasama).		Gas liquid chromatogram [Chromatogram 0001] [Chromatogram 0002] (provided by Dr. Akiko Horiuchi).	Generally considerd to be predominant fatty acid in nature (few fats known to contain less than 10%; Separation from olive oil by double fraction via urea adduct(Ref. 4003). Major constituent in plant oils e.g. olive oil (about 80%), almond oil (about 80%), mainly as glyceride.	Purest product (98%) obtained when the oil was saponified with 3% KOH solution; Synthesis(Ref. 4008)	In animals oleic acid is synthsized from stearoyl CoA by oxidative desaturation using O₂, NADPH, cytochrome b₅. Oleic acid is further metabolized to 20:9n-9 via reactions of desaturation and elongation. Essential fatty acid deficincy causes the accumulation of 20:9n-9.			[4003] / [4008]
112		9-Elaidic acid	trans-9-Octadecenoic acid	DFA0112	Tetsuyuki Kobayashi	C18:1	C₁₈H₃₄O₂	282.461			44.5-46.5C	234C at 15 mmHg	d 0.8565	1.4405 at 70C		soluble in alcohol,chloroform, ether and petroleum ether(Ref. 0189)							Fat of ruminants; human-mother's milk (Ref. 4002)					[0189] / [4002]
113		cis-10-Oleic acid	cis-10-Octadecenoic acid	DFA0113	Tetsuyuki Kobayashi	C18:1	C₁₈H₃₄O₂	282.461			22.2-22.8C					(Ref. 0012)(Ref. 0013)(Ref. 0262)(Ref. 0478)							Root nodules of Pinellia ternate					[0012] / [0013] / [0262] / [0478]
114			trans-10-Octadecenoic acid	DFA0114	Tetsuyuki Kobayashi	C18:1	C₁₈H₃₄O₂	282.461								(Ref. 0012)(Ref. 0013)(Ref. 0262)(Ref. 0478)							Root of nodules of Pinellia					[0012] / [0013] / [0262] / [0478]
115		cis-Vaccenic acid	cis-11-Octadecenoic acid	DFA0115	Tetsuyuki Kobayashi	cis-Vac / C18:1n-7	C₁₈H₃₄O₂	282.461			14.5-15.5C					(Ref. 0064)(Ref. 0199)(Ref. 0238)(Ref. 0473)							Found in butterfat and in other animal fats. (Ref. 4004)	Synthesis (Ref. 4005)(Ref. 4006)(Ref. 4007)				[0064] / [0199] / [0238] / [0473] / [4004] / [4005] / [4006] / [4007]
116		trans-Vaccenic acid	trans-11-Octadecenoic acid	DFA0116	Tetsuyuki Kobayashi	trans-Vac / C18:1n-7	C₁₈H₃₄O₂	282.461			44C		d 0.8563	1.4406 at 70C		soluble in acetone and mathanol(Ref. 0062)(Ref. 0083)(Ref. 0209)(Ref. 0262)(Ref. 0474)							Small proportion in ox and sheep body fats; butter					[0062] / [0083] / [0209] / [0262] / [0474]
117		cis-12-Oleic acid	cis-12-Octadecenoic acid	DFA0117	Tetsuyuki Kobayashi	C18:1	C₁₈H₃₄O₂	282.461			9.8-10.4 / 26.5-27.5C	196C at 1.5 mmHg				(Ref. 0044)(Ref. 0064)(Ref. 0199)(Ref. 0207)(Ref. 0473)(Ref. 0474)							Soybean oil					[0044] / [0064] / [0199] / [0207] / [0473] / [0474]
118		trans-12-Elaidic acid	trans-12-Octadecenoic acid	DFA0118	Tetsuyuki Kobayashi	C18:1	C₁₈H₃₄O₂	282.461			39.7-40.1C	196C at 1.5 mmHg				(Ref. 0044)(Ref. 0199)(Ref. 0473)												[0044] / [0199] / [0473]
119			trans-15-Octadecenoic acid	DFA0119	Tetsuyuki Kobayashi	C18:1	C₁₈H₃₄O₂	282.461			61-61.5C(Ref. 0001)					(Ref. 0054)(Ref. 0494)								Synthetic by partial hydrogenation of linolenic acid.				[0054] / [0494]
120			trans-16-Octadecenoic acid	DFA0120	Tetsuyuki Kobayashi	C18:1	C₁₈H₃₄O₂	282.461			65.6-66.2C					(Ref. 0213)(Ref. 0214)							Hydrolysates of betterfat and of ox and sheep fats					[0213] / [0214]
121			cis-17-Octadecenoic acid	DFA0121	Tetsuyuki Kobayashi	C18:1	C₁₈H₃₄O₂	282.461			55-55.5C					(Ref. 0208) (Ref. 0262)							Kamala-seed oil	Synthetic, by reduction of ethyl undecanoate with LiAlH₄ to 10-undecenol, followed by further reactions to cis-17-octadecenoic acid.				[0208] / [0262]
122			2-Nonadecenoic acid	DFA0122	Tetsuyuki Kobayashi	C19:1	C₁₉H₃₆O₂	296.488			66.5C	297-298C at 100 mmHg				(Ref. 0384)								Synthetic, by dehydrohalogenation of 2-bromononadecanoic acid.				[0384]
123		cis-Gadoleic acid	cis-9-Eicosenoic acid / cis-9-icosenoic acid	DFA0123	Tetsuyuki Kobayashi	C20:1	C₂₀H₃₈O₂	310.515			23-23.5C	170C at 0.1 mmHg	d 0.882	1.4597 at 25C		soluble in acetone, methylalcohol and petroleumether (Ref. 0106) (Ref. 0234) (Ref. 0332) (Ref. 0487)							Natural fats; codfish; shark- and ray-liver oils; whale oil	Synthetic				[0106] / [0234] / [0332] / [0487]
124		cis-Gondoic acid	cis-11-Eicosenoic acid / cis-11-icosenoic acid	DFA0124	Tetsuyuki Kobayashi	C20:1	C₂₀H₃₈O₂	310.515			23-24/50C	267C at 15 mmHg				soluble in ethanol and methylalcohol (Ref. 0044) (Ref. 0250) (Ref. 0255)						Gas liquid chromatogram [Chromatogram 0001] [Chromatogram 0002] (provided by Dr. Akiko Horiuchi).	Seed oils of Cardiospermum halicacabum (balloon vine), rape, mustard, and other Brassicaceae; reported in oils of menhaden, Atlantic cod, Squalus acanthias (dogfish) liver, and Dalphinapterus leucas (beluga, or white whale) blubber					[0044] / [0250] / [0255]
125		trans-Gondoic acid	trans-11-Eicosenoic acid / trans-11-icosenoic acid	DFA0125	Tetsuyuki Kobayashi	C20:1	C₂₀H₃₈O₂	310.515			52-53C					(Ref. 0254)							Oils of pilot whale, menhaden, Atlantic cod, Squalus acanthias (dogfish) liver, and blubber of Delphinap terus leucas (beluga, or white whale); many plants, especially Buxaceae.					[0254]
126			cis-14-Eicosenoic acid / cis-14-icosenoic acid	DFA0126	Tetsuyuki Kobayashi	C20:1	C₂₀H₃₈O₂	310.515			42.5C					(Ref. 0512)								Synthetic				[0512]
127		cis-Cetoleic acid	cis-11-Docosenoic acid	DFA0127	Tetsuyuki Kobayashi	C22:1	C₂₂H₄₂O₂	338.568			33-33.7C					soluble in ethanol (Ref. 0126) (Ref. 0482) (Ref. 0483)							As the ester in oils of marine animals, especially in liver oils of fish, e.g., Gadus morhua (Atlantic codfish).					[0126] / [0482] / [0483]
128		cis-Erucic acid	cis-13-Docosenoic acid	DFA0128	Tetsuyuki Kobayashi	C22:1	C₂₂H₄₂O₂	338.568			34.7C	281C at 30 mmHg	d 0.85321	1.44438 at 70C		very soluble in ether and methylalchol (Ref. 0091) (Ref. 0151) (Ref. 0172) (Ref. 0235) (Ref. 0337)				[Spectrum 0001] (provided by Dr. Takeshi Kasama).		Gas liquid chromatogram [Chromatogram 0001] (provided by Dr. Akiko Horiuchi).	Seed oils of Brassicaceae and Tropaeolaceae (40-80% of total fatty acids); seeds of rape, wallflower, mustard and jamba; nastutium; Pringlea antiscorbutica (Kerguelen cabbage); Thlaspi arvense (fenchweed); Argentine avocados; 3 Ximenia spp.	Synthetic				[0091] / [0151] / [0172] / [0235] / [0337]
129		trans-Brassidic acid	trans-13-Docosenoic acid	DFA0129	Tetsuyuki Kobayashi	C22:1	C₂₂H₄₂O₂	338.568			61.9C	265C at 15 mmHg	d 0.85002	1.44349 at 70C		sparingly solbule in cold ethanol (Ref. 0091) (Ref. 0096) (Ref. 0097) (Ref. 0550)								Synthetic, by (1) the malonic ester method, and (2) treating erucic acid with a variety of isomerizing agents.				[0091] / [0096] / [0097] / [0550]
130			22-Tricosenoic acid	DFA0130	Tetsuyuki Kobayashi	C23:1	C₂₃H₄₄O₂	352.594			75.1-75.2C					(Ref. 0463)								Synthetic, by lengthening the chain of 10-undecenoic acid.				[0463]
131		Nervonic acid / cis-Selacholeic acid	cis-15-Tetracosenoic acid	DFA0131	Tetsuyuki Kobayashi	C24:1	C₂₄H₄₆O₂	366.621			42.5-43C					soluble in acetone, ethanol and ether (Ref. 0092) (Ref. 0210) (Ref. 0290) (Ref. 0503) (Ref. 0504) (Ref. 0506)				[Spectrum 0001] (provided by Dr. Takeshi Kasama).		Gas liquid chromatogram [Chromatogram 0001] [Chromatogram 0002] (provided by Dr. Akiko Horiuchi).	Liver oil of Centrophorus granulosus (spiny dogfish shark); cerebroside of brain tissue; reported in kernel oils of several Ximenia spp.					[0092] / [0210] / [0290] / [0503] / [0504] / [0506]
132		trans-Selacholeic acid	trans-15-Tetracosenoic acid	DFA0132	Tetsuyuki Kobayashi	C24:1	C₂₄H₄₆O₂	366.621			65.5C					(Ref. 0092)								Synthetic				[0092]
133			9-Hexacosenoic acid	DFA0133	Tetsuyuki Kobayashi	C26:1	C₂₆H₅₀O₂	394.674								(Ref. 0059)							Reported to be a component of lipids in Spheciospongia vesparia (a sponge)					[0059]
134		Ximenic acid	cis-17-Hexacosenoic acid	DFA0134	Tetsuyuki Kobayashi	C26:1	C₂₆H₅₀O₂	394.674			45-45.5C(?)					soluble in benzene, chloroform, ether and petoleumether (Ref. 0082) (Ref. 0407)							Reported in the seed oil of Ximenia americana (an Indian shrub).					[0082] / [0407]
135			cis-19-Octacosenoic acid	DFA0135	Tetsuyuki Kobayashi	C28:1	C₂₈H₅₄O₂	422.727			57-58C					(Ref. 0336)							Small proportion of South African Ximenia spp.; 4.7-12.2% of seed oils of various Ximenia spp.					[0336]
136		Lumepueic acid	cis-21-Triacontenoic acid	DFA0136	Tetsuyuki Kobayashi	C30:1	C₃₀H₅₈O₂	450.780								soluble in benzene, chloroform, ether and petroleumether (Ref. 0082)							Reported to be 3-7% of fatty acids in various African Ximenia oils.					[0082]
137			cis-Dotriacontenoic acid	DFA0137	Tetsuyuki Kobayashi	C32:1	C₃₂H₆₂O₂	478.833								(Ref. 0336)							Approx. 1% in seed oils of Ximenia americana & X. caffra.					[0336]
138		b-Vinylacrylic acid	2, 4-Pentadienoic acid	DFA0138	Tetsuyuki Kobayashi	C5:2	C₅H₆O₂	98.100			80C	decomposes, 100C				very soluble in ethanol and ether / soluble in hot water / slightly soluble in petroleumether (Ref. 0162)								Synthetic				[0162]
139		Sorbic acid	2, 4-Hexadienoic acid	DFA0139	Tetsuyuki Kobayashi	C6:2	C₆H₈O₂	112.127			134.5C	decomposes, 228C				soluble in ethanol / slightly solubule in hot water (Ref. 0080) (Ref. 0229) (Ref. 0242)							Berries of mountain ash; unripe sorb apples.					[0080] / [0229] / [0242]
140		cis, cis-Stillingic acid	cis-2, cis-4-Decadienoic acid	DFA0140	Tetsuyuki Kobayashi	C10:2	C₁₀H₁₆O₂	168.233						1.4896 at 17C		soluble in acetone, ether and hexane (Ref. 0146)							Stillingia oils.					[0146]
141			cis-2, trans-4-Decadienoic acid	DFA0141	Tetsuyuki Kobayashi	C10:2	C₁₀H₁₆O₂	168.233				112-114C at 0.45 mm Hg		1.5007 at 18C		soluble in acetone, ether and petroleumether (Ref. 0146)							Sebastiania fruticosa seeds.					[0146]
142		trans, cis-Stillingic acid	trans-2, cis-4-Decadienoic acid	DFA0142	Tetsuyuki Kobayashi	C10:2	C₁₀H₁₆O₂	168.233				107C at 0.2 mm Hg		1.5078 at 18C		(Ref. 0146)							Stillingia oils.					[0146]
143			trans-2, trans-4-Decadienoic acid	DFA0143	Tetsuyuki Kobayashi	C10:2	C₁₀H₁₆O₂	168.233			49-50C	121-124C at 0.3 mmHg		1.5058 at 31C		(Ref. 0146) (Ref. 0348)								Synthetic				[0146] / [0348]
144			cis-2, cis-6-Decadienoic acid	DFA0144	Tetsuyuki Kobayashi	C10:2	C₁₀H₁₆O₂	168.233			Oil			1.4730 at 17C		(Ref. 0158) (Ref. 0233) (Ref. 0261) (Ref. 0399)								Synthetic				[0158] / [0233] / [0261] / [0399]
145			trans-2, cis-6-Decadienoic acid	DFA0145	Tetsuyuki Kobayashi	C10:2	C₁₀H₁₆O₂	168.233								(Ref. 0144)							Stillingia oils.					[0144]
146			trans-2, trans-6-Decadienoic acid	DFA0146	Tetsuyuki Kobayashi	C10:2	C₁₀H₁₆O₂	168.233			42-43C					(Ref. 0144)								Synthetic				[0144]
147			trans-4, trans-6-Decadienoic acid	DFA0147	Tetsuyuki Kobayashi	C10:2	C₁₀H₁₆O₂	168.233								(Ref. 0529)								Synthetic				[0529]
148			9, 12-Hexadecadienoic acid	DFA0148	Tetsuyuki Kobayashi	C16:2	C₁₆H₂₈O₂	252.392								soluble in acetone, ether and petroleumether (Ref. 0101) (Ref. 0122) (Ref. 0223)							Seed oils of Acacia giraffae, Asclepias syriaca, and Macadamia ternifolia.					[0101] / [0122] / [0223]
149			cis-5, cis-12-Octadecadienoic acid	DFA0149	Tetsuyuki Kobayashi	C18:2	C₁₈H₃₂O₂	280.445								(Ref. 0018)								Synthetic				[0018]
150			cis-5, trans-12-Octadecadienoic acid	DFA0150	Tetsuyuki Kobayashi	C18:2	C₁₈H₃₂O₂	280.445			-4 to -2C			1.4677 at 20C		(Ref. 0018)								Synthetic				[0018]
151			trans-5, cis12-Octadecadienoic acid	DFA0151	Tetsuyuki Kobayashi	C18:2	C₁₈H₃₂O₂	280.445			-12C to -9C	168C to 170C at 0.3mmHg		1.4684 at 20C		(Ref. 0018)												[0018]
152			trans-5, trans-12-Octadecadienoic acid	DFA0152	Tetsuyuki Kobayashi	C18:2	C₁₈H₃₂O₂	280.445			16C to 19C	175C to 176C at 0.4mmHg		1.4671 at 20C		(Ref. 0018)												[0018]
153			6, 8-Octadecadienoic acid	DFA0153	Tetsuyuki Kobayashi	C18:2	C₁₈H₃₂O₂	280.445				153C to 155C at 0.1mmHg				(Ref. 0138)												[0138]
154			trans-8, trans-10-Octadecadienoic acid	DFA0154	Tetsuyuki Kobayashi	C18:2	C₁₈H₃₂O₂	280.445			56C to 56.5C		d⁶⁰₄ 0.8808	1.4682 at 60C		(Ref. 0356)												[0356]
155			cis-8, cis-11-Octadecadienoic acid	DFA0155	Tetsuyuki Kobayashi	C18:2	C₁₈H₃₂O₂	280.445			-12.5C to -9.5C	11.8C to 20C at 0.0001mmHg		1.4663 at 25C		(Ref. 0187)(Ref. 0287)(Ref. 0295)												[0187] / [0287] / [0295]
156			cis-9, cis-11-Octadecadienoic acid	DFA0156	Tetsuyuki Kobayashi	C18:2	C₁₈H₃₂O₂	280.445			42C to 43.2C					(Ref. 0456)												[0456]
157			cis-9, trans-11-Octadecadienoic acid	DFA0157	Tetsuyuki Kobayashi	C18:2	C₁₈H₃₂O₂	280.445			-6C to -3C					(Ref. 0377)												[0377]
158			trans-9, trans-11-Octadecadienoic acid	DFA0158	Tetsuyuki Kobayashi	C18:2	C₁₈H₃₂O₂	280.445			54C		d⁷⁷₄ 0.8659	1.4624 at 77C		(Ref. 0150)(Ref. 0349)(Ref. 0377)												[0150] / [0349] / [0377]
159		Linoleic acid	cis-9, cis-12-Octadecadienoic acid	DFA0159	Tetsuyuki Kobayashi	LA / C18:2n-6 / C18:2w6	C₁₈H₃₂O₂	280.445		There are two groups of essential fatty acids for mammals, the n-6 (or w6) and the n-3 (or w3). Linoleic acid (LA) is one of the n-6 essential fatty. Animals deficient in LA show the growth retardation, skin lesions, reproductive failure, fatty liver and polydipsia (Ref. 2009/2010). Dietary supplementation of either linoleate, g-linoleate or arachidonate prevents such symptoms completely. Its physiological functions appear to be mediated mainly through the hormone-like eicosanoids (prostaglandins, leukotriens and thromboxanes et al.) derived from arachidonic acid which is biosynthesized from LA. LA is also shown to be involved in control of the water impermeability of the skin and regulation of cholesterol synthesis and transport.	-5C	229C to 230C at 16mmHg	d 0.9031	1.4711 at 20C		soluble in acetone, alcohol, ether and petroleum ether.(Ref. 0193)(Ref. 0351)(Ref. 0378)(Ref. 0409)(Ref. 0410)						Gas liquid chromatogram [Chromatogram 0001] (provided by Dr. Akiko Horiuchi).	Constituent of the essential fatty acids (vitamin F) and of various microorganisms; oils of cottonseed, soybean, peanut, corn, sunflower and poppy seed.		Linoleic acid (18:2n-6) is synthesized from oleic acid (18:1n-9) by desaturation of D12-desaturase, and a-linolenic acid (18:3n-3) is formed from linoleic acid by desaturation reaction of D15-desaturase. Since both D12- and 15-desaturases are present in plant cells but not in animal cells, linoleic and a-linolenic acid are not biosynthesized in animal cells in vivo. When ingested by animals, linoleic acid is desaturated, elongated to form g-linolenic acid (18:3n-6), dihomo-g-linolenic acid (20:3n-6), arachidonic acid (20:4n-6) and adrenic acid (22:4n-6). Docosapentaenoic acid (22:5n-6) is synthesized from adrenic acid in significant amounts only under conditions of prolonged n-3 fatty acid deficiency. No interconversion between the n-6 and n-3 series in mammals. Nutritionally, it is important to note that different foods contain different proportions of n-6/n-3 and therefore the n-6/n-3 ratio in tissue lipids change significantly depending on the choice of foods.(Ref. 2003) Although plants synthesize and store linoleic acid and a-linolenic acid as well as saturated and monounsaturated fatty acids in grains, the proportions of these fatty acids in different vegetable oils differ greatly. Safflower and sunflower oil contain high levels of linoleate, while perilla and linseed oil are rich in a-linolenic acid.			[0193] / [0351] / [0378] / [0409] / [0410] / [2003] / [2009] / [2010]
160			cis-9, trans-12-Octadecadienoic acid	DFA0160	Tetsuyuki Kobayashi	C18:2	C₁₈H₃₂O₂	280.445			1C			1.4650 at 27C		(Ref. 0011)(Ref. 0266)(Ref. 0405)								Synthetic by dehydration of ricinoleic acid or elaidinization of linoleic acid.				[0011] / [0266] / [0405]
161			trans-9, cis-12-Octadecadienoic acid	DFA0161	Tetsuyuki Kobayashi	C18:2	C₁₈H₃₂O₂	280.445			1C			1.4690 at 27C		(Ref. 0193)												[0193]
162		Linolelaidic	trans-9, trans-12-Octadecadienoic acid	DFA0162	Tetsuyuki Kobayashi	C18:2	C₁₈H₃₂O₂	280.445			28C to 29C	179C to 183C at 0.8mmHg		1.4641 at 27C		soluble in alcohol, ether, methyl alcohol and petroleum ether.(Ref. 0127)(Ref. 0193)(Ref. 0275)							Seed fat of Chilopsis linearis.					[0127] / [0193] / [0275]
163			cis-10, cis-12-Octadecadienoic acid	DFA0163	Tetsuyuki Kobayashi	C18:2	C₁₈H₃₂O₂	280.445			38.2C to 39C					(Ref. 0119)(Ref. 0252)(Ref. 0456)												[0119] / [0252] / [0456]
164			trans-10, cis-12-Octadecadienoic acid	DFA0164	Tetsuyuki Kobayashi	C18:2	C₁₈H₃₂O₂	280.445			22.23C					(Ref. 0118)(Ref. 0266)(Ref. 0378)(Ref. 0379)							Seed fat of Chilopsis linearis.					[0118] / [0266] / [0378] / [0379]
165			trans-10, trans-12-Octadecadienoic acid	DFA0165	Tetsuyuki Kobayashi	C18:2	C₁₈H₃₂O₂	280.445			56C to 57C		d 0.8686	1.4656 at 70C		soluble in acetone, cyclohexane and ether.(Ref. 0085)(Ref. 0117)(Ref. 0252)(Ref. 0266)												[0085] / [0117] / [0252] / [0266]
166			cis-10, cis-13-Octadecadienoic acid	DFA0166	Tetsuyuki Kobayashi	C18:2	C₁₈H₃₂O₂	280.445			-9C to -6.5C	121C to 128C at 0.0001mmHg		1.4670 at 25C		(Ref. 0194)												[0194]
167			cis-11, cis-14-Octadecadienoic acid	DFA0167	Tetsuyuki Kobayashi	C18:2	C₁₈H₃₂O₂	280.445			6C to 8C	112C to 115C at 0.0001mmHg		1.4664 at 25C		(Ref. 0194)												[0194]
168			cis-10, cis-13-Nonadecadienoic acid	DFA0168	Tetsuyuki Kobayashi	C19:2	C₁₉H₃₄O₂	294.472								(Ref. 0274)							Liver oil of Carcharodon carcharias; Cambodiafish oil.					[0274]
169			11, 14-Eicosadienoic acid / 11, 14-icosadienoic acid	DFA0169	Tetsuyuki Kobayashi	C20:2	C₂₀H₃₆O₂	308.499								soluble in acetone, ether and petroleum ether.(Ref. 0287)(Ref. 0292)							Herring and menhaden oils; cattle-liver phosphatides; swine brain lipids; shark liver oil.					[0287] / [0292]
170			5, 13-Docosadienoic acid	DFA0170	Tetsuyuki Kobayashi	C22:2	C₂₂H₄₀O₂	336.552								(Ref. 0034)							Fish oils.					[0034]
171			13, 16-Docosadienoic acid	DFA0171	Tetsuyuki Kobayashi	C22:2	C₂₂H₄₀O₂	336.552								soluble in acetone and ether.(Ref. 0045)(Ref. 0241)												[0045] / [0241]
172			17, 20-Hexacosadienoic acid	DFA0172	Tetsuyuki Kobayashi	C26:2	C₂₆H₄₈O₂	392.658								soluble inether and petroleum ether.(Ref. 0059)							Fish oils; Spheciospongia vesparia (sponge).					[0059]
173			4, 7, 10-Hexadecatrienoic acid	DFA0173	Tetsuyuki Kobayashi	C16:3	C₁₆H₂₆O₂	250.376								soluble in alcohol and ether.(Ref. 0295)							Sardine oil.					[0295]
174			trans-5, trans-8, trans-11-Hexadecatrienoic acid	DFA0174	Tetsuyuki Kobayashi	C16:3	C₁₆H₂₆O₂	250.376								soluble in methyl alcohol and petroleum ether.(Ref. 0347)												[0347]
175			6, 9, 12-Hexadecatrienoic acid	DFA0175	Tetsuyuki Kobayashi	C16:3	C₁₆H₂₆O₂	250.376								soluble in alcohol and ether.(Ref. 0295)(Ref. 0464)(Ref. 0465)			CMR (METHYL ESTER) : C12, 127.797; C13, 130.127; C14, 29.308; C15, 22.753; C16: 13.760ppm (Ref. 6001) PMR(METHYL ESTER): CH3-C-C-C=C- (TERMINAL METHYL GROUP) , 0.83-0.98ppm (TRIPLETS) (Ref. 6001)	HR-EI-MS (METHYL ESTER) : M/Z; 264.20910(M) 001) EI-MS (PYRROLIDIDE) : M/Z; 154, 166, 194, 206, 234, 246(Ref. 6001).			Herring, menhaden and rapeseed oils. Muscle lipids and internal lipids in a sardine. ( The concentration of internal lipids in total fatty acid is higher than that of muscle lipids. ) (Ref. 6001)					[0295] / [0464] / [0465] / [6001]
176		Hiragonic acid	6,10,14-Hexadecatrienoic acid	DFA0176	Tetsuyuki Kobayashi	C16:3	C₁₆H₂₆O₂	250.376				180-190C at 15mmHg	d 0.9296	1.4850 at 50C		soluble in acetone, ethanol, ether and methylalcohol.(Ref. 0488)(Ref. 0489)							Oil of Sardinops melanosticta.					[0488] / [0489]
177			7, 10, 13-Hexadecatrienoic acid	DFA0177	Tetsuyuki Kobayashi	C16:3	C₁₆H₂₆O₂	250.376								soluble in acetone, ethanol, ether and pentane.(Ref. 0231)(Ref. 0295)(Ref. 0465)							Menhaden oil.					[0231] / [0295] / [0465]
178			9, 12, 15-Hexadecatrienoic acid	DFA0178	Tetsuyuki Kobayashi	C16:3	C₁₆H₂₆O₂	250.376								very soluble in acetone, ethanol, pentane, and petroleumether.(Ref. 0295)							Jacaranda oils.					[0295]
179		Calea	trans-3, cis-9, cis-12-Octadecatrienoic acid	DFA0179	Tetsuyuki Kobayashi	C18:3	C₁₈H₃₀O₂	278.430			61-61.5C					soluble in acetone, ethanol, ether, and petroleumether.(Ref. 0040)							Linseed, perilla, and hemp oils.					[0040]
180		g-Linolenic acid	cis-6, cis-9, cis-12-Octadecatrienoic acid	DFA0180	Tetsuyuki Kobayashi	C18:3n-6 / C18:3w6 / gLnn / gLnA	C₁₈H₃₀O₂	278.430		There are two groups of essential fatty acids, the n-6 (or w6) and the n-3 (or w3). g-linolenic acid is n-6 fatty acids. Essential fatty acid deficiency causes skin lesion and growth retardation. Dietary supplementation of either linoleate, g-linoleate or arachidonate prevents such symptoms completely. The n-6 essential fatty acids have at least four roles (Ref. 2014): 1) Modulation of membrane structure. 2) Formation of short-lived giologically active molecules. Oxygenated derivatives of g-linolenic acid is a Arachidonic acid may have a role in the regulation of cell devision in cancer and other cells. There are other bioactive substance, PGE1 and 15-OH-dihomogamma-linolenic acid which are both formed from g-linolenic acid after its rapid elongation to dihomogamma-linolenic acid. 3) Control of the water impermeability of the skin. 4) Regulation of cholesterol synthesis and transport.	-11.3 to -11C	125C at 0.05mmHg	d 0.9164	1.4800 at 20C		soluble in acetone, ether, methylalcohol and petroleum ether.(Ref. 0352)(Ref. 0383)(Ref. 0415)							Isolated from seeds of Oenothera biennis and O. lamarckiana (evening primroses); drying oils. A minor component of many animal lipids.		Linoleic acid (18:2n-6) is synthesized from oleic acid (18:1n-9) by desaturation of D12-desaturase, and a-linolenic acid (18:3n-3) is formed from linoleic acid by desaturation reaction of D15-desaturase. Since both D12- and 15-desaturases are present in plant cells but not in animal cells, linoleic and a-linolenic acid are not biosynthesized in animal cells in vivo. When ingested by animals, linoleic acid is desaturated, elongated to form g-linolenic acid (18:3n-6), dihomo-g-linolenic acid (20:3n-6), arachidonic acid (20:4n-6) and adrenic acid (22:4n-6). Docosapentaenoic acid (22:5n-6) is synthesized from adrenic acid in significant amounts only under conditions of prolonged n-3 fatty acid deficiency. No interconversion between the n-6 and n-3 series in mammals. Nutritionally, it is important to note that different foods contain different proportions of n-6/n-3 and therefore the n-6/n-3 ratio in tissue lipids change significantly depending on the choice of foods.(Ref. 2003)			[0352] / [0383] / [0415] / [2003] / [2014]
181			6, 10, 14-Octadecatrienoic acid	DFA0181	Tetsuyuki Kobayashi	C18:3	C₁₈H₃₀O₂	278.430					d 0.9221	1.4794 at 20C		soluble in ethanol, pentane and petroleum ether.(Ref. 0495)(Ref. 0498)(Ref. 0499)							Trichosanthes oils.					[0495] / [0498] / [0499]
182			cis-8, trans-10, cis-12-Octadecatrienoic acid	DFA0182	Tetsuyuki Kobayashi	C18:3	C₁₈H₃₀O₂	278.430			43.5-44C					very soluble in petroleumether and soluble in acetone, ethanol, CS₂ and pentane.(Ref. 0125)							Catalpa ovata seed oil; Jacaranda oils.					[0125]
183		a-Calendic acid	trans-8, trans-10, cis-12-Octadecatrienoic acid	DFA0183	Tetsuyuki Kobayashi	C18:3	C₁₈H₃₀O₂	278.430			40-40.5C					soluble in acetone, ethanol, cyclohexane, ether, pentane and petroleum ether.(Ref. 0123)							Neou, po-yak, and tung oils.					[0123]
184		b-Calendic acid	trans-8, trans-10, trans-12-Octadecatrienoic acid	DFA0184	Tetsuyuki Kobayashi	C18:3	C₁₈H₃₀O₂	278.430			77-78C					soluble in ethanol, CS₂, ether, heptane, metylalcohol and petroleum ether.(Ref. 0123)(Ref. 0279)							Cattle-liver phosphatides.					[0123] / [0279]
185		Punicic acid / trichosanic acid	cis-9, trans-11, cis-13-Octadecatrienoic acid	DFA0185	Tetsuyuki Kobayashi		C₁₈H₃₀O₂	278.430			43.5-44C		d⁵⁰₄ 0.9025	1.5113 at 50C		soluble in ethanol, pentane and petroleum ether.(Ref. 0125)(Ref. 0128)(Ref. 0129)(Ref. 0130)(Ref. 0251)							Seed oils of Punica granatum (pomegranate) and Catalpa speciosa; Chilopsis sp.; C. linearis.					[0125] / [0128] / [0129] / [0130] / [0251]
186		a-Eleostearic acid	cis-9, trans-11, trans-13-Octadecatrienoic acid	DFA0186	Tetsuyuki Kobayashi	C18:3	C₁₈H₃₀O₂	278.430			49-49.2C	235C at 15 mmHg	d⁵⁰₄ 0.9028	1.5112 at 50C		soluble in ethanol, cyclohexane and petroleum ether.(Ref. 0128)							Aleurites spp. (tung) , neou, and po-yak oils; oils of tropical and subtropical species.					[0128]
187			trans-9, trans-11, trans-13-Octadecatrienoic acid	DFA0187	Tetsuyuki Kobayashi	C18:3	C₁₈H₃₀O₂	278.430			61.5-62.5C					soluble in acetone, ethanol, CS₂, heptane, methylalcohol and pentane.(Ref. 0131)							Cattle-liver phosphatides.					[0131]
188		b-Eleostearic acid	trans-9, trans-11, trans-13-Octadecatrienoic acid	DFA0188	Tetsuyuki Kobayashi	C18:3	C₁₈H₃₀O₂	278.430			71-71.5C	188C at 1 mmHg	d 0.8909	1.5011 at 75C		soluble in ethanol, methylalcohol and petroleum ether.(Ref. 0010)(Ref. 0067)(Ref. 0387)								Synthetic, by isomerization of the a-acid in the presence of intense light and various catalysts, especially I₂.				[0010] / [0067] / [0387]
189		Isomerized punicic acid	trans-9, trans-11, trans-13-Octadecatrienoic acid	DFA0189	Tetsuyuki Kobayashi	C18:3	C₁₈H₃₀O₂	278.430			70-71C					(Ref. 0131)								Synthetic, by isomerization of the a-acid.				[0131]
190			9, 12, 14-Octadecatrienoic acid	DFA0190	Tetsuyuki Kobayashi	C18:3	C₁₈H₃₀O₂	278.430								(Ref. 0278)								Synthetic, by isomerization of a-linolenic acid.				[0278]
191		a-Linolenic acid	cis-9, cis-12, cis-15-Octadecatrienoic acid	DFA0191	Tetsuyuki Kobayashi	aLnA / C18:3n-3 / C18:3w3 / aLnn	C₁₈H₃₀O₂	278.430		Dietary a-linolenic acid can be further elongated and desaturated to form the long-chain n-3 fatty acids, such as eicosapentaenoic acid (EPA) and docosapentaenoic acid (DHA), which are uniquely rich in neural membranes of retina and brain in mammals. It has been reported that n-3 fatty acid deficiency produces reduced learning ability(Ref. 2005), impaired vision, abnormal electroretinogram(Ref. 2006/2007) and polydipsia(Ref. 2008). Dietary fat manipulation of perilla oil rich in a-linolenic acid reduces colonic damage in experimental Crohn's disease (Ref. 2015/2016).	-11.3 to -11C	125C at 0.05 mmHg	d 0.9164	1.4678 at 50C		soluble in acetone, ethanol, ether and petroleum ether.(Ref. 0400)						Gas liquid chromatogram [Chromatogram 0001] (provided by Dr. Akiko Horiuchi).	Linseed, perilla, and hemp oils; drying oils.		Linoleic acid (18:2n-6) is synthesized from oleic acid (18:1n-9) by desaturation of D12-desaturase, and a-linolenic acid (18:3n-3) is formed from linoleic acid by desaturation reaction of D15-desaturase. Since both D12- and 15-desaturases are present in plant cells, a-linolenic acid is synthesized in plants, and relatively enriched in leaves (photosynthetic tissues). On the other hand, these desaturases are not present in animal cells, neither linoleic nor a-linolenic acid is biosynthesized in animal cells in vivo. When ingested by animals, a-linolenic acid is desaturated, elongated and chain-shortened to form eicosapantaenoic acid (20:5n-3, EPA) and docosahexaenoic acid (22:6n-3, DHA)(Ref. 2001/2002). No interconversion between the n-6 and n-3 series in mammals. Nutritionally, it is important to note that different foods contain different proportions of n-6/n-3 and therefore the n-6/n-3 ratio in tissue lipids change significantly depending on the choice of foods. Although plants synthesize and store linoleic acid and a-linolenic acid as well as saturated and monounsaturated fatty acids in grains, the proportions of these fatty acids in different vegetable oils differ greatly. Safflower and sunflower oil contain high levels of linoleate, while perilla and linseed oil are rich in a-linolenic acid.			[0400] / [2001] / [2002] / [2005] / [2006] / [2007] / [2008] / [2015] / [2016]
192		Elaidolinoleic acid	trans-9, trans-12, trans-15-Octadecatrienoic acid	DFA0192	Tetsuyuki Kobayashi	C18:3	C₁₈H₃₀O₂	278.430			29.5-30C					solubule in methylalcohol and petroleum ether.(Ref. 0279)								Synthetic, by treatment of the ester form of a-linolenic acid with 1% Se at 205-215C to yield this acid ester (melting point, 29-30C).				[0279]
193			10, 12, 14-Octadecatrienoic acid	DFA0193	Tetsuyuki Kobayashi	C18:3	C₁₈H₃₀O₂	278.430			79C					(Ref. 0276)(Ref. 0278)												[0276] / [0278]
194		Pseudoeleostearic acid	trans-10, trans-12, trans-14-Octadecatrienoic acid	DFA0194	Tetsuyuki Kobayashi	C18:3	C₁₈H₃₀O₂	278.430			77-77.5C					(Ref. 0010)								Synthetic, by alkali isomerization of a-linolenic acid.				[0010]
195			10, 12 ,15-Octadecatrienoic acid	DFA0195	Tetsuyuki Kobayashi	C18:3	C₁₈H₃₀O₂	278.430								(Ref. 0276)								Synthetic, by alkali isomerization of a-linolenic acid.				[0276]
196			5, 8, 11-Eicosatrienoic acid / 5, 8, 11-icosatrienoic acid	DFA0196	Tetsuyuki Kobayashi	C20:3	C₂₀H₃₄O₂	306.483								solubule in CS₂, heptane and methylalcohol.(Ref. 0292)							Fish oils; phosphatides of liver and suprarenals of land animals and of brain.					[0292]
197		bishomo-g-linolenic acid / dihomo-g-linolenic acid	8, 11, 14-Eicosatrienoic acid/8, 11, 14-icosatrienoic acid	DFA0197	Tetsuyuki Kobayashi	C20:3n-6 / C20:3w6 / DHLA	C₂₀H₃₄O₂	306.483								solubule in CS₂, heptane and methylalcohol.(Ref. 0292)(Ref. 0294)							Fish oils; phosphatides of liver and suprarenals of land animals and of brain; liver oil of Carcharodon carcharias (a shark).					[0292] / [0294]
198			11, 14, 17-Eicosatrienoic acid / 11, 14, 17-icosatrienoic acid	DFA0198	Tetsuyuki Kobayashi	C20:3	C₂₀H₃₄O₂	306.483								(Ref. 0050)(Ref. 0051)							Shark-liver and herring oil.					[0050] / [0051]
199		Podocarpric acid	x, y, z-Eicosatrienoic acid/x, y, z-icosatrienoic acid	DFA0199	Tetsuyuki Kobayashi	C20:3	C₂₀H₃₄O₂	306.483								(Ref. 0303)(Ref. 0304)							Podocarpus oil.					[0303] / [0304]
200			7, 10, 13-Docosatrienoic acid	DFA0200	Tetsuyuki Kobayashi	C22:3	C₂₂H₃₈O₂	334.536								(Ref. 0296)							Reported in brain and cattle-liver phosphatides.					[0296]
201			8, 11, 14-Docosatriennoic acid	DFA0201	Tetsuyuki Kobayashi	C22:3	C₂₂H₂₈O₂	324.457								(Ref. 0293)							Reported in liver oil of Carcharodon carcharias (a shark); cattle-suprarenal phosphatides.					[0293]
202			4, 7, 10, 13-Hexadesatetraenoic acid	DFA0202	Tetsuyuki Kobayashi	C16:4	C₁₆H₂₄O₂	248.361								soluble in acetone, alcohol, ether and petroleum ether.(Ref. 0448)							South Africa pilchad oil; Japanease sardine oil.					[0448]
203			4, 7, 11, 14-Hexadesatetraenoic acid	DFA0203	Tetsuyuki Kobayashi	C16:4	C₁₆H₂₄O₂	248.361								soluble in acetone, alcohol, ether, carbon disuifide and petroleum ether.(Ref. 0510)(Ref. 0511)							Japanease sardine oil.					[0510] / [0511]
204			4, 8, 12, 16-Hexadesatetraenoic acid	DFA0204	Tetsuyuki Kobayashi	C16:4	C₁₆H₂₄O₂	248.361								soluble in acetone, alcohol, ether and petroleum ether.(Ref. 0268)(Ref. 0295)							Japanease sardine oil.					[0268] / [0295]
205			6, 9, 12, 15-Hexadesatetraenoic acid	DFA0205	Tetsuyuki Kobayashi	C16:4	C₁₆H₂₄O₂	248.361						1.4870 at 29C		soluble in acetone, alcohol, ether, carbon disuifide and petroleum ether.(Ref. 0280)(Ref. 0281)(Ref. 0508)(Ref. 0510)			""CMR(METHYL ESTER): C12, 127.093; C13, 128.939; C14, 31.529; C15, 136.736 C16: 114.741ppm PMR(METHYL ESTER): CH2=CH-C(TERMINAL OLEFINIC PROTON), 4.92-4.96, 5.62-5.88ppm(MULTIPLETS).""(Ref. 6001)	""HR-EI-MS(METHYL ESTER): M/Z; 262.19326(M) EI-MS(PYRROLIDIDE): M/Z; 154,166,194,206,260(M-41), 272(M=29), 286(M-15)EI-MS(PICOLINYL ESTER): M/Z; 339(M), 338(M-1), 324(M-15), 298(M-41), 272, 258, 232, 218, 192 ""(Ref. 6002)			Sardine sagax (South African pilchard); herring oil (0.7%); menhaden body oil (1.9%). Lipids from Mytilus galloprovincialis or Nitzschia pungens. It is enriched from Japanese sardine oil during purification of EPA and DHA.					[0280] / [0281] / [0508] / [0510] / [6001] / [6002]
206			trans-3, cis-9, cis-12, cis-15-Octadecatetraenoic acid	DFA0206	Tetsuyuki Kobayashi	C18:4	C₁₈H₂₈O₂	276.414								(Ref. 0253)							Seed oil of Stenolobium stans.					[0253]
207		Moroctic acid / Moritic acid	4, 8, 12, 15-Octadecatetraenoic acid	DFA0207	Tetsuyuki Kobayashi	C18:4	C₁₈H₂₈O₂	276.414				208-215C at 15 mmHg	0.9297 at 20C	1.4911at 20C		soluble in acetone, alcohol, ether and petroleum ether.(Ref. 0103)(Ref. 0472)(Ref. 0489)(Ref. 0500)							Sardine oil; head oil of the white whale.					[0103] / [0472] / [0489] / [0500]
208			6, 9, 12, 15-Octadecatetraenoic acid	DFA0208	Tetsuyuki Kobayashi	C18:4	C₁₈H₂₈O₂	276.414			-57.4 to -56.6C			14888 at 16C		soluble in carbon disulfide and methyl alcohol.(Ref. 0269)(Ref. 0350)							Seed oil of Onosmodium occidentale; South African pilchard; Newfoundland squid; sevral other genera and species.					[0269] / [0350]
209		a-Parinaric acid	9, 11, 13, 15-Octadecatetraenoic acid	DFA0209	Tetsuyuki Kobayashi	C18:4n-3	C₁₈H₂₈O₂	276.414			85 to 86 C					soluble in acetone, alcohol and petroleum ether.(Ref. 0169)						Gas liquid chromatogram [Chromatogram 0001] (provided by Dr. Akiko Horiuchi).	Seed oil of Impatient and Parinarium; Iris sp.; Nymphaea aiba.					[0169]
210		b-Parinaric acid	trans-9, trans-11, trans-13, trans-15-Octadecatetraenoic acid	DFA0210	Tetsuyuki Kobayashi	C18:4	C₁₈H₂₈O₂	276.414			95 to 96 C					soluble in ether and petroleum ether.(Ref. 0509)								Synthetic by isomerization of a-acid.				[0509]
211			9, 12, 15, 18-Octadecatetraenoic acid	DFA0211	Tetsuyuki Kobayashi	C18:4	C₁₈H₂₈O₂	276.414								soluble in carbon disulfide and methyl alcohol.(Ref. 0347)												[0347]
212			4, 8, 12, 16-Eicosatetraenoic acid / 4, 8, 12, 16-icosatetraenoic acid	DFA0212	Tetsuyuki Kobayashi	C20:4	C₂₀H₃₂O₂	304.467				217 to 220 C at 20 mmHg	0.9263 at 20 C	1.4915 at 20 C		soluble in acetone, methyl alcohol, ether and petroleum ether.(Ref. 0442)(Ref. 0489)(Ref. 0496)							Brain phosphatides; sardine oil; whale oils; swine liver.					[0442] / [0489] / [0496]
213		Arachidonic acid	5, 8, 11, 14-Eicosatetraenoic acid / 5, 8, 11, 14-icosatetraenoic acid	DFA0213	Tetsuyuki Kobayashi	AA / Ara / C20:4n-6 / C20:4w6	C₂₀H₃₂O₂	304.467		There are two groups of essential fatty acids, the n-6 (or w6) and the n-3 (or w3). Arachidonic acid is n-6 fatty acids. Essential fatty acid deficiency causes skin lesion and growth retardation. Dietary supplementation of either linoleate, g-linoleate or arachidonate prevents such symptoms completely. The n-6 essential fatty acids have at least four roles (Ref. 2014): 1) Modulation of membrane structure. 2) Formation of bioactive molecules called eicosanoids. Arachidonic acid, which is nomally found esterifing sn-2 position of phospholipids, is released by the action of phospholipase A₂. Free arachidonate is used for precursors of eicosanoids, such as PG₂ series of prostaglandins, leukotrienes and thromboxanes. 3) Control of the water impermeability of the skin. 4) Regulation of cholesterol synthesis and transport.	-49.5 C	163 C at 1 mmHg	0.9082 at 20 C	1.4824 at 20 C		soluble in acetone, methyl alcohol, ether and petroleum ether.(Ref. 0224)(Ref. 0225)(Ref. 0328)(Ref. 0347)							Constituent of many animal phospholipids, also of some ferns and mosses. Confinded to fats of land animals; brain, liver, glandular and egg lipids.		Metabolic product of linoleic acid (9,12-18:2). The synthesis of 5,8,11,14-20:4 occurs via the following reaction sequence in the endoplasmic reticulum (Ref. 2013): 9,12-18:2 --> 6,9,12-18:3 --> 8,11,14-20:3 --> 5,8,11,14-20:4.			[0224] / [0225] / [0328] / [0347] / [2013] / [2014]
214			6, 10, 14, 18-Eicosatetraenoic acid / 6, 10, 14, 18-icosatetraenoic acid	DFA0214	Tetsuyuki Kobayashi	C20:4	C₂₀H₃₂O₂	304.467					0.9263 at 20 C	1.4935 at 20 C		soluble in acetone, methyl alcohol, ether and petroleum ether.(Ref. 0267)							Fish and whale oils.					[0267]
215			8, 11, 14, 17-Eicosatetraenoic acid / 8, 11, 14, 17-icosatetraenoic acid	DFA0215	Tetsuyuki Kobayashi	C20:4	C₂₀H₃₂O₂	304.467								soluble in acetone, methyl alcohol and petroleum ether.(Ref. 0464)(Ref. 0465)							Sardine oil.					[0464] / [0465]
216			4, 7, 10, 13-Docosatetraenoic acid	DFA0216	Tetsuyuki Kobayashi	C22:4	C₂₂H₃₆O₂	332.520								soluble in acetone, methyl alcohol and petroleum ether.(Ref. 0292)(Ref. 0294)							Brain phosphatides.					[0292] / [0294]
217			7, 10, 13, 16-Docosatetraenoic acid	DFA0217	Tetsuyuki Kobayashi	C22:4	C₂₂H₃₆O₂	332.520								soluble in carbon disulfide, heptane and methyl alcohol.(Ref. 0292)(Ref. 0294)							Brain and cattle-liver phosphatides.					[0292] / [0294]
218		Stearidonic acid	8, 12, 16, 19 (20)-Docosatetraenoic acid	DFA0218	Tetsuyuki Kobayashi	C22:4	C₂₂H₃₆O₂	332.520								soluble in acetone, methyl alcohol and petroleum ether.(Ref. 0050)(Ref. 0051)							Liver oil of Carcharodon carcharias (a shark).					[0050] / [0051]
219		Timnodonic acid	4, 8, 12, 15, 18-Eicosapentaenoic acid / 4, 8, 12, 15, 18-icosapentaenoic acid	DFA0219	Tetsuyuki Kobayashi	C20:5	C₂₀H₃₀O₂	302.451					0.9399 at 15 C	1.5109 at 15 C		soluble in benzene, chloroform, ether and petroleum ether.(Ref. 0489)							Sardine and bonito oils.					[0489]
220		Eicosapentanoic acid	5, 8, 11, 14, 17-Eicosapentaenoic acid / 5, 8, 11, 14, 17-icosapentaenoic acid	DFA0220	Tetsuyuki Kobayashi	EPA / C20:5n-3 / C20:5w3	C₂₀H₃₀O₂	302.451		Considered to be the major reason for the beneficial effects of fish oils on the cardiovascular system. EPA is a precursor to series 3 eicosanoids that promote dilation of blood vessels and a slower blood clotting reaction and, as such, has been found to be critical to the maintenance of normal cardiovascular health. (Ref. 2019/2020)	-54.4 to -53.8 C			1.4977 at 23 C		soluble in heptane and methyl alcohol.(Ref. 0265)(Ref. 0269)			""METHYL ESTER:	""METHYL ESTER:316,300,287,262,247,234,215,201,180,161,152 "" (Ref. 6056)		Gas liquid chromatogram [Chromatogram 0001] (provided by Dr. Akiko Horiuchi).	Present in fish oils as an acylglycerol and animal phospholipids. Cattle-liver lipids; various fish and seal oils.		Metabolic product of a-linolenic acid (9,12,15-18:3). The synthesis of 5,8,11,14,17-20:5 (=EPA) occurs via the following reaction sequence in the endoplasmic reticulum (Ref. 2013): 9,12,15-18:3 --> 6,9,12,15-18:4 --> 8,11,14,17-20:4 --> 5,8,11,14,17-20:5 --> 7,10,13,16,19-22:5. EPA is further metabolized to DHA. Precursor of PG3 series of prostaglandins.			[0265] / [0269] / [2013] / [2019] / [2020] / [6056] / [6058]
221			4, 7, 10, 13, 16-Docosapentaenoic acid	DFA0221	Tetsuyuki Kobayashi	C22:5n-6 / C22:5w6	C₂₂H₃₄O₂	330.504								soluble in chloroform, heptane and methyi alcohol.(Ref. 0269)							Brain phosphatides.		The synthesis of 4,7,10,13,16-22:5 occurs via the following reaction sequence (Ref. 2013): 9,12-18:2 --> 6,9,12-18:3 --> 8,11,14-20:3 --> 5,8,11,14-20:4 --> 7,10,13,16-22:4 --> 9,12,15,18-24:4 --> 6,9,12,15,18-24:5 --> 4,7,10,13,16-22:5. According to these pathways the 24-carbon acids that are made in the endoplasmic reticulum move to a site for partial beta-oxidation, which is most likely peroxisomes.			[0269] / [2013]
222		Clupanodonic acid	4, 8, 12, 15, 19-Docosapentaenoic acid	DFA0222	Tetsuyuki Kobayashi	C22:5	C₂₂H₃₄O₂	330.504			-78 C	207 to 212 at 2 mmHg	0.9356 at 20 C	1.5014 at 20 C		soluble in acetone, ether and petroleum ether.(Ref. 0470)(Ref. 0501)(Ref. 0502)(Ref. 0505)							Marine oils; body oils of teleost fish.					[0470] / [0501] / [0502] / [0505]
223			7, 10, 13, 16, 19-Docosapentaenoic acid	DFA0223	Tetsuyuki Kobayashi	C22:5n-3 / C22:5w3	C₂₂H₃₄O₂	330.504								soluble in benzene, chloroform, ether, methyl alcohol and petroleum ether.(Ref. 0005)(Ref. 0006)						Gas liquid chromatogram [Chromatogram 0001] (provided by Dr. Akiko Horiuchi).	Liver lipids of cattle; herring oil.					[0005] / [0006]
224		Docosahexaenoic acid / cervonic acid	cis-4, cis-7, cis-10, cis-13, cis-16, cis-19-Docosahexaenoic acid	DFA0224	Tetsuyuki Kobayashi	DHA / C22:6n-3 / C22:6w3	C₂₂H₃₂O₂	328.488		DHA is one of the n-3 (w3) fatty acids. It is uniquely rich in neural membranes of retina and brain in mammals. n-3 fatty acid deficiency causes the reduction of DHA level in these tissues and produces reduced learning ability (Ref. 2005), impaired vision, abnormal electroretinogram (Ref. 2006/2007) and polydipsia (Ref. 2008). It is believed to be important for the full development of the nervous system in the fetus and newborn.(Ref. 2003) Considered, along with EPA, to be the major reason for the beneficial effects of fish oils on the cardiovascular system. Anti-inflammatory (Ref. 2021/2022/2024), anti-thrombotic (Ref. 2023), anti-arteriosclerosis (Ref. 2022/2025) and anti-cancer activities (Ref. 2026/2027) have been reported. Production of bioactive metabolites, eicosanoids, is suppressed by DHA. DHA can be also involved in the modulation of membrane structures (Ref. 2017/2018).	-44.2 to -44.1 C			1.5017 at 26 C		soluble in benzene, chloroform, methyl alcohol, ether and petroleum ether.(Ref. 0292)(Ref. 0294)(Ref. 0526)						Gas liquid chromatogram [Chromatogram 0002] (provided by Dr. Akiko Horiuchi).	South African pilchard oil; brain phosphatides; liver lipids of cattle. It is found mainly in fish and marine microorganisms and plants. DHA is also an essential component of the brain, eyes, and other nervous system tissues. Tuna eyeballs are one of the major source (Ref. 2012).		Metabolic product of a-linolenic acid (9,12,25-18:3). The synthesis of 4,7,10,13,16,19-22:6 (=DHA) occurs via the following reaction sequence (Ref. 2013): 9,12,15-18:3 --> 6,9,12,15-18:4 --> 8,11,14,17-20:4 --> 5,8,11,14,17-20:5 --> 7,10,13,16,19-22:5 --> 9,12,15,18,21-24:5 --> 6,9,12,15,18,21-24:6 --> 4,7,10,13,16,19-22:6. According to these pathways the 24-carbon acids that are made in the endoplasmic reticulum move to a site for partial beta-oxidation, which is most likely peroxisomes.			[0292] / [0294] / [0526] / [2003] / [2005] / [2006] / [2007] / [2008] / [2012] / [2013] / [2017] / [2018] / [2021] / [2022] / [2023] / [2024] / [2025] / [2026] / [2027]
225			4, 8, 12, 15, 19, 21-Tetracosahexaenoic acid	DFA0225	Tetsuyuki Kobayashi	C24:6	C₂₄H₃₆O₂	356.541					0.9452 at 20 C	1.5122 at 20 C		soluble in benzene, chloroform, methyl alcohol, ether and petroleum ether.(Ref. 0004)							Japanese sardine, fish-liver and whale oils.					[0004]
226		Isovaleric acid	3-Methylbutanoic acid	DFA0226	Tetsuyuki Kobayashi		C₅H₁₀O₂	102.132			-37.6C	176.7C at 760mmHg	d0.937	1.40178 at 22.4C		soluble in ethanol , chloroform , ether and 23 parts water.(Ref. 0019)(Ref. 0020)(Ref. 6027)(Ref. 6028)(Ref. 6029)(Ref. 6030)		""Methyl : 2968cm-1 Methyl , Methylene : 2935 , 2877 , 2855cm-1""		""M/E : 39 , 41 , 42 , 43 , 45 , 60 , 69""			Tabacco; valerian root; hemp,pineapple, & lavender oils; volatile acids of sheep tallow; rumen of sheep; head & body oils of porpoise; hair grease of dog.					[0019] / [0020] / [6027] / [6028] / [6029] / [6030]
227		6-Methylcaprylic acid	d-6-Methyloctanoic acid	DFA0227	Tetsuyuki Kobayashi		C₉H₁₈O₂	158.238								soluble in acetone , ether , methyl alcohol and petroleum ether.(Ref. 0110)(Ref. 0147)(Ref. 0325)(Ref. 0326)							Degradation product of polymycins; wool grease.					[0110] / [0147] / [0325] / [0326]
228		7-Methylcaprylic acid	7-Methyloctanoic acid	DFA0228	Tetsuyuki Kobayashi		C₉H₁₈O₂	158.238			-18.5C					(Ref. 0108)(Ref. 0320)							Minor constituent of wool grease (degras).					[0108] / [0320]
229		Isolauric acid	10-Methylhendecanoic acid	DFA0229	Tetsuyuki Kobayashi		C₁₂H₂₄O₂	200.318			41.2C	140-145C at 3 mmHg				soluble in acetone , ether , methyl alcohol and petroleum ether.(Ref. 0099)(Ref. 0522)(Ref. 6015)(Ref. 6021)							Wool grease ; butter ; sheep tallow ; cattle fat ; whale oil.					[0099] / [0522] / [6015] / [6021]
230			d-10-Methyldodecanoic acid	DFA0230	Tetsuyuki Kobayashi		C₁₃H₂₆O₂	214.344			6.2-6.5C	178-180C at 10 mmHg		1.4424 at 25C		soluble in benzene , chloroform , methyl alcohol and petroleum ether.(Ref. 0382)(Ref. 6015)(Ref. 6021)							Wool grease; sheep tallow; butter; traces in cattle milk fat; cattle fat; whale oil.	Synthetic.				[0382] / [6015] / [6021]
231		Isoundecylic acid / 11-methyllauric acid	11-Methyldodecanoic acid	DFA0231	Tetsuyuki Kobayashi		C₁₃H₂₆O₂	214.344			39.4-40C			1.4293at 60C		soluble in acetone , ethanol , methyl alcohol and petroleum ether.(Ref. 0445)(Ref. 6015)(Ref. 6021)							Traces in butter fat; wool grease; sheep tallow; cattle fat; whale oil.					[0445] / [6015] / [6021]
232		Isomyristic acid / 12-methyltridecylic acid	(+)-12-Methyltridecanoic acid	DFA0232	Tetsuyuki Kobayashi		C₁₄H₂₈O₂	228.371			53.6C					soluble in acetone , methyl alcohol and petroleum ether.(Ref. 0216)(Ref. 6061)							Wool grease; butterfat.					[0216] / [6061]
233		12-methylmyristic acid	(+)-12-Methyltetradecanoic acid	DFA0233	Tetsuyuki Kobayashi		C₁₅H₃₀O₂	242.398			25.8C			0.4327 at 59C		soluble in chloroform , ether , methyl alcohol and petroleum ether.(Ref. 0357)							Wool grease; sheep tallow ; butterfat.					[0357]
234		Isopentadecylic acid / 13-methylmyristic acid	13-Methyltetradecanoic acid	DFA0234	Tetsuyuki Kobayashi		C₁₅H₃₀O₂	242.398			52.2C			1.4312 at 59C		soluble in methyl alcohol and petroleum ether.(Ref. 0215)(Ref. 0217)(Ref. 0444)(Ref. 6120)(Ref. 6138)							External tissue of sheep; butterfat.	Synthetic , by heating a product , which is gained by warming 11-methyldodecylmalonic acid diethyl with solution of ethanolic KOH, at 170C in vacuo.				[0215] / [0217] / [0444] / [6120] / [6138]
235		Isopalmitic acid / 14-methylpentadecylic acid	14-Methypentadecanoic acid	DFA0235	Tetsuyuki Kobayashi		C₁₆H₃₂O₂	256.424			62.4C		d1.012	1.4293 at 70C		soluble in acetone , ether , methyl alcohol and petroleum ether.(Ref. 0216)(Ref. 6061)(Ref. 6065)(Ref. 6064)(Ref. 6009)		Isopropyl : Doublet in 1360-1380cm-1					Butterfat; wool grease; traces in ewternal tissue of sheep.	Synthetic.				[0216] / [6009] / [6061] / [6064] / [6065]
236		14-methylpalmitic acid	(+)-14-Methylhexadecanoic acid	DFA0236	Tetsuyuki Kobayashi		C₁₇H₃₄O₂	270.451			38.0C					soluble in acetone , ether , methyl alcohol and petroleum ether.(Ref. 0244)(Ref. 0513)(Ref. 6132)(Ref. 6009)		7.25m(1380cm-1) ; CH3					Wool grease; external tissue fat of sheep.	Synthetic, by treatment hydrazine hydrate, KOH and diethylene glycol to 14-methyl-13-oxohexadecanoic acid.				[0244] / [0513] / [6009] / [6132]
237		15-methylpalmitic acid	15-Methylhexadecanoic acid	DFA0237	Tetsuyuki Kobayashi		C₁₇H₃₄O₂	270.451			60.5C			1.4315 at 70C		soluble in acetone , ether and petroleum ether.(Ref. 0218)(Ref. 6067)(Ref. 6068)							Wool grease; cattle tallow.					[0218] / [6067] / [6068]
238			10-Methylheptadecanoic acid	DFA0238	Tetsuyuki Kobayashi		C₁₈H₃₆O₂	284.477			33.5C					soluble in acetone and glacial acetic acid(Ref. 0459)(Ref. 0525)							Butter fat.					[0459] / [0525]
239		Isostearic acid / 16-Methylmargaric acid	(+)-16-Methylheptadecanoic acid	DFA0239	Tetsuyuki Kobayashi		C₁₈H₃₆O₂	284.477			69.5C					soluble in acetone , ether , petroleum ether.(Ref. 0179)(Ref. 6070)(Ref. 6009)		Isopropyl : Doublet in 1360-1380cm-1					Wool grease.					[0179] / [6009] / [6070]
240		Tuberculostearic acid / 10-methylstearic acid	l-(+)-10-Methyloctadecanoic acid	DFA0240	Tetsuyuki Kobayashi		C₁₉H₃₈O₂	298.504			13.2C	175-178C at 760mmHg	d0.887	1.4512 at 25C		soluble in acetone , ethanol , methyl alcohol and pentane.(Ref. 0407)(Ref. 0430)(Ref. 0459)(Ref. 0524)							Lipids of human tubercle bacilli.	Synthetic.				[0407] / [0430] / [0459] / [0524]
241		16-methylstearic acid	(+)-16-Methyloctadecanoic acid	DFA0241	Tetsuyuki Kobayashi		C₁₉H₃₈O₂	298.504			49.9-50.7C			1.4342 at 70C		soluble in acetone , methyl alcohol and petroleum ether.(Ref. 0110)				[Spectrum 0001] (provided by Dr. Takeshi Kasama).			Wool grease.					[0110]
242		Isoarachidic acid	18-Methylnonadecanoic acid	DFA0242	Tetsuyuki Kobayashi		C₂₀H₄₀O₂	312.530			75.3C					soluble in ethanol , ether and petroleum ether.(Ref. 0357)							Wool grease.					[0357]
243			(+)-18-Methyleicosanoic acid / (+)-18-Methylicosanoic acid	DFA0243	Tetsuyuki Kobayashi		C₂₁H₄₂O₂	326.557			55.6C					soluble in acetone , chloroform and petroleum ether.(Ref. 0357)				[Spectrum 0001] (provided by Dr. Takeshi Kasama).			Wool grease.					[0357]
244		Isobehenic acid	20-Methylheneicosanoic acid / 20-Methylhenicosanoic acid	DFA0244	Tetsuyuki Kobayashi		C₂₂H₄₄O₂	340.584			79.5C					soluble in chloroform , ether , methyl alcohol and petroleum ether.(Ref. 0357)							Wool grease.					[0357]
245			(+)-20-Methyldocosanoic acid	DFA0245	Tetsuyuki Kobayashi		C₂₃H₄₆O₂	354.610			62.1C					soluble in acetone , chloroform , ether , and petroleum ether.(Ref. 0357)							Wool grease.					[0357]
246			22-Methyltricosanoic acid	DFA0246	Tetsuyuki Kobayashi		C₂₄H₄₈O₂	368.637			83.1C					soluble in acetone , chloroform and petroleum ether.(Ref. 0027)							Wool grease.					[0027]
247			3, 13, 19-Trimethyltricosanoic acid	DFA0247	Tetsuyuki Kobayashi		C₂₆H₅₂O₂	396.690			-8C	208C at 760mmHg				(Ref. 0111)(Ref. 0112)(Ref. 0395)(Ref. 0457)							Fatty acids in the tubercle bacilli.					[0111] / [0112] / [0395] / [0457]
248		Isopentacosanoic acid	(+)-23-Methyltetracosanoic acid	DFA0248	Tetsuyuki Kobayashi		C₂₅H₅₀O₂	382.663			82.4-82.6C					soluble in ethanol , benzene , chloroform and petroleum ether.(Ref. 0027)							Wool grease.					[0027]
249		Isocerotic acid	24-Methylpentacosanoic acid	DFA0249	Tetsuyuki Kobayashi		C₂₆H₅₂O₂	396.690			86.9C					soluble in acetone , chloroform and glacial acetic acid.(Ref. 0027)							Wool grease.					[0027]
250			(+)-24-Methylhexacosanoic acid	DFA0250	Tetsuyuki Kobayashi		C₂₇H₅₄O₂	410.716			72.9C					soluble in benzene, chloroform , glacial acetic acid and petroleum ether.(Ref. 0357)							Wool grease.					[0357]
251		Isomontanic acid	26-methylheptacosanoic acid	DFA0251	Tetsuyuki Kobayashi		C₂₈H₅₆O₂	424.743			89.3 C					soluble in benzene, chloroform, glacial acetic acid and petroleum ether.(Ref. 0357)							Wool grease.					[0357]
252		Mycoceranic acid / Mycocerosic acid	2,4,6-(D)-Trimethyloctacosanoic acid	DFA0252	Tetsuyuki Kobayashi		C₃₁H₆₂O₂	466.823			27-28 C					soluble in chloroform and petroleum ether.(Ref. 0113)							Lipids of tubercle bacilli.	Synthetic.				[0113]
253			(+)-28-Methyltriacontanoic acid	DFA0253	Tetsuyuki Kobayashi		C₃₁H₆₂O₂	466.823			80.7 C					soluble in benzene, chloroform, glacial acetic acid and petroleum ether.(Ref. 0357)							Wool grease.					[0357]
254		Angelic acid / a-Methylisocrotonic acid	2-Methyl-cis-2-butenoic acid	DFA0254	Tetsuyuki Kobayashi		C₅H₈O₂	100.116			45 C	185 C at 760 mm Hg / 88-90 C at 12 mmHg	d⁴⁷₄0.983	1.4434 at 47 C		very soluble in ether ; soluble in ethanol ; slightly soluble in water.(Ref. 0109)(Ref. 6076)(Ref. 6077)(Ref. 6078)(Ref. 6012)(Ref. 6013)	lMAX : 216nm, eMAX : 9500	C=C : 1645cm-1					As the ester in Angelica archangelica root and Roman camomile oils.					[0109]
255		Tiglic acid / a,b-Dimethylacrylic acid	2-Methyl-trans-2-butenoic acid	DFA0255	Tetsuyuki Kobayashi		C₅H₈O₂	100.116			65.5-66.5 C	198.5 C at 760 mm Hg / 95-96 C at 12 mmHg	d0.9641	1.4342 at 81 C / 1.4330 at 76 C		very soluble in hot water ; slightly soluble in ethanol, cold water and ether.(Ref. 0145)(Ref. 6012)(Ref. 6014)(Ref. 6077)(Ref. 6079)	lMAX : 216-217nm(e 10700)MAX : 9500	C=C : 1645cm-1 / C=O : 1689cm-1, 1387,1282,1161,1082,1017, 939, 786, 737cm-1					As the glyceride in oil of Croton tiglium; as the ester in Roman camomile oil; bacteria-free Ascaris.					[0145]
256		Pyroterebic acid	4-Methyl-3-pentenoic acid	DFA0256	Tetsuyuki Kobayashi		C₆H₁₀O₂	114.142			Oil	207 C / 99 C at 10 mm Hg / 103-106 C at 13 mmHg				soluble in ethanol, chloroform and ether.(Ref. 0109)(Ref. 6086)(Ref. 6113)							Esterified with a diterpene alcohol in the sap of Calotropis procera.	Acetone reacts with Methyl b-bromopropionate in the presence of magnesium, followed by saponification to give 4-Methyl-3-pentanoic acid.				[0109]
257		C₂₇-Phthienoic acid / Mycolipenic acid	(+)-2, 4(l), 6(l)-Trimethyl-trans-2-tetracosenoic acid	DFA0257	Tetsuyuki Kobayashi		C₂₇H₅₂O₂	408.701			39.5-41 C			1.4598 at 25 C		soluble in acetone, chloroform, methyl alcohol and petroleum ether ; rosettes from acetone at - 8 C.(Ref. 0358)							Mixture of acids of the tubercle bacilli known as ""phthioic acid"".					[0358]
258		Aleprolic acid / Lowest homolog of the chaulmoogra series.	Cyclopent-2-enyl -1-oic acid / 2-Cyclopentenyl-1-oic acid	DFA0258	Tetsuyuki Kobayashi		C₆H₈O₂	112.127			Liquid	97-98 C at 17 mmHg ( Volatile in steam ; sublimes )				soluble in acetone, ethanol, ether, hot water and petroleum ether.(Ref. 0142)							In small proportion in Hydnocarpus wightiana.					[0142]
259		Aleprestic acid	2-Cyclopentene-1-pentanoic acid / 5-(2-cyclopenten-1-yl)pentanoic acid / 5-(Cyclopent-2-enyl)pentanoic acid	DFA0259	Tetsuyuki Kobayashi		C₁₀H₁₆O₂	168.233			Liquid					(Ref. 0140)(Ref. 0141)(Ref. 0142)							In small proportion in seed oils of Hydnocarpus wightiana and Hydnocarpus anthelmintica.					[0140] / [0141] / [0142]
260		Aleprylic acid	2-Cyclopentene-1-heptanoic acid / 7-(2-cyclopenten-1-yl)heptanoic acid / 7-(Cyclopent-2-enyl)heptanoic acid	DFA0260	Tetsuyuki Kobayashi		C₁₂H₂₀O₂	196.286			12.0 C					soluble in acetone, ether and petroleum ether.(Ref. 0140)(Ref. 0141)(Ref. 0142)							Oil of Hydnocarpus anthelmintica and Hydnocarpus wightiana.					[0140] / [0141] / [0142]
261		Sterculic acid	w-(2-n-Octylcycloprop-1-enyl)octanoic acid	DFA0261	Tetsuyuki Kobayashi		C₁₉H₃₄O₂	294.472			18 C					soluble in ether.(Ref. 0239)(Ref. 0240)							Sterculia foetida ; usually in small proportion in a variety of oils together with malvalic acid.					[0239] / [0240]
262		Alepric acid	2-Cyclopentene-1-nonanoic acid / 9-(2-cyclopenten-1-yl)nonanoic acid / 9-(Cyclopent-2-enyl)nonanoic acid	DFA0262	Tetsuyuki Kobayashi		C₁₄H₂₄O₂	224.339			48.0 C	165-168 C at 1mmHg				soluble in ethanol, ether, methyl alcohol and petroleum ether.(Ref. 0141)							Oil of Hydnocarpus anthelmintica and Hydnocarpus wightiana.					[0141]
263		Lactobacillic acid / Phytomonic acid	w-(2-n-Hexylcycloprop-1-enyl)decanoic acidDisagreement concerning structure in England and the United States ; also suggested to be 2-hexylcyclopropanedecanoic acid and w-(2-n-octylcyclopropyl)octanoic acid.	DFA0263	Tetsuyuki Kobayashi		C₁₉H₃₆O₂	296.488			27.8-28.8 C					soluble in acetone, chloroform, ether and petroleum ether.(Ref. 0215)(Ref. 0243)(Ref. 0245)(Ref. 0246)							31% in Lactobacillus arabinosus; 16-19% in Lactobacillus casei; 13% in Agrobacterium tumefaciens (Synonym: Phytomonas tumefaciens.).					[0215] / [0243] / [0245] / [0246]
264		Hydnocarpic acid	2-Cyclopentene-1-undecanoic acid / 11-(2-cyclopenten-1-yl)undecanoic acid / 11-(Cyclopent-2-enyl)hendecanoic acid	DFA0264	Tetsuyuki Kobayashi		C₁₆H₂₈O₂	252.392			60.5 C	247.5 C at 20 mmHg				soluble in ethanol, chloroform (readily) and petroleum ether ; sparingly soluble in most organic solvents.(Ref. 0048)(Ref. 0141)(Ref. 0160)(Ref. 0401)(Ref. 0402)							Saponifiable matter of chaulmoogra and other oils; Carpotroche brasiliensis; Hydnocarpus anthelmintica; Hydnocarpus wightiana; Taraktogenos kurzii (Synonym: Hydnocarpus kurzii.).					[0048] / [0141] / [0160] / [0401] / [0402]
265		Chaulmoogric acid	2-Cyclopentene-1-tridecanoic acid / 13-(2-cyclopenten-1-yl)tridecanoic acid / 13-(Cyclopent-2-enyl)-n-tridecanoic acid	DFA0265	Tetsuyuki Kobayashi		C₁₈H₃₂O₂	280.445			68.5 C	247.5 C at 20 mmHg				soluble in acetone, chloroform and ether.(Ref. 0048)(Ref. 0142)(Ref. 0401)(Ref. 0402)							Seed of Taraktogenos kurzii (Synonym: Hydnocarpus kurzii.); oil of Gynocardia odorata (chaulmoogra); 2 Oncoba spp..					[0048] / [0142] / [0401] / [0402]
266		Gorlic acid	2-Cyclopentene-1-tridecenoic acid / 13-(2-cyclopenten-1-yl)tridecenoic acid / 13-(Cyclopent-2-enyl)-6-tridecenoic acid	DFA0266	Tetsuyuki Kobayashi		C₁₈H₃₀O₂	278.430			6.0 C [Liquid]	232.5 C	d0.9436	1.4782 at 25 C		soluble in hot ethanol.(Ref. 0048)(Ref. 0107)(Ref. 0401)(Ref. 0402)							Glycerides of Oncoba echinata; several Hydnocarpus oils.					[0048] / [0107] / [0401] / [0402]
267		Glycolic acid	Hydroxyacetic acid	DFA0267	Tetsuyuki Kobayashi		C₂H₄O₃	76.051			80 C	Decomposes at 100 C	d1.49			very soluble in ether and water ; soluble in ethanol.(Ref. 0282)							Cane-sugar juice; unripe grapes.					[0282]
268		Lactic acid	2-Hydroxypropionic acid	DFA0268	Tetsuyuki Kobayashi		C₃H₆O₃	90.078			52.8 C [ L(+)- and D(-)- ] ; 18 C [ DL- ]	122 C at 15 mmHg	d1.2060	1.43915 at 20 C (Value for the DL-form)		very soluble in acetone, ethanol, ether and water.(Ref. 0264)							Widely distributed in nature.					[0264]
269		b-Lactic acid / Hydracrylic acid	3-Hydroxypropionic acid	DFA0269	Tetsuyuki Kobayashi		C₃H₆O₃	90.078			Syrup					very soluble in ethanol, ether and water.(Ref. 0283)(Ref. 0411)							Juice of muscular tissue; bile.					[0283] / [0411]
270			dl-2-Hydroxybutyric acid	DFA0270	Tetsuyuki Kobayashi		C₄H₈O₃	104.105			43-44 C					very soluble in ethanol, ether and water.(Ref. 0256)							Fermentation of molasses, starch.					[0256]
271		b-Hydroxybutyric acid	D(-)-3-Hydroxybutyric acid	DFA0271	Tetsuyuki Kobayashi		C₄H₈O₃	104.105			49-50 C					very soluble in ethanol, ether and water ; insoluble in benzene.(Ref. 0385)								Synthetic, by (1) reduction and hydrolysis of ethyl acetoacetate, (2) direct oxidation of butyric acid (see entry 4) by H₂O₂, (3) partial oxidation of aldol.				[0385]
272			4-Hydroxybutyric acid	DFA0272	Tetsuyuki Kobayashi		C₄H₈O₃	104.105			Liquid at -17 C	130 C				(Ref. 0386)(Ref. 0479)							Urine of diabetics.					[0386] / [0479]
273		2-Hydroxyvaleric acid	DL-2-Hydroxypentanoic acid	DFA0273	Tetsuyuki Kobayashi		C₅H₁₀O₃	118.131			34 C	187 C	d0.942	1.4086 at 20 C		soluble in ethanol and water.(Ref. 0322)								Synthetic, through corresponding a-harogen or cyanohydrin.				[0322]
274		3-Hydroxyvaleric acid / 3-Ethylhydracrylic acid	3-Hydroxypentanoic acid	DFA0274	Tetsuyuki Kobayashi		C₅H₁₀O₃	118.131			Liquid at -32 C					soluble in ethanol, benzene, chloroform and ether.(Ref. 0327)								Synthetic, from butene-1-chlorohydrin.				[0327]
275		4-Hydroxyvaleric acid	4-Hydroxypentanoic acid	DFA0275	Tetsuyuki Kobayashi		C₅H₁₀O₃	118.131			Unstable					soluble in ethanol, ether and water.(Ref. 0324)								Synthetic, by reduction of levulinic acid (see entry 396) with NaHg or catalytic hydrogenation (exists only in solution).				[0324]
276		5-Hydroxyvaleric acid / d-hydroxyvaleric acid	5-Hydroxypentanoic acid	DFA0276	Tetsuyuki Kobayashi		C₅H₁₀O₃	118.131								soluble in alcohol , ether and water.(Ref. 0321)(Ref. 0323)								Synthetic, by (1) reduction of glutaric acid anhydride with AlHg, (2) action of alcoholic sodium ethoxide on 5-iodovaleric acid, or (3) malonic acid or ethyl acetoacetate synthesis.				[0321] / [0323]
277		2-Hydroxycaproic acid	DL-2-Hydroxyhexanoic acid	DFA0277	Tetsuyuki Kobayashi		C₆H₁₂O₃	132.158			60 C					very soluble in alcohol , chloroform , ether and water.(Ref. 0313)(Ref. 0528)								Synthetic, by (1) action of HNO₂ on norleucine, or (2) debromination of a-bromo-n-caproic acid.				[0313] / [0528]
278		3-Hydroxycaproic acid	DL-3-Hydroxyhexanoic acid	DFA0278	Tetsuyuki Kobayashi		C₆H₁₂O₃	132.158			13 C					very soluble in water.(Ref. 0313)								Synthetic, by (1) debromination of b-bromo-n-caproic acid in alkaline solution, or (2) treatment of 2-hexenoic acid (see entry 47) with NaOH solution.				[0313]
279		4-Hydroxycaproic acid	DL-4-Hydroxyhexanoic acid	DFA0279	Tetsuyuki Kobayashi		C₆H₁₂O₃	132.158			Reverts to lactone					(Ref. 0174)(Ref. 0311)								Synthetic, by (1) treatment of the corresponding bromo acid with NaOH solution, or (2) treatment of hydrosorbic acid (see entry 48) with concentrated H₂SO₄ and hydrolysis of the reaction product.				[0174] / [0311]
280		5-Hydroxycaproic acid	5-Hydroxyhexanoic acid	DFA0280	Tetsuyuki Kobayashi		C₆H₁₂O₃	132.158			Reverts to lactone					(Ref. 0311)								Synthetic, by (1) debromination of the corresponding bromo acid or (2) reduction of 5-keto-n-caproic acid (see entry 400) with NaHg.				[0311]
281		6-Hydroxycaproic acid	6-Hydroxyhexanoic acid	DFA0281	Tetsuyuki Kobayashi		C₆H₁₂O₃	132.158								(Ref. 0419)								Synthetic, but difficult to prepare in the free state.				[0419]
282		2-Hydroxyenanthoic acid	2-Hydroxyheptanoic acid	DFA0282	Tetsuyuki Kobayashi		C₇H₁₄O₃	146.184			65 C					soluble in cold water (difficultly).(Ref. 0024)(Ref. 0170)(Ref. 0311)(Ref. 0422)(Ref. 0518)(Ref. 0519)								Synthetic, by debromination of the corresponding 2-bromo acid with H₂O under pressure or with a solution of NaOH.				[0024] / [0170] / [0311] / [0422] / [0518] / [0519]
283		4-Hydroxyenanthoic acid	4-Hydroxyheptanoic acid	DFA0283	Tetsuyuki Kobayashi		C₇H₁₄O₃	146.184			Reverts to g-lactone					(Ref. 0256)								Synthetic, by (1) heating 4-bromoheptanoic acid with H₂O, or (2) decomposition of g-propyl-paraconic acid.				[0256]
284		d-Hydroxyenanthoic acid	5-Hydroxyheptanoic acid	DFA0284	Tetsuyuki Kobayashi		C₇H₁₄O₃	146.184			Syrupy liquid					(Ref. 0170)(Ref. 0171)								Synthetic, by debromination of 5-bromoheptanoic acid with H₂O.				[0170] / [0171]
285		w-Hydroxyenanthoic acid	7-Hydroxyheptanoic acid	DFA0285	Tetsuyuki Kobayashi		C₇H₁₄O₃	146.184								(Ref. 0468)								Synthetic, by reduction of pimelic acid.				[0468]
286		2-Hydroxycaprylic acid	2-Hydroxyoctanoic acid	DFA0286	Tetsuyuki Kobayashi		C₈H₁₆O₃	160.211			69.5 C					very soluble in alcohol and ether ; sparingly soluble in water.(Ref. 0084)(Ref. 0256)(Ref. 0333)								Synthetic, by action of Ba(OH)₂ solution on 2-bromocaprylic acid followed by acidification.				[0084] / [0256] / [0333]
287		3-Hydroxycaprylic acid	3-Hydroxyoctanoic acid	DFA0287	Tetsuyuki Kobayashi		C₈H₁₆O₃	160.211			48-51 C					(Ref. 0008)(Ref. 0313)								Synthetic.				[0008] / [0313]
288		6-Hydroxycaprylic acid	6-Hydroxyoctanoic acid	DFA0288	Tetsuyuki Kobayashi		C₈H₁₆O₃	160.211			Viscous liquid					(Ref. 0076)(Ref. 0333)								Synthetic, by reduction of 6-keto-n-caprylic acid (see entry 410) with Zn and KOH.				[0076] / [0333]
289		8-Hydroxycaprylic acid	8-Hydroxyoctanoic acid	DFA0289	Tetsuyuki Kobayashi		C₈H₁₆O₃	160.211			58 C					very soluble in alcohol and benzene ; soluble in water ; sparingly soluble in petroleum and ether.(Ref. 0132)(Ref. 0167)								Synthetic, by partial reduction of potassium methyl suberate with Na in ethanol.				[0132] / [0167]
290		2-Hydroxypelargonic acid	2-Hydroxynonanoic acid	DFA0290	Tetsuyuki Kobayashi		C₉H₁₈O₃	174.237				freezing point , 70 C				very soluble in alcohol and ether ; soluble in water ( difficultly).(Ref. 0015)(Ref. 0070)(Ref. 0071)								Synthetic, by action of Ba(OH)₂ solution on 2-bromononanoic acid followed by acidification.				[0015] / [0070] / [0071]
291		3-Hydroxypelargonic acid	(+)-3-Hydroxynonanoic acid	DFA0291	Tetsuyuki Kobayashi		C₉H₁₈O₃	174.237			48-51 C	freezing point , 48-51 C				soluble in alcohol , ether and hot light petroleum ; insoluble in water.(Ref. 0032)(Ref. 0308)								Synthetic, along with heptanoic acid (see entry 7) and 1,2,4-decanetriol by oxidation of hexyl allyl carbinol.				[0032] / [0308]
292		4-Hydroxypelargonic acid	4-Hydroxynonanoic acid	DFA0292	Tetsuyuki Kobayashi		C₉H₁₈O₃	174.237			Reverts of g-lactone	117-120 C at 10 mm Hg , Value for the g-lactone				(Ref. 0530)												[0530]
293		7-Hydroxypelargonic acid	7-Hydroxynonanoic acid	DFA0293	Tetsuyuki Kobayashi		C₉H₁₈O₃	174.237				204 C at 25 mmHg				(Ref. 0074)(Ref. 0076)(Ref. 0422)								Synthetic, by reduction of the corresponding keto acid with Zn and KOH.				[0074] / [0076] / [0422]
294		9-Hydroxypelargonic acid	9-Hydroxynonanoic acid	DFA0294	Tetsuyuki Kobayashi		C₉H₁₈O₃	174.237			51-51.5 C ; 24-26.5 C					(Ref. 0132)(Ref. 0343)(Ref. 0530)								Synthetic, by partial reduction of potassium methyl azelate with Na in ethanol (also by other methods).				[0132] / [0343] / [0530]
295		2-Hydroxycapric acid	2-Hydroxydecanoic acid	DFA0295	Tetsuyuki Kobayashi		C₁₀H₂₀O₃	188.264			70.5 C	decomposes				Crystals from chloroform , petroleum and ether.(Ref. 0037)								Synthetic, by treatment of 2-bromocapric acid with KOH.				[0037]
296			l-2-Hydroxydecanoic acid	DFA0296	Tetsuyuki Kobayashi		C₁₀H₂₀O₃	188.264			77.6-78 C , Reverts to lactone					(Ref. 0256)								Synthetic, results with lactone from treatment of 2-bromocapric acid with NaOH.				[0256]
297		4-Hydroxycapric acid	4-Hydroxydecanoic acid	DFA0297	Tetsuyuki Kobayashi		C₁₀H₂₀O₃	188.264			Reverts to lactone					(Ref. 0176)								Synthetic, reportedly , by action of fuming HCl on the oxime of 9-keto-12-hydroxystearic acid.				[0176]
298		5-Hydroxycapric acid	5-Hydroxydecanoic acid	DFA0298	Tetsuyuki Kobayashi		C₁₀H₂₀O₃	188.264			Reverts to lactone	117-120 C at 0.02 mm Hg , Value for the lactone.				(Ref. 0354)								Synthetic, by partial reduction of various sebacic acid derivatives.				[0354]
299		10-Hydroxycapric acid	10-Hydroxydecanoic acid	DFA0299	Tetsuyuki Kobayashi		C₁₀H₂₀O₃	188.264			75.5-76.5 C					soluble in ether; sparingly soluble in petroleum and ether.(Ref. 0132)(Ref. 0343)								Synthetic, by partial reduction of sebacic acid derivatives (easily from mono- and di-etholides).				[0132] / [0343]
300		2-Hydroxyhendecanoic acid	2-Hydroxyundecanoic acid	DFA0300	Tetsuyuki Kobayashi		C₁₁H₂₂O₃	202.291			69 C	freezing point , 69 C , Converts to capric aldehyde on distillation				soluble in alcohol and ether; sparingly soluble in cold water.(Ref. 0037)								Synthetic, by debromination of 2-bromoundecanoic acid with KOH.				[0037]
301		w-Hydroxyhendecanoic acid	11-Hydroxyundecanoic acid	DFA0301	Tetsuyuki Kobayashi		C₁₁H₂₂O₃	202.291				71.5C				soluble in ethyl alcohol and ether ; sparingly soluble in cold water.(Ref. 0132)								Synthetic, by debromination of 11-bromoundecanoic acid with Ag₂O in alkaline solution / by hydrolysis of 11-hydroxydecanenitrile (also other methods)				[0132]
302		a-Hydroxylauric acid	2-Hydroxydodecanoic acid	DFA0302	Tetsuyuki Kobayashi		C₁₂H₂₄O₃	216.317								soluble in ethyl alcohol and ether ; sparingly soluble in cold water.(Ref. 0132)							Aceric fraction of wool grease	Synthesis, by debromination of 2-bromolauric acid with Ag₂O				[0132]
303		b-Hydroxylauric acid	3-Hydroxydodecanoic acid	DFA0303	Tetsuyuki Kobayashi		C₁₂H₂₄O₃	216.317								soluble in ethyl alcohol and methyl alcohol.(Ref. 0132)(Ref. 0202)(Ref. 0468)							Acidic fraction of wool grease	Synthesis, by treatment of 3-bromolauric acid with aqueous KOH				[0132] / [0202] / [0468]
304		4-Hydroxylauric acid	4-Hydroxydodecanoic acid	DFA0304	Tetsuyuki Kobayashi		C₁₂H₂₄O₃	216.317			62.3-63.5C	170-171C at 11 mm Hg				soluble in ethyl alcohol, hexsane and benzene; needlls from benzene-petroleum ether(Ref. 0134)(Ref. 0202)								Synthetic, by saponification of the lactone				[0134] / [0202]
305		12-Hydroxylauric acid	12-Hydroxydodecanoic acid	DFA0305	Tetsuyuki Kobayashi		C₁₂H₂₄O₃	216.317			84-85C	164-166C at 11 mm Hg				soluble in ethanol, hexsane and benzene(Ref. 0132)(Ref. 0343)							As the etholide in the waxlike substances in various species of conifers, including Juniperus sabina					[0132] / [0343]
306			2-Hydroxytridecanoic acid	DFA0306	Tetsuyuki Kobayashi		C₁₃H₂₆O₃	230.344			78C					soluble in ethyl alcohol and ether / insoluble in benzene and petroleum ether								Synthetic, through the corresponding bromo acid
307			4-Hydroxytridecanoic acid	DFA0307	Tetsuyuki Kobayashi		C₁₃H₂₆O₃	230.344			66-66.5C					soluble in ethyl alcohol and ether / insoluble in benzene and petroleum ether(Ref. 0134)								Synthetic, by saponification of the g-lactone				[0134]
308			13-Hydroxytridecanoic acid	DFA0308	Tetsuyuki Kobayashi		C₁₃H₂₆O₃	230.344			79-79.5C					soluble in ethyl alcohol and ether / insoluble in benzene and petroleum ether(Ref. 0086)(Ref. 0468)								Synthetic, by partial reduction of tridecanedioic acid dimethyl ester with Na and ethanol				[0086] / [0468]
309		a-Hydroxymyristic acid	2-Hydroxytetradecanoic acid	DFA0309	Tetsuyuki Kobayashi		C₁₄H₂₈O₃	244.370			51-51.5C					soluble in ethyl alcohol, chloroform and ether (Ref. 0257)(Ref. 0309)(Ref. 0522)							Beeswax / wool grease	Synthetic, debromination of 2-bromomyristic acid				[0257] / [0309] / [0522]
310		w-Hydroxymyristic acid	14-Hydroxytetradecanoic acid	DFA0310	Tetsuyuki Kobayashi		C₁₄H₂₈O₃	244.370			54-54.5C	196-198C at 10 mmHg				(Ref. 0132)								Synthetic, by condensation of dimethyl sodium malonate with 12-bromo-1-dodecanol				[0132]
311			2-Hydroxypentadecanoic acid	DFA0311	Tetsuyuki Kobayashi		C₁₅H₃₀O₃	258.397			84.5C					readily soluble in ethyl alcohol / difficulty soluble in cold benzene								Synthetic, by action of NaOH on 2-bromopentadecanoic acid
312		Convolvulinolic acid	11-Hydroxypentadecanoic acid	DFA0312	Tetsuyuki Kobayashi		C₁₅H₃₀O₃	258.397			63.5-64C	166C at 2 mm Hg				soluble in ethyl alcohol, chloroform and ether(Ref. 0154)(Ref. 0476)								Synthetic, by reaction of n-butylmagnesium bromide and methyl 11-aldoundecanoate / by partial reduction of pentadecanedioic acid demethyl ester				[0154] / [0476]
313		2-Hydroxypalmitic acid	2-Hydroxyhexadecanoic acid	DFA0313	Tetsuyuki Kobayashi	C16h:0	C₁₆H₃₂O₃	272.423			85.8-86.6C					soluble in ethyl alcohol and methyl alcohol / insoluble in petroleum ether(Ref. 0256)						Gas liquid chromatogram [Chromatogram 0001] (provided by Dr. Etsuko Yasugi).		Synthetic, by the action of KOH on 2-bromopalmitic acid				[0256]
314		4-Hydroxypalmitic acid	4-Hydroxyhexadecanoic acid	DFA0314	Tetsuyuki Kobayashi		C₁₆H₃₂O₃	272.423			79-79.6C					soluble in ethyl acetate(Ref. 0258)							Jalap resin (along with jalaponolic acid) from Vera Cruz and Brazil / Ipomoea and scammony resins					[0258]
315		11-Hydroxypalmitic acid/builic acid/jalapinoic acid	11-Hydroxyhexadecanoic acid	DFA0315	Tetsuyuki Kobayashi		C₁₆H₃₂O₃	272.423			68-69C	183-186C at 3 mm Hg				soluble in ethyl alcohol and ether(Ref. 0155)(Ref. 0263)(Ref. 0438)							Shellac; root wax of Ipomoea orizabensis (Mexican scammony)					[0155] / [0263] / [0438]
316		14-Hydroxypalmitic acid	14-Hydroxyhexadecanoic acid	DFA0316	Tetsuyuki Kobayashi		C₁₆H₃₂O₃	272.423								soluble in hot ether / sparingly soluble in coid ether(Ref. 0485)(Ref. 0486)							Juniperus sabina wax					[0485] / [0486]
317		Juniperic acid	16-Hydroxyhexadecanoic acid	DFA0317	Tetsuyuki Kobayashi		C₁₆H₃₂O₃	272.423			95C	194-196C at 2 mm Hg				soluble in ethyl alcohol, benzene, hexane and ether / sparingly soluble in cold ether / insoluble in cold water(Ref. 0055)							Juniperus sabina wax					[0055]
318			2-Hydroxyheptadecanoic acid	DFA0318	Tetsuyuki Kobayashi		C₁₇H₃₄O₃	286.450			89C					(Ref. 0315)						Gas liquid chromatogram [Chromatogram 0001] (provided by Dr. Etsuko Yasugi).		Synthetic, by the action of KOH on 2-bromomargaric acid				[0315]
319			17-Hydroxyheptadecanoic acid	DFA0319	Tetsuyuki Kobayashi		C₁₇H₃₄O₃	286.450			87.5-88C	210C at 3 mm Hg				(Ref. 0132)(Ref. 0270)(Ref. 0467)								Synthetic, by paratial reduction of heptadecanedioic acid dimethyl ester				[0132] / [0270] / [0467]
320		2-Hydroxystearic acid	DL-2-Hydroxyoctadecanoic acid	DFA0320	Tetsuyuki Kobayashi		C₁₈H₃₆O₃	300.477			93C					soluble in ethyl alcohol, hexane, benzene methyl alcohol and ether (Ref. 0315)				[Spectrum 0001] (provided by Dr. Takeshi Kasama).		Gas liquid chromatogram [Chromatogram 0001] [Chromatogram 0002] (provided by Dr. Etsuko Yasugi).		Synthetic, by the action of KOH on 2-bromo- or 2-iodostearic acid				[0315]
321		3-Hydroxystearic acid	DL-3-Hydroxyoctadecanoic acid	DFA0321	Tetsuyuki Kobayashi		C₁₈H₃₆O₃	300.477			91C					soluble in ether / sparingly soluble in hot ethyl alcohol and chloroform(Ref. 0060)(Ref. 0397)								Synthetic				[0060] / [0397]
322		4-Hydroxystearic acid	DL-4-Hydroxyoctadecanoic acid	DFA0322	Tetsuyuki Kobayashi		C₁₈H₃₆O₃	300.477			89C					soluble in ether / sparingly soluble in hot ethyl alcohol and chloroform(Ref. 0060)(Ref. 0446)								Synthetic				[0060] / [0446]
323		5-Hydroxystearic acid	DL-5-Hydroxyoctadecanoic acid	DFA0323	Tetsuyuki Kobayashi		C₁₈H₃₆O₃	300.477			81.9-82.1C					soluble in acetone(Ref. 0060)(Ref. 0271)								Synthetic				[0060] / [0271]
324		6-Hydroxystearic acid	DL-6-Hydroxyoctadecanoic acid	DFA0324	Tetsuyuki Kobayashi		C₁₈H₃₆O₃	300.477			83C					soluble in acetone(Ref. 0060)(Ref. 0087)								Synthetic				[0060] / [0087]
325		7-Hydroxystearic acid	DL-7-Hydroxyoctadecanoic acid	DFA0325	Tetsuyuki Kobayashi		C₁₈H₃₆O₃	300.477			77.6-77.8C					soluble in petroleum ether(Ref. 0060)(Ref. 0389)								Synthetic, by the Grignard reaction				[0060] / [0389]
326		8-Hydroxystearic acid	DL-8-Hydroxyoctadecanoic acid	DFA0326	Tetsuyuki Kobayashi		C₁₈H₃₆O₃	300.477			81.5-81.7C					soluble in light petroleum(Ref. 0060)(Ref. 0335)								Synthetic, by the Grignard reaction of 9-aldopelargonic acid with nonylmagnesium btomide				[0060] / [0335]
327		9-Hydroxystearic acid	DL-9-Hydroxyoctadecanoic acid	DFA0327	Tetsuyuki Kobayashi		C₁₈H₃₆O₃	300.477			75.4-75.9C	212-216C at 4 mm Hg				soluble in petroleum(Ref. 0016)(Ref. 0043)(Ref. 0060)								Synthetic, by the Grignard reaction				[0016] / [0043] / [0060]
328		10-Hydroxystearic acid/rosilic acid	DL-10-Hydroxyoctadecanoic acid	DFA0328	Tetsuyuki Kobayashi		C₁₈H₃₆O₃	300.477			84C	213-217C at 4 mm Hg				soluble in petroleum(Ref. 0060)(Ref. 0480)							Wax of the Druschky rose	Synthetic, by the Grignard reaction / by the action of Ag₂O on 10-iodostearic acid				[0060] / [0480]
329		11-Hydroxystearic acid	DL-11-Hydroxyoctadecanoic acid	DFA0329	Tetsuyuki Kobayashi		C₁₈H₃₆O₃	300.477			81-82C	204-206C at 4 mm Hg				soluble in petroleum(Ref. 0060)(Ref. 0480)								Synthetic, by the Grignard reaction / by the reaction of Zn + HCl on the HBr addition product of ricinoleic acid				[0060] / [0480]
330		12-Hydroxystearic acid	DL-12-Hydroxyoctadecanoic acid	DFA0330	Tetsuyuki Kobayashi		C₁₈H₃₆O₃	300.477			76.6-76.7C	185-189C at 2 mm Hg				soluble in petroleum(Ref. 0060)(Ref. 0480)								Synthetic, by the Grignard reaction				[0060] / [0480]
331		13-Hydroxystearic acid	DL-13-Hydroxyoctadecanoic acid	DFA0331	Tetsuyuki Kobayashi		C₁₈H₃₆O₃	300.477			77.2-77.5C					soluble in light petroleum(Ref. 0060)(Ref. 0469)(Ref. 0480)								synthetic by the Grignard reaction				[0060] / [0469] / [0480]
332		14-Hydroxystearic acid	14-Hydroxyoctadecanoic acid	DFA0332	Tetsuyuki Kobayashi		C₁₈H₃₆O₃	300.477			76.6-76.8C					soluble in petroleum and ehtanol(Ref. 0060)(Ref. 0480)								synthetic by the Grignard reaction				[0060] / [0480]
333		15-Hydroxystearic acid	15-Hydroxyoctadecanoic acid	DFA0333	Tetsuyuki Kobayashi		C₁₈H₃₆O₃	300.477			75.3-75.5C					soluble in petroleum and ehtanol(Ref. 0060)								synthetic by the Grignard reaction				[0060]
334		16-Hydroxystearic acid	16-Hydroxyoctadecanoic acid	DFA0334	Tetsuyuki Kobayashi		C₁₈H₃₆O₃	300.477			78.4-78.6C					soluble in petroleum and ehtanol(Ref. 0060)								synthetic by the Grignard reaction				[0060]
335		17-Hydroxystearic acid	17-Hydroxyoctadecanoic acid	DFA0335	Tetsuyuki Kobayashi		C₁₈H₃₆O₃	300.477			76.4-76.6C					soluble in petroleum and ehtanol(Ref. 0060)								synthetic by the Grignard reaction				[0060]
336		18-Hydroxystearic acid	18-Hydroxyoctadecanoic acid	DFA0336	Tetsuyuki Kobayashi		C₁₈H₃₆O₃	300.477			87-88C (unstable)					soluble in petroleum and ehtanol(Ref. 0149)(Ref. 0370)(Ref. 0412)(Ref. 0439)							Carnauba wax	synthetic by (i) partial reduction of octadecanedioic acid dimethyl ester, or (ii)hydrogenation of kamlolenic acid (see entries 381 and 382)				[0149] / [0370] / [0412] / [0439]
337			2-Hydroxynonadecanoic acid	DFA0337	Tetsuyuki Kobayashi		C₁₉H₃₈O₃	314.503			83-84C					(Ref. 0132)						Gas liquid chromatogram [Chromatogram 0001] [Chromatogram 0002] (provided by Dr. Etsuko Yasugi).		synthetic by treatment of the corresponding bromo acid with KOH				[0132]
338			19-Hydroxynonadecanoic acid	DFA0338	Tetsuyuki Kobayashi		C₁₉H₃₈O₃	314.503			91-91.5C					(Ref. 0132)								synthetic by the partial reduction of nonadecanedionic acid dimethyl ester				[0132]
339			2-Hydroxyeicosanoic acid	DFA0339	Tetsuyuki Kobayashi		C₂₀H₄₀O₃	328.530			91-92C					(Ref. 0036)								synthetic by heating 2-bromoarachidic acid with ethanolic NaOH				[0036]
340			3-Hydroxyeicosanoic acid	DFA0340	Tetsuyuki Kobayashi		C₂₀H₄₀O₃	328.530			93C					(Ref. 0450)												[0450]
341			20-Hydroxyeicosanoic acid	DFA0341	Tetsuyuki Kobayashi		C₂₀H₄₀O₃	328.530			97.4-97.8C (acetyl derivative), 68.5C (methyl ester)					(Ref. 0132)								synthetic by partial reductionof eicosanedioic acid dimethyl ester				[0132]
342			21-Hydroxyheneicosanoic acid	DFA0342	Tetsuyuki Kobayashi		C₂₁H₄₂O₃	342.556			92.5-93C					(Ref. 0132)							seed oil of Mallotus philippinensis (kamala)	synthetic by the partial reduction of heneicosanedioic acid dimethyl ester				[0132]
343		2-Hydroxybehenic	2-Hydroxydocosanoic acid	DFA0343	Tetsuyuki Kobayashi		C₂₂H₄₄O₃	356.583			99.3-99.6C					(Ref. 0203)(Ref. 0413)(Ref. 0439)				[Spectrum 0001] (provided by Dr. Takeshi Kasama).		Gas liquid chromatogram [Chromatogram 0001] [Chromatogram 0002] (provided by Dr. Etsuko Yasugi).		hydrolysis of suberin; synthetic by the action of aqueous KOH on 2-bromobehenic acid				[0203] / [0413] / [0439]
344		3-Hydroxybehenic	(+)-3-Hydroxydocosanoic acid	DFA0344	Tetsuyuki Kobayashi		C₂₂H₄₄O₃	356.583			95.8-96C					(Ref. 0008)(Ref. 0440)(Ref. 0450)(Ref. 0515)								synthetic				[0008] / [0440] / [0450] / [0515]
345		w-Hydroxybehenic/phellonic acid	22-Hydroxydocosanoic acid	DFA0345	Tetsuyuki Kobayashi		C₂₂H₄₄O₃	356.583			99.2-100.5C					soluble in acetone, chloroform, ethanol, glacial acetic acid and pyridine(Ref. 0203)(Ref. 0273)(Ref. 0370)(Ref. 0440)(Ref. 0515)							cork; birch bark; carnauba wax					[0203] / [0273] / [0370] / [0440] / [0515]
346		Cerebronic acid	DL-2-Hydroxytetracosanoic acid	DFA0346	Tetsuyuki Kobayashi		C₂₄H₄₈O₃	384.636			99.5-100.5C [(+)-]					(Ref. 0116)						Gas liquid chromatogram [Chromatogram 0001] (provided by Dr. Etsuko Yasugi).	brain lipids					[0116]
347		3,11-dihydroxymyristoic acid/ipurolic acid	3,11-Dihydroxytetradecanoic acid	DFA0347	Tetsuyuki Kobayashi		C₁₄H₂₈O₄	260.370			100-101C					soluble in chloroform and ethanol(Ref. 0262)(Ref. 0342)(Ref. 0371)(Ref. 0403)							Ipomoea purpurea					[0262] / [0342] / [0371] / [0403]
348		2,15-dihydroxypentadecylic acid	2,15-Dihydroxypentadecanoic acid	DFA0348	Tetsuyuki Kobayashi		C₁₅H₃₀O₄	274.396			102-103C					soluble in methanol and alcohol(Ref. 0030)(Ref. 0031)								syanthetic from ustilic acid A (see entry 350)				[0030] / [0031]
349		3,12-dihydroxypalmitic acid	3,12-Dihydroxyhexadecanoic acid	DFA0349	Tetsuyuki Kobayashi		C₁₆H₃₂O₄	288.423			83-84C					soluble in methanol and alcohol(Ref. 0441)							Fermentaion of Ustilago zeae					[0441]
350		Ustilic acid A	15,16-Dihydroxyhexadecanoic acid	DFA0350	Tetsuyuki Kobayashi		C₁₆H₃₂O₄	288.423			112-113C					soluble in hot alcohol, methanol ; slightly soluble in ethanol and water(Ref. 0312)							castor oil					[0312]
351		2,3-Dihydroxystearic acid	2,3-Dihydroxyoctadecanoic acid	DFA0351	Tetsuyuki Kobayashi		C₁₈H₃₆O₄	316.476			126C					soluble in alcohol, ethanol and hot water(Ref. 0316)							straw, soils					[0316]
352		5,6-Dihydroxystearic acid	5,6-Dihydroxyoctadecanoic acid	DFA0352	Tetsuyuki Kobayashi		C₁₈H₃₆O₄	316.476			94C					soluble in acetone and ethanol(Ref. 0398)							seed oils of hare's-ear and mustard					[0398]
353		6,7-Dihydroxystearic acid	6,7-Dihydroxyoctadecanoic acid	DFA0353	Tetsuyuki Kobayashi		C₁₈H₃₆O₄	316.476			122C (erythro), 117.5C (threo)					soluble in methanol and alcohol(Ref. 0460)							fermentation of Ustilago zeae					[0460]
354		7,8-Dihydroxystearic acid	7,8-Dihydroxyoctadecanoic acid	DFA0354	Tetsuyuki Kobayashi		C₁₈H₃₆O₄	316.476			96.5C					soluble in methanol and alcohol(Ref. 0189)(Ref. 0398)								synthetic				[0189] / [0398]
355		8,9-Dihydroxystearic acid	8,9-Dihydroxyoctadecanoic acid	DFA0355	Tetsuyuki Kobayashi		C₁₈H₃₆O₄	316.476			98.5C					soluble in alcohol, ehtanol ; insoluble in water(Ref. 0026)(Ref. 0189)								synthetic by oxidationof cis- or trans-7-octadecenoic acid (see entries 107 and 108) with performic acid				[0026] / [0189]
356		9,10-Dihydroxystearic acid	9,10-Dihydroxyoctadecanoic acid	DFA0356	Tetsuyuki Kobayashi		C₁₈H₃₆O₄	316.476			133-136.5C (erythro)					soluble in alcohol, ethanol, hot water, methanol and alcohol(Ref. 0454)							castor oil	synthetic				[0454]
357		9,12-Dihydroxystearic acid	9,12-Dihydroxyoctadecanoic acid	DFA0357	Tetsuyuki Kobayashi		C₁₈H₃₆O₄	316.476			90C					soluble in alcohol ; sparingly soluble in ethanol ; insoluble in petroleum and ethanol(Ref. 0200)							many animal and seed fats and oils					[0200]
358		10,11-Dihydroxystearic acid	10,11-Dihydroxyoctadecanoic acid	DFA0358	Tetsuyuki Kobayashi		C₁₈H₃₆O₄	316.476			77-78C					soluble in ehtanol and alcohol(Ref. 0427)(Ref. 0428)								synthetic				[0427] / [0428]
359		11,12-Dihydroxystearic acid	11,12-Dihydroxyoctadecanoic acid	DFA0359	Tetsuyuki Kobayashi		C₁₈H₃₆O₄	316.476			129-130C (erythro), 95-96C (threo)					soluble in methanol and alcohol(Ref. 0065)(Ref. 0177)(Ref. 0178)(Ref. 0436)								synthetic				[0065] / [0177] / [0178] / [0436]
360		12,13-Dihydroxystearic acid	12,13-Dihydroxyoctadecanoic acid	DFA0360	Tetsuyuki Kobayashi		C₁₈H₃₆O₄	316.476			97.8-98C [(+)-threo], 98.5C [(-)-threo], 98.5-99C [(+-)-threo]					soluble in methanol and alcohol(Ref. 0064)(Ref. 0124)(Ref. 0436)												[0064] / [0124] / [0436]
361		11,12-Dihydroxyarachidic acid	11,12-Dihydroxyeicosanoic acid	DFA0361	Tetsuyuki Kobayashi		C₂₀H₄₀O₄	344.529			130C					soluble in acetone, ether . (Ref. 0249)							Seed oil of hare's ear and mustard.					[0249]
362		D-Threonic acid	2,2,4-Trihydroxybutyric acid	DFA0362	Tetsuyuki Kobayashi		C₄H₈O₅	136.103								(Ref. 0196)/(Ref. 0222)/(Ref. 0272)								Synthetic				[0196] / [0222] / [0272]
363		DL-Erythronic acid	2,3,4-Trihydroxybutyric acid	DFA0363	Tetsuyuki Kobayashi		C₄H₈O₅	136.103			102-103C					soluble in water.(readily) (Ref. 0196)/(Ref. 0222)/(Ref. 0272)								Synthetic				[0196] / [0222] / [0272]
364		Digitoxic acid	3,4,5-Trihydroxyhexanoic acid	DFA0364	Tetsuyuki Kobayashi		C₆H₁₂O₅	164.156								soluble in acetone, water. (Ref. 0532)												[0532]
365		2,15,16-Trihydroxypalmitic acid/Ustilic acid	2,15,16-Trihydroxyhexadecanoic acid	DFA0365	Tetsuyuki Kobayashi		C₁₆H₃₂O₅	304.422			140C					soluble in methyl alcohol. (Ref. 0312)							Hydrolytic breakdown of Ustilago (fungal smut of cereal grain)					[0312]
366		8,9,16-Trihydroxypalmitic acid	8,9,16-Trihydroxyhexadecanoic acid	DFA0366	Tetsuyuki Kobayashi		C₁₆H₃₂O₅	304.422			100C					(Ref. 0190)							Shellac	Synthetic				[0190]
367		9,10,16-Trihydroxypalmitic acid/aleuritic acid	9,10,16-Trihydroxyhexadecanoic acid	DFA0367	Tetsuyuki Kobayashi		C₁₆H₃₂O₅	304.422			102C/104C					soluble in aqueous alcohol, methyl alcohol, ; needles from water. (Ref. 0373)/(Ref. 0374)/(Ref. 0375)/(Ref. 0376)							Shellac					[0373] / [0374] / [0375] / [0376]
368		11,12,15-Trihydroxypalmitic acid	11,12,15-Trihydroxyhexadecanoic acid	DFA0368	Tetsuyuki Kobayashi		C₁₆H₃₂O₅	304.422			100C					(Ref. 0114)/(Ref. 0155)							Shallac					[0114] / [0155]
369		Phloionolic acid	9,10,18-Trihydroxyoctadecanoic acid	DFA0369	Tetsuyuki Kobayashi		C₁₈H₃₆O₅	332.475			104C					(Ref. 0533)							Cork	Synthetic				[0533]
370		Apionic acid	2,3,4,4-Tetrahydroxyisovaleric acid	DFA0370	Tetsuyuki Kobayashi		C₅H₁₀O₆	166.129								(Ref. 0431)/(Ref. 0517)								Synthetic				[0431] / [0517]
371		Sativic acid	9,10-threo-12,13-threo-Tetrahydroxyoctadecanoic acid	DFA0371	Tetsuyuki Kobayashi		C₁₈H₃₆O₆	348.475			147.5C/148C					(Ref. 0064)/(Ref. 0068)								Synthetic, by ring opening of vernolic acid with performic acid (4 optically active pairs of acids produced)				[0064] / [0068]
372		Ambrettolic acid	16-Hydroxyhexadec-7-enoic acid	DFA0372	Tetsuyuki Kobayashi		C₁₆H₃₀O₃	270.408			53-55C for a, 26-27C for b	185-190C at 13 mm Hg				soluble in ethanol, ether. (Ref. 0285)/(Ref. 0466)							As the lactone (ambrettolide) in musk (ambrette) seed oil	synthetic from the lactone				[0285] / [0466]
373			9-Hydroxy-cis-12-octadecenoic acid	DFA0373	Tetsuyuki Kobayashi		C₁₈H₃₄O₃	298.461								soluble in acetone, ethanol, ether. (Ref. 0063)/(Ref. 0204)/(Ref. 0205)/(Ref. 0206)							Seed fat of Strophanthus spp.; 6-14% in seed oils of 13 Strophanthus spp.					[0063] / [0204] / [0205] / [0206]
374		Ricinoleic acid	12-Hydroxy-cis-9-octadecenoic acid	DFA0374	Tetsuyuki Kobayashi		C₁₈H₃₄O₃	298.461			5.0, 7.7 and 16.0C (trimorphic)	225C at 10 mm Hg	d²⁷^.⁴₄0.940	1.4716 at 20C		soluble in acetone, ethanol, ether ; slightly soluble in chloroform ; insoluble in water. (Ref. 0148)/(Ref. 0197)/(Ref. 0228)/(Ref. 0284)/(Ref. 0345)							Seed oils of Ricinus, Strophanthus sarmentosus, ergot, and a few other plants.					[0148] / [0197] / [0228] / [0284] / [0345]
375		Ricinelaidic acid	12-Hydroxy-trans-9-octadecenoic acid	DFA0375	Tetsuyuki Kobayashi		C₁₈H₃₄O₃	298.461			52-53C					very soluble in acetone, ethanol, ether ; soluble in petroleum ether, ; very slightly soluble in ether. (Ref. 0089)/(Ref. 0090)/(Ref. 0307)/(Ref. 0344)/(Ref. 0392)							Not natural fats and oils.	Synthetic, by treatment of castor oil with N oxides.				[0089] / [0090] / [0307] / [0344] / [0392]
376			9-Hydroxy-trans-10,cis-12-octadecadienoic acid	DFA0376	Tetsuyuki Kobayashi		C₁₈H₃₂O₃	296.445								(Ref. 0123)/(Ref. 0365)							Seed oil of Tragopogon porrifolius.					[0123] / [0365]
377		Dimorphecolic acid / a-dimorphecolic acid	9-Hydroxy-trans-10,trans-12-octadecadienoic acid	DFA0377	Tetsuyuki Kobayashi		C₁₈H₃₂O₃	296.445								(Ref. 0366)/(Ref. 0452)/(Ref. 0453)							Several Dimorphotheca spp.; 34% in seed oil of D.aurantiaca (Cape marigold); species of other genera.					[0366] / [0452] / [0453]
378		Densipolic acid	12-Hydroxy-cis-9,cis-15-octadecadienoic acid	DFA0378	Tetsuyuki Kobayashi		C₁₈H₃₂O₃	296.445								(Ref. 0355)/(Ref. 0455)							Seed oil of Lesquerella densipila.					[0355] / [0455]
379			13-Hydroxy-cis-9,trans-11-octadecadienoic acid	DFA0379	Tetsuyuki Kobayashi		C₁₈H₃₂O₃	296.445								soluble in acotone, ethanol, pentane. (Ref. 0123)/(Ref. 0365)							Seed oils of 4 species of Asteraceae including Tragopogon porrifolius, 1 species of Fabaceae, and 1 species of Zygophyllaceae.					[0123] / [0365]
380		a-Artemisic acid	13-Hydroxy-trans-9,trans-11-octadecadienoic acid	DFA0380	Tetsuyuki Kobayashi		C₁₈H₃₂O₃	296.445								(Ref. 0364)/(Ref. 0365)							4% in the seed oil of Tragopogon porrifolius along with dimorphecolic acid.					[0364] / [0365]
381		a-Kamlolenic acid	18-Hydroxy-cis-9,trans-11,trans-13-octadecatrienoic acid	DFA0381	Tetsuyuki Kobayashi		C₁₈H₃₀O₃	294.429			77-78C					(Ref. 0066)/(Ref. 0211)/(Ref. 0227)							Primary constituent of Mallotus phillippinensis (kamala) and other Mallotus spp.					[0066] / [0211] / [0227]
382		b-Kamlolenic acid	18-Hydroxy-trans-9,trans-11,trans-13-octadecatrienoic acid	DFA0382	Tetsuyuki Kobayashi		C₁₈H₃₀O₃	294.429			88-89C					(Ref. 0066)/(Ref. 0211)/(Ref. 0227)								Synthetic, by isomerization of the a-acid.				[0066] / [0211] / [0227]
383		Lesquerolic acid	14-Hydroxy-cis-11-eicosenoic acid	DFA0383	Tetsuyuki Kobayashi		C₂₀H₃₈O₃	326.514								(Ref. 0038)/(Ref. 0359)							Seed oils of various Lesquerella spp.					[0038] / [0359]
384		Hydroxynervonic acid	2-Hydroxy-15-tetracosenoic acid	DFA0384	Tetsuyuki Kobayashi		C₂₄H₄₆O₃	382.620			65C					soluble in acetone, ethanol, chloroform, ether, pyridine (readily) ; slightly soluble in petroleum ether. (Ref. 0289)/(Ref. 0291)							Brain lipids - first prepared from a cerebroside fraction partially soluble in petroleum benzin.					[0289] / [0291]
385		Pyruvic acid / a-ketopropionic acid	2-Oxopropionic acid	DFA0385	Tetsuyuki Kobayashi		C₃H₄O₃	88.062			13.6C	165C at 760 mm Hg	d¹⁵^.³₄1.2668	1.43025 at 15.3C		miscible in all proportions with ethanol, ether, water. (Ref. 0161)/(Ref. 0166)/(Ref. 0188)/(Ref. 0195)/(Ref. 0259)								Synthetic, by distillation of tartaric acid in the presence of KHSO₄(good yield)				[0161] / [0166] / [0188] / [0195] / [0259]
386		3-Methylpyruvic acid	2-Oxobutyric acid	DFA0386	Tetsuyuki Kobayashi		C₄H₆O₃	102.089			31-32C	74-78C at 25 mm Hg	d1.3974			miscible in all proportions with water. (Ref. 0095)/(Ref. 0212)/(Ref. 0433)								Synthetic				[0095] / [0212] / [0433]
387		Acetoacetic acid / b-ketobutyric acid	3-Oxobutyric acid	DFA0387	Tetsuyuki Kobayashi		C₄H₆O₃	102.089			36-37C	decomposes, <100				soluble in ethanol, benzene, chloroform, ether, water. (Ref. 0347)								Synthetic, by treatment of butyryl chloride with AgCN and hydrolysis of the cyanide.				[0347]
388		2-Ketovaleric acid	2-Oxopentanoic acid	DFA0388	Tetsuyuki Kobayashi		C₅H₈O₃	116.115			6-7C	179C at 760 mm Hg				(Ref. 0008)/(Ref. 0072)								Synthetic, by (i) the action of ethylmagnesium iodide on ethyl cyanoacetate, and (ii) hydrolysis of bytyryl chloride with AgCN.				[0008] / [0072]
389		3-Ketovaleric acid	3-Oxopentanoic acid	DFA0389	Tetsuyuki Kobayashi		C₅H₈O₃	116.115			33-35C	191C at 760 mm Hg				very soluble in ethanol, ether, water ; insolble in aliphatic hydrocarbons. (Ref. 0414)								Synthetic, by reaction of a-substituted fatty acids with etyl acetoacetate, followed by alkaline hydrolysis of the condensation product.				[0414]
390		Levulinic acid	4-Oxopentanoic acid	DFA0390	Tetsuyuki Kobayashi		C₅H₈O₃	116.115			37.2C	246C / 154C at 15 mm Hg	d1.1395	1.442 at 15.8C		very soluble in ethanol, ether, water. (Ref. 0143)/(Ref. 0314)/(Ref. 0340)								Synthetic, by heating sugars, particularly hexoses (good yield).				[0143] / [0314]
391		2-Keto-n-caproic acid	2-Oxohexanoic acid	DFA0391	Tetsuyuki Kobayashi		C₆H₁₀O₃	130.142			15 C	93-94 C at 14 mmHg				(Ref. 0047)(Ref. 0232)(Ref. 0299)								Synthetic, by saponification of the ethyl ester				[0047] / [0232] / [0299]
392		3-Keto-n-caproic acid	3-Oxohexanoic acid	DFA0392	Tetsuyuki Kobayashi		C₆H₁₀O₃	130.142								(Ref. 0003)								Synthetic, by action of propylmagnesium iodide on cyanoacetic acid, followed by hydrolysis of the complex formed				[0003]
393		4-Keto-n-caproic acid	4-Oxohexanoic acid	DFA0393	Tetsuyuki Kobayashi		C₆H₁₀O₃	130.142			40 C	89 C at 0.4 mmHg / 183 C at 20 mmHg				(Ref. 0423)								Synthetic, by hydrolysis of the oxime ( also by other methods )				[0423]
394		5-Keto-n-caproic acid	5-Oxohexanoic acid	DFA0394	Tetsuyuki Kobayashi		C₆H₁₀O₃	130.142			13-14 C	180 C at 20 mmHg				soluble in most organic solvents (Ref. 0058)(Ref. 0248)								Synthetic, by hydrolytic cleavage of dihydroresorcinol ( also by other methods )				[0058] / [0248]
395		2-Keto-n-heptylic acid	2-Oxoheptanoic acid	DFA0395	Tetsuyuki Kobayashi		C₇H₁₂O₃	144.168			29-30 C	108-111 C at 17 mmHg				soluble in most organic solvents (Ref. 0008)												[0008]
396		n-Valerylacetic acid	3-Oxoheptanoic acid	DFA0396	Tetsuyuki Kobayashi		C₇H₁₂O₃	144.168								(Ref. 0077)								Synthetic, by condensation of ethyl valerate and ethyl acetate				[0077]
397		3-Butyrylpropionic acid	4-Oxoheptanoic acid	DFA0397	Tetsuyuki Kobayashi		C₇H₁₂O₃	144.168			48 C	123-126 C at 3.5 mmHg				(Ref. 0338)								Synthetic, by treatment of butyrylsuccinic acid dimethyl ester with HCl				[0338]
398		4-Propionylbutyric acid	5-Oxoheptanoic acid	DFA0398	Tetsuyuki Kobayashi		C₇H₁₂O₃	144.168			50 C	110 C at 16 mmHg				(Ref. 0078)								Synthetic, by oxidation of 1-ethyl-2-propionyl-1-cyclopentene, also from one of the reactions of ethylcyclopenetene				[0078]
399		5-Acetovaleric acid	6-Oxoheptanoic acid	DFA0399	Tetsuyuki Kobayashi		C₇H₁₂O₃	144.168			31-32 C / 40-42 C	250-253 C at 280 mmHg				(Ref. 0394)								Synthetic, by action of methylzinc iodide on the acid chloride of monomethyl adipate ( also by other methods )				[0394]
400		2-Keto-n-caprylic acid	2-Oxooctanoic acid	DFA0400	Tetsuyuki Kobayashi		C₈H₁₄O₃	158.195			32-33 C	104 C at 6 mmHg				(Ref. 0008)												[0008]
401		3-Keto-n-caprylic acid	3-Oxooctanoic acid	DFA0401	Tetsuyuki Kobayashi		C₈H₁₄O₃	158.195			74 C ( Decomposes to 2-heptanone / methyl valeryl ketone. )					soluble in water, most organic solvents; insoluble in petroleum ether (Ref. 0186)								Synthetic, by treatment of 3-octynoic acid with ethanolic KOH and monoethyl succinate				[0186]
402		4-Keto-n-caprylic acid	4-Oxooctanoic acid	DFA0402	Tetsuyuki Kobayashi		C₈H₁₄O₃	158.195			53 C	168-170 C at 15 mmHg				insoluble in water (Ref. 0338)								Synthetic, by action of butylzinc iodide on the acid chloride of monoethyl succinate				[0338]
403		5-Keto-n-caprylic acid	5-Oxooctanoic acid	DFA0403	Tetsuyuki Kobayashi		C₈H₁₄O₃	158.195			34 C	280-285 C at 760 mmHg				soluble in alcohol, ether, water (Ref. 0185)(Ref. 0186)								Synthetic, by ring cleavage of coniine ( a hemlock alkaloid ), C₈H₁₇N				[0185] / [0186]
404		6-Keto-n-caprylic acid	6-Oxooctanoic acid	DFA0404	Tetsuyuki Kobayashi		C₈H₁₄O₃	158.195			52 C	160-161 C at 9 mmHg				(Ref. 0073)(Ref. 0075)								Synthetic, by action of ethylzinc iodide on the acid chloride of monomethyl adipate ( also by other methods )				[0073] / [0075]
405		7-Keto-n-caprylic acid	7-Oxooctanoic acid	DFA0405	Tetsuyuki Kobayashi		C₈H₁₄O₃	158.195			29-30 C	184-185 C at 15 mmHg	d0.9708	1.4375 at 25 C		(Ref. 0311)								Synthetic, by oxidation of 1-methylcycloheptene				[0311]
406		n-Heptanoylacetic acid	2-Oxononanoic acid	DFA0406	Tetsuyuki Kobayashi		C₉H₁₆O₃	172.222			43-44 C ( With decomposition ) / 98-98.5 C [ oxime ]					(Ref. 0008)(Ref. 0009)								Synthetic, by action of ethanolic KOH on 2-nonynoic acid				[0008] / [0009]
407		3-Caproylpropionic acid	4-Oxononanoic acid	DFA0407	Tetsuyuki Kobayashi		C₉H₁₆O₃	172.222			70-71 C ( Crystalline mass decomposes at ordinary temperatures to 2-octanone / methyl hexyl ketone. )					(Ref. 0458)								Synthetic, by action of pentylmagnesium bromide on N-methylsuccinimide				[0458]
408		4-n-Valerylbutyric acid	5-Oxononanoic acid	DFA0408	Tetsuyuki Kobayashi		C₉H₁₆O₃	172.222			44 C / 142 C [ semi-carbazone ]					(Ref. 0185>												[0185]
409		n-Butyryl-n-valeric acid	6-Oxononanoic acid	DFA0409	Tetsuyuki Kobayashi		C₉H₁₆O₃	172.222			43 C / 154-155 C [ semi-carbazone ]	140-142 C at 1 mmHg				(Ref. 0393>												[0393]
410		6-Propionyl-n-caproic acid	7-Oxononanoic acid	DFA0410	Tetsuyuki Kobayashi		C₉H₁₆O₃	172.222			42 C	42 C at 760 mmHg ( freezing point )				(Ref. 0075>								Synthetic, by action of ethylzinc iodide on the acid chloride of monoethyl pimelate				[0075]
411		2-Oxocapric acid	2-Oxodecanoic acid	DFA0411	Tetsuyuki Kobayashi		C₁₀H₁₈O₃	186.248			46-47 C / 85-86 C [ oxime ]	148-151 C at 18 mmHg				(Ref. 0008>												[0008]
412		3-Oxocapric acid	3-Oxodecanoic acid	DFA0412	Tetsuyuki Kobayashi		C₁₀H₁₈O₃	186.248			80-85 C ( Decomposes to 2-nonanone / methyl heptyl ketone. ) [ Leaflets ]					(Ref. 0458>												[0458]
413		4-Oxocapric acid	4-Oxodecanoic acid	DFA0413	Tetsuyuki Kobayashi		C₁₀H₁₈O₃	186.248			70-71 C					(Ref. 0339>								Synthetic, by action of hexylmagnesium bromide on N-methylsuccinimide				[0339]
414		5-Oxocapric acid	5-Oxodecanoic acid	DFA0414	Tetsuyuki Kobayashi		C₁₀H₁₈O₃	186.248			58 C	155-161 C at 2 mmHg				(Ref. 0185>								Synthetic, by H₂O₂ oxidation of coniine in presence of spongy platinum				[0185]
415		6-Oxocapric acid	6-Oxodecanoic acid	DFA0415	Tetsuyuki Kobayashi		C₁₀H₁₈O₃	186.248			46-47 C					(Ref. 0159>								Synthetic, by oxidation of (1) 1-cyclohexene-1 with KMnO₄, or (2) 1-methylcyclohexanone-2 with CrO₃-H₂SO₄				[0159]
416		8-Oxocapric acid	8-Oxodecanoic acid	DFA0416	Tetsuyuki Kobayashi		C₁₀H₁₈O₃	186.248			64 C					(Ref. 0075>								Synthetic, by action of ethylzinc iodide on the acid chloride of monomethyl suberate				[0075]
417		9-Oxocapric acid	9-Oxodecanoic acid	DFA0417	Tetsuyuki Kobayashi		C₁₀H₁₈O₃	186.248			48 C					(Ref. 0046>								Synthetic, by action of monomethyl ester chloride of azelaic acid + Zn ( or Cu )				[0046]
418		Pelargonylacetic acid	3-Oxoundecanoic acid	DFA0418	Tetsuyuki Kobayashi		C₁₁H₂₀O₃	200.275			55 C [ White crystals ]					(Ref. 0008>												[0008]
419		3-Caprylpropionic acid	4-Oxoundecanoic acid	DFA0419	Tetsuyuki Kobayashi		C₁₁H₂₀O₃	200.275			77 C / 62 C [ crystals ]					(Ref. 0458>								Synthetic, from the appropriate monoester acid chloride and alkyl iodide				[0458]
420		4-Heptanoylbutyric acid	5-Oxoundecanoic acid	DFA0420	Tetsuyuki Kobayashi		C₁₁H₂₀O₃	200.275			62 C					(Ref. 0185>								Synthetic, from the monoethyl ester chloride of the appropriate dibasic acid				[0185]
421		8-Propionylcaprylic acid	9-Oxoundecanoic acid	DFA0421	Tetsuyuki Kobayashi		C₁₁H₂₀O₃	200.275			43.5C ; 56C					(Ref. 0002)								Synthetic, by hydration of 9-nudecynoic acid				[0002]
422		9-Acetylpelargonic acid	10-Oxoundecanoic acid	DFA0422	Tetsuyuki Kobayashi		C₁₁H₂₀O₃	200.275			58.5-59.5C	166-167C at 1 mm Hg				(Ref. 0133)								Synthetic, by (i) oxidation of nudecane-1,10-diol, or (ii) hydration of 10-undecynoic acid				[0133]
423		4-Ketolauric acid	4-Oxododecanoic acid	DFA0423	Tetsuyuki Kobayashi		C₁₂H₂₂O₃	214.301			50C					(Ref. 0100) (Ref. 0475)								Synthetic, by action of ethanolic KOH on 3-dodecynoic acid				[0100] / [0475]
424		9-Ketolauric acid	9-Oxododecanoic acid	DFA0424	Tetsuyuki Kobayashi		C₁₂H₂₂O₃	214.301			50C					(Ref. 0032)								Synthetic, by action of propylzinc iodide on the acid chloride of monoethyl azelate				[0032]
425		2-Ketotridecanoic acid	2-Oxotridecanoic acid	DFA0425	Tetsuyuki Kobayashi		C₁₃H₂₄O₃	228.328			39-40.5C					(Ref. 0008)												[0008]
426		10-Ketotridecanoic acid	10-Oxotridecanoic acid	DFA0426	Tetsuyuki Kobayashi		C₁₃H₂₄O₃	228.328			63C					(Ref. 0416)								Synthetic, by reaction of ethylsodio-2-acetylbutyrate with 9-carbethoxynonanoyl chloride				[0416]
427		12-Ketotridecanoic acid	12-Oxotridecanoic acid	DFA0427	Tetsuyuki Kobayashi		C₁₃H₂₄O₃	228.328			70-71C	185-186C at 1 mm Hg				(Ref. 0418)								Synthetic, by oxidation of tridecane-1,12-diol				[0418]
428		4-Ketomyristic acid	4-Oxotetradecanoic acid	DFA0428	Tetsuyuki Kobayashi		C₁₄H₂₆O₃	242.354			87C					(Ref. 0418)								Synthetic, by hydrolysis of the condensation product of undecanoyl chloride & the Na derivative of ethyl acetylsuccinate				[0418]
429		10-Ketomyristic acid	10-Oxotetradecanoic acid	DFA0429	Tetsuyuki Kobayashi		C₁₄H₂₆O₃	242.354			69C					(Ref. 0134)								Synthetic, by action of ethyl sodioacetoacetate on ethyl 11-chloroundecanoate & hydrolysis of the reaction product, ethyl 2-acetylbrassylate				[0134]
430		13-Ketomyristic acid	13-Oxotetradecanoic acid	DFA0430	Tetsuyuki Kobayashi		C₁₄H₂₆O₃	242.354			87C	164-166C at 1 mm Hg				(Ref. 0198) (Ref. 0425)								Synthetic, by hydrolysis of ethyl sodioacetoacetate by action on ethyl 11-chloroundecanoate				[0198] / [0425]
431		4-Ketopentadecanoic acid	4-Oxopentadecanoic acid	DFA0431	Tetsuyuki Kobayashi		C₁₅H₂₈O₃	256.381			92.6C					(Ref. 0139)								Synthetic, by oxidation with KMnO₄ of either 4-hydroxy-3,5-dicarboxypentadecanoic acid or its lactone				[0139]
432		11-Ketopentadecanoic acid	11-Oxopentadecanoic acid	DFA0432	Tetsuyuki Kobayashi		C₁₅H₂₈O₃	256.381			70-71C					(Ref. 0154)								Synthetic, by oxidation of convolvulinolic acid with CrO₃				[0154]
433		14-Ketopentadecanoic acid	14-Oxopentadecanoic acid	DFA0433	Tetsuyuki Kobayashi		C₁₅H₂₈O₃	256.381			78.4-79.4C	205-206C at 15 mm Hg				(Ref. 0134)								Synthetic, by oxidation of 1,14-pentadecanediol with CrO₃				[0134]
434		2-Ketopalmitic acid	2-Oxohexadecanoic acid	DFA0434	Tetsuyuki Kobayashi		C₁₆H₃₀O₃	270.408			65-66C ; 47C ; 81-82C					(Ref. 0008)												[0008]
435		3-Ketopalmitic acid	3-Oxohexadecanoic acid	DFA0435	Tetsuyuki Kobayashi		C₁₆H₃₀O₃	270.408			98C ; 40-41C ; 81-82C	165-170C				(Ref. 0458)												[0458]
436		4-Ketopalmitic acid	4-Oxohexadecanoic acid	DFA0436	Tetsuyuki Kobayashi		C₁₆H₃₀O₃	270.408			91-92C					(Ref. 0258)								Synthetic, by action of the Na derivative of ethyl 2-acetyltridecanoate on 3-carbomethoxypropionyl chloride				[0258]
437		5-Ketopalmitic acid	5-Oxohexadecanoic acid	DFA0437	Tetsuyuki Kobayashi		C₁₆H₃₀O₃	270.408			88C					(Ref. 0416)								Synthetic, by action of lauroyl chloride & diethyl sodio-2-acetylglutarate				[0416]
438		7-Ketopalmitic acid	7-Oxohexadecanoic acid	DFA0438	Tetsuyuki Kobayashi		C₁₆H₃₀O₃	270.408			78C					(Ref. 0416)								Synthetic, by action of ethyl sodio-2-acetyldecanoate & 6-carbomethoxyhexanoyl chloride				[0416]
439		8-Ketopalmitic acid	8-Oxohexadecanoic acid	DFA0439	Tetsuyuki Kobayashi		C₁₆H₃₀O₃	270.408			77-78C					(Ref. 0416)(Ref. 0417)								Synthetic, by reaction of 7-carbethoxyheptanoyl chloride and ethyl sodio-2-acetylnonanoate				[0416] / [0417]
440		9-Ketopalmitic acid	9-Oxohexadecanoic acid	DFA0440	Tetsuyuki Kobayashi		C₁₆H₃₀O₃	270.408			73.5-74.5C					(Ref. 0154)								Synthetic, by reaction of the half-ester chloride of the appropriate dibasic acid and alkyl iodide				[0154]
441		10-Ketopalmitic acid	10-Oxohexadecanoic acid	DFA0441	Tetsuyuki Kobayashi		C₁₆H₃₀O₃	270.408			75-75.8C					(Ref. 0179)								Synthetic, by reaction of hexylmagnesium bromide and the acid chloride of monomethyl sebacate				[0179]
442		11-Ketopalmitic acid	11-Oxohexadecanoic acid	DFA0442	Tetsuyuki Kobayashi		C₁₆H₃₀O₃	270.408			74-75C / 91-92C					(Ref. 0154)								Synthetic, by oxidation of 11-hydroxypalmitic acid				[0154]
443		9-Ketoheptadecylic acid / 9-Ketomargaric acid	9-Oxoheptadecanoic acid	DFA0443	Tetsuyuki Kobayashi		C₁₇H₃₂O₃	284.434			78.5C					(Ref. 0318)(Ref. 0319)								Synthetic, by oxidation of 2-hydroxy2-octylsebasic acid with KMnO₄				[0318] / [0319]
444		3-Ketostearic acid	3-Oxooctadecanoic acid	DFA0444	Tetsuyuki Kobayashi		C₁₈H₃₄O₃	298.461			102-103C					easily soluble in acetic acid, ether and hot alcohol / insoluble in water (Ref. 0458)								Synthetic, by saponification of the ethyl ester				[0458]
445		4-Ketostearic acid	4-Oxooctadecanoic acid	DFA0445	Tetsuyuki Kobayashi		C₁₈H₃₄O₃	298.461			97C					easily soluble in acetic acid, ether and hot alcohol / insoluble in water (Ref. 0462)								Po-yak oil; synthetic, by oxidation of the lactone of 4-hydroxystearic acid				[0462]
446		5-Ketostearic acid	5-Oxooctadecanoic acid	DFA0446	Tetsuyuki Kobayashi		C₁₈H₃₄O₃	298.461			85C / 91C					easily soluble in acetic acid, ether and hot alcohol / insoluble in water (Ref. 0104)(Ref. 0105)								Synthetic, by reaction of the half-ester chloride of glutaric acid with 1-iodotridecane				[0104] / [0105]
447		6-Ketostearic acid	6-Oxooctadecanoic acid	DFA0447	Tetsuyuki Kobayashi		C₁₈H₃₄O₃	298.461			87C					easily soluble in acetic acid, ether and hot alcohol / insoluble in water (Ref. 0432)								Synthetic, by reaction of 5-carboxypentanoyl chloride and the Na derivative of ethyl 2-acetyltridecanoate				[0432]
448		7-Ketostearic acid	7-Oxooctadecanoic acid	DFA0448	Tetsuyuki Kobayashi		C₁₈H₃₄O₃	298.461			75C					easily soluble in acetic acid, ether and hot alcohol / insoluble in water (Ref. 0025)								Synthetic, by reaction of concentrated H₂SO₄ and 6-octadecynoic ( tariric ) acid				[0025]
449		9-Ketostearic acid	9-Oxooctadecanoic acid	DFA0449	Tetsuyuki Kobayashi		C₁₈H₃₄O₃	298.461			83C					easily soluble in acetic acid, ether and hot alcohol / insoluble in water (Ref. 0418)								Synthetic, by reduction of 12-chloro-9-ketostearic acid with Zn and HCl ( also by othe methods )				[0418]
450		10-Ketostearic acid	10-Oxooctadecanoic acid	DFA0450	Tetsuyuki Kobayashi		C₁₈H₃₄O₃	298.461			76C					Easily soluble in acetic acid, ether and hot alcohol / insoluble in water (Ref. 0418)								Synthetic, by (1) oxidation of 10-hydroxystearic acid with a mixture of CrO₃ and acetic acid, or (2) pyrolysis of 9,10-dihydroxystearic acid Zn salt ( also by othe methods )				[0418]
451			2,6-Dimethylnonadecanoic Acid	DFA7001	Tetsuyuki Kobayashi		C₁₁H₂₂O₂	186.291															Oil gland of natatorial bird tail.(Ref. 7114)					[7114]
452			2,6-Dimethylundecanoic Acid	DFA7002	Tetsuyuki Kobayashi		C₁₃H₂₆O₂	214.344															Tail oil gland of natatorial bird.(Ref. 7114)					[7114]
453			2,6-Dimethyldodecanoic Acid	DFA7003	Tetsuyuki Kobayashi		C₁₄H₂₈O₂	228.371															Tail oil gland of natatorial bird.(Ref. 7114)					[7114]
454			4,8-Dimethyldodecanoic Acid	DFA7004	Tetsuyuki Kobayashi		C₁₄H₂₈O₂	228.371															Placenta oil. (Ref. 7145)Tail oil gland of natatorial bird.(Ref. 7144)					[7144] / [7145]
455			4,12-Dimethyltridecanoic Acid	DFA7005	Tetsuyuki Kobayashi		C₁₅H₃₀O₂	242.398															Placenta oil. (Ref. 7145)Tail oil gland of natatorial bird.(Ref. 7144)					[7144] / [7145]
456			2,6-Dimethyltetradecanoic Acid	DFA7006	Tetsuyuki Kobayashi		C₁₆H₃₂O₂	256.424												[Spectrum 0001] (provided by Dr. Takeshi Kasama).			Placenta oil. (Ref. 7145)Tail oil gland of natatorial bird.(Ref. 7144) Harderian gland of guinea pig.(Ref. 7146)					[7144] / [7145] / [7146]
457			2,8-Dimethyltetradecanoic Acid	DFA7007	Tetsuyuki Kobayashi		C₁₆H₃₂O₂	256.424															Placenta oil.(Ref. 7145) Tail oil gland of natatorial bird.(Ref. 7144)					[7144] / [7145]
458			2,6-Dimethylpentadecanoic Acid	DFA7008	Tetsuyuki Kobayashi		C₁₇H₃₄O₂	270.451												[Spectrum 0001] (provided by Dr. Takeshi Kasama).			Placenta oil.(Ref. 7145) Harderian gland of guinea pig.(Ref. 7146)					[7145] / [7146]
459			4,8-Dimethylpentadecanoic Acid	DFA7009	Tetsuyuki Kobayashi		C₁₇H₃₄O₂	270.451												[Spectrum 0001] (provided by Dr. Takeshi Kasama).		Gas chromatography (Ref. 7145)	Placenta oil.(Ref. 7145) Tail oil gland of natatorial bird.(Ref. 7144) Harderian gland of guinea pig.(Ref. 7146)					[7144] / [7145] / [7146]
460			2,6-Dimethylhexadecanoic Acid	DFA7010	Tetsuyuki Kobayashi		C₁₈H₃₆O₂	284.477												[Spectrum 0001] (provided by Dr. Takeshi Kasama).			Tail oil gland of natatorial bird.(Ref. 7144) Harderian gland of guinea pig.(Ref. 7146)					[7144] / [7146]
461			4,8-Dimethylhexadecanoic Acid	DFA7011	Tetsuyuki Kobayashi		C₁₈H₃₆O₂	284.477												[Spectrum 0001] (provided by Dr. Takeshi Kasama).			Tail oil gland of natatorial bird.(Ref. 7144> Harderian gland of guinea pig.(Ref. 7146)					[7144] / [7146]
462			2,14-Dimethylhexadecanoic Acid	DFA7012	Tetsuyuki Kobayashi		C₁₈H₃₆O₂	284.477												[Spectrum 0001] (provided by Dr. Takeshi Kasama).			Harderian gland of guinea pig.(Ref. 7146)					[7146]
463			4,14-Dimethylhexadecanoic Acid	DFA7013	Tetsuyuki Kobayashi		C₁₈H₃₆O₂	284.477												[Spectrum 0001] (provided by Dr. Takeshi Kasama).		Gas chromatography (Ref. 7145)	Placenta oil.(Ref. 7145) Harderian gland of guinea pig.(Ref. 7146)					[7145] / [7146]
464			6,14-Dimethylhexadecanoic Acid	DFA7014	Tetsuyuki Kobayashi		C₁₈H₃₆O₂	284.477												[Spectrum 0001] (provided by Dr. Takeshi Kasama).		Gas chromatography (Ref. 7145)	Placenta oil.(Ref. 7145) Harderian gland of guinea pig.(Ref. 7146)					[7145] / [7146]
465			4,14-Dimethylheptadecanoic Acid	DFA7015	Tetsuyuki Kobayashi		C₁₉H₃₈O₂	298.504												[Spectrum 0001] (provided by Dr. Takeshi Kasama).			Harderian gland of guinea pig.(Ref. 7146)					[7146]
466			2,14-Dimethyloctadecanoic Acid	DFA7016	Tetsuyuki Kobayashi		C₂₀H₄₀O₂	312.530															Harderian gland of guinea pig.(Ref. 7146)					[7146]
467			4,14-Dimethyloctadecanoic Acid	DFA7017	Tetsuyuki Kobayashi		C₂₀H₄₀O₂	312.530															Harderian gland of guinea pig.(Ref. 7146)					[7146]
468			6,14-Dimethyloctadecanoic Acid	DFA7018	Tetsuyuki Kobayashi		C₂₀H₄₀O₂	312.530															Harderian gland of guinea pig.(Ref. 7146)					[7146]
469			4,16-Dimethyloctadecanoic Acid	DFA7019	Tetsuyuki Kobayashi		C₂₀H₄₀O₂	312.530												[Spectrum 0001] (provided by Dr. Takeshi Kasama).			Harderian gland of guinea pig.(Ref. 7146)					[7146]
470			6,16-Dimethyloctadecanoic Acid	DFA7020	Tetsuyuki Kobayashi		C₂₀H₄₀O₂	312.530												[Spectrum 0001] (provided by Dr. Takeshi Kasama).			Harderian gland of guinea pig.(Ref. 7146)					[7146]
471			2-Methylundecanoic Acid	DFA7021	Tetsuyuki Kobayashi		C₁₂H₂₄O₂	200.318			13C	140-142C/2mmHg(Ref. 7147)		h25/D=1.4397(Ref. 7147)									Tail oil gland of natatorial bird.(Ref. 7148)					[7147]
472			3-Methylundecanoic Acid	DFA7022	Tetsuyuki Kobayashi		C₁₂H₂₄O₂	200.318				147.5-148C/2mmHg(Ref. 7147)	D20/ =0.8906, D25/ =0.8868,D30/ =0.8832, d20/ =0.8906, d25/ =0.8868, d30 /=0.8832, d35/ =0.8795(Ref. 7147)	h25/D=1.4389(Ref. 7147)						D20/ =0.8906, D25/ =0.8868,D30/ =0.8832, d20/ =0.8906, d25/ =0.8868, d30 /=0.8832, d35/ =0.8795(Ref. 7147)								[7147]
473			4-Methylundecanoic Acid	DFA7023	Tetsuyuki Kobayashi		C₁₂H₂₄O₂	200.318				158-162C/12mmHg(Ref. 7147)		h25/D=1.4393(Ref. 7147)									Placenta oil. (Ref. 7145)Tail oil gland of natatorial bird.(Ref. 7144)					[7144] / [7145] / [7147]
474			5-Methylundecanoic Acid	DFA7024	Tetsuyuki Kobayashi		C₁₂H₂₄O₂	200.318				153-154C/6mmHg (Ref. 7147)																[7147]
475			6-Methylundecanoic Acid	DFA7025	Tetsuyuki Kobayashi		C₁₂H₂₄O₂	200.318				173-174C/11mmHg (Ref. 7147)											Placenta oil.(Ref. 7145)					[7145] / [7147]
476			8-Methylundecanoic Acid	DFA7026	Tetsuyuki Kobayashi		C₁₂H₂₄O₂	200.318				170-172C/10mmHg (Ref. 7147)		h25/D=1.4420 (Ref. 7147)									Placenta oil.(Ref. 7145)					[7145] / [7147]
477			9-Methylundecanoic Acid	DFA7027	Tetsuyuki Kobayashi		C₁₂H₂₄O₂	200.318			-1.8C(Ref. 7147)	170-171C/10mmHg (Ref. 7147)																[7147]
478		Isolauric Acid	10-Methylundecanoic Acid	DFA7028	Tetsuyuki Kobayashi		C₁₂H₂₄O₂	200.318			41.2C(Ref. 7147)	140-145C/3mmHg(Ref. 7147)											Wool oil, butter, sheep oil, cattle oil, whale oil.(Ref. 7149)					[7147] / [7149]
479			2-Methyldodecanoic Acid	DFA7029	Tetsuyuki Kobayashi		C₁₃H₂₆O₂	214.344			23.3-24.1C(Ref. 7147)	140-142C/1.6mmHg(Ref. 7147)		h25/D=1.4401(Ref. 7147)									Tail oil gland of natatorial bird.(Ref. 7144/7148)					[7144] / [7147]
480			3-Methyldodecanoic Acid	DFA7030	Tetsuyuki Kobayashi		C₁₃H₂₆O₂	214.344			22C (Ref. 7147)	149-154C/5mmHg (Ref. 7147)		h25/D=1.4400 (Ref. 7147)														[7147]
481			4-Methyldodecanoic Acid	DFA7031	Tetsuyuki Kobayashi		C₁₃H₂₆O₂	214.344				174-176C/14mmHg (Ref. 7147)											Placenta oil,(Ref. 7145) tail oil gland of natatorial bird.(Ref. 7144/7148)					[7144] / [7145] / [7147]
482			5-Methyldodecanoic Acid	DFA7032	Tetsuyuki Kobayashi		C₁₃H₂₆O₂	214.344				163-166C/11mmHg (Ref. 7147)																[7147]
483			6-Methyldodecanoic Acid	DFA7033	Tetsuyuki Kobayashi		C₁₃H₂₆O₂	214.344				176-178C/10mmHg(Ref. 7147)											Placenta oil.(Ref. 7145)					[7145] / [7147]
484			7-Methyldodecanoic Acid	DFA7034	Tetsuyuki Kobayashi		C₁₃H₂₆O₂	214.344				176-178C/10mmHg(Ref. 7147)																[7147]
485			8-Methyldodecanoic Acid	DFA7035	Tetsuyuki Kobayashi		C₁₃H₂₆O₂	214.344				179-181C/10mmHg (Ref. 7147)											Placenta oil.(Ref. 7145)					[7145] / [7147]
486			9-Methyldodecanoic Acid	DFA7036	Tetsuyuki Kobayashi		C₁₃H₂₆O₂	214.344				176-178C/12mmHg (Ref. 7147)																[7147]
487			2-Methyltridecanoic Acid	DFA7037	Tetsuyuki Kobayashi		C₁₄H₂₈O₂	228.371				182-184C/11mmHg (Ref. 7147)		h25/D=1.4437(Ref. 7147)									Tail oil gland of natatorial bird.(Ref. 7144/7148)					[7144] / [7147]
488			4-Methyltridecanoic Acid	DFA7038	Tetsuyuki Kobayashi		C₁₄H₂₈O₂	228.371				160-162C/10mmHg(Ref. 7147)											Placenta oil,(Ref. 7145) tail oil gland of natatorial bird.(Ref. 7144)					[7144] / [7145] / [7147]
489		Isobutyric Acid	2-Methyl-Propanoic Acid	DFA7039	Tetsuyuki Kobayashi		C₄H₈O₂	88.105			-47	84.8-85.1/50mmHg, 153.5-153.8C/750.3	1.024(-60C)-0.6982(240C),D20/4 : 0.9490					Methyl: 2979, 2939cm^-¹/methyl, methylene: 2880, 2850cm^-¹ (Ref. 7002)		m/e: 88, 73, 55, 45, 44, 43, 42, 41, 39(Ref. 7003) 1.024(-60C)-0.6982(240C),D20/4 : 0.9490	(Ref. 7002)/(Ref. 7003)			Synthesized by oxidation of isobutyric alcohol with sulfuric acid and potassium bichromate.				[7002] / [7003]
490		a-Methyl-Butyric Acid	2-Methyl-Butanoic Acid	DFA7040	Tetsuyuki Kobayashi		C₅H₁₀O₂	102.132				174C, 86.5-87.5C/26mmHg (Ref. 7027)	D20/4: 0.938(S), D20/4: 0.934(R) (Ref. 7027)	h25/D: 1.4040 (Ref. 7029), h20/D: 1.4058 (Ref. 7030)						D20/4: 0.938(S), D20/4: 0.934(R) (Ref. 7027)								[7027] / [7029] / [7030]
491		Pivalic Acid	2,2-Dimethyl-Propanoic Acid	DFA7041	Tetsuyuki Kobayashi		C₅H₁₀O₂	102.132			35.5-35.7C	163.7-163.9C/760mmHg, 76.5C/20mmHg	D18/4: 0.8580	h25/D: 1.4030 (Ref. 7004)				n: 2907, 1704, 1433cm^-¹ (Ref. 7038)		D18/4: 0.8580	(Ref. 7038)			Isobutylene was treated with concentrated sulfuric acid, carbon monooxide and H₂O.				[7004] / [7038]
492		2-Methyl Valeric Acid	2-Methyl-Pentanoic Acid	DFA7042	Tetsuyuki Kobayashi		C₆H₁₂O₂	116.158				192C/750mmHg (Ref. 7031)	D20/4: 0.9309 (Ref. 7031)	h20/D: 1.4170 (Ref. 7031)						D20/4: 0.9309 (Ref. 7031)								[7031]
493		3-Methyl Valeric Acid	3-Methyl-Pentanoic Acid	DFA7043	Tetsuyuki Kobayashi		C₆H₁₂O₂	116.158				196-198C/770mmHg(S), 105C/30mmHg(S),88-91	D25/: 0.923(S), D24/4: 0.924(R) <7032>>	h25/D: 1.4152(S) (Ref. 7032)						D25/: 0.923(S), D24/4: 0.924(R) <7032>>								[7032]
494		Isocaproic Acid	3-Methyl-Pentanoic Acid	DFA7044	Tetsuyuki Kobayashi		C₆H₁₂O₂	116.158			-33C (Ref. 7034)	201C/761mmHg, 118-120C/20mmHg, 102-104	D:0.9535(-20C)-0.6744(280C), D20/20:0.9192 (Ref. 7035)	h20/D: 1.4146, h25/D: 1.4124 (Ref. 7035)						D:0.9535(-20C)-0.6744(280C), D20/20:0.9192 (Ref. 7035)								[7005] / [7034] / [7035]
495		Diethyl-Acetic Acid	2-Ethyl-Butanoic Acid	DFA7045	Tetsuyuki Kobayashi		C₆H₁₂O₂	116.158			-31.8C (Ref. 7034)	192.6C/754mmHg, 90-91C/13mmHg (Ref. 7034)	D20/4: 0.9239 (Ref. 7034)	h20/D: 1.4132 (Ref. 7034)				nC-H: 2910cm^-¹; n: 1706, 1433cm^-¹ (Ref. 7037)/(Ref. 7038)		D20/4: 0.9239 (Ref. 7034)								[7034] / [7037] / [7038]
496		Dimethyl-Ethyl-Acetic Acid	2,2-Dimethyl-Butanoic Acid	DFA7046	Tetsuyuki Kobayashi		C₆H₁₂O₂	116.158				104-105C/32mmHg, 94-96C/15mmHg,186C/752mmHg		h20/D: 1.4142, h25/D: 1.4127 (Ref. 7039)														[7039]
497			3,3-Dimethyl-Butanoic Acid	DFA7047	Tetsuyuki Kobayashi		C₆H₁₂O₂	116.158			6-7C	184.2-184.5C/763-764mmHg, 98-99C/25mmHg (Ref. 7040)	D20/4: 0.915 (Ref. 7041)	h20/D: 1.4110, h25/D: 1.4084 (Ref. 7041)						D20/4: 0.915 (Ref. 7041)								[7040] / [7041]
498			2-Methyl-Hexanoic Acid	DFA7048	Tetsuyuki Kobayashi		C₇H₁₄O₂	130.185				207-208C/737mmHg, 216.5-218C,112C/13mmHg (Ref. 7042)	D25/4: 0.7962 (Ref. 7043)	h25/D: 1.4062(Ref. 7043)				Methyl : 2957, 2872cm^-¹(Ref. 7006)/methylene: 2932, 2860cm^-¹(Ref. 7006)/methyl, methylene: 1234cm^-¹(Ref. 7007)		D25/4: 0.7962 (Ref. 7043)								[7006] / [7007] / [7042] / [7043]
499			3-Methyl-Hexanoic Acid	DFA7049	Tetsuyuki Kobayashi		C₇H₁₄O₂	130.185				96C/4mmHg(R), 93C/5mmHg(S) (Ref. 7044)	D22/4: 0.913(S) (Ref. 7045)	h18/D: 1.4308(R), h21/D : 1.4212(S) (Ref. 7045)				Methyl: 2957, 2872cm^-¹(Ref. 7006)/methylene: 2932cm^-¹(Ref. 7006)/methyl, methylene: 1230cm^-¹(Ref. 7007)		D22/4: 0.913(S) (Ref. 7045)								[7006] / [7007] / [7044] / [7045]
500			4-Methyl-Hexanoic Acid	DFA7050	Tetsuyuki Kobayashi		C₇H₁₄O₂	130.185				112C/9mmHg(S) (Ref. 7047)	D20/4: 0.9215 (Ref. 7048)	h25/D: 1.4232(S) (Ref. 7047)				Methyl: 2958, 2872cm^-¹(Ref. 7006)/methylene: 2929cm^-¹(Ref. 7006)/methyl, methylene: 1220cm^-¹(Ref. 7007)		D20/4: 0.9215 (Ref. 7048)								[7006] / [7007] / [7047] / [7048]
501			5-Methyl-Hexanoic Acid	DFA7051	Tetsuyuki Kobayashi		C₇H₁₄O₂	130.185				211-215C/760mmHg,120C/24mmHg,101-102C/11mmHg		h25/D: 1.4199, h20/D: 1.4220 (Ref. 7049)				Methyl: 2959, 2872cm^-¹(Ref. 7006)/methylene: 2932cm^-¹(Ref. 7006)/methyl, methylene: 1209cm^-¹(Ref. 7007)										[7006] / [7007] / [7049]
502		a-Ethyl-Valeric Acid	2-Ethyl-Pentanoic Acid	DFA7052	Tetsuyuki Kobayashi		C₇H₁₄O₂	130.185				209-210C (Ref. 7050)		h22/D: 1.4180 (Ref. 7050)														[7050]
503		a,a-Dimethyl-Valeric Acid	2,2-Dimethyl-Pentanoic Acid	DFA7053	Tetsuyuki Kobayashi		C₇H₁₄O₂	130.185				199-200C,111C/20mmHg,101-102C/11mmHg (Ref. 7051)		h20/D: 1.4210 (Ref. 7051)														[7051]
504		b,b-Dimethyl-Valeric Acid	3,3-Dimethyl-Pentanoic Acid	DFA7054	Tetsuyuki Kobayashi		C₇H₁₄O₂	130.185				203-204C (Ref. 7052)	D25/: 0.9348, D20/4: 0.9246 (Ref. 7052)	h25/D: 1.4280, h20/D: 1.4238 (Ref. 7052)						D25/: 0.9348, D20/4: 0.9246 (Ref. 7052)								[7052]
505		a-Ethyl Caproic Acid	2-Ethylhexoic Acid	DFA7055	Tetsuyuki Kobayashi		C₈H₁₆O₂	144.211				227.6C/760mmHg, 117-119C/15mmHg(S) (Ref. 7053)	D17/4: 0.908(S), D32/4: 0.8954(Ref. 7053)	h25/D: 1.4231(S), h30/D: 1.4195 (Ref. 7053)				1724, 1449, 1351, 1266, 1235, 943cm^-¹(Ref. 7008)		D17/4: 0.908(S), D32/4: 0.8954(Ref. 7053)								[7008] / [7053]
506			2-Methyloctanoic Acid	DFA7056	Tetsuyuki Kobayashi		C₉H₁₈O₂	158.238				163C/2mmHg, 244-246C/760mmHg (Ref. 7054)	D0/4: 0.9098, D18/: 0.90325 (Ref. 7054)	h25/D: 1.4274 (Ref. 7055)						D0/4: 0.9098, D18/: 0.90325 (Ref. 7054)								[7054] / [7055]
507			2-Methylnonaoic Acid	DFA7057	Tetsuyuki Kobayashi		C₁₀H₂₀O₂	172.265				149C/14mmHg, 115-117C/3mmHg (Ref. 7056)	D23/4: 0.895(R)(Ref. 7057)	h25/D: 1.4312(R) (Ref. 7057)						D23/4: 0.895(R)(Ref. 7057)								[7056] / [7057]
508			2-Methyldecanoic Acid	DFA7058	Tetsuyuki Kobayashi		C₁₁H₂₂O₂	186.291				127C/1.5mmHg, 135-137C/4mmHg (Ref. 7058)																[7058]
509			2-Methyltetradecanoic Acid	DFA7059	Tetsuyuki Kobayashi		C₁₅H₃₀O₂	242.398			36.5C (Ref. 7061)	172-175C/2-3mmHg (Ref. 7062)																[7061] / [7062]
510			2-Methylhexadecanoic Acid	DFA7060	Tetsuyuki Kobayashi		C₁₇H₃₄O₂	270.451			45.5-46.5C, 47.5-48C (Ref. 7065)	174-177C/1-2mmHg (Ref. 7062)								[Spectrum 0001] (provided by Dr. Takeshi Kasama).								[7062] / [7065]
511		l-Isostearic Acid	2-Methylheptadecanoic Acid	DFA7061	Tetsuyuki Kobayashi		C₁₈H₃₆O₂	284.477			49-49.5C (Ref. 7068)	180C/2mmHg (Ref. 7068)								[Spectrum 0001] (provided by Dr. Takeshi Kasama).								[7068]
512		Neostearic Acid	15,15-Dimethylhexadecanoic Acid	DFA7062	Tetsuyuki Kobayashi		C₁₈H₃₆O₂	284.477			49.8-50.2C (Ref. 7009)	145-153C/0.05Torr (Ref. 7009)						1704(C=O)cm^-¹, 1455, 1414, 1366cm^-¹(Ref. 7009)										[7009]
513			2-Methyloctadecanoic Acid	DFA7063	Tetsuyuki Kobayashi		C₁₉H₃₈O₂	298.504			54.7-55C(R), 54.6-55.1C (Ref. 7070)	176C/0.5mmHg (Ref. 7071)	D: 1.015(SOLID)(R), 0.998 (Ref. 7072)				carboxyl: l max 213, e max 67.2(Ref. 7011)	-1700cm^-¹(C=O), 1379cm^-¹, 1294cm^-¹, 1236cm^-¹(Ref. 7010)		D: 1.015(SOLID)(R), 0.998 (Ref. 7072)								[7010] / [7011] / [7070] / [7071] / [7072]
514			17-Methyloctadecanoic Acid	DFA7064	Tetsuyuki Kobayashi		C₁₉H₃₈O₂	298.504			66.5-67C (Ref. 7073)	180C/0.3mmHg (Ref. 7073)	D70/4: 0.8420 (Ref. 7074)	h70/D: 1.4336 (Ref. 7074)				-1700cm^-¹(C=O), 1379cm^-¹, 1284cm^-¹, 1236cm^-¹(Ref. 7010)		D70/4: 0.8420 (Ref. 7074)								[7010] / [7073] / [7074]
515		b,b-Dimethylacrylic Acid	3-Methyl-2-Butenoic Acid	DFA7065	Tetsuyuki Kobayashi		C₅H₈O₂	100.116			69.5-70.5C (Ref. 7079)						l max : 216nm, emax: 10000 (Ref. 7015)	C=O: 1689cm^-¹, 1645, 1342, 1292, 1258, 1176, 1110, 1073, 929, 855cm^-¹(Ref. 7014)										[7014] / [7015] / [7079]
516			4-Methyl-4-Pentenoic Acid	DFA7066	Tetsuyuki Kobayashi		C₆H₁₀O₂	114.142			-3C (Ref. 7035)	76-82C/2mmHg, 93-94C/9mmHg (Ref. 7035)	D20/4: 0.9863(Ref. 7035)	h20/D: 1.4380 (Ref. 7035)						D20/4: 0.9863(Ref. 7035)								[7035]
517			2,2-Dimethyl-3-Butenoic Acid	DFA7067	Tetsuyuki Kobayashi		C₆H₁₀O₂	114.142				100-102C/28mmHg(Ref. 7016)		h20/D: 1.4295(016), h25/D: 1.4272(Ref. 7017)														[7016] / [7017]
518			(Z)2-Methyl-2-Hexenoic Acid	DFA7068	Tetsuyuki Kobayashi		C₇H₁₂O₂	128.169				110C/10mmHg(Ref. 7012)		h25/D: 1.4525(Ref. 7012)			lmax: 218nm, emax: 8780(Ref. 7012)	1637, 1462, 1420, 1285, 1250cm^-¹, 1232, 1171, 1101, 1072, 1047, 948cm^-¹(Ref. 7012)										[7012]
519			(E)2-Methyl-2-Hexenoic Acid	DFA7069	Tetsuyuki Kobayashi		C₇H₁₂O₂	128.169				118-119C/11mmHg (Ref. 7012)		h25/D: 1.4602(Ref. 7012)			lmax : 217nm, emax : 13580(Ref. 7012)	1642, 1460, 1422, 1289, 1258cm^-¹, 1227, 1163, 1101, 1059, 1031cm^-¹, 935,917cm^-¹(Ref. 7012)										[7012]
520			(E)2-Methyl-2-Heptenoic Acid	DFA7070	Tetsuyuki Kobayashi		C₈H₁₄O₂	142.196				129.5-131C/11mmHg (Ref. 7012)		h25/D: 1.4605(Ref. 7012)				C=C: 1638cm^-¹ (Ref. 7012)										[7012]
521			6-Methyl-5-Octenoic Acid	DFA7071	Tetsuyuki Kobayashi		C₉H₁₆O₂	156.222				153C/24mmHg (Ref. 7018)	D22/4: 0.932 (Ref. 7018)	h22/D: 1.4518(Ref. 7018)						D22/4: 0.932 (Ref. 7018)								[7018]
522		Citronellic Acid	3,7-Dimethyl-6-Octenoic Acid	DFA7072	Tetsuyuki Kobayashi		C₁₀H₁₈O₂	170.249				119C/3mmHg(R), 90-93C/0.05mmHg() (Ref. 7019)	""D20/4: 0.9255(R), D21/4: 0.9234() (Ref. 7019)	h20/D: 1.4530(R), h21/D: 1.4517() (Ref. 7019)						""D20/4: 0.9255(R), D21/4: 0.9234() (Ref. 7019)								[7019]
523			3,7-Dimethyl-2-Octenoic Acid	DFA7073	Tetsuyuki Kobayashi		C₁₀H₁₈O₂	170.249				140C/15mmHg, 108-112C/2.5mmHg (Ref. 7020)	D18/4: 0.931 (Ref. 7080)	h18/D: 1.4542 (Ref. 7080)			lmax: 218nm, loge: 4.04 (Ref. 7020)			D18/4: 0.931 (Ref. 7080)								[7020] / [7080]
524			5-Methyl-2-Undecenoic Acid	DFA7074	Tetsuyuki Kobayashi		C₁₂H₂₂O₂	198.302				162-163C/7mmHg (Ref. 7021)		h25/D: 1.4596 (Ref. 7021)			lmax: 210nm, emax: 13160(Ref. 7021)	C=O: 1704cm^-¹, C=C: 1653cm^-¹, Methyl: 1379cm^-¹(Ref. 7022)										[7021] / [7022]
525			2-Methyl-2-Dodecenoic Acid	DFA7075	Tetsuyuki Kobayashi		C₁₃H₂₄O₂	212.328			33C (Ref. 7023)	146-147C/1.4mmHg (Ref. 7081)		h25/D: 1.4698 (Ref. 7023)			l%max: 218nm, emax: 11330(Ref. 7023)	C=O: 1692cm^-¹, C=C: 1645cm^-¹, Methyl: 1379cm^-¹(Ref. 7022)										[7022] / [7023] / [7081]
526			(E)5-Methyl-2-Tridecenoic Acid	DFA7076	Tetsuyuki Kobayashi		C₁₄H₂₆O₂	226.355				168-170C/2.5mmHg (Ref. 7024)	D25/4: 0.908 (Ref. 7024)	h25/D: 1.4620 (Ref. 7024)			lmax: 210nm, emax: 13900(Ref. 7024)			D25/4: 0.908 (Ref. 7024)								[7024]
527			(E)2,5-Dimethyl-2-Tridecenoic Acid	DFA7077	Tetsuyuki Kobayashi		C₁₅H₂₈O₂	240.382				182C/3mmHg (Ref. 7024)		h25/D: 1.4663 (Ref. 7024)			lmax: 218.5nm, emax: 14870(Ref. 7024)											[7024]
528		Isopropenylacetic Acid	3-Methyl-3-Butenoic Acid	DFA7078	Tetsuyuki Kobayashi		C₅H₈O₂	100.116				92-93C/29-30mmHg(Ref. 7082)												3-Methyl-3-butanoic acid is prepared from b-methallyl chloride and carbon dioxide in the presence of magnesium(Ref. 7082).				[7082]
529		2-Ethyl Acrylic Acid	2-Ethyl-2-Propenoic Acid	DFA7079	Tetsuyuki Kobayashi		C₅H₈O₂	100.116			-15 - -16C(Ref. 7083)	40-41C/0.25mmHg(Ref. 7083),52-54/4mmHg(Ref. 7084)	D25/4 = 0.991(Ref. 7083)	h25/D = 1.4332(Ref. 7083), 1.4358(Ref. 7084)			(Ref. 7014)	(Ref. 7014)		D25/4 = 0.991(Ref. 7083)				2-Ethyl-2-propenoic acid is prepared from a-hydroxy-methylbutyronitrile and sodium hydroxide(Ref. 7083).				[7014] / [7083] / [7084]
530		3-Isopropyl Acrylic Acid	4-Methyl-2-Pentenoic Acid	DFA7080	Tetsuyuki Kobayashi		C₆H₁₀O₂	114.142			-25C(Ref. 7086)	114 - 116C/17mmHg (Ref. 7087)		h21/D = 1.454(Ref. 7087)										4-Methyl-2-pentenoic acid is prepared from isobutyraldehyde and malonic acid(Ref. 7113).				[7086] / [7087] / [7113]
531			3-Methyl-4-Pentenoic Acid	DFA7081	Tetsuyuki Kobayashi		C₆H₁₀O₂	114.142				78 - 80C/25mmHg(Ref. 7088/7089)		h20/D = 1.4366 (Ref. 7088/7089)				5.85, 6.09, 10.06, 10.91m(Ref. 7089)						3-methyl-4-pentenoic acid is obtained by fractionating a mixture of ethyl b-ethoxyacrylate and crotyl alcohol, followed by saponification (Ref. 7089).				[7088] / [7089]
532			3-Methyl-2-Pentenoic Acid	DFA7082	Tetsuyuki Kobayashi		C₆H₁₀O₂	114.142			13 - 14C(Ref. 7090)		D20 = 0.9851 (Ref. 7090)	h20/D = 1.4651 (Ref. 7090)						D20 = 0.9851 (Ref. 7090)				3-Methyl-2-pentenoic acid was prepared from 3-methyl-3-hydroxy pentenoic acid (Ref. 7090).				[7090]
533			3-Methyl-3-Pentenoic Acid	DFA7083	Tetsuyuki Kobayashi		C₆H₁₀O₂	114.142			14.5 - 15.5C (Ref. 7091)	40hC/0.005mmHg(Ref. 7091)												3-Methyl-3-pentenoic acid is obtained from isomerization of 3-methyl-2-pentenoic acid with 25% koh, followed by separation of the isomer(Ref. 7114).				[7091] / [7114]
534		Trimethyl Acrylic Acid	2,3-Dimethyl-Crotonic Acid	DFA7084	Tetsuyuki Kobayashi		C₆H₁₀O₂	114.142			70 - 71C(Ref. 7092)	104C/13mmHg(Ref. 7092)					lmax 221nm(e9700 in c2h5oh)(Ref. 7092)							2,3-Dimethyl-crotonic acid was prepared from 2-brom-3-methyl-2-butene with lithium (Ref. 7092).				[7092]
535			5-Methyl-5-Hexenoic Acid	DFA7085	Tetsuyuki Kobayashi		C₇H₁₂O₂	128.169				109C/12mmHg (Ref. 7093)	D21/4 = 0.9507 ,(Ref. 7093)	h21/D = 1.4422 (Ref. 7093)						D21/4 = 0.9507 ,(Ref. 7093)				5-Methyl-5-hexenoic acid was prepared from 2-(methane sulfonyloxymethyl)-2-methyl-cyclopentanone and koh (Ref. 7093).				[7093]
536			2-Butyl-Acrylic Acid	DFA7086	Tetsuyuki Kobayashi		C₇H₁₂O₂	128.169				111 - 111.5C/10mmHg (Ref. 7012)		h25/D = 1.4435 (Ref. 7012)			lmax 208.5mm(emax 8,480)(Ref. 7012)	6.13vs, 6.93vs, 7.77vs, 7.95s, 8.15vs, 8.43s, 8.55s, 9.2m, 10.54vs (Ref. 7012)						2-Butyl-acrylic acid was prepared from 2-butyl-acrylic acid terriary butyl ester (Ref. 7012).				[7012]
537			4,4-Dimethyl-2(E)-Pentenoic Acid	DFA7087	Tetsuyuki Kobayashi		C₇H₁₂O₂	128.169			62 - 63C (Ref. 7094)													4,4-Dimethyl-2(E)-pentenoic acid was prepared from pivalinaldehyde and malonic acid(Ref. 7094).				[7094]
538			4,4-Dimethyl-2(Z)-Pentenoic Acid	DFA7088	Tetsuyuki Kobayashi		C₇H₁₂O₂	128.169			11 - 12C (Ref. 7086)	60 - 61C/0.8mmHg(Ref. 7086)		h25/D = 1.4432 (Ref. 7086)										4,4-Dimethyl-2(Z)-pentenoic acid is prepared from 1,3-dibromo-4,4-dimethyl-2-pentanone (Ref. 7086).				[7086]
539			2,2-Dimethyl-4-Pentenoic Acid	DFA7089	Tetsuyuki Kobayashi		C₇H₁₂O₂	128.169				92 - 93C/8.5mmHg (Ref. 7095)		h20/D = 1.4338 (Ref. 7095)										2,2-Dimethyl-4-pentenoic acid was prepared from 2,2-dimethyl-4-pentenal with koh (Ref. 7095).				[7095]
540		2-Isopropyl-E-Crotonic Acid	2-Isopropyl-2(E)-Butenoic Acid	DFA7090	Tetsuyuki Kobayashi		C₇H₁₂O₂	128.169			54.5C (Ref. 7096)													2-Isopropyl-2-(E)-butenoic acid is prepared from the rection of 2-isopropyl-3-hydroxybutenoic acid ethyl with phosphorus pentoxide, followed by saponification (Ref. 7096).				[7096]
541			3-Isopropyl-3-Butenoic Acid	DFA7091	Tetsuyuki Kobayashi		C₇H₁₂O₂	128.169			-72C (Ref. 7097)	80C/2mmHg (Ref. 7097)	D25/4 = 0.9480(Ref. 7097)	h25/D = 1.4380 (Ref. 7097)						D25/4 = 0.9480(Ref. 7097)				3-Isopropyl-3-butenoic acid is prepared from 2,3-dimethyl-1-butene, pentylnatrium and CO₂ (Ref. 7097).				[7097]
542			6-Methyl-5-Heptenoic Acid	DFA7092	Tetsuyuki Kobayashi		C₈H₁₄O₂	142.196				129 - 130C/12mmHg (Ref. 7098)	D20/4 = 0.937 (Ref. 7018)	h20/D = 1.4484 (Ref. 7018)						D20/4 = 0.937 (Ref. 7018)				6-Methyl-5-heptenoic acid is prepared from 5-methyl-4-hexenylmagnesium and CO₂ (Ref. 7098).				[7018] / [7098]
543			2-Ethyl-3(E)-Hexenoic Acid	DFA7093	Tetsuyuki Kobayashi		C₈H₁₄O₂	142.196				125 - 128C/15mmHg (Ref. 7099)	D22.5/4 = 0.967(Ref. 7099)	h22.5/D = 1.4510(Ref. 7099)				5.5 - 6.5mm, 10 - 13.5mm(Ref. 7099)		D22.5/4 = 0.967(Ref. 7099)				2-Ethyl-3(E)-hexenoic acid is prepared from 2-ethyl-3-hexenal, silber nitrare and NAOH (Ref. 7099).				[7099]
544			3-Tert-Butyl-3-Butenoic Acid	DFA7094	Tetsuyuki Kobayashi		C₈H₁₄O₂	142.196			26.5 - 27.5C (Ref. 7097)	70C/1mmHg (Ref. 7097)	D25/4 = 0.9412(Ref. 7097)	h25/D = 1.4440 (Ref. 7097)						D25/4 = 0.9412(Ref. 7097)				3-Tertiary butyl-3-butenoic acid is prepared from 2,3,3-trimethyl-1-butene, pentylnatrium and CO₂ (Ref. 7097).				[7097]
545		2-Amyl-3-Butenoic Acid	2-Pentyl-3-Butenoic Acid	DFA7095	Tetsuyuki Kobayashi		C₉H₁₆O₂	156.222				128C/11mmHg (Ref. 7100)	D25/4 = 0.9183(Ref. 7097)	h25/D = 1.4387 (Ref. 7097)						D25/4 = 0.9183(Ref. 7097)				2-Pentyl-3-butenoic acid is prepared from the bromination of 1-octene, followed by the reaction with magnesium and carbon dioxide (Ref. 7100).				[7097] / [7100]
546			3-Methyl-2-Nonenoic Acid	DFA7096	Tetsuyuki Kobayashi		C₁₀H₁₈O₂	170.249				113 - 114C/1mmHg (Ref. 7011)		h25/D = 1.4648 (Ref. 7011)			lmax 219mm (Ref. 7011)	5.90(C=O), 6.10(C=C) (Ref. 7022)						3-Methyl-2-nonenoic acid is prepared from 3-hydroxy-3-methyl-pelargonic acid and acetanhydride (Ref. 7115).				[7011] / [7022] / [7115]
547			2,7-Dimethyl-6-Octenoic Acid	DFA7097	Tetsuyuki Kobayashi		C₁₀H₁₈O₂	170.249				146 - 147C/13mmHg (Ref. 7101)	D16/4 = 0.9257 (Ref. 7101)	h16/D = 1.4502 (Ref. 7101)						D16/4 = 0.9257 (Ref. 7101)				2,7-Dimethyl-6-octenoic acid was prepared from methyl-(5-methyl-4-hexenyl)-malonic acid diethyl and koh (Ref. 7101).				[7101]
548			2,7-Dimethyl-6-Nonenoic Acid	DFA7098	Tetsuyuki Kobayashi		C₁₁H₂₀O₂	184.275				125 - 126C/3mmHg (Ref. 7018)	D27/4 = 0.929 (Ref. 7018)	h27/D = 1.4532 (Ref. 7018)						D27/4 = 0.929 (Ref. 7018)				2,7-dimethyl-6-nonenoic acid is prepared from methyl-(5-methyl-4-heptenyl)-malonic acid dimethyl and KOH (Ref. 7107).				[7018] / [7107]
549			4-Ethyl-2-Methyl-2-Octenoic Acid	DFA7099	Tetsuyuki Kobayashi		C₁₁H₂₀O₂	184.275				141 - 142C/4.6mmHg (Ref. 7102)		h25/D = 1.4628 (Ref. 7102)			200 - 270nm (Ref. 7102)							4-Ethyl-2-methyl-2-octenoic acid was prepared from the reaction of 4-ethyl-3-hydroxy-2-methyl-octanoic acid ethyl and phosphoryl chloride, followed by heating with sulfuric acid (Ref. 7102).				[7102]
550			2,4-Dimethyl-2-(E)-Dodecenoic Acid	DFA7100	Tetsuyuki Kobayashi		C₁₄H₂₆O₂	226.355					D25 = 0.901 (Ref. 7103)	h25/D = 1.4636 (Ref. 7103)			lmax 217nm (Ref. 7103)			D25 = 0.901 (Ref. 7103)				2,4-Dimethyl-2-(E)-dodecenoic acid is prepared from 2,4-dimethyl-2-(E)-dodecenoic acid methyl (Ref. 7103).				[7103]
551			2,4-Dimethyl-2(E)-Tetradecenoic Acid	DFA7101	Tetsuyuki Kobayashi		C₁₆H₃₀O₂	254.408				176 - 177C/1.5mmHg (Ref. 7102)		h25/D = 1.4634 (Ref. 7102)			lmax 219nm (Ref. 7102)	10.08, 12.38, 13.33, 15.03m(Ref. 7102)						2,4-Dimethyl-2-(E)-tetradecenoic acid was prepared from the reation of 2-mrthyl-dodecanal with 2-bromo-propanoic acid ethyl, followed by dehydration and saponification (Ref. 7102).				[7102]
552			2,4-Dimethyl-Icosenoic Acid	DFA7102	Tetsuyuki Kobayashi		C₂₂H₄₂O₂	338.568			53 - 54C (Ref. 7104)	199 - 201C/0.1mmHg, 195 - 198C/0.15mmHg (Ref. 7104)					Me ester: lmax 214nm							2,4-Dimethyl-icosenoic acid is prepared from the reaction of 2-bromo-2,4-dimethyl-icosanoic acid methyl with pyridine, followed by saponification with KOH (Ref. 7104).				[7104]
553			2-Propyl Octadec-9-(Z)-Enoic Acid	DFA7103	Tetsuyuki Kobayashi		C₂₁H₄₀O₂	324.541				193 - 195C/0.5 - 1mmHg (Ref. 7105)												2-Propyl-octadec-9(Z)-enoic acid was repared from 7(Z)-hexadecenyl propyl marlonic diethyl and KOH (Ref. 7105).				[7105]
554			2-Methyl-2-Icosenoic Acid	DFA7104	Tetsuyuki Kobayashi		C₂₁H₄₀O₂	324.541			66.3 - 67.6C (Ref. 7081)	203 - 205C/2.5mmHg(Me ESTER) (Ref. 7106)					lmax 217nm (emax 13,490) (Ref. 7081)	C=C: 12.60m, 13.52m, 15.50m (Ref. 7106)						2-Metyl-2-icosenoic acid was prepared from 2-methyl-2-icosenoic acid methyl (Ref. 7081).				[7081] / [7106]
555		Phytenoic Acid	3,7,11,15-Tetramethyl-2(Z)-Hexadecenoic Acid	DFA7105	Tetsuyuki Kobayashi		C₂₀H₃₈O₂	310.515				210 - 220C/11.5mmHg, 174C/0.4mmHg (Ref. 7107)	D20/4 = 0.893 (Ref. 7107)							D20/4 = 0.893 (Ref. 7107)				Phytenoic acid is prepared from phytol (Ref. 7107).				[7107]
556			4-Heptyl-2-Methyl-2-Undecenoic Acid	DFA7106	Tetsuyuki Kobayashi		C₁₉H₃₆O₂	296.488				183 - 184C/0.5mmHg (Ref. 7102)		h25/D = 1.4643 (Ref. 7102)			lmax 219nm (emax 13,800) (Ref. 7102)	C=CH: 9.91, 12.42, 13.29, 15.01m (Ref. 7102)						4-Heptyl-2-methyl-2-undecenoic acid is prepared from 2-bromooropanoic acid ethyl, Zn and 2-heptylnonanal (Ref. 7102).				[7102]
557			2,5-Dimethyl-2-Heptadecenoic Acid	DFA7107	Tetsuyuki Kobayashi		C₁₉H₃₆O₂	296.488				170C/0.1mmHg (Ref. 7024)		h25/D = 1.4662 (Ref. 7024)			lmax 218.5nm (Ref. 7024)							2,5-Dimethyl-2-heptadecenoic acid was prepared from 2,5-dimethyl-2-heptadecenoic acid methyl (Ref. 7024).				[7024]
558			14-Methyl-4-Pentadecenoic Acid	DFA7108	Tetsuyuki Kobayashi		C₁₆H₃₀O₂	254.408			45 -46C (Ref. 7108)													14-Methyl-4-penttadenoic acid is obtained from oyster as glycolipid (Ref. 7108).				[7108]
559			2-Hexyl-2-Decenoic Acid	DFA7109	Tetsuyuki Kobayashi		C₁₆H₃₀O₂	254.408				170 - 175C/0.02mmHg (Ref. 7109)		h19/D = 1.4642 (Ref. 7109)			lmax 216.5nm (Ref. 7109)							2-Hexyl-2-decenoic acid is prepared from 2-hexyl-3-hydroxy decanoic acid with acetic anhydride (Ref. 7109).				[7109]
560			6-Isopentyl-9-Methyl-5-Decenoic Acid	DFA7110	Tetsuyuki Kobayashi		C₁₆H₃₀O₂	254.408				142 - 145C/0.2mmHg (Ref. 7110)		h20/D = 1.4562 (Ref. 7110)										6-Isopentyl-9-methyl-5-decenoic acid is prepared from the reaction of 9-methyl-6-oxo-decanoic acid ethyl with isopentylmagnesium bromide, followed by saponification with KOH (Ref. 7110).				[7110]
561		2-Methylenedodecanoic Acid	2-Decyl-Acrylic Acid	DFA7111	Tetsuyuki Kobayashi		C₁₃H₂₄O₂	212.328			33.3 - 34.2C (Ref. 7141)						lmax 210nm (Ref. 7111)	C=CH2: 10.54m (Ref. 7022)						2-Decyl acrylic acid was prepared from the reaction of 2-methyl dodecanoic acid with phosphor chloride, followed by hydrolysis (Ref. 7023).				[7022] / [7023] / [7111] / [7141]
562		4,4-Dimethyl-Valeric Acid	4,4-Dimethyl-Pentanoic Acid	DFA7112	Tetsuyuki Kobayashi		C₇H₁₄O₂	130.185				100-102C/15mmHg,83-85C/3mmHg (Ref. 7116)												4,4-Dimethyl valenic acid was heated with sulfuric acid and aq. sodium nitrite.				[7116]
563		3,4-Dimethyl-Valeric Acid	3,4-Dimethyl-Pentanoic Acid	DFA7113	Tetsuyuki Kobayashi		C₇H₁₄O₂	130.185				75C/2mmHg (Ref. 7097)	D25/4=0.9239 (Ref. 7097)	h25/D=1.4235 (Ref. 7097)						D25/4=0.9239 (Ref. 7097)				Treatment of 1-bromo-2, 3-dimethylbutane and magnesium in ether with carbon dioxide.				[7097]
564			2-Ethyl-2-Methyl-Butanoic Acid	DFA7114	Tetsuyuki Kobayashi		C₇H₁₄O₂	130.185				123-125C/27mmHg (Ref. 7039)		h25/D = 1.4212 (Ref. 7039)										2-Ethyl-butan-1-ol was treated with CO, water, nickel tetra carbonyl and a small amount of nickel chloride (II) in aqueous hydrochloric acid at 300C under the pressure of 1280 atm.				[7039]
565			3-Methyl-Heptanoic Acid	DFA7115	Tetsuyuki Kobayashi		C₈H₁₆O₂	144.211				121C/15mmHg (Ref. 7117)		h16/D=1.4276 (Ref. 7117)										(1-Methyl-pentyl) malonic acid was heated at 185C(Ref. 7117).				[7117]
566			5-Methyl-Heptanoic Acid	DFA7116	Tetsuyuki Kobayashi		C₈H₁₆O₂	144.211				120C/15mmHg(119), 236-238C (Ref. 7119)						3000-2800 cm^-¹ (Ref. 7006)						Diethyl (3-methyl-pentyl) malonate was heated with ethanolic KOH, then acidified(Ref. 7119).				[7006] / [7119]
567			4-Ethyl-Hexanoic Acid	DFA7117	Tetsuyuki Kobayashi		C₈H₁₆O₂	144.211				121-122C/10mmHg (Ref. 7120)	D17.5/ =0.940 (Ref. 7120)	h17.5/D=1.4412 (Ref. 7120)				3.3-3.6m(Ref. 7119)		D17.5/ =0.940 (Ref. 7120)				4-Vinyl-hexa-3,5-dienoic acid was hydroxylated with Raner nickel catalyst at 25C under the pressure of 100 atm(Ref. 7120).				[7119] / [7120]
568			2,2-Dimethyl-Hexanoic Acid	DFA7118	Tetsuyuki Kobayashi		C₈H₁₆O₂	144.211				216-220C/726mmHg(Ref. 7121), 119-122C/18mmHg(Ref. 7122)		h25/D=1.4240 (Ref. 7121)										Methyl 2,2-dimethylhexanoate was treatd with ethanolic KOH(Ref. 7121).				[7121] / [7122]
569		2-Ethyl-2-Methyl-Valeric Acid	2-Ethyl-2-Methyl-Pentanoic Acid	DFA7119	Tetsuyuki Kobayashi		C₈H₁₆O₂	144.211				115-117C/14mmHg (Ref. 7123)	D25/ =0.9177 (Ref. 7124)	h25/D=1.4288 (Ref. 7123)						D25/ =0.9177 (Ref. 7124)				1,1-diethyl-propyl 2-methylbutanoic acid was treated with liquid ammonia solution of sodium amide or potassium amide in ether. Then the product was further treated with propyl halide in ether, followed by treatment with dioxane and conc. hydrochloric acid(Ref. 7123).				[7123] / [7124]
570			2-Isopropyl-Hexanoic Acid	DFA7120	Tetsuyuki Kobayashi		C₉H₁₈O₂	158.238				121C/12mmHg (Ref. 7125)	D25/4=0.9017 (Ref. 7126)	h25/D=1.4266 (Ref. 7125)				3.38- 3.50m, 6.5 - 8.5 m (Ref. 7119)		D25/4=0.9017 (Ref. 7126)				2-Isopropyl-cyclohexan-1-ol was treated with the mixture of KOH and sodium acetate at 350C(Ref. 7126).				[7119] / [7125] / [7126]
571			3,5,5-Trimethyl-Hexanoic Acid	DFA7121	Tetsuyuki Kobayashi		C₉H₁₈O₂	158.238				120C/13mmHg (Ref. 7127)		h26/D=1.4270 (Ref. 7127)										3,5,5-Trimethyl-hexan-1-ol was treated with chromium(VI) oxide and acetic acid(Ref. 7127).				[7127]
572			3-Methyl-Nonanoic Acid	DFA7122	Tetsuyuki Kobayashi		C₁₀H₂₀O₂	172.265				122-125C/3mmHg (Ref. 7128)	D23/ =0.888 (Ref. 7128)	h23/D=1.4318 (Ref. 7128)						D23/ =0.888 (Ref. 7128)				2-Octylmalonic acid was heated at 165-170c for an hour.				[7128]
573			3,3-Dimethyl-Nonanoic Acid	DFA7123	Tetsuyuki Kobayashi		C₁₁H₂₂O₂	186.291				130-133C/5mmHg (Ref. 7129)	D25/ =0.8995(Ref. 7129)	h25/D=1.4370 (Ref. 7129)						D25/ =0.8995(Ref. 7129)				Methyl 3,3-dimethylnonanoate was treated with ethanolic KOH.				[7129]
574			(R)-3-Methyl-Undecanoic Acid	DFA7124	Tetsuyuki Kobayashi		C₁₂H₂₄O₂	200.318				117C/0.5mmHg (Ref. 7130)		h26/D=1.4350 (Ref. 7130)										A mixture of octanoic acid, methyl 3-methylglutarate, methyl alcohol and a small amount of sodium were electrolysed, and the product was treated with ethanolic KOH.				[7130]
575			(S)-4-Methyl-Dodecanoic Acid	DFA7125	Tetsuyuki Kobayashi		C₁₃H₂₆O₂	214.344				162-164C/5.5mmHg (Ref. 7024)	D25/ =0.888 (Ref. 7024)	h25/D=1.4424 (Ref. 7024)						D25/ =0.888 (Ref. 7024)				1-Bromo-3-methyl undecane was incubated with potassium cyanide in ethanol, followed by heating in aq. Potassium hydroxide.				[7024]
576			2-Ethyl-Dodecanoic Acid	DFA7126	Tetsuyuki Kobayashi		C₁₄H₂₈O₂	228.371				175-180C/11mmHg (Ref. 7133)	D70/4=0.8535 (Ref. 7132)	h25/D=1.4450(134),h70/D=1.4258(Ref. 7132)						D70/4=0.8535 (Ref. 7132)				Silver salt of ethyl ethyldecylmalonate was incubated with bromine in carbon tetrachloride.				[7132] / [7133]
577			9-Methyltridecanoic Acid	DFA7127	Tetsuyuki Kobayashi		C₁₄H₂₈O₂	228.371				154C/2mmHg(Ref. 7134)		h 25/D = 1.4462 (Ref. 7134)										9-Hydroxy-9-methyltridecanitril was warmed with ethanolic KOH. The product was heated with a small amount of iodine at 200C, followed by hydrogenation with Pt in ethanol(Ref. 7134).				[7134]
578			6-Ethyldodecanoic Acid	DFA7128	Tetsuyuki Kobayashi		C₁₄H₂₈O₂	228.371				131-132C/1mmHg(Ref. 7135)												Barium 6-oxododecanate was treated with ethyl magnesium iodide in Ether, then the hydrolysate was heated with iodine at 180C, followed by hydrogenation with Pt in methyl alchol(Ref. 7135).				[7135]
579			2,4-Dimethyldodecanoic Acid	DFA7129	Tetsuyuki Kobayashi		C₁₄H₂₈O₂	228.371				148-150C/2mmHg(Ref. 7136)	D20/4 = 0.8869 (Ref. 7136)	h 20/D = 1.4456 (Ref. 7136)						D20/4 = 0.8869 (Ref. 7136)				2-Bromo-4-methyl dodecane was treated with magnesium in ether, followed by reaction with carbon dioxide(Ref. 7136).				[7136]
580			3-Methyltetradecanoic Acid	DFA7130	Tetsuyuki Kobayashi		C₁₅H₃₀O₂	242.398			24-24.5 (Ref. 7119)	170		n32/D = 1.4487 (Ref. 7059)										Diethyl 1-methyl dodecyl malonate was heated with ethanolic KOH. After acidification, the product was obtained by heating at 170C under diminished pressure(Ref. 7119).				[7059] / [7119]
581			11-Methyltetradecanoic Acid	DFA7131	Tetsuyuki Kobayashi		C₁₅H₃₀O₂	242.398			18.5-19C (Ref. 7119)	170-171C/0.4mmHg (Ref. 7119)												Diethyl 9-methyl dodecyl malonate was heated with ethanolic KOH. After acidification, the product was obtained by heating at 170C under diminished pressure(Ref. 7119).				[7119]
582			3-Methylpentadecanoic Acid	DFA7132	Tetsuyuki Kobayashi		C₁₆H₃₂O₂	256.424			37.2-37.6C (Ref. 7023)													It was produced by hydrolysis of methyl 3-methylpentadecanoate(Ref. 7023).				[7023]
583			2-Propyltridecanoic Acid	DFA7133	Tetsuyuki Kobayashi		C₁₆H₃₂O₂	256.424			20-21C (Ref. 7138)	180-183C/3.5mmHg(Ref. 7138)	D70/4 = 0.8486 (Ref. 7139)	h 20/D = 1.4425 (Ref. 7138)						D70/4 = 0.8486 (Ref. 7139)				Diethyl propylundecylmalonate was heated in ethanolic KOH. After acidification the product was obtained by heating at 180C under a vacuum of 20 Torr(Ref. 7138).				[7138] / [7139]
584			2-Hexyldecanoic Acid	DFA7134	Tetsuyuki Kobayashi		C₁₆H₃₂O₂	256.424				140-150C/0.02mmHg(Ref. 7109)	D70/4 = 0.8463 (Ref. 7132)	h 24/D = 1.4432(Ref. 7109)						D70/4 = 0.8463 (Ref. 7132)				It was synthesized from 2-hexyl-2-decenoic acid by hydrogenation with Pt in ethanol(Ref. 7109).				[7109] / [7132]
585			3-Ethyl-3-Methyltridecanoic Acid	DFA7135	Tetsuyuki Kobayashi		C₁₆H₃₂O₂	256.424				168-171C/1mmHg (Ref. 7140)		h 25/D = 1.4515 (Ref. 7140)										A mixture of 3-ethyl-3-methylglutarate monomethyl, decanoic acid, methylalcohol and small amount of sodium was electrolysed, followed by treatment with aq. potassium hydroxide(Ref. 7140).				[7140]
586			2-Heptyl Nonanoic Acid	DFA7136	Tetsuyuki Kobayashi		C₁₆H₃₂O₂	256.424			26C (Ref. 7110)	158-160C/1.5mmHg (Ref. 7110)												2-Peptyl nonanitril was heated with hydrobromic acid at 160C (Ref. 7110).				[7110]
587			6-Ethyl Tetradecanoic Acid	DFA7137	Tetsuyuki Kobayashi		C₁₆H₃₂O₂	256.424				140-142C/0.01mmHg (Ref. 7135)												Barium 6-oxotetradecanate was treated with ethyl magnesium iodide in ether, followed by treatment with hydrochloric acid. Then the product was heated with iodine at 180C. The product isolated was hydrogenated with Pt in methyl alcohol to give 6-etHYL TETRADECANOIC ACID(Ref. 7135).				[7135]
588			2,4-Dimethyl Tetradecanoic Acid	DFA7138	Tetsuyuki Kobayashi		C₁₆H₃₂O₂	256.424				144-145C/0.5mmHg (Ref. 7136)	D20/4=0.8843 (Ref. 7136)	h20/D=1.4487 (Ref. 7136)						D20/4=0.8843 (Ref. 7136)				2-Bromo-4-methyltetradecane was treated with magnesium in ether, followed by reaction with carbon dioxide(Ref. 7136).				[7136]
589			3,5-Dimethyl Tetradecanoic Acid	DFA7139	Tetsuyuki Kobayashi		C₁₆H₃₂O₂	256.424				147-149C/0.5mmHg (Ref. 7136)	D20/4=0.8859 (Ref. 7136)	h20/D=1.4491(Ref. 7136)						D20/4=0.8859 (Ref. 7136)				Sodium diethylmalonate and 2-bromo-4-methyl tridecane were heated in ethylalcohol and the reaction product was treated with sodium hydroxide. The final product was obtained by vacuum distillation after acidification(Ref. 7136).				[7136]
590			4-Hexyl Decanoic Acid	DFA7140	Tetsuyuki Kobayashi		C₁₆H₃₂O₂	256.424				147-148C/0.8mmHg (Ref. 7110)		h27/D=1.4450(Ref. 7110)										Diethyl (2-hexyloctyl)malonate was heated with ethanolic KOH, and the product was heated after acidification(Ref. 7110).				[7110]
591			2-Ethyl-2-Butyl Decanoic Acid	DFA7141	Tetsuyuki Kobayashi		C₁₆H₃₂O₂	256.424				138-139C/0.4mmHg (Ref. 7123)		h25/D=1.4500(Ref. 7123)										2-Ethylhexanate(1,1-diethylpropyl)ester was treated with potassium amide in liquid ammonia, and further treated with octyl bromide. Then the product was heated in a mixture of hydrochloric acid/dioxane(Ref. 7123).				[7123]
592			5-Methyl Hexadecanoic Acid	DFA7142	Tetsuyuki Kobayashi		C₁₇H₃₄O₂	270.451			34.5-35C (Ref. 7065)	158-160C/0.2mmHg (Ref. 7065)												Diethyl (3-methyl tetradecyl) malonate was heated in ethanolic KOH, and the product was obtained by vacuum distillation after acidification(Ref. 7065).				[7065]
593			11,15-Dimethyl Hexadecanoic Acid	DFA7143	Tetsuyuki Kobayashi		C₁₈H₃₆O₂	284.477				165-172C/0.5Torr		h20/D=1.4480										It was produced by electrolysis of a mixture of sebacic acid monoethyl ester, 3,7-dimethyloctanate, potassium carbonate and ethyl alchol (pH6.8-7), followed by treatment with ethanolic KOH.
594			15-Methyl Octadecanoic Acid	DFA7144	Tetsuyuki Kobayashi		C₁₉H₃₈O₂	298.504		(Ref. 7010)	40.9-42.4C (Ref. 7046)	183C/0.4mmHg(Ref. 7073)						7.78m, 8.10m, 13.5m(CS2) (Ref. 7010)						Ethylester of 15-methyl-12-oxooctadecanate was heated at 200C with hydrazine hydrate, sodium hydroxide and diethylene glycol(Ref. 7046).				[7010] / [7046] / [7073]
595			5-Methyl Octadecanoic Acid	DFA7145	Tetsuyuki Kobayashi		C₁₉H₃₈O₂	298.504		(Ref. 7010/7011)	44.5-45C (Ref. 7143)	174C/0.1mmHg(Ref. 7073)					209nm (Ref. 7011)	7.76m, 8.25m(CS2) (Ref. 7010)						Diethyl ester of (3-methyl tetradecyl) malonate was heated with ethanolic KOH. After acidification the product was obtained by distillation under deminished pressure(Ref. 7073).				[7010] / [7011] / [7073] / [7143]
596			9-Hydroperoxy-10,12-Octadecadienoic Acid/9-Hydroperoxy-10,12-Octadecadienoate	DFA8001	Tetsuyuki Kobayashi		C₁₈H₃₂O₄	312.444		Pysiological damages are induced by these hydroperoxides which are incorporated into bodies or synthesized endogenously.(Ref. 8043/8044/8045/8046/8047/8048/8049)							Trans, cis isomer: l max=236nm, e =25900, trans, trans isomer: l max=233nm, e=28600 (Ref. 8001/8002/8003/8004/8005/8011)	Methyl ester: (Ref. 8001/8005/8006/8007/8008/8009/8010/8011): trans, cis isomer: 986 and 949cm^-¹, trans, trans isomer: 989cm^-¹, OOH group: 3550cm^-¹	¹H-NMR(Ref. 8001/8012), ¹H-NMR( after methanolyzation and reduction)(Ref. 8005/8017): trans,cis isomer: C10-13 (5.42-6.48ppm), C14 (2.10-2.18ppm), C9(4.15ppm), J10-11= 15.4Hz(trans), J12-13= 10.8Hz (cis), trans, trans isomer: olefinic protons (5.41ppm), C14 (2.07ppm), C9 (4.20ppm)	GC/EI-MS(after methanolysis, reduction and trimethylsilylation) (Ref. 8012/8018/8013/8019/8014): m/e= 382[M], 292[M-HOTMS], 311[M-(CH2)4CH3], 225[M-(CH2)7COOCH3] standard peak/ GC-EI-MS(after methylation, reduction and hydrogenation) (Ref. 8020/8015/8016): m/e= 187[CH(OH)(CH2)7COOCH3], 158[(CH2)7COOCH3+H], 155[C(OH)-(CH)7CO]			Auto oxidation of methyllinoleate(Ref. 8021/8022/8023/8024/8025/8026/8027/8039/8028/8029/8030). Oxidation of methyl linoleate by singlet oxygen(Ref. 8022/8023/8025/8026/8027/8039/8030/8024). Oxidation of linoleic acid by lipoxygenase(Ref. 8023/8031/8032/8033/8034/8035/8037/8038/8036). Production mechanism (auto oxidation): bis-allylic hydrogen at C11.					[8001] / [8002] / [8003] / [8004] / [8005] / [8006] / [8007] / [8008] / [8009] / [8010] / [8011] / [8012] / [8013] / [8014] / [8015] / [8016] / [8017] / [8018] / [8019] / [8020] / [8021] / [8022] / [8023] / [8024] / [8025] / [8026] / [8027] / [8028] / [8029] / [8030] / [8031] / [8032] / [8033] / [8034] / [8035] / [8036] / [8037] / [8038] / [8039] / [8043] / [8044] / [8045] / [8046] / [8047] / [8048] / [8049]
597			13- Hydroperoxy-9,11-Octadecadienoic Acid/13- Hydroperoxy-9,11-Octadecadienoate	DFA8002	Tetsuyuki Kobayashi		C₁₈H₃₂O₄	312.444		Pysiological damages are induced by these hydroperoxides which are incorporated into bodies or synthesized endogenously.(Ref. 8043/8044/8045/8046/8047/8048)							Trans, cis isomer: l max= 236nm, e= 26000, trans, trans isomer: l max= 233nm, e=28600 (025/027/028/029/036)	Methyl ester(Ref. 8001/8006/8007/8008/8009/8010/8011): cis, trans isomer: 986 and 949cm^-¹, trans, trans isomer: 989cm^-¹, OOH group: 3550cm^-¹	¹H-NMR (Ref. 8001/8012): C9-13 (5.45-6.53ppm), C13 (4.37ppm), J9-10= 11Hz (cis),J11-12=15Hz (trans) /¹H-NMR (after methanolyzation and reduction )(Ref. 8005/8017): cis, trans isomer : olefinic protons(5.91ppm), C8 (2.10ppm), C13(4.15ppm), trans, trans isomer: olefinic protons (5.41ppm), C8 (2.07ppm)	GC-EI-MS(after methanolysis, reduction and trimethylsilylation) (Ref. 8012/8018/8019/8013/8014): m/e= 382[M], 292[M-HOTMS], 311[M-(CH2)4CH3] standard peak,225[M-(CH2)7COOCH3] / GC-EI-MS(after methylation, reduction and hydrogenation) (Ref. 8020/8015/8016): m/e= 243[CH(OH)(CH2)11COOCH3], 214[(CH2)11COOCH3+H], 211[C(OH(CH2)11CO]			Auto oxidation of methyl linoleate(Ref. 8029/8021/8022/8023/8024/8025/8026/8039/8028/8030). Oxidation of methyl linoleate by singlet oxygen(Ref. 8022/8023/8025/8026/8027/8030/8024). Oxidation of linoleic acid by lipoxygenase(Ref. 8023/8031/8032/8033/8034/8035/8037/8038/8036). Production mechanism (auto oxidation): bis-allylic hydrogen at C11.					[8001] / [8005] / [8006] / [8007] / [8008] / [8009] / [8010] / [8011] / [8012] / [8013] / [8014] / [8015] / [8016] / [8017] / [8018] / [8019] / [8020] / [8021] / [8022] / [8023] / [8024] / [8025] / [8026] / [8027] / [8028] / [8029] / [8030] / [8031] / [8032] / [8033] / [8034] / [8035] / [8036] / [8037] / [8038] / [8039] / [8043] / [8044] / [8045] / [8046] / [8047] / [8048]
598			10-Hydroperoxy-8,12-Octadecadienoic Acid/10-Hydroperoxy-8,12-Octadecadienoate	DFA8003	Tetsuyuki Kobayashi		C₁₈H₃₂O₄	312.444		Pysiological damages are induced by these hydroperoxides which are incorporated into bodies or synthesized endogenously.(Ref. 8043/8044/8045/8046/8047/8048/8049)								After methanolyzation and reduction(Ref. 8091/8090): isolated double bond (3013-3010, 972-971cm^-¹)	¹H-NMR(after methanolyzation and reduction)(Ref. 8091): olefinic protons(5.55-5.59ppm), C10 (4.08-4.11ppm)	GC-EI-MS(after methanolysis, reduction and trimethylsilylation)(Ref. 8090/8019): m/e= 271[SMTO=CH-CH=CH-(CH2)6COOCH3], GC-EI-MS (after methylation, reduction and hydrogenation)(Ref. 8020):m/e= 201[CH(OH)(CH2)8COOCH3], 172[(CH2)8COOCH3+H], 169[C(OH)(CH2)8CO] GC-EI-MS(after methylation, reduction, hydrogenation and trimethylsilylation)(Ref. 8090)			Oxidation of methyl linoleate by singlet oxygen(Ref. 8043/8044/8045/8046/8047/8048/8049).					[8019] / [8020] / [8043] / [8044] / [8045] / [8046] / [8047] / [8048] / [8049] / [8090] / [8091]
599			12-Hydroperoxy-9,13-Octadecadienoic Acid/12-Hydroperoxy-9,13-Octadecadienoate	DFA8004	Tetsuyuki Kobayashi		C₁₈H₃₂O₄	312.444		Pysiological damages are induced by these hydroperoxides which are incorporated into bodies or synthesized endogenously.(Ref. 8043/8044/8045/8046/8047/8048/8049)								After methanolyzation and reduction(Ref. 8091/8090): isolated double bond (3013-3010, 972-971cm^-¹)	¹H-NMR(after methanolyzation and reduction)(Ref. 8091): olefinic protons(5.55-5.59ppm), C10 (4.08-4.11ppm)	GC-EI-MS(after methanolysis, reduction and trimethylsilylation)(Ref. 8090/8019): m/e= 185[SMTO=CH-CH=CH-(CH2)3CH3], GC-EI-MS (after methylation, reduction and hydrogenation)(Ref. 8020): m/e= 229[CH(OH)(CH2)10COOCH3], 200[(CH2)10COOCH3+H], 197[C(OH)(CH2)10CO] GC-EI-MS(after methylation, reduction, hydrogenation and trimethylsilylation)(Ref. 8090)			Oxidation of methyl linoleate by singlet oxygen(Ref. 8024/8022/8023/8025/8026/8027/8039/8030).					[8019] / [8020] / [8022] / [8023] / [8024] / [8025] / [8026] / [8027] / [8030] / [8039] / [8043] / [8044] / [8045] / [8046] / [8047] / [8048] / [8049] / [8090] / [8091]
600			8-Hydroperoxy-9,12-Octadecadienoic Acid	DFA8005	Tetsuyuki Kobayashi		C₁₈H₃₂O₄	312.444											¹H-NMR (after methanolyzation, reduction and 400MHz )(Ref. 8050): olefinic protons(5.91-5.51ppm), C8 (4.45ppm), C11(2.84ppm), C14(2.05ppm),J9-10= J12-13= 10.7Å }0.2Hz (cis)	GC-EI-MS(after methanolysis, reduction and trimethylsilylation) (Ref. 8050>: m/e= 292[M-HOTMS], 271[CH=CH-CH(OTMS)-(CH2)6COOCH3], 239[M-(CH2)6C00CH3], 173[SMTO=CH-(CH2)6COOCH3-TMS+H], 149[239-HOTMS] standard peak			A minor component of monohydroperoxide generated from linoleic acid or methyllinoleate by autooxidation(Ref. 8050/8051). A minor component of hydroperoxide generated from linoleic acid through oxidation by soy bean lipoxygenase (type-2)(Ref. 8050).				8-OOH and 14-OOH are known as small amount components of monohydroperoxidate from auto oxidation of linoleic acid and oxidation of soybean lipoxygenase(type-2). Their amount does not change by temperature or addition of a-tocopherol(Ref. 8050).	[8050] / [8051]
601			14-Hydroperoxy-9,12-Octadecadienoic Acid	DFA8006	Tetsuyuki Kobayashi		C₁₈H₃₂O₄	312.444											¹H-NMR(after methanolyzation, reduction and 400MHz)(Ref. 8050): olefinic protons(5.32-5.47ppm) C14(4.45ppm), C11(2.85ppm), C8(2.05ppm), J9-10= J12-13= 10.08Å }0.1Hz(cis)	GC-EI-MS(after methanolysis, reduction and trimethylsilylation)(Ref. 8050): m/e= 325[M-(CH2)3CH3] standard peak, 292[M-HOTMS], 235[325-HOTMS], 185[CH=CH-CH(OTMS)-(CH2)3CH3]			A minor component of monohydroperoxide generated from linoleic acid or methyllinoleate by autooxidation(Ref. 8050/8051). A minor component of hydroperoxide generated from linoleic acid through oxidation by soy bean lipoxygenase (type-2)(Ref. 8050).				8-OOH and 14-OOH are known as small amount components of monohydroperoxidate from auto oxidation of linoleic acid and oxidation of soybean lipoxygenase(type-2). Their amount does not change by temperature or addition of a-tocopherol(Ref. 8050).	[8050] / [8051]
602			9,10-Epoxy-12-Octadecenoic Acid/9,10-Epoxy-12-Octadecenoate	DFA8007	Tetsuyuki Kobayashi		C₁₈H₃₂O₃	296.445		Antimicrobial compounds for Piricularia oryzae, a pathogenic fungus of rice blast disease (Imochi-byo)(Ref. 8072)								Olefinic(3002cm^-¹), cis unsaturation(718cm^-¹), cis epoxide(835-815cm^-¹)(Ref. 8017)	¹H-NMR(Ref. 8017): olefinic protons(5.44ppm), isolated cis epoxide(2.92ppm)	GC-EI-MS(Ref. 8017): m/e= 310[M], 279[M-OCH3], 199[M-CH3(CH2)4CH=CHCH2], 153[M-(CH2)7-COOCH3], GC-EI-MS(after solvolysation-trimethylsilylation in MeOH)(Ref. 8062)			In autooxidated methyllinoleate(Ref. 8017). A major secondary product by autooxidation in a lipid film of linoleate(Ref. 8062).				8, 9-; 10, 11- and 11, 12-Epoxide were detected in autooxidated methyl linoleate as well as 9, 10-epoxide(Ref. 8017).	[8017] / [8062] / [8072]
603			12,13-Epoxy-9-Octadecenoic Acid	DFA8008	Tetsuyuki Kobayashi		C₁₈H₃₂O₃	296.445		Antimicrobial compounds for Piricularia oryzae, a pathogenic fungus of rice blast disease (Imochi-byo)(Ref. 8072)								Trans olefin(960cm^-¹), cis olefin(720cm^-¹), trans epoxide(885cm^-¹), cis epoxide(840 and 820cm^-¹)(Ref. 8071)	¹H-NMR(Ref. 8071): C8(2.01ppm), C9, 10(5.45ppm), C2, 11(2.29ppm), C12, 13(2.91ppm), J9-10= 10Hz(cis olefin)	GC-EI-MS(after solvolysation-trimethylsilylation in MeOH)(Ref. 8018/8062/8071): m/e= 299[SNTO=CH-CH2-CH=CH(CH2)7COOCH3], 217[CH3(CH2)4CH(OCH3)CHOTMS], 195[OHCCH2CH=CH(CH2)7CO], 173[ SMTO=CH(CH2)4CH3]			A major secondary product by autooxidation in a lipid film of linoleate(Ref. 8062). A bitter substance in lecithin(Ref. 8071).					[8018] / [8062] / [8071] / [8072]
604			12,13-Epoxy-9-Hydroperoxy-10-Octadecenoic Acid	DFA8009	Tetsuyuki Kobayashi		C₁₈H₃₂O₅	328.444		It showed a slightly higher toxicity than linoleate monohydroxyperoxide.(Ref. 8045/8047)								Isorated trans unsaturation(970cm^-¹), trans epoxide(885cm^-¹), OOH(3600 AND 3430cm^-¹) (Ref. 8052)	¹H-NMR(methyl ester)(Ref. 8052): C9(4.33ppm), C10(5.85ppm), C11(5.47ppm), C12(3.11ppm), C13(2.84ppm) J10-11=16Hz(trans olefin), J12-13=2Hz(trans epoxide)	GC-EI-MS(after methanolysis, reduction and trimethylsilylation)(Ref. 8052/8061)			Major reactive products between 13-hydroperoxylinoleate (or linoleate) and soy bean extracts(pH=6.9)(Ref. 8052). Copper-catalyzed degradation products of linoleate methylhydroperoxide(Ref. 8062). Production mechanism (Ref. 8026/8030/8073/8074).					[8026] / [8030] / [8045] / [8047] / [8052] / [8061] / [8062] / [8073] / [8074]
605			12,13-Epoxy-11-Hydroperoxy-9-Octadecenoic Acid	DFA8010	Tetsuyuki Kobayashi		C₁₈H₃₂O₅	328.444										After methylation and reduction(Ref. 8066/8013/8052)	¹H-NMR(after methylation and reduction)(Ref. 8066/8013/8052)	GC-EI-MS(after methylation, reduction and trimethylsilylation)(Ref. 8052/8093): m/e= 285[SMTO=CH-CH=CH-(CH2)7COOCH3]			Major reactive products between 13-hydroperoxylinoleate (or linoleate) and soy bean extracts(pH=6.9)(Ref. 8052). Production mechanism(Ref. 8026/8030/8073/8074).					[8013] / [8026] / [8030] / [8052] / [8066] / [8073] / [8074] / [8093]
606			9,10-Epoxy-11-Hydroxy-12-Octadecenoic Acid/9,10-Epoxy-11-Hydroxy-12- Octadecenoate	DFA8011	Tetsuyuki Kobayashi		C₁₈H₃₂O₄	312.444										Methyl ester(Ref. 8013/8057/8059/8066/8071): trans olefin(980cm^-¹), trans epoxide(900-890cm^-¹), OH(3620-3300cm^-¹)	¹H-NMR(Ref. 8013): trans-epoxy-cis-ene: C9(2.98ppm), C10(2.77ppm), C11(4.63ppm), C12(5.32ppm), C13(5.60ppm), C14(2.06ppm), J9-10=2Hz, J10-11=4Hz, J11-12=8Hz J12-13=11Hz / trans-epoxy-trans-ene: C9(2.93ppm), C10(2.77ppm), C11(4.25ppm), C12, 13(5.54ppm), C14(2.06ppm)	GC-EI-MS(after methanolysis and trimethylsilylation)(Ref. 8013/8059/8012/8063/8071/8017): m/e= 398[M], 383[M-CH3], 241[M-(CH2)7COOCH3], 199[SMTO=CH-CH=CH(CH2)4CH3 or CH(-O-)-CH(CH2)7COOCH3], GC-EI-MS(after methanolysis, reduction and hydrogenation)(078), GC-EI-MS(after aceto-hydrolyzation, methanolysis and trimethylsilylation)(Ref. 8066/8059): m/e=361[SMTO			A minor component of epoxy-hydroxy compounds generated from linoleic acid by autooxidation [the epoxy ring shows trans configuration](Ref. 8017/8012). Soy bean lipoxygenase-catalyzed degradation products of linoleate hydroperoxide(Ref. 8059). A degradation product of 9-hydroperoxylinoleate in the presence of Fe(III)-cystein.					[8012] / [8013] / [8017] / [8057] / [8059] / [8063] / [8066] / [8071]
607			9,10-Epoxy-13-Hydroxy-11-Octadecenoic Acid/9,10-Epoxy-13-Hydroxy-11-Octadecenoate	DFA8012	Tetsuyuki Kobayashi		C₁₈H₃₂O₄	312.444									l=277 and 316nm(very weak absorption)(Ref. 8009)	Metyl ester(Ref. 8017/8056/8009): trans olefin(965-958cm^-¹), trans epoxide(890-874 cm^-¹), cis epoxide(weak absorprion; 845 AND 830cm^-¹), free OH(3600cm^-¹),bonded OH(3640-3380cm^-¹)	¹H-NMR(methyl ester)(Ref. 8017/8056/8009): C9(2.83ppm), C10(3.09-3.1ppm;trans epoxide), C11(5.45-5.53ppm), C12(5.93-5.95ppm), C13(3.9-4.2ppm), C12, 13(2.9-3.4ppm;cis epoxide), OH proton(3.6ppm), J11-12=15.6Hz(trans unsaturation), J9-10=2-2.2Hz(trans epoxide)	GC-EI-MS(after methanolysis and trimethylsilylation)(Ref. 8017/8056/8009/8012): m/e= 398[M], 383[M-CH3], 367[M-OCH3], 327[M-(CH2)4CH3], 241[M-(CH2)7COOCH3]			A degradation product of 13-hydroperoxymethyllinoleate(Ref. 8056/8057). A major compound generated by autooxidation of methyllinoleate[the epoxide ring and double bond show trans configuration](Ref. 8017/8012). Oxidation of linoleic acid by wheat lipoxygenase[the epoxy ring shows cis configuration].					[8009] / [8012] / [8017] / [8056] / [8057]
608			12,13-Epoxy-9-Hydroxy-10-Octadecenoic Acid/12,13-Epoxy-9-Hydroxy-10-Octadecenoate	DFA8013	Tetsuyuki Kobayashi		C₁₈H₃₂O₄	312.444									l=277 and 316nm(very weak absorption)(Ref. 8009)	Methyl ester(Ref. 8017/8056/8009/8063/8071): trans olefin(965-958cm^-¹), trans epoxide( 890-874cm^-¹), cis epoxide(weak absorption; 845 and 830cm^-¹), free OH(3600cm^-¹)bonded OH(3640-3380cm^-¹)	¹H-NMR(Ref. 8052/8017/8056/8009): C9(3.9-4.2ppm), C10(5.93-5.95ppm), C11(5.41-5.53ppm), C12(3.09-3.1ppm; trans epoxide), C13(2.81-2.83ppm; trans epoxide), C12, 13(2.9- 3.4ppm; cis epoxide),OH proton(3.6ppm), J10-11=15.6Hz(trans unsaturation),J12-13=2-2.2Hz(trans epoxide)	GC-EI-MS(after methanolysis and trimethylsilylation)(Ref. 8017/8056/8009/8012/8071): m/e=398[M], 383[M-CH3], 367[M-OCH3], 327[M-(CH2)4CH3], 241[M-(CH2)7COOCH3], 285[CH=CH-CH(OTMS)-(CH2)7COOCH3], 259[SMTO=CH-(CH2)7COOCH3]GC-EI-MS(after methanolysis and trimethylsiltlation under acidity)(Ref. 8052) GC-EI-MS(after BF3-MeOH treatment and trimethylsilylation)(Ref. 8057)	ORD analysis(Ref. 8063)		A degradation product of 13-hydroperoxylinoleate in the presence of Fe(III)-cystein(Ref. 8063) or hemoglobin(Ref. 8014/8054). Degradation products of 13-hydroperoxymethyllinoleate by radical reactions(Ref. 8056/8057). A major component of epoxy-hydroxy compounds generated from methyllinoleate by autooxydation.					[8009] / [8012] / [8014] / [8017] / [8052] / [8054] / [8056] / [8057] / [8063] / [8071]
609			12,13-Epoxy-11-Hydroxy-9-Octadecenoic Acid/12,13-Epoxy-11-Hydroxy-9-Octadecenoate	DFA8014	Tetsuyuki Kobayashi		C₁₈H₃₂O₄	312.444										Methyl ester: trans olefin(980-962cm^-¹), trans epoxide(900-890cm^-¹), OH(3590-3300cm^-¹) (Ref. 8093/8013/8066/8059/8057)	¹H-NMR(Ref. 8013/8066/8060/8063/8017):trans-epoxy-cis-ene: C8(2.08ppm), C9(5.60-5.65ppm), C10(5.32-5.46ppm), C11(4.25-4.63ppm), C12(2.77-2.78ppm), C13(2.92-3.0ppm), J9-10=11Hz, J10-11=8Hz, J11-12=3-5Hz, J12-13=2-2.5Hz, trans-epoxy-trans-ene: C8(2.06ppm), C9, 10(5.54ppm)	GC-EI-MS(after methanolysis and trimethylsilylation)(Ref. 8093/8013/8059/8060/8063/8017/8014): m/e=398[M], 298[M-CH3(CH2)4CHO], 285[SMTO=CH-CH=CH(CH2)7COOCH3], 241[M-(CH2)7-COOCH3], 113[CH-(-O-)-CH-(CH2)4CH3]; GC-EI-MS(after methanolysis, trimethylsilylation and hydrogenation)(Ref. 8059)	ORD analysis(Ref. 8063/8069/8070)		13-Hydroperoxylinoleate in EtOH-water[the epoxide ring and OH show threo configuration](Ref. 8093). A degradation product in the presence of Fe(III)-cystein[the epoxy ring: trans, the double bond: cis or trans](Ref. 8013/8063) or hemoglobin[threo type: 80%, erythro type: 20%](Ref. 8014/8054).					[8013] / [8014] / [8017] / [8054] / [8057] / [8059] / [8060] / [8063] / [8066] / [8069] / [8070] / [8093]
610			12,13-Epoxy-11-Methoxy-9-Octadecenoic Acid	DFA8015	Tetsuyuki Kobayashi		C₁₉H₃₄O₄	326.471										Methyl ester: cis olefin(758-740cm^-¹), trans epoxide(900 AND 890cm^-¹), cis epoxide(852 and 842cm^-¹) (Ref. 8070)	¹H-NMR: C8(2.08ppm), C9(5.69-5.74ppm), C10(5.28-5.32ppm), C11(3.76-4.03ppm), C12(2.74-2.98ppm), C13(2.74-2.92ppm), J9-10=11.7-11.9Hz(cis unsaturation) (Ref. 8070)	GC-EI-MS(methyl ester)(Ref. 8070): m/e=309[M-OCH3], 240[M-CH3(CH2)4CHO], 227[CH3OCH-CH=CH(CH2)7COOCH3], 209[240-OCH3], 195[227-CH3OH]	ORD analysis(Ref. 8070)		Oxidative products of 13-hydroperoxylinoleate in MeOH(Ref. 8070).					[8070]
611			9,10-Epoxy-13-Oxo-11-Octadecenoic Acid	DFA8016	Tetsuyuki Kobayashi		C₁₈H₃₀O₄	310.428									l ether/max=229-230nm; e=16500 (a,b-unsaturated carbonyl)(Ref. 8013/8056)	Methyl ester: trans monoene(973cm^-¹), trans epoxide(885cm^-¹), cis epoxide(825 cm^-¹), conjugated carbonyl(1700, 1680, and 1635cm^-¹)(Ref. 8013)	¹H-NMR(Ref. 8013): C9(2.9ppm;trans epoxide), C10(3.20ppm; trans epoxide), C9(3.14ppm; cis-epoxide),C10(3.47ppm; cis epoxide), C11(6.57-6.63ppm), C12(6.34-6.36ppm), C14(2.52ppm), J9-10=2Hz(trans epoxide), J9-10=4Hz(cis epoxide), J11-12=16Hz(trans olefin)	GC-EI-MS(after methanolysis and trimethylsilylation )(Ref. 8013), GC-EIMS(after BF3-MeOH treatment and trimethylsilylation)(075/072): m/e=428[M], 413[M-CH3], 259[SMTO=CH(CH2)7- COOCH3], 242[CH3OCH-CH=CH-C(OTMS)(CH2)4CH3]			A degradation product of hydroperoxylinoleate in the presence of Fe(III)-cystein[the epoxide ring: trans or cis, the double bond: trans](Ref. 8013/8063). A minor reactive product between linoleate and soy bean extracts(Ref. 8053).					[8013] / [8053] / [8056] / [8063]
612			12,13-Epoxy-9-Oxo-10-Octadecenoic Acid	DFA8017	Tetsuyuki Kobayashi		C₁₈H₃₀O₄	310.428									lether/max=229-230nm; e=16500 (a,b-unsaturated carbonyl)(Ref. 8013/8056)	Methyl ester: trans monoene(973cm^-¹), trans epoxide(885cm^-¹), cis epoxide(825 cm^-¹), conjugated carbonyl(1700, 1680, and 1635cm^-¹) (Ref. 8013)	¹H-NMR: C8(2.52ppm), C10(6.34-6.36ppm), C11(6.57-6.63ppm), C12(3.2ppm; trans epoxide), C13(2.9ppm; trans epoxide), C12(3.47ppm; cis epoxide), C13(3.14ppm; cis epoxide), J12-13=2Hz(trans epoxide), J12-13=4Hz(cis epoxide), J10-11=16Hz(trans olefin)	GC-EI-MS(after methanolysis and trimethylsilylation)(Ref. 8013), GC-EI-MS(after NaBH4-reduction, methanolysis and trimethylsilylation)(Ref. 8053/8014) GC-EI-MS(after BF3-MeOH treatment and trimethylsilylation)(Ref. 8056/8053): m/e=428[M], 413[M-CH3], 328[CH3OCH-CH=CH-C(O)-(CH2)7-C(OTMS)OCH3], 173[SMTO=CH(CH2)4CH3]	ORD analysis		A degradation product of hydroperoxylinoleate in the presence of Fe(III)-cystein[the epoxide ring: trans or cis, the double bond: trans](Ref. 8013/8063). A minor reactive product between linoleate and soy bean extracts(Ref. 8053).					[8013] / [8014] / [8053] / [8056] / [8063]
613			10-Ethoxy-9,13-Dihydroxy-11-Octadecenoic Acid	DFA8018	Tetsuyuki Kobayashi		C₂₀H₃₈O₅	358.513										Isolated trans olefin(980-978cm^-¹), ether alcohol CO stretch(1090cm^-¹), OH(3500-3420cm^-¹) (Ref. 8013/8071)	¹H-NMR: C9, 10(3.62ppm), C11, 12(5.63ppm), C13(4.12ppm), OH(5.6ppm), -OCH2CH3(1.16ppm), -OCH2CH3(3.44ppm)(Ref. 8013/8017)	GC-EI-MS(after methanolysis and trimethylsilylation)(Ref. 8013/8017): m/e=343[M-173], 259[SMTO=CH-(CH2)7COOCH3], 173[SMTO=CH-(CH2)4CH3]			A degradation product of hydroperoxylinoleate in the presence of Fe(III)-cystein[the double bond: trans](Ref. 8013). A bitter substansce in lecithin(Ref. 8071). Production mechanism(Ref. 8074).					[8013] / [8017] / [8071] / [8074]
614			12-Ethoxy-9,13-Dihydroxy-10-Octadecenoic Acid	DFA8019	Tetsuyuki Kobayashi		C₂₀H₃₈O₅	358.513										Isolated trans olefin(980-978cm^-¹), ether alcohol CO stretch(1090cm^-¹), OH(3500-3420cm^-¹) (Ref. 8013/8017)	¹H-NMR: C9(4.12ppm), C10, 11(5.63ppm), C12, 13(3.62ppm), OH(5.6ppm), -OCH2CH3(1.16ppm), -OCH2CH3(3.44ppm) (Ref. 8013/8017)	GC-EI-MS(after methanolysis and trimethylsilylation)(Ref. 8013/8017): m/e=343[M-173], 259[SMTO=CH-(CH2)7COOCH3], 173[SMTO=CH-(CH2)4CH3], 416[CH3CH2OCH-CH=CH-CH(OTMS)-(CH2)7-C(OTMS)OCH3: rearrangement peak]			A degradation product of hydroperoxylinoleate in the presence of Fe(III)-cystein[the double bond: trans](Ref. 8013). A bitter substansce in lecithin(Ref. 8071). Production mechanism(Ref. 8074).					[8013] / [8017] / [8071] / [8074]
615			9-Hydroperoxy-12,13-Dihydroxy-10-Octadecenoic Acid	DFA8020	Tetsuyuki Kobayashi		C₁₈H₃₄O₆	346.459												GC-EI-MS(after methanolysis, reduction and trimethylsilylation), GC-EI-MS(aftre methanolysis, reduction, hydrogenation and trimethylsilylation )(Ref. 8059)			Reaction products of linolate hydroperoxide by soy bean lipoxygenase(Ref. 8059). Production mechanism(Ref. 8024).					[8024] / [8059]
616			13-Hydroperoxy-9,10-Dihydroxy-11-Octadecenoic Acid	DFA8021	Tetsuyuki Kobayashi		C₁₈H₃₄O₆	346.459												GC-EI-MS(after methanolysis, reduction and trimethylsilylation), GC-EI-MS(aftre methanolysis, reduction, hydrogenation and trimethylsilylation )(Ref. 8059)			Reaction products of linolate hydroperoxide by soy bean lipoxygenase(Ref. 8059). Production mechanism(Ref. 8024).					[8024] / [8059]
617			9-Hydroxy-10,12-Octadecadienoic Acid/9-Hydroxy-10,12-Octadecadienoate	DFA8022	Tetsuyuki Kobayashi		C₁₈H₃₂O₃	296.445		Trans, trans isomer showed a slightly lower toxicity than linoleate monohydroxyperoxide(Ref. 8045/8047).							Methyl ester: l/max=231, 233, 234nm (Ref. 8071)	Methyl ester: trans, trans isomer: trans, trans conjugated diene(985cm^-¹), free OH(3600cm^-¹), bonded OH(3695-3318cm^-¹), trans, cis isomer: trans, cis conjugated diene(990, 968cm^-¹), olefinic(3005cm^-¹), free OH(3600cm^-¹), bonded OH(3700-3160cm-	¹H-NMR(methyl ester): trans, trans olefinic protons(5.41ppm), trans,cis olefinic protons(5.91ppm), C9(4.15-4.20ppm), C14(2.07-2.10ppm)(Ref. 8017/8071)	GC-EI-MS(after methanolysis and trimethylsilylation)(Ref. 8059/8018/8012): m/e=382[M], 367[M-CH3], 351[M-OCH3], 311[M-(CH2)4CH3], 225[M-(CH2)7COOCH3], GC-EI-MS(after methanolysis, hydrogenation and trimethylsilylation)(Ref. 8059), GC-EI-MS(after methanolysis and hydrogenation)(Ref. 8064)			Minor degradation products of linoleate hydroperoxide in the presence of Fe(III)-cystein(Ref. 8013). A degradation product of hydroperoxymethyllinoleate in the presence of di-t-butyl diperoxyoxalate or Co(II)(Ref. 8058). Reaction products bstween hydroperoxylinoleate and soy bean lipoxygenase(Ref. 8059).					[8012] / [8013] / [8017] / [8018] / [8045] / [8047] / [8058] / [8059] / [8064] / [8071]
618			13-Hydroxy-9,11-Octadecadienoic Acid/13-Hydroxy-9,11-Octadecadienoate	DFA8023	Tetsuyuki Kobayashi		C₁₈H₃₂O₃	296.445		Trans, trans configuration showed a slightly lower toxicity than linoleate monohydroxyperoxide(Ref. 8045/8047).							lEtOH/max=234nm(conjugated diene)(Ref. 8014/8071)	Methyl ester: trans, trans isomer: trans, trans conjugated dinen(985cm^-¹), free OH(3600cm^-¹), bonded OH(3695-3318cm^-¹); cis, trans isomer: cis, trans conjugated diene(990, 968cm^-¹), olefinic(3005cm^-¹), free OH(3600cm^-¹), bonded OH(3700-3160cm	¹H-NMR(methyl ester): trans, trans olefinic protons(5.41ppm), cis,trans olefinic protons(5.91ppm), C13(4.15-4.20ppm), C8(2.07-2.10ppm) (Ref. 8017/8071)	GC-EI-MS(after methanolysis and trimethylsilylation)(Ref. 8013/8059/8018/8012/8004): m/e=382[M], 367[M-CH3], 351[M-OCH3], 311[M-(CH2)4CH3], 225[M-(CH2)7COOCH3], GC-EI-MS(after methanolysis, hydrogenation and trimethylsilylation)(Ref. 8059/8014), GC-EI-MS(after methanolysis and hydrogenation) (Ref. 8064)			Minor degradation products of linoleate hydroperoxide in the presence of Fe(III)-cystein(Ref. 8013). A degradation product of hydroperoxymethyllinoleate in the presence of di-t-butyl diperoxyoxalate or Co(II)(Ref. 8058). Reaction products bstween hydroperoxylinoleate and soy bean lipoxygenase(Ref. 8059).					[8004] / [8012] / [8013] / [8014] / [8017] / [8018] / [8045] / [8047] / [8058] / [8059] / [8064] / [8071]
619			9,10-Dihydroxy-12-Octadecenoic Acid	DFA8024	Tetsuyuki Kobayashi		C₁₈H₃₄O₄	314.460										Methyl ester(Ref. 8071)		GC-EI-MS(after methanolysis and trimethylsilylation)(Ref. 8059/8071): m/e=457[M-CH3], 441[M-OCH3], 382[M-HOTMS], 361[SMTO=CH-CH(OTMS)-(CH2)7COOCH3], 271[361-HOTMS], 259[SMTO=CH-(CH2)7COOCH3], GC-EI-MS(after methanolysis, hydrogenation and trimethylsilylation)(Ref. 8059)			Reaction products bstween hydroperoxylinoleate and soy bean lipoxygenase(Ref. 8059). A bitter substance in lecithin(Ref. 8071).					[8059] / [8071]
620			9,13-Dihydroxy-10-Octadecenoic Acid/9,13-Dihydroxy-10-Octadecenoate	DFA8025	Tetsuyuki Kobayashi		C₁₈H₃₄O₄	314.460										Trans unsaturation(980cm^-¹), olefinic(3010cm^-¹), OH(3620-3500cm^-¹)(Ref. 8017)	¹H-NMR(90MHz,CDCl3): trans olefinic protons(5.6-6.22ppm), carbinol methine protons(4.12ppm), J10-11=12.1Hz(trans unsaturation) (Ref. 8017)	GC-EI-MS(after methanolysis and trimethylsilylation)(Ref. 8059/8017/8092/8012): m/e=429[M-43], 355, 285[CH=CH-CH(OTMS) -(CH2)7COOCH3], 259[SMTO=CH-(CH2)7COOCH3], 173[SMTO=CH-(CH2)4CH3], GC-EI-MS(after methanolysis, hydrogenation and trimethylsilylation)(Ref. 8059/8092)			Reaction products bstween hydroperoxylinoleate and soy bean lipoxygenase(Ref. 8059). Autooxydation products of methyllinoleate(Ref. 8017/8092/8012).					[8012] / [8017] / [8059] / [8092]
621			9,13-Dihydroxy-11-Octadecenoic Acid/9,13-Dihydroxy-11-Octadecenoate	DFA8026	Tetsuyuki Kobayashi		C₁₈H₃₄O₄	314.460										Trans unsaturation(980cm^-¹), olefinic(3010cm^-¹), OH(3620-3500cm^-¹)(Ref. 8017)	¹H-NMR(90MHz,CDCl3): trans olefinic protons(5.6-6.22ppm), carbinol methine protons(4.12ppm), J11-12=12.1Hz(trans unsaturation) (Ref. 8017)	GC-EI-MS(after methanolysis and trimethylsilylation)(Ref. 8059/8017/8012): m/e=429[M-43], 355, 259[SMTO=CH-CH(CH2)7 COOCH3], 199[CH=CH-CH(OTMS)-(CH2)4CH3], 173[SMTO=CH-(CH2)4CH3], GC-EI-MS(after methanolysis, hydrogenation and trimethylsilylation)(Ref. 8059/8092)			Reaction products bstween hydroperoxylinoleate and soy bean lipoxygenase(Ref. 8059). Autooxydation products of methyllinoleate(Ref. 8017/8092/8012). Production mechanism(Ref. 8024/8030).					[8012] / [8017] / [8024] / [8030] / [8059] / [8092]
622			12,13-Dihydroxy-9-Octadecenoic Acid	DFA8027	Tetsuyuki Kobayashi		C₁₈H₃₄O₄	314.460										Methyl ester(Ref. 8071)		GC-EI-MS(after methanolysis and trimethylsilylation)(Ref. 8059/8071): m/e=457[M-CH3], 441[M-OCH3], 382[M-HOTMS], 299[M-173], 275[SMTO=CH-CH(OTMS)-(CH2)4CH3], 185[275-HOTMS], 173[SMTO=CH-( CH2)4CH3],GC-EI-MS(after methanolysis, hydrogenation and trimethylsilylation)(Ref. 8059)			Reaction products bstween hydroperoxylinoleate and soy bean lipoxygenase(Ref. 8059). A bitter substance in lecithin(Ref. 8071).					[8059] / [8071]
623			11,12,13-Trihydroxy-9-Octadecenoic Acid	DFA8028	Tetsuyuki Kobayashi		C₁₈H₃₄O₅	330.460										Methyl ester(CS2): cis olefin(758cm^-¹), bonded OH(3400-3240cm^-¹) (Ref. 8069)	¹H-NMR(methyl ester): C8(2.04-2.11ppm), C9, 10(5.53-5.68ppm), C11(4.23-4.65ppm), C12(3.56-3.74ppm), C13(3.26-3.48ppm)(Ref. 8069)	GC-EI-MS(after methanolysis and trimethylsilylation)(Ref. 8069): m/e=285[SMTO=CH-CH=CH-(CH2)7COOCH3], 275[SMTO=CH-CH(OTMS)-(CH2)4CH3], 185[275-HOTMS], 173[SMTO=CH-(CH2)4CH3], 387[M-173]	ORD analysis (Ref. 8069)		Oxidative products of 13-hydroperoxylinoleate(Ref. 8069).					[8069]
624			8,13-Dihydroxy-9,11-Octadecadienoic Acid	DFA8029	Tetsuyuki Kobayashi		C₁₈H₃₂O₄	312.444									Methyl ester: lMeOH/max=230nm(224nm and 238nm)(Ref. 8054/8055)	trans trans unsaturation(990-981cm^-¹)(Ref. 8054/8055)		GC-EI-MS(after methanolysis and trimethylsilylation)(Ref. 8054): m/e=455[M-CH3], 439[M-OCH3], 380[M-HOTMS], 245[SMTO=CH-(CH2)6COOCH3], 237[M-(CH2)6COOCH3-HOTMS], 173[SMTO=CH-(CH2)4CH3], GC-EI-MS(after methanolysis, hydrogenation and trimethylsilylation)(Ref. 8054): m/e=459[M-CH3], 403[M-(CH2)4CH3], 374[(CH2)4 -CH(OTMS)-(CH2)6-C(OTMS)OCH]			Reaction products between 13-Hydroperoxylinoleate and human hemoglobin in EtOH(Ref. 8054). Autooxydation products of linoleic acid in EtOH-water(Ref. 8055).					[8054] / [8055]
625			9,14-Dihydroxy-10,12-Octadecadienoic Acid	DFA8030	Tetsuyuki Kobayashi		C₁₈H₃₂O₄	312.444												GC-EI-MS(after methanolysis and trimethylsilylation)(Ref. 8055): m/e=455[M-CH3], 439[M-OCH3], 413[M-(CH2)CH3], 323[413-HOTMS], 313[M-(CH2)7COOCH3], 259[SMTO=CH-(CH2)7COOCH3], 159[SMTO=CH- (CH2)3CH3]/ GC-EI-MS(after methanolysis, hydrogenation and trimethylsilylation)(074): m/e=459[M-CH3], 417[M-(CH2)3CH3], 388[(CH2)4-CH(OTMS)-(CH2)7COOCH3]			Autooxydation products of linoleic acid in EtOH-water(Ref. 8055).					[8055]
626			9,10,13-Trihydroxy-11-Octadecenoic Acid/9,10,13-Trihydroxy-11-Octadecenoate	DFA8031	Tetsuyuki Kobayashi		C₁₈H₃₄O₅	330.460		It showed a toxicity corresponding to linoleate monohydroxyperoxide(Ref. 8045/8047).								Methyl ester: olefinic trans unsaturation(990-965cm^-¹), free OH(3620-3595 cm^-¹), bonded OH(3640-3160cm^-¹) (Ref. 8059/8017/8056/8069/8009/8071/8066)	¹H-NMR(methyl ester)(Ref. 8017/8009): olefinic protons(5.76ppm), C10, 13(3.7-4.2ppm) C9(3.2-3.6ppm), OH(3.6ppm)	GC-EI-MS(after methanolysis and trimethylsilylation)(Ref. 8059/8017/8056/8069/8009/8066/8012): m/e=545[M-CH3], 529[M-OCH3], 259[SMTO=CH-(CH2)7COOCH3], 173[SMTO=CH-(CH2)4CH3], 387[M-173], 298[387-HOTMS]GC-EI-MS(after methanolysis, trimethylsilylation and isopropyliden derivative treatment)(Ref. 8056), GC-EIMS(after methanolysis, hydrogenation and trimethylsilylation)(Ref. 8009/8092): m/e=562[M], 547[M-CH3]	ODR analysis (Ref. 8069)		Reaction products between hydroperoxylinoleate and soy bean lipoxygenase(Ref. 8059) or potato extracts(Ref. 8066). Oxidative products of 13-hydroperoxylinoleate(Ref. 8069). A degradation product of 13-hydroperoxylinoleate in the presence of Fe(III)-cystein(Ref. 8013).					[8009] / [8012] / [8013] / [8017] / [8045] / [8047] / [8056] / [8059] / [8066] / [8069] / [8071] / [8092]
627			9,12,13-Trihydroxy-10-Octadecenoic Acid/9,12,13-Trihydroxy-10-Octadecenoate	DFA8032	Tetsuyuki Kobayashi		C₁₈H₃₄O₅	330.460		It showed a toxicity corresponding to linoleate monohydroxyperoxide(Ref. 8045/8047).								Methyl ester: olefinic trans unsaturation(990-965 cm^-¹), free OH(3620-3595 cm^-¹), bonded OH(3640-3160cm^-¹)(Ref. 8059/8017/8056/8009/8071)	¹H-NMR(methyl ester)(Ref. 8017/8069/8009):olefinic protons(5.74-5.86ppm), C9, 12(3.7-4.2ppm), C13(3.2-3.77ppm), OH(3.6ppm)	GC-EI-MS(after methanolysis and trimethylsilylation)(Ref. 8059/8017/8056/8069/8009/8066/8012): m/e=545[M-CH3], 529[M-OCH3], 460[rearrangment peak], 259[SMTO=CH-(CH2)7COOCH3], 173[SMTO=CH-(CH2)4CH3], 387[M-173], 301[M-259], 298[M-HOTMS], GC-EI-MS(after methanolysis, trimethylsilylation and isopropylidene treatment), GC-EI-MS(after methanolysis, hydrogenation and trimethylsilylation)	ODR analysis (Ref. 8069)		Reaction products between hydroperoxylinoleate and soy bean lipoxygenase(Ref. 8059) or potato extracts(Ref. 8066). Major reactive products between 13-hydroperoxylinoleate and hemathin(Ref. 8124). Oxidative products of 13-hydroperoxylinoleate(Ref. 8069). A degradation product of 13-hydroperoxylinoleate in the presence of Fe(III)-cystein(Ref. 8013).					[8009] / [8012] / [8013] / [8017] / [8045] / [8047] / [8056] / [8059] / [8066] / [8069] / [8071] / [8124]
628			13-Hydroxy-8-Methoxy-9,11-Octadecadienoic Acid	DFA8033	Tetsuyuki Kobayashi		C₁₉H₃₄O₄	326.471									lMeOH/max=230mm(Ref. 8054)			GC-EI-MS(after methanolysis and trimethylsilylation)(Ref. 8054): m/e=397[M-CH3], 380[M-CH3OH], 341[M-(CH2)4CH3], 322[M-HOTMS], 309[M-(CH2)4CH3-CH3OH], 269[M-(CH2)6COOCH3], 237[269-CH3OH], 187[CH3OCH-(CH2)6COOCH3], 179[269-HOTMS], 173[SMTO=CH-(CH2)4CH3], 133[CH3O-CH=OTMS]			Reaction products between 13-hydroperoxylinoleate and human hemoglobin in MeOH(Ref. 8054).					[8054]
629			12-Hydroxy-11,13-Dimethoxy-9-Octadecenoic Acid	DFA8034	Tetsuyuki Kobayashi		C₂₀H₃₈O₅	358.513										Methyl ester(CS2)(Ref. 8070): cis olefin(756cm^-¹), bonded OH(3460cm^-¹), free OH(3555cm^-¹)	¹H-NMR(methyl ester;CDCl3,300MHz)(Ref. 8070): C9(5.70ppm), C10(5.27ppm), C11(3.98ppm), C12(3.56ppm), C13(3.13ppm), OH(2.48ppm), C11OCH3(3.36ppm), C13OCH3(3.28ppm), J9-10=11.2Hz(cis unsaturation)	GC-EI-MS(after methanolysis and trimethylsilylation)(Ref. 8070): m/e=329[M-CHOCH3(CH2)4CH3], 309[M-CH3(CH2)4-2CH3OH], 227[CHOCH3CH=CH(CH2)7COOCH3], 217[M-227](standard peak), 300[227+TMS], 115[CHOCH3(CH2)4CH3]	ORD analysis(Ref. 8070)		Oxidative products of 13-hydroperoxylinoleate in MeH(Ref. 8070).					[8070]
630			13-Hydroxy-9,10-Dimethoxy-11-Octadecenoic Acid	DFA8035	Tetsuyuki Kobayashi		C₂₀H₃₈O₅	358.513										Methyl ester(CS2)(Ref. 8070): trans olefin(973-970cm^-¹), OH(3600 and 3440cm^-¹)	¹H-NMR(methyl ester; CDCl3, 300MHz)(Ref. 8070): C9(3.15-3.19ppm), C10(3.58-3.62ppm), C11(5.55-5.58ppm), C12(5.71ppm), C13(4.15ppm), C9OCH3(3.27-3.29ppm), C10OCH3(3.40-3.41ppm), J11-12=15.7Hz(trans unsaturation)	GC-EI-MS(after methanolysis and trimethylsilylation)(Ref. 8070): m/e=201[CHOCH3(CH2)7COOCH3](standard peak), 243[M-201] 173[SMTO=CH(CH2)4CH3]	ODR analysis(Ref. 8070)		Oxidative products of 13-hydroperoxylinoleate in MeH(Ref. 8070).					[8070]
631			13-Hydroxy-9,12-Dimethoxy-10-Octadecenoic Acid	DFA8036	Tetsuyuki Kobayashi		C₂₀H₃₈O₅	358.513										Methyl ester(CS2)(Ref. 8070): trans olefin(975cm^-¹), OH(3570 and 3460cm^-¹)	¹H-NMR(methyl ester; CDCl3,300MHz)(Ref. 8070): C9(3.54-3.55ppm), C10(5.49-5.56ppm), C11(5.40-5.58ppm), C12(3.35-3.52ppm), C13(3.46-3.71ppm), C12OCH3(3.28-3.31ppm), C9OCH3(3.25-3.27ppm), J10-11=15.7Hz(trans unsaturation)	GC-EI-MS(after methanolysis and trimethylsilylation)(Ref. 8070): m/e=173[SMTO=CH(CH2)4CH3](standard peak), 240[M-173-OCH3]	ODR analysis(Ref. 8070)		Oxidative products of 13-hydroperoxylinoleate in MeH(Ref. 8070).					[8070]
632			12,13-Dihydroxy-11-Methoxy-9-Octadecenoic Acid	DFA8037	Tetsuyuki Kobayashi		C₁₉H₃₆O₅	344.486										Methyl ester(CS2)(Ref. 8070): cis olefin(750cm^-¹), OH(3550 and 3490cm^-¹)	¹H-NMR(methyl ester; CDCl3,300MHz)(Ref. 8070): C9(5.74ppm), C10(5.37ppm), C11(4.11ppm), C12(3.62ppm), C13(3.45ppm), C11OCH3(3.27ppm), C12OH(2.39ppm), C13OH(2.70ppm), J9-10=11.2Hz(cis unsaturation)	GC-EI-MS(after methanolysis and trimethylsilylation)(Ref. 8070): m/e=227[CHOCH3CH=CH(CH2)7COOCH3], 300[227+TMS], 275[M-227], 185[275-HOTMS], 173[SMTO=CH(CH2)4CH3]			Oxidative products of 13-hydroperoxylinoleate in MeH(Ref. 8070).					[8070]
633			9-Hydroxy-10-Oxo-12-Octadecenoic Acid	DFA8038	Tetsuyuki Kobayashi		C₁₈H₃₂O₄	312.444									lEtOH/max=226nm(e=2900Å }400), lEtOH/max=277nm(e=1300Å }200) (Ref. 8067)		¹H-NMR(Ref. 8067): C9(4.21ppm), C11(3.22ppm), C12,13(5.54ppm), C14(2.00ppm)				Oxidative products of linoleate by corn germ extracts(Ref. 8067). Reaction products between 9-hydroperoxylinoleate and corn hydroperoxide isomerase(Ref. 8067). Prodaction mechanism(Ref. 8023/8067/8073/8074).					[8023] / [8067] / [8073] / [8074]
634			9-Hydroxy-12-Oxo-10-Octadecenoic Acid	DFA8039	Tetsuyuki Kobayashi		C₁₈H₃₂O₄	312.444									l EtOH /max=226nm(e=9900Å }1100),l EtOH /max=275nm(e=260Å }30) (Ref. 8067)	Trans unsaturation(973cm^-¹), conjugated C=O(1617cm^-¹), OH(3460,1070cm^-¹) (Ref. 8067)					Reaction products between 9-hydroperoxylinoleate and corn hydroperoxide isomerase(Ref. 8067). Prodaction mechanism(Ref. 8035/8067/8073/8074).					[8035] / [8067] / [8073] / [8074]
635			9-Hydroxy-13-Oxo-10-Octadecenoic Acid	DFA8040	Tetsuyuki Kobayashi		C₁₈H₃₂O₄	312.444										Metyl ester: isolated trans olefin(970cm^-¹), keto carbonyl(1717cm^-¹), OH(3460cm^-¹) (Ref. 8013/8071)	¹H-NMR(methyl ester, trans ene)(Ref. 8013): C9(4.08ppm), C10(5.56ppm), C11(5.7ppm), C12(3.11ppm), C2,14(2.33ppm)	GC-EI-MS(after methanolysis and trimethylsilylation)(Ref. 8013/8071/8068): m/e=398[M], 383[M-CH3], 367[M-OCH3], 327[M-(CH2)4CH3], 259[SMTO=CH-(CH2)7COOCH3], 241[M-(CH2)7COOCH3], 99[CH3(CH2)4CO] GC-EI-MS(after methanolysis, hydrogenation and trimethylsilylation)(Ref. 8068)			A degradation product of hydroperoxylinoleate in the presence of Fe(III)-cystein[the double bond shows trans configuration](Ref. 8013/8068). A bitter substance in lecithin(Ref. 8071). Production mechanism(Ref. 8074).					[8013] / [8068] / [8071] / [8074]
636			13-Hydroxy-9-Oxo-11-Octadecenoic Acid	DFA8041	Tetsuyuki Kobayashi		C₁₈H₃₂O₄	312.444										Metyl ester(CS2): isolated trans olefin(970cm^-¹), keto carbonyl(1717cm^-¹), OH(3460cm^-¹) (Ref. 8013/8071)	¹H-NMR(methyl ester, trans ene)(Ref. 8013): C2, 8(2.33ppm), C10(3.11ppm), C11(5.7ppm) C12(5.56ppm), C13(4.08ppm)	GC-EI-MS(after methanolysis and trimethylsilylation)(Ref. 8013/8071/8068): m/e=398[M], 383[M-CH3], 367[M-OCH3], 327[M-(CH2)4CH3], 241[M-(CH2)7COOCH3], 199[CH2CO(CH2)7COOCH3], 185[CO(CH2)7COOCH3], 173[SMTO=CH-(CH2)4CH3]GC-EI-MS(after methanolysis, hydrogenation and trimethylsilylation)(Ref. 8068)			A degradation product of hydroperoxylinoleate in the presence of Fe(III)-cystein[the double bond shows trans configuration](Ref. 8013/8068). A bitter substance in lecithin(Ref. 8071). Production mechanism(Ref. 8074). Oxidative products of 13-hydroperoxylinoleate(Ref. 8069).					[8013] / [8068] / [8069] / [8071] / [8074]
637			13-Hydroxy-10-Oxo-11-Octadecenoic Acid	DFA8042	Tetsuyuki Kobayashi		C₁₈H₃₂O₄	312.444									l EtOH /max=226nm(e=9900Å }1100), l EtOH /max=275nm(e260Å }30)(Ref. 8067)	Trans unsaturation(973cm^-¹), conjugated C=O(1617cm^-¹), OH(3460,1070cm^-¹) (Ref. 8067)	¹H-NMR(Ref. 8067): C9(2.56ppm), C11(6.28ppm), C12(6.80ppm), C13(4.29ppm)	GC-EI-MS(after methanolysis and hydrogenation)(Ref. 8067): m/e=328[M], 257[M-(CH2)4CH3], 225[257-CH3OH], 199[CO(CH2)8COOCH3], 167[199-CH3OH](standard peak), 157[(CH2)7COOCH3 or CH3(CH2)4CH(OH)-(CH2)2CO]			Oxidative products of linoleate by corn germ extracts(Ref. 8067). Reaction products between 9-hydroperoxylinoleate and corn hydroperoxide isomerase(Ref. 8067). Production mechanism(Ref. 8035/8067/8073/8074).					[8035] / [8067] / [8073] / [8074]
638			13-Hydroxy-12-Oxo-9-Octadecenoic Acid	DFA8043	Tetsuyuki Kobayashi		C₁₈H₃₂O₄	312.444									l EtOH /max=226nm(e=2900Å }400), l EtOH /max=277nm(e=1300Å }200) (Ref. 8067)		¹H-NMR(Ref. 8067): C8(2.00ppm), C9, 10(5.54ppm), C11(3.22ppm), C13(4.21ppm)				Reaction products between 13-hydroperoxylinoleate and corn hydroperoxide isomerase(Ref. 8067). Production mechanism(Ref. 8023/8035/8067/8073/8074).					[8023] / [8035] / [8067] / [8073] / [8074]
639			Methyl 9,12-Dihydroxy-13-Oxo-10-Octadecenoate	DFA8044	Tetsuyuki Kobayashi		C₁₉H₃₄O₅	342.470												GC-EI-MS(TMS)(Ref. 8056): m/e=486[M], 471[M-CH3], 455[M-OCH3], 386[M-C(O)(CH2)4CH3-H], 259[SMTO=CH-(CH2)7COOCH3]			Degradation products of radical reactions from 13-hydroperoxymethyllinoleate(Ref. 8056/8057).					[8056] / [8057]
640			Methyl 10,13-Dihydroxy-9-Oxo-11-Octadecenoate	DFA8045	Tetsuyuki Kobayashi		C₁₉H₃₄O₅	342.470												GC-EI-MS(TMS)(Ref. 8056): m/e=486[M], 471[M-CH3], 455[M-OCH3], 300[M-C(O)(CH2)7CH3-H], 173[SMTO=CH-(CH2)4CH3]			Degradation products of radical reactions from 13-hydroperoxymethyllinoleate(Ref. 8056/8057).					[8056] / [8057]
641			9-Oxo-10,12-Octadecadienoic Acid/9-Oxo-10,12-Octadecadienoate	DFA8046	Tetsuyuki Kobayashi		C₁₈H₃₀O₃	294.429		It showed a slightly lower toxicity than linoleate monohydroxyperoxide(Ref. 8045/8047).							l MeOH /max=277-278nm(e=20300),lmax=267nm(cyclohexane)(Ref. 8013/8059/8056/8071)	Trans, trans unsaturations(strong absorption at 1000-990cm^-¹), trans,cis unsaturations(960-955cm^-¹), unsaturated ketone(1695-1600cm^-¹) (Ref. 8013/8059/8056/8071/8069)	¹H-NMR(Ref. 8013/8071): C8(2.54ppm), C10, 12, 13(6.06-6.21ppm), C11(7.02-7.51ppm), C14(2.20-2.23ppm)	GC-EI-MS(after methanolysis and hydrogenation)(Ref. 8056/8071/8012/8069): m/e=308[M], 277[M-OCH3], 237[M-(CH2)4CH3], 185[C(O)(CH2)6COOCH3], 166[CH3(CH2)4-CH=CH-CH=CH-C(OH)=CH2; Maclafferty transposition] 151[M-(CH2)7COOCH3]GC-EI-MS(TMS)(Ref. 8013): m/e=366[M], 341[M-CH3], 295[ [M-(CH2)4CH3], 276[M-HOTMS]			A degradation product of hydroperoxylinoleate in the presence of Fe(III)-cystein[trans, trans; or trans, cis](Ref. 8013). A degradation product of hydroperoxymethyllinoleate in the presence of di-t-butyl diperoxyoxalate or Co(II)(Ref. 8058).					[8012] / [8013] / [8045] / [8047] / [8056] / [8058] / [8059] / [8069] / [8071]
642			13-Oxo-9,11-Octadecadienoic Acid/13-Oxo-9,11-Octadecadienoate	DFA8047	Tetsuyuki Kobayashi		C₁₈H₃₀O₃	294.429		It showed a slightly lower toxicity than linoleate monohydroxyperoxide(Ref. 8045/8047).							lMeOH/max=277-278nm(e=20300)(Ref. 8013/8059/8056)(038/078/075), l EtOH /max=278nm(Ref. 8013), lmax=267nm(cyclohexane)(Ref. 8071), DNP hydrazone: lCHCl3/max=388, 304, 265nm(Ref. 8075)	Trans, trans unsaturations(strong absorption at 1000-990cm^-¹), cis, trans unsaturations(960-955cm^-¹), unsaturated ketone(1695-1600cm^-¹)(Ref. 8013/8059/8056/8071)	¹H-NMR(Ref. 8013/8071): C8(2.20-2.23ppm), C9, 10, 12(6.06-6.21ppm), C11(7.02-7.51ppm) C14(2.54ppm)	GC-EI-MS(after methanolysis and trimethylsilylation)(Ref. 8014/8071/8012/8069): m/e=308[M], 277[M-OCH3], 252[M-CH2=C H-CH2CH3], 237[M-(CH2)4CH3], 209[M-C(O)(CH2)4CH3], 151[M-(CH2)7COOCH3], GC-EI-MS(TMS)(Ref. 8013): m/e=366[M], 341[M-CH3], 295[M-(CH2)4CH3], 276[M-HOTMS], 166[M-(CH2)6C(=O)OTMS]; REARRA			A degradation product of hydroperoxylinoleate in the presence of Fe(III)-cystein[trans, trans; or trans, cis](Ref. 8013). A degradation product of hydroperoxymethyllinoleate in the presence of di-t-butyl diperoxyoxalate or Co(II)(Ref. 8058).					[8012] / [8013] / [8014] / [8045] / [8047] / [8056] / [8058] / [8059] / [8069] / [8071] / [8075]
643			Methyl 9-Butylperoxy-10,12-Octadecadienoate	DFA8048	Tetsuyuki Kobayashi		C₂₃H₄₂O₄	382.577									lether/max=234nm(Ref. 8057)	Ester carbonyl(1740cm^-¹), trans, trans diene(991cm^-¹)(Ref. 8057)	¹H-NMR(Ref. 8057): C10-C13(5.5-6.1ppm), C9(4.1ppm), C14(2.1ppm)	GC-EI-MS(hydrogenation with palladium-charcoal)(Ref. 8057)			A degradation product of 13-hydroperoxymethyllinoleate in the presence of di-tert-butyl peroxyoxalate(Ref. 8057).					[8057]
644			Methyl 13-Butylperoxy-9,11-Octadecadienoate	DFA8049	Tetsuyuki Kobayashi		C₂₃H₄₂O₄	382.577									lether/max=234nm(Ref. 8057)	Ester carbonyl(1740cm^-¹), trans, trans diene(991cm^-¹)(Ref. 8057)	¹H-NMR(Ref. 8057): C9-C12(5.5-6.1ppm), C13(4.1ppm), C8(2.1ppm)	GC-EI-MS(hydrogenation with palladium-charcoal)(Ref. 8057)			A degradation product of 13-hydroperoxymethyllinoleate in the presence of di-tert-butyl peroxyoxalate(Ref. 8057).					[8057]
645			9-Hydroperoxy-10,12,15-Octadecatrienoic Acid/9-Hydroperoxy-10,12,15-Octadecatrienoate	DFA8050	Tetsuyuki Kobayashi		C₁₈H₃₀O₄	310.428		Pysiological damages are induced by these hydroperoxides which are incorporated into bodies or synthesized endogenously.(Ref. 8043/8044/8045/8046/8047/8048/8049). It reacts with DNA in the presence of Fe ions and ascorbic acid(Ref. 8096).							(Me-ester; after reduction; in etoh)(Ref. 8076), trans, cis, cis isomer: lmax=236nm trans, trans, cis isomer: lmax=232nm	(Me-ester; after reduction)(Ref. 8076/8077), trans, cis, cis isomer:9 88-983 AND 951-945cm^-¹; trans, trans, cis isomer: 992-983cm^-¹ (Me-ester)(Ref. 8078), OOH group: 3400cm^-¹		EI-MS(Me-ester; after reduction and hydrogenation)(Ref. 8020/8076): m/e=187[O=CH(CH2)7C(=OH)OCH3]; 158[CH2(CH2)6C(=OH)OCH3]; 155[O=CH(CH2)7C=O], GC-EI-MS(Me-ester; after reduction and TMS)(Ref. 8090/8077): m/e=380[M]; 365[M-CH3]; 223[SMTO=CH-CH=CH-CH=CH-CH2-CH=CH-CH2CH3]			Auto oxidation of linoleate(Ref. 8090/8022/8023/8021/8024/8025/8026/8027/8030/8028). Oxidation of linoleate by singlet oxygen(Ref. 8022/8023/8024/8025/8026/8027/8030). Reaction products between linoleate and linseed lipoxygenase(pH6.5, 24C)(Ref. 8016).					[8016] / [8020] / [8021] / [8022] / [8023] / [8024] / [8025] / [8026] / [8027] / [8028] / [8030] / [8043] / [8044] / [8045] / [8046] / [8047] / [8048] / [8049] / [8076] / [8077] / [8078] / [8090] / [8096]
646			12-Hydroperoxy-9,13,15-Octadecatrienoic Acid/12-Hydroperoxy-9,13,15-Octadecatrienoate	DFA8051	Tetsuyuki Kobayashi		C₁₈H₃₀O₄	310.428		Pysiological damages are induced by these hydroperoxides which are incorporated into bodies or synthesized endogenously.(Ref. 8043/8044/8045/8046/8047/8048/8049). It reacts with DNA in the presence of Fe ions and ascorbic acid(Ref. 8096).							(Me-ester;after reduction;in etoh)(Ref. 8076), cis, trans, cis isomer: lmax=233nm , cis, trans, trans isomer: lmax=232nm	(Me-ester; after reduction)(Ref. 8076/8077), cis, trans,cis isomer: 990-983 and 951-945cm^-¹; cis, trans, trans isomer: 992-983cm^-¹, (Me-ester)(Ref. 8078), OOH group: 3400cm^-¹		EI-MS(Me-ester; after reduction and hydrogenation)(Ref. 8020/8076): m/e=229[O=CH(CH2)10C(=OH)OCH3]; 200[CH2(CH2)9C(=OH)OCH3]; 197[O=CH(CH2)10C=O], GC-EI-MS(Me-ester; after reduction and TMS)(Ref. 8090/8077): m/e=380[M]; 365[M-CH3]; 183[SMTO=CH-CH=CH-CH=CH-CH2-CH3]			Auto oxidation of linoleate(Ref. 8029/8022/8023/8021/8024/8025/8026/8027/8030/8028). Oxidation of linoleate by singlet oxygen(Ref. 8022/8023/8024/8025/8026/8027/8030).				Isomerization of hydroperoxides: Positional isomers at 9, 12, 13, and 16 and their geometric isomers of cis, cis, trans- or cis, trans, trans are formed. The proportion of 9-, 16- isomers is higher than that of 12-, 13- isomers.	[8020] / [8021] / [8022] / [8023] / [8024] / [8025] / [8026] / [8027] / [8028] / [8029] / [8030] / [8043] / [8044] / [8045] / [8046] / [8047] / [8048] / [8049] / [8076] / [8077] / [8078] / [8090] / [8096]
647			13-Hydroperoxy-9,11,15-Octadecatrienoic Acid/13-Hydroperoxy-9,11,15-Octadecatrienoate	DFA8052	Tetsuyuki Kobayashi		C₁₈H₃₀O₄	310.428		Pysiological damages are induced by these hydroperoxides which are incorporated into bodies or synthesized endogenously.(Ref. 8043/8044/8045/8046/8047/8048/8049). It reacts with DNA in the presence of Fe ions and ascorbic acid(Ref. 8096).							(Me-ester; after reduction; in etoh)(Ref. 8076), cis, trans, cis isomer: lmax=233nm, trans, trans, cis isomer: lmax=232nm	(Me-ester; after reduction)(Ref. 8076/8077), cis, trans, cis isomer: 989-983 and 950-945cm^-¹; trans, trans, cis isomer: 992-983cm^-¹, (Me-ester)(Ref. 8078), OOH group: 3400cm^-¹	¹H-NMR(cis,trans,cis-isomer)(Ref. 8011): C10: 5.95ppm; C11: 6.54ppm; C12: 5.54ppm; C13: 4.38ppm; J10-11=11Hz; J11-12=15Hz[C11-12: trans]; J12-13=8Hz ¹H-NMR(cis,trans,cis-isomer; after reduction)(Ref. 8011): C10: 5.94ppm; C11: 6.49ppm; C12: 5.64ppm; C13: 4.20ppm	EI-MS(Me-ester; after reduction and hydrogenation)(Ref. 8020/8076): m/e=243[O=CH(CH2)11C(=OH)OCH3]; 214[CH2(CH2)10C(=OH)OCH3]; 211[O=CH(CH2)11C=O], GC-EI-MS(Me-ester; after reduction and TMS)(Ref. 8090/8077): m/e=380[M]; 365[M-CH3]; 311[SMTO=CH-CH=CH-CH=CH-(CH2)7-COOCH3]			Auto oxidation of linoleate(Ref. 8029/8022/8023/8021/8024/8025/8026/8027/8030/8028). Oxidation of linoleate by singlet oxygen(Ref. 8022/8023/8024/8025/8026/8027/8030). Reaction products between linoleate and soy bean lipoxygenase(pH:8.7,25					[8011] / [8016] / [8020] / [8021] / [8022] / [8023] / [8024] / [8025] / [8026] / [8027] / [8028] / [8029] / [8030] / [8043] / [8044] / [8045] / [8046] / [8047] / [8048] / [8049] / [8076] / [8077] / [8078] / [8090] / [8096]
648			16-Hydroperoxy-9,12,14-Octadecatrienoic Acid/16-Hydroperoxy-9,12,14-Octadecatrienoate	DFA8053	Tetsuyuki Kobayashi		C₁₈H₃₀O₄	310.428		Pysiological damages are induced by these hydroperoxides which are incorporated into bodies or synthesized endogenously.(Ref. 8043/8044/8045/8046/8047/8048/8049). It reacts with DNA in the presence of Fe ions and ascorbic acid(Ref. 8096).							(Me-ester; after reduction; in etoh)(Ref. 8076), cis, cis, trans isomer: lmax=236nm, cis, trans, trans isomer: lmax=232nm	(Me-ester; after reduction)(Ref. 8076/8077), cis, cis, trans isomer: 989-983 and 951-945cm^-¹; cis, trans, trans isomer: 991-983cm^-¹, (Me-ester)(Ref. 8078), OOH group: 3400cm^-¹		EI-MS(Me-ester; after reduction and hydrogenation)(Ref. 8020/8077): m/e=285[O=CH(CH2)14C(=OH)OCH3]; 256[CH2(CH2)13C(=OH)OCH3]; 253[O=CH(CH2)14C=O], GC-EI-MS(Me-ester; after reduction,tms)(Ref. 8077): m/e=380[M]; 365[M-CH3]; 351[SMTO=CH-CH=CH-CH=CH-CH2-CH=CH-(CH2)7-COOCH3]			Auto oxidation of linoleate(Ref. 8029/8022/8023/8021/8024/8025/8026/8027/8030/8028). Oxidation of linoleate by singlet oxygen(Ref. 8022/8023/8024/8025/8026/8027/8030).				Isomerization of hydroperoxides: Positional isomers at 9, 12, 13, and 16 and their geometric isomers of cis, cis, trans- or cis, trans, trans are formed. The proportion of 9-, 16- isomers is higher than that of 12-, 13- isomers.	[8020] / [8021] / [8022] / [8023] / [8024] / [8025] / [8026] / [8027] / [8028] / [8029] / [8030] / [8043] / [8044] / [8045] / [8046] / [8047] / [8048] / [8049] / [8076] / [8077] / [8078] / [8096]
649			Methyl-10-Hydroperoxy-8,12,15-Octadecatrienoate	DFA8054	Tetsuyuki Kobayashi		C₁₉H₃₂O₄	324.455		Pysiological damages are induced by these hydroperoxides which are incorporated into bodies or synthesized endogenously.(Ref. 8043/8044/8045/8046/8047/8048/8049). It reacts with DNA in the presence of Fe ions and ascorbic acid(Ref. 8096).										EI-MS(Me-ester; after reduction and hydrogenation)(Ref. 8020): m/e=201[O=CH(CH2)8C(=OH)OCH3]; 172[CH2(CH2)7C(=O)OCH3];169[O=CH(CH2)8C=O]; GC-EI-MS (Me-ester; after reduction, TMS)(Ref. 8090): m/e=271[SMTO=CH-CH=CH(CH2)6COOCH3], GC-EI-MS(Me-ester;after reduction, hydrogenation)			Oxidation of linoleate by singlet oxygen(Ref. 8022/8023/8024/8025/8026/8027/8030).				Isomerization of hydroperoxides: Positional isomers at 9, 10, 12, 13, 15, and 16 and their geometric isomers of cis, cis, trans- or cis, trans, trans are formed. The proportion of 9-, 16- isomers is higher than that of 12-, 13- isomers.	[8020] / [8022] / [8023] / [8024] / [8025] / [8026] / [8027] / [8030] / [8043] / [8044] / [8045] / [8046] / [8047] / [8048] / [8049] / [8090] / [8096]
650			Methyl-15-Hydroperoxy-9,12,16-Octadecatrienoate	DFA8055	Tetsuyuki Kobayashi		C₁₉O₃₂O₄	804.182		Pysiological damages are induced by these hydroperoxides which are incorporated into bodies or synthesized endogenously.(Ref. 8043/8044/8045/8046/8047/8048/8049). It reacts with DNA in the presence of Fe ions and ascorbic acid(Ref. 8096).										EI-MS(Me-ester; after reduction and hydrogenation)(Ref. 8020): m/e=271[O=CH(CH2)13C(=OH)OCH3]; 242[CH2(CH2)12C(=OH)OCH3]; 239[O=CH(CH2)13C=O]; GC-EI-MS(Me-ester; after reduction and hydroganation)(Ref. 8090): m/e=143[SMTO=CH-CH=CH-CH3]			Oxidation of linoleate by singlet oxygen(Ref. 8022/8023/8024/8025/8026/8027/8030).				Isomerization of hydroperoxides: Positional isomers at 9, 10, 12, 13, 15 and 16 and their geometric isomers of cis, cis, trans- or cis, trans, trans are formed. The proportion of 9-, 16- isomers is higher than that of 12-, 13- isomers.	[8020] / [8022] / [8023] / [8024] / [8025] / [8026] / [8027] / [8030] / [8043] / [8044] / [8045] / [8046] / [8047] / [8048] / [8049] / [8090] / [8096]
651			Methyl-10,12-Epidioxy-9-Hydroperoxy-13,15-Octadecadienoate	DFA8056	Tetsuyuki Kobayashi		C₁₉H₃₂O₆	356.454		It reacts with DNA in the presence of Fe ions and ascorbic acid(Ref. 8096).							Conjugated diene: lmax=231-236nm (Ref. 8078/8081/8083/8084)	OOH group: 3520 cm^-¹[free], 3700-3100cm^-¹[bonded]; olefinic protons: 3020-3000cm^-¹; CONJUGATE TRANS, CIS DIENES: 990-980cm^-¹, 955-947cm^-¹(Ref. 8079/8081/8083/8084/8085)	¹H-NMR(Ref. 8081/8084/8083): C9: 3.92-4.21; C10: 4.45-4.47; C11: 2.19-2.47, 2.81-2.87; C12: 4.77-4.80; C13: 5.57-5.62; C14: 6.65-6.68; C15: 5.96-6.65; C16: 5.50-5.55; OOH: 9.05-9.56ppm; J13-14=15Hz[C13-14 : trans]; J15-16=10Hz[C15-16: cis]13C-NMR(Ref. 8081/8084): C9: 86.0; C10, 12: 83.8, 83.0	GC-EI-MS(after reduction(PH3P) and TMS)(Ref. 8081): m/e=397[M-CH3]; 259[SMTO=CH(CH2)7COOCH3]; GC-EI-MS(after reduction with NaBH4 or KI andTMS)(Ref. 8077): m/e=259[SMTO=CH(CH2)7COOCH3]; 183[SMTO=CH-CH=CH-CH=CH-CH2CH3]			Auto oxydation of linoleate(Ref. 8081/8083). Oxydation of linoleate in the presence of Fe(III)-ascorbic acid(Ref. 8078). Photoenhancemant of linoleate peroxydation[Type II](Ref. 8084/8085). Production mechanism(Ref. 8026/8039).				Major secondary products of linolenate by autooxidation(Ref. 8026/8081). It is formed through 1, 3 cyclization of 12-peroxy radical of linolenate(Ref. 8025/8026/8027/8039/8028/8083). A level of epidioxy hydroperoxides produced by autooxidation of linolenate decreased by supplementation of antioxidants(Ref. 8094).	[8025] / [8026] / [8027] / [8028] / [8039] / [8077] / [8078] / [8079] / [8081] / [8083] / [8084] / [8085] / [8094] / [8096]
652			Methyl-13,15-Epidioxy-16-Hydroperoxy-9,11-Octadecadienoate	DFA8057	Tetsuyuki Kobayashi		C₁₉H₃₂O₆	356.454		It reacts with DNA in the presence of Fe ions and ascorbic acid(Ref. 8096).							Conjugated cis, trans diene: lmax=234-237nm, conjugated trans, trans diene: lmax=231-234nm (Ref. 8078/8081/8083/8084/8088)	OOH group: 3720-3140cm^-¹[bonded], 3530-3520cm^-¹[FREE]; olefinic protons: 3020-3000cm^-¹; conjugated cis, trans diene : 989-980cm^-¹, 955-947cm^-¹; conjugatedtrans, trans diene: 992-984cm^-¹, 955cm^-¹(Ref. 8078/8081/8083/8084/8085/8088)	¹H-NMR(Ref. 8081/8083/8084/8088): C9: 5.46-5.78; C10: 5.99-6.05; C11: 6.26-6.67; C12: 5.53- 5.62; C13: 4.75-4.84; C14: 2.23-2.47, 2.79-2.88; C15: 4.47-4.49; C16: 3.86-4.15; OOH: 8.98-9.55ppm; J9-15=10.0-11.0[cis]; J9-10=15.1-15.5[trans]; J11-12=14.5-15.4Hz[trans]	GC-EI-MS(after reduction(PH3P) and TMS-derivatization)(Ref. 8081): m/e=397[M-CH3], 131[SMTO=CHCH2CH3]; GC-EI-MS(after reduction(NaBH4 or KI) and TMS-derivatization)(Ref. 8077): m/e=311[SMTO=CH-CH=CH-CH=CH-(CH2)7COOCH3]; 131[SMTO=CHCH2CH3]			Auto oxydation of linoleate(Ref. 8081/8083). Oxydation of linoleate in the presence of Fe(III)-ascorbic acid(Ref. 8078). Photoenhancemant of linoleate peroxydation[Type II](Ref. 8084/8085). Production mechanism(Ref. 8026/8039).				Major secondary products of linolenate by autooxidation(Ref. 8026/8081). It is formed through 1, 3 cyclization of 13-peroxy radical of linolenate(Ref. 8025/8026/8027/8039/8028/8083).	[8025] / [8026] / [8027] / [8028] / [8039] / [8077] / [8078] / [8081] / [8083] / [8084] / [8085] / [8088] / [8096]
653			Methyl-10,12-Epidioxy-13-Hydroperoxy-8,15-Octadecadienoate	DFA8058	Tetsuyuki Kobayashi		C₁₉H₃₂O₆	356.454		It reacts with DNA in the presence of Fe ions and ascorbic acid(Ref. 8096).								OOH group: 3660-3150cm^-¹[bonded], 3520cm^-¹[free]; OLEFINIC PROTONS: 3020-3002cm^-¹; isolated trans unsaturation: 960cm^-¹(Ref. 8084)	¹H-NMR(105): C17[terminal methyl group attached ton the vinyl group]: 1.78ppm (Ref. 8084)	GC-EI-MS(after reduction(PH3P) and TMS-derivatization)(Ref. 8084): m/e=307[M-CH3- HOTMS]; 241[M-171]; 171[SMTO=CHCH2CH=CHCH2CH3], GC-EI-MS(after reduction, hydrogenation, and tms-derivatization)(Ref. 8084)			Photoenhancemant of linoleate peroxydation[Type II](Ref. 8084). Production of 10-hydroperoxyradical by singlet-oxygen mediated oxydation of linolate via 1,3-cyclization(Ref. 8026/8084).					[8026] / [8084] / [8096]
654			Methyl-13,15-Epidioxy-12-Hydroperoxy-9,16-Octadecadienoate	DFA8059	Tetsuyuki Kobayashi		C₁₉H₃₂O₆	356.454		It reacts with DNA in the presence of Fe ions and ascorbic acid(Ref. 8096>.								OOH GROUP: 3660-3150cm^-¹[bonded], 3520cm^-¹[free]; olefinic protons: 3020-3002cm^-¹; isolated trans unsaturation: 960cm^-¹(Ref. 8084)	¹H-NMR(Ref. 8084)	GC-EI-MS(after reduction(PH3P) and TMS-derivatization)(Ref. 8084): m/e=307[M-CH3- HOTMS]; 299[SMTO=CHCH2CH=CH(CH2)7COOCH3]; 113[M-299]; GC-EI-MS(after reduction, hydrogenation and TMS-derivatization)(Ref. 8084): m/e=457[M-CH3-HOTMS]			Photoenhancemant of linoleate peroxydation[Type II](Ref. 8084). Production of 10-hydroperoxyradical by singlet-oxygen mediated oxydation of linolate via 1,3-cyclization(Ref. 8026/8084).					[8026] / [8084] / [8096]
655			Methyl-9,12-Dihydroperoxy-10,13,15-Octadecatrienoate	DFA8060	Tetsuyuki Kobayashi		C₁₉H₃₂O₆	356.454		It reacts with DNA in the presence of Fe ions and ascorbic acid(Ref. 8096).							Conjugated diene: lmax=233-235nm(Ref. 8081/8084)	OOH group: 3712-3140cm^-¹[bonded], 3530-3510cm^-¹[free]; olefinic protons: 3005cm^-¹; conjugated trans, cis diene: 988-979cm^-¹, 953-935cm^-¹; isolated trans unsaturation: 968-960cm^-¹(Ref. 8081/8084)	¹H-NMR(Ref. 8081/8084): C2: 2.3ppm; C8, 17: 1.8-2.2ppm; C9, 12: 4.40-4.42, 4.86ppm; C10, 11, 13, 14, 15, 16: 5.26-6.28ppm; C18: 1.02ppm; OOH: 8.07ppm	GC-EI-MS(after reduction and TMS-derivatization)(Ref. 8084): m/e=453[M-CH3]; 437[M-OCH3]; 378[M-HOTMS]; 311[M-(CH2)7COOCH3]; 221[311-HOTMS]; 157[(CH2)7COOCH3], GC-EI-MS(after reduction, hydrogenation and TMS-derivatization)(102) m/e=443[M-OCH3]			It is produced from a 9-hydroperoxy isomer during autooxidation of linoleate(Ref. 8025/8026/8081). It is produced from 9- or 12-hydroperoxy isomer during oxidation of linoleate by singlet-oxygen (Ref. 8026/8084/8085).					[8025] / [8026] / [8081] / [8084] / [8085] / [8096]
656			Methyl-9,16-Dihydroperoxy-10,12,14-Octadecatrienoate	DFA8061	Tetsuyuki Kobayashi		C₁₉H₃₂O₆	356.454		It reacts with DNA in the presence of Fe ions and ascorbic acid(Ref. 8096).							Conjugated triene: lmax=258-260, 268-269, 278-280nm(Ref. 8078/8081/8084)	OOH group: 3712-3140cm^-¹[bonded], 3530-3510cm^-¹[free]; olefinic protons: 3005cm^-¹; conjugated trans, cis, trans triene: 960cm^-¹; conjugated trans, trans, trans triene: 996-991cm^-¹(Ref. 8078/8081/8084)	¹H-NMR(Ref. 8081/8084): C2: 2.30-2.37ppm; C8,17: 1.50-1.85ppm; C9, 16: 4.34-4.42ppm; C10, 11, 12, 13, 14, 15: 5.25-6.90ppm; C18: 0.94-0.95ppm; OOH:7.70-7.94ppm	GC-EI-MS(after reduction and TMS-derivatization)(Ref. 8084), GC-EI-MS(after reduction, hydrogenation and TMS-derivatization)(Ref. 8078/8084), GC-EIMS(after reduction,hydrogenation and TBDMS-derivatization)(Ref. 8078),CI-MS(Ref. 8089)			It is produced from 9- or 16-hydroperoxy isomer during autooxidation of linoleate(Ref. 8025/8026/8078/8081). Oxidation of linoleate in presence of Fe(III)-ascorbic acid(Ref. 8078). It is produced from 9- or 16-hydroperoxy isomer during oxidation of linoleate by singlet-oxygen(Ref. 8026/8084/8085).					[8025] / [8026] / [8078] / [8081] / [8084] / [8085] / [8089] / [8096]
657			Methyl-13,16-Dihydroperoxy-9,11,14-Octadecatrienoate	DFA8062	Tetsuyuki Kobayashi		C₁₉H₃₂O₆	356.454		It reacts with DNA in the presence of Fe ions and ascorbic acid(Ref. 8096).							Conjugated diene: lmax=233-235nm(Ref. 8081/8084)	OOH group: 3712-3140cm^-¹[bonded], 3530-3510cm^-¹[free]; olefinic protons: 3005cm^-¹; conjugated cis, trans diene: 988-979cm^-¹, 953-935cm^-¹; isolated trans unsaturation: 968-960cm^-¹(Ref. 8081/8084)	¹H-NMR(Ref. 8081/8084): C2: 2.3ppm; C8, 17: 1.8-2.2ppm; C9, 10, 11, 12, 14, 15: 5.26-6.28ppm, C13, 16: 4.40-4.42ppm; C18: 1.02ppm; OOH: 8.07ppm	GC-EI-MS(after reduction and TMS-derivatization)(Ref. 8084): m/e=453[M-CH3]; 439[M -CH2CH3]; 437[M-OCH3]; 378[M-HOTMS]; 143[(CH2)6C00CH3], GC-EI-MS(after reduction, hydrogenation and TMS-derivatization)(102) m/e=443[M-OCH3]; 315[SMTO=CH(CH2)11COOCH3]			It is produced from a 16-hydroperoxy isomer during autooxidation of linoleate(Ref. 8025/8026/8081). It is produced from 13- or 16-hydroperoxy isomer during oxidation of linoleate by singlet-oxygen(Ref. 8026/8084/8085).					[8025] / [8026] / [8081] / [8084] / [8085] / [8096]
658			Methyl-10,12-Dihydroperoxy-8,13,15-Octadecatrienoate	DFA8063	Tetsuyuki Kobayashi		C₁₉H₃₂O₆	356.454		It reacts with DNA in the presence of Fe ions and ascorbic acid(Ref. 8096).							Conjugated diene: lmax=231-233nm(Ref. 8084)	OOH group: 3700-3140cm^-¹[bonded], 3520-3510cm^-¹[free]; conjugated trans, cis diene: 985-979cm^-¹, 953-935cm^-¹; isolated trans unsaturation: 968-960cm^-¹(Ref. 8084)	¹H-NMR(Ref. 8084): C2, 7, 11, 17: 1.8-2.5ppm; C8, 9, 13, 15, 16: 5.3-6.1ppm; C10, 12: 4.49- 4.51ppm; C14: 6.60-6.63ppm; C18: 1.01-1.10ppm; OOH: 8.02-8.05ppm	GC-EI-MS(after reduction and TMS-derivatization)(Ref. 8084): m/e=468[M]; 453[M-OCH3]; 437[M-OC H3]; 378[M-HOTMS]; 271[SMTO=CHCH=CH(CH2)6COOCH3]; 183[SMTO=CHCH=CHCH=CHCH2 CH3]; CI-MS(110) m/e=339[M+H-H20]; 323[M-OOH]; 305[323-H20]; 199[CHOCH=CH(CH2)6COOCH3+H]			It is produced from 10- or 12-hydroperoxy isomer during oxidation of linoleate by singlet-oxygen(Ref. 8026/8084/8085).					[8026] / [8084] / [8085] / [8096]
659			Methyl-13,15-Dihydroperoxy-9,11,16-Octadecatrienoate	DFA8064	Tetsuyuki Kobayashi		C₁₉H₃₂O₆	356.454		It reacts with DNA in the presence of Fe ions and ascorbic acid(Ref. 8096).							Conjugated diene: lmax=234-235nm(Ref. 8084)	OOH group: 3700-3140cm^-¹[bonded], 3520-3510cm^-¹[free]; conjugated cis, trans diene: 985-979cm^-¹, 953-935cm^-¹; isolated trans unsaturation: 968-960cm^-¹(Ref. 8084)	¹H-NMR(Ref. 8084): C2: 2.31-2.32ppm; C8, 14: 1.8-2.2ppm; C9, 10, 12, 16, 17: 5.25-6.20ppm; C11: 6.63ppm; C13, 15: 4.48-4.50ppm; C18: 1.8ppm; OOH: 7.94-8.08ppm(Ref. 8084)	GC-EI-MS(after reduction and TMS-derivatization)(Ref. 8084): m/e=468[M]; 453[M-OCH3]; 437[M-OCH3]; 378[M-HOTMS]; 311[SMTO=CHCH=CHCH=CH(CH2)7COOCH3]; 143[SMTO=CHCH=CHCH3]			It is produced from 13- or 15-hydroperoxy isomer during oxidation of linoleate by singlet-oxygen(Ref. 8026/8084/8085).					[8026] / [8084] / [8085] / [8096]
660			Methyl-10,16-Dihydroperoxy-8,12,14-Octadecatrienoate	DFA8065	Tetsuyuki Kobayashi		C₁₉H₃₂O₆	356.454		It reacts with DNA in the presence of Fe ions and ascorbic acid(Ref. 8096).							Conjugated diene: lmax=232nm(Ref. 8084)	OOH group: 3700-3140cm^-¹[bonded], 3520-3510cm^-¹[free]; conjugated cis,trans diene: 985-979cm^-¹, 953-935cm^-¹; isolated trans unsaturation: 968-960cm^-¹(Ref. 8084)	¹H-NMR(Ref. 8084): C2: 2.31ppm; C7, 11, 17: 2.08ppm; C8, 9, 12, 13, 15: 5.25-6.25ppm; C10, 16: 4.34ppm; C14: 6.55ppm; C18: 0.93ppm; OOH: 8.04ppm(Ref. 8084)	GC-EI-MS(after reduction and TMS-derivatization)(Ref. 8084): m/e=468[M]; 439[M-CH2CH3]; 437[M-OCH3]; 378[M-HOTMS]; 349[439-HOTMS]; 271[SMTO=CHCH=CH(CH2)6COOCH3]; 197[M-271]; CI-MS(110): m/e=339[M+H-H20]; 323[M-OOH]; 305[323-H2O]; 199[CHOCH=CH(CH2)6COOCH3+H]			It is produced from 10- or 16-hydroperoxy isomer during oxidation of linoleate by singlet-oxygen(Ref. 8026/8084/8085).					[8026] / [8084] / [8085] / [8096]
661			Methyl-9,15-Dihydroperoxy-10,12,16-Octadecatrienoate	DFA8066	Tetsuyuki Kobayashi		C₁₉H₃₂O₆	356.454		It reacts with DNA in the presence of Fe ions and ascorbic acid(Ref. 8096).							Conjugated diene: lmax=237nm(Ref. 8084)	OOH group: 3700-3140cm^-¹[bonded], 3520-3510cm^-¹[free]; conjugated trans, cis diene: 985-979cm^-¹, 953-935cm^-¹; isolated trans unsaturation: 968-960cm^-¹(Ref. 8084)	¹H-NMR(Ref. 8084): C2: 2.31ppm; C8, 14: 1.75-1.85ppm; C9, 15: 4.40ppm; C10, 11, 12, 13, 16, 17: 5.25-6.90ppm; C18: 1.8ppm; OOH: 7.83-7.88ppm(Ref. 8084)	GC-EI-MS(after reduction and TMS-derivatization)(Ref. 8084): m/e=157[(CH2)7COOCH3] 143[SMTO=CHCH=CHCH3]			It is produced from 9- or 15-hydroperoxy isomer during oxidation of linoleate by singlet-oxygen(Ref. 8026/8084/8085).					[8026] / [8084] / [8085] / [8096]
662			Methyl-10,12,13,15-Bisepidioxy-9-Hydroperoxy-16-Octadecenoate	DFA8067	Tetsuyuki Kobayashi		C₁₉H₃₂O₈	388.453		It reacts with DNA in the presence of Fe ions and ascorbic acid(Ref. 8096).								OOH group: 3700-3150cm^-¹[bonded], 3530cm^-¹[free], isolated trans unsaturation: 960cm^-¹(Ref. 8084)	¹H-NMR(Ref. 8084): C2: 2.3ppm; C9: 3.88ppm[C9-10 erythro], 4.17ppm[C9-10 threo]; C10, 12, 13, 15: 4.47ppm; C11, 14: 2.1-2.8ppm; C16: 5.88ppm; C17: 5.35ppm; C18: 1.73ppm; OOH: 8.73ppm[C9-10 erythro], 9.20ppm[C9-10 threo] (Ref. 8084)	GC-EI-MS(after reduction(PH3P) and TMS-derivatization)(Ref. 8084): m/e=259[SMTO=CH(CH2)7COOCH3]; 185[M-259]; GC-EI-MS(after reduction, hydrogenation, and TMS-derivatization)(105): m/e=261[SMTO=CHCH2CH(OTMS)(CH2)2CH3]; 259[SMTO=CH(CH2)7COOCH3]			It is produced from a 15-peroxyradical by singlet-oxygen mediated oxidation of linoleate via succesive 1,3-cyclization(Ref. 8026/8039/8084).					[8026] / [8039] / [8084] / [8096]
663			Methyl-10,12,13,15-Bisepidioxy-16-Hydroperoxy-8-Octadecenoate	DFA8068	Tetsuyuki Kobayashi		C₁₉H₃₂O₈	388.453		It reacts with DNA in the presence of Fe ions and ascorbic acid(Ref. 8096).								OOH group: 3700-3150cm^-¹[bonded], 3530cm^-¹[free]; isolated trans unsaturation: 960cm^-¹(Ref. 8084)	¹H-NMR(Ref. 8084): C2: 2.3ppm; C8: 5.35ppm; C9: 5.88ppm; C10, 12, 13, 15: 4.47ppm; C11, 14: 2.1-2.8ppm; C16: 3.88ppm[C15-16 erythro], 4.17ppm[C15-16 threo]; C18: 1.05ppm; OOH: 8.73ppm[C15-16 erythro], 9.20ppm[C15-16 threo] (Ref. 8084)	GC-EI-MS(after reduction(PH3P) and TMS-derivatization)(105): m/e=313[M-131]; 131[SMTO=CHCH2CH3]; GC-EI-MS(after reduction,hydrogenation, and TMS-derivatization)(Ref. 8084): m/e=349[SMTO=CHCH2CH(OTMS)CH(OTMS)CH2CH3]; 273[SMTO=CH(CH2)8COOCH3]			It is produced from a 10-peroxyradical by singlet-oxygen mediated oxidation of linoleate via succesive 1,3-cyclization(Ref. 8026/8039/8084).					[8026] / [8039] / [8084] / [8096]
664			Methyl-11-(3,5-Epidioxy-2-Ethylcyclopentyl)-9-Hydroperoxy-10-Undecenoate	DFA8069	Tetsuyuki Kobayashi		C₁₉H₃₂O₆	356.454		It reacts with DNA in the presence of Fe ions and ascorbic acid(Ref. 8096).								OOH group: 3620-3010cm^-¹[bonded], 3520cm^-¹[free]; isolated trans unsaturation: 960cm^-¹(Ref. 8084)	¹H-NMR(Ref. 8086/8087): C9: 4.26-4.35; C10: 5.47-5.52; C11: 5.44-6.03; C12: 2.66-2.92; C13: 4.42-4.53; C15: 4.53-4.66; C16: 1.90-2.16; OOH: 7.89-7.94; 13C-NMR(Ref. 8086/8087): C9: 86.3-86.6; C10: 129.8-132.4; C11: 132.4-135.0; C12: 45.9-50.8; C13: 79.8-80.5C14: 39.3-44.1; C15: 81.7-83.0;	EI-MS(after reduction and TMS)(Ref. 8087): m/e=543[M-CH3]; 468[M-HOTMS]; 401[M-(CH2)7COOCH3]; 378[M-2xHOTMS]; 352[468-SMTO=CHCH2]; 323[352-CH2CH3]; 285[CH=CHCH(OTMS)(CH2)7COOCH3]; 259[SMTO=CH(CH2)7COOCH3]; 217[SMTO-CH=CH-CH=OTMS]			Photoenhancement of linoleate peroxidation(TypeII)(Ref. 8026/8039/8084). It is produced from a 13-peroxyradical of linoleate via 1,3-cyclization(Ref. 8026/8039/8084/8086/8087).					[8026] / [8039] / [8084] / [8086] / [8087] / [8096]
665			Methyl-8-[3,5-Epidioxy-2-(3-Hydroperoxy-1-Pentenyl)Cyclopentyl]Octanoate	DFA8070	Tetsuyuki Kobayashi		C₁₉H₃₂O₆	356.454		It reacts with DNA in the presence of Fe ions and ascorbic acid(Ref. 8096).								OOH group: 3620-3010cm^-¹[bonded], 3520cm^-¹[free]; isolated trans unsaturation: 960cm^-¹(Ref. 8084)		GC-EI-MS(after reduction and hydrogenation and TMS-derivatization)(Ref. 8084): m/e=545[M-CH3]; 455[545-HOTMS]; 401[M-(CH2)2CH(OTMS)CH2CH3]; 131[SMTO=CHCH2CH3]			Photoenhancement of linoleate peroxidation(TypeII)(Ref. 8026/8039/8084). It is produced from a 12-peroxyradical of linoleate via 1,3-cyclization(Ref. 8026/8039/8084).					[8026] / [8039] / [8084] / [8096]
666			Methyl-9,10-Epoxy-12,15-Octadecadienoate	DFA8071	Tetsuyuki Kobayashi		C₁₉H₃₂O₃	308.456										Cis unsaturation: 3002cm^-¹(Ref. 8081)	GC-EI-MS(Ref. 8084): m/e=308[M]; 277[M-OCH3]; 199[CH-(O)-CH(CH2)7COOCH3]; 171[199-28]; 151[M-(CH2)7COOCH3]; 123[151-28]; GC-EI-MS(after hydrogenation)(Ref. 8084): m/e=281[M-OCH3]; 199[CH-(O)-CH(CH2)7COOCH3]; 171[199-28]; 155[M-(CH2)7COOCH3]127[155-28]				Autooxidation of linoleate(Ref. 8081). Photoenhancement of linoleate peroxidation(Ref. 8084).					[8081] / [8084]
667			Methyl-12,13-Epoxy-9,15-Octadecadienoate	DFA8072	Tetsuyuki Kobayashi		C₁₉H₃₂O₃	308.456										Cis unsaturation: 3002cm^-¹(Ref. 8081)	¹H-NMR(Ref. 8081): cis unsaturationS: 5.43ppm[4H]; cis epoxide ring:2.79 AND 2.98ppm[2H]	GC-EI-MS(Ref. 8084): m/e=308[M]; 277[M-OCH3]; 211[CH-(O)-CHCH2CH=CH(CH2)7COOCH3-28] 83[M-CH2CH=CH(CH2)7COOCH3-28], GC-EI-MS(after hydrogenation)(105): m/e=281[M-OCH3]; 241[CH-(O)-CH(CH2)10CO OCH3]; 213[214-28]; 113[M-(CH2)10COOCH3]; 85[113-28]			Autooxidation of linoleate(Ref. 8081). Photoenhancement of linoleate peroxidation(Ref. 8084).					[8081] / [8084]
668			Methyl-15,16-Epoxy-9,12-Octadecadienoate	DFA8073	Tetsuyuki Kobayashi		C₁₉H₃₂O₃	308.456										Cis unsaturation: 3002cm^-¹(Ref. 8081)	¹H-NMR(Ref. 8081): cis unsaturationS: 5.43ppm[4H]; cis epoxide ring:2.79 AND 2.98ppm[2H]	GC-EI-MS(Ref. 8084): m/e=308[M]; 279[CH-(O)-CHCH2CH=CHCH2CH=CH(CH2)7COOCH3]; 277[M -OCH3]; 251[279-28]; 71[CH3CH2CH-(O)-CH]; 43[71-28]; GC-EI-MS(after hydrogenation)(105): m/e=281[M-OCH3]; 255[CH-(O)-CH(CH2)13COOCH3-28]; 71[CH3CH2CH-(O)-CH]; 43[71-28]			Auto oxidation of linoleate(Ref. 8081). Photoenhancement of linoleate peroxidation(Ref. 8084).					[8081] / [8084]
669			Methyl-10,13-Epdioxy-9-Hydroperoxy-11,15-Octadecadienoate	DFA8074	Tetsuyuki Kobayashi		C₁₉H₃₂O₆	356.454										OOH group: 3635-3300cm^-¹[bonded]; olefinic protons: 3005cm^-¹; isolated trans unsaturation: 965cm^-¹ (Ref. 8085)	¹H-NMR(Ref. 8085): C8: 1.6ppm; C9: 4.22ppm; C10: 4.65ppm; C11, 12: 5.98ppm; C13: 4.48ppm; C14: 2.0ppm; C15, 16: 5.45ppm; C17: 2.05ppm; OOH: 8.65ppm	GC-EI-MS(after reduction(PH3P) and TMS-derivatization)(Ref. 8085): m/e=412[M]; 322[M-HOTMS]; 259[SMTO=CH(CH2)7COOCH3]; 153[M-259]; 69[CH2CH=CHCH2CH3]; 55[CH=CHCH2CH3]; GC-EI-MS(after reduction, hydrogenation, and TMS-derivatization)(106): m/e=457[M-CH3-HOTMS]			It is produced from a 9-hydroperoxide isomer of linoleate by 1,4-adduct of singlet-oxygen(Ref. 8026/8085).					[8026] / [8085]
670			Methyl-12,15-Epdioxy-16-Hydroperoxy-9,13-Octadecadienoate	DFA8075	Tetsuyuki Kobayashi		C₁₉H₃₂O₆	356.454										OOH group: 3635-3300cm^-¹[bonded]; olefinic protons: 3005cm^-¹; isolated trans unsaturation: 965cm^-¹ (Ref. 8085)	¹H-NMR(Ref. 8085): C8: 2.05ppm; C9, 10: 5.45ppm; C11: 2.0ppm; C12: 4.48ppm; C13, 14: 5.98ppm; C15: 4.65ppm; C16: 4.22ppm; C17: 1.6ppm; OOH: 8.65ppm	GC-EI-MS(after reduction(PH3P) and TMS-derivatization)(Ref. 8085): m/e=412[M]; 322[M-HOTMS]; 281[M-131]; 197[CH2CH=CH(CH2)7COOCH3]; 183[CH=CH(CH2)7COOCH3]; 131[SMTO=CHCH2CH3]; GC-EI-MS(after reduction, hydrogenation and TMS-derivatization)(Ref. 8085)			It is produced from a 16-hydroperoxide isomer of linoleate by 1,4-adduct of singlet-oxygen(Ref. 8026/8085).					[8026] / [8085]
671			Methyl-10,12,13,16-Bisepidioxy-9-Hydroperoxy-14-Octadecenoate	DFA8076	Tetsuyuki Kobayashi		C₁₉H₃₂O₈	388.453											¹H-NMR(Ref. 8085): C8: 1.6ppm; C9: 4.08ppm; C10, 12, 13, 16: 4.45ppm; C11: 2.1-2.7ppm; C14, 15: 5.68ppm; OOH: 8.45ppm	GC-EI-MS(after reduction(PH3P) and TMS-derivatization)(Ref. 8085): m/e=259[SMTO=CH(CH2)7COOCH3]; 185[M-259]; GC-EI-MS(after reduction, hydrogenation, and TMS-derivatization)(Ref. 8085): m/e=389[M-259-HOTMS]; 387[M-261-HOTMS]; 297[387-HOTMS]			It is produced from 10,12-epidioxy-9-hydroperoxides by singlet-oxygen mediated oxidation of 12-peroxyradical linoleate via 1,3-cyclization(Ref. 8026/8085).					[8026] / [8085]
672			Methyl-9,12,13,15-Bisepidioxy-16-Hydroperoxy-10-Octadecenoate	DFA8077	Tetsuyuki Kobayashi		C₁₉H₃₂O₈	388.453											¹H-NMR(Ref. 8085): C9, 12, 13, 15: 4.45ppm; C10, 11: 5.68ppm; C14: 2.1-2.7ppm; C16: 4.08 ppm; C17: 1.6ppm; OOH: 8.45ppm	GC-EI-MS(after reduction(PH3P) and TMS-derivatization)(Ref. 8085): m/e=313[M-131]; 131[SMTO=CHCH2CH3]; GC-EI-MS(after reduction, hydrogenation, and TMS-derivatization)(Ref. 8085): m/e=389[SMTO=CH(CH2)2CH(OTMS)(CH2)7COOCH3]; 299[389-HOTMS]; 259[SMTO=CH(CH2)7COOCH3]			It is produced from 13,15-epidioxy-16-hydroperoxides by 1,4-adduct of singlet-oxygen mediated oxidation of 13-peroxyradical linoleate via 1,3-cyclization(Ref. 8026/8085).					[8026] / [8085]
673			Methyl-8-[2-(2-Formylvinyl)-3-Hydroxy-5-Oxocyclopentyl]Octanoate	DFA8078	Tetsuyuki Kobayashi		C₁₇H₂₆O₅	310.385										Keto carbonyl: 1740cm^-¹[the peak corresponded with ester carbonyl] conjugated aldehyde: 1688cm^-¹ (Ref. 8082)		GC-EI-MS(after reduction(NaBH4) and TMS-derivatization)(Ref. 8082): m/e=530[M]; 515[M-CH3]; 440[M-HOTMS]; 425[440-CH3]; 399[515-SMTO=CHCH2]; 324[440-SMTO= CHCH2]; 311[M-SMTOC3H5OTMS]; 243[SMTOC5H5OTMS]; 217[EMTOC3H3OTMS]; 191[SMT OCHOTMS]; 167[C6H6OTMS]			It is prodused from 12-hydroperoxy isomer via PGG-like endoperoxide during autooxidation of linoleate(Ref. 8082).					[8082]
674			5-Hydroperoxy-6,8,11,14-Eicosatetraenoic Acid/5-Hydroperoxy-6,8,11,14-Eicosatetraenoate	DFA8079	Tetsuyuki Kobayashi		C₂₀H₃₂O₄	336.466		5-HPETE generated by 5-lipoxygenase is enzymatically converted to bioactive compounds such as leukotriene and HETE(Ref. 8100/8101/8103/8104).							UV(Ref. 8099)conjugated diene: lmax=235nm, UV(Me-ester)(Ref. 8098) conjugated diene: lmax=232.5nm, UV(Me-ester; after reduction)(Ref. 8105/8114) conjugated trans, cis diene: lmax=235-236nm, conjugated trans, trans diene: lm	IR(Me-ester; after reduction)(Ref. 8105)conjugated trans, cis diene: 985, 950cm^-¹, conjugated trans, trans diene: 989cm^-¹		GC-EI-MS(Me-ester; after reduction and TMS)(Ref. 8080/8098/8114/8116/8117/8118/8119)GC-EI-MS(Me-ester; after reduction and TBDMS)(114), GC-EI-MS(Me-ester; after reduction, hydrogenation and TMS)(Ref. 8080/8098/8099/8105/8114/8116/8120)			Autooxidation of arachidonic acid(Ref. 8080/8097/8105). Oxidation of arachidonic acid by singlet-oxygen(Ref. 8098/8099). Reaction products between arachidonic acid and lipoxygenase from living cells(5-HPETE)(Ref. 8031/8100/8101/8102/8103).				Isomerization of hydroperoxides : Both 5- and 15-hydroperoxide were generated predominantly by autooxidation or singlet-oxygen mediated oxidation(Ref. 8080/8097/8106). However, the proportion of each isomer generated become almost equal by supplementation of hydrogen donor such as tocopherol(Ref. 8041/8080/8106).	[8031] / [8041] / [8080] / [8097] / [8098] / [8099] / [8100] / [8101] / [8102] / [8103] / [8104] / [8105] / [8106] / [8114] / [8116] / [8117] / [8118] / [8119] / [8120]
675			8-Hydroperoxy-5,9,11,14-Eicosatetraenoic Acid/8-Hydroperoxy-5,9,11,14-Eicosatetraenoate	DFA8080	Tetsuyuki Kobayashi		C₂₀H₃₂O₄	336.466		8-HPETE generated by 8-lipoxygenase is enzymatically converted to bioactive compounds such as leukotriene and HETE(Ref. 8100).							UV(Ref. 8099) conjugated diene: lmax=235nm, UV(Me-ester)(Ref. 8098) conjugated diene: lmax=232.5nm, UV(Me-ester; after reduction)(Ref. 8105) conjugated trans, cis diene:lmax=236nm, conjugated trans, trans diene: lmax=232.5n	IR(me-ester; after reduction)(Ref. 8105) conjugated trans, cis diene: 985, 950cm^-¹, conjugated trans, trans diene: 989cm^-¹; IR(Me-ester)(Ref. 8098): OOH group: 3400cm^-¹	¹H-NMR(Me-ester)(Ref. 8098): OOH: 8.3ppm	GC-EI-MS(Me-ester; after reduction and TMS)(Ref. 8080/8098/8116): m/e=406[M]; 316[M-HOTMS]; 65[SMTO=CHCH=CHCH=CHCH2CH=CH(CH2)4CH3]; GC-EI-MS(Me-ester; after reduction and TBDMS)(114): m/e=448[M], 391[M-(CH3)3C]; GC-EI-MS(Me-ester;after reduction, hydrogenation and TMS)	Rogenation and TBDMS)(Ref. 8098)		Autooxidation of arachidonic acid(Ref. 8080/8097/8105). Oxidation of arachidonic acid by singlet-oxygen(Ref. 8098/8099). Reaction products between arachidonic acid and lipoxygenase from living cells(8-HPETE)(Ref. 8100/8101/8102).				Isomerization of hydroperoxides : Both 5- and 15-hydroperoxide were generated predominantly by autooxidation or singlet-oxygen mediated oxidation(Ref. 8080/8097/8106). However, the proportion of each isomer generated become almost equal by supplementation of hydrogen donor such as tocopherol(Ref. 8041/8080/8106).	[8041] / [8080] / [8097] / [8098] / [8099] / [8100] / [8101] / [8102] / [8105] / [8106] / [8116]
676			9-Hydroperoxy-5,7,11,14-Eicosatetraenoic Acid/9-Hydroperoxy-5,7,11,14-Eicosatetraenoate	DFA8081	Tetsuyuki Kobayashi		C₂₀H₃₂O₄	336.466		9-HPETE generated by 9-lipoxygenase is enzymatically converted to bioactive compounds such as leukotriene and HETE(Ref. 8100).							UV(Ref. 8099) conjugated diene: lmax=235nm, UV(Me-ester)(Ref. 8098) conjugated diene: lmax=232.5nm, UV(Me-ester; after reduction)(Ref. 8105) conjugated cis, trans diene: lmax=236nm, conjugated trans, trans diene: lmax=232.	IR(me-ester; after reduction)(Ref. 8105) conjugated cis, trans diene: 985, 950cm^-¹, conjugated trans, trans diene: 989cm^-¹		GC-EI-MS(Me-ester; after reduction and TMS)(Ref. 8080/8098/8116): m/e=406[M]; 316[M-HOTMS]; 255[SMTO=CHCH=CHCH=CH(CH2)3COOCH3]; GC-EI-MS(Me-ester; after reduction and TBDMS)(114): m/e=448[M], 391[M-(CH3)3C]; GC-EI-MS(Me-ester; after reduction hydrogenation and TMS)	Rogenation and TBDMS)(Ref. 8098)		Autooxidation of arachidonic acid(Ref. 8080/8097/8105). Oxidation of arachidonic acid by singlet-oxygen(Ref. 8098/8099). Reaction products between arachidonic acid and lipoxygenase from living cells(9-HPETE)(Ref. 8100/8102).				Isomerization of hydroperoxides : Both 5- and 15-hydroperoxide were generated predominantly by autooxidation or singlet-oxygen mediated oxidation(Ref. 8080/8097/8106). However, the proportion of each isomer generated become almost equal by supplementation of hydrogen donor such as tocopherol(Ref. 8041/8080/8106).	[8041] / [8080] / [8097] / [8098] / [8099] / [8100] / [8102] / [8105] / [8106] / [8116]
677			11-Hydroperoxy-5,8,12,14-Eicosatetraenoic Acid/11-Hydroperoxy-5,8,12,14-Eicosatetraenoate	DFA8082	Tetsuyuki Kobayashi		C₂₀H₃₂O₄	336.466		11-HPETE generated by 11-lipoxygenase is enzymatically converted to bioactive compounds such as leukotriene and HETE(Ref. 8100/8101/8102/8103/8104).							UV(Ref. 8099) conjugated diene: lmax=235nm, UV(Me-ester)(Ref. 8098) conjugated diene: lmax=232.5nm, UV(Me-ester; after reduction)(Ref. 8105) conjugated trans, cis diene:lmax=236nm, conjugated trans, trans diene: lmax=232.5	IR(Ref. 8099): conjugated trans, cis diene: 985, 950cm^-¹, OOH group: 3400cm^-¹, IR(Me-ester; after reduction)(Ref. 8105)conjugated trans, cis diene: 985, 950cm^-¹, conjugated trans, trans diene: 989cm^-¹		GC-EI-MS(Me-ester; after reduction and TMS)(Ref. 8080/8098/8116), GC-EI-MS(Me-ester; after reduction and TBDMS)(114), GC-EI-MS(Me-ester; after reduction, hydrogenation and TMS)(Ref. 8080/8098/8099/8105/8120), GC-EI-MS(Me-ester; after reduction, hydrogenation and TBDMS)			Autooxidation of arachidonic acid(Ref. 8080/8097/8105). Oxidation of arachidonic acid by singlet-oxygen(Ref. 8098/8099). Reaction products between arachidonic acid and lipoxygenase from living cells(11-HPETE)(Ref. 8100/8102).				Isomerization of hydroperoxides : Both 5- and 15-hydroperoxide were generated predominantly by autooxidation or singlet-oxygen mediated oxidation(Ref. 8080/8097/8106). However, the proportion of each isomer generated become almost equal by supplementation of hydrogen donor such as tocopherol(Ref. 8041/8080/8106).	[8041] / [8080] / [8097] / [8098] / [8099] / [8100] / [8101] / [8102] / [8103] / [8104] / [8105] / [8106] / [8116] / [8120]
678			12-Hydroperoxy-5,8,10,14-Eicosatetraenoic Acid/12-Hydroperoxy-5,8,10,14-Eicosatetraenoate	DFA8083	Tetsuyuki Kobayashi		C₂₀H₃₂O₄	336.466		12-HPETE generated by 12-lipoxygenase is enzymatically converted to bioactive compounds such as leukotriene and HETE(Ref. 8100/8101/8103/8104).							UV(Ref. 8099)conjugated diene: lmax=235nm, UV(Me-ester)(Ref. 8098)conjugated diene: lmax=232.5nm, UV(Me-ester; after reduction)(Ref. 8105) conjugated cis, trans diene: lmax=236nm, conjugated trans, trans diene: lmax=232.5n	IR(Me-ester; after reduction)(Ref. 8105) conjugated cis, trans diene: 985,950cm^-¹, conjugated trans, trans diene: 989cm^-¹		GC-EI-MS(Me-ester;after reduction and TMS)(Ref. 8080/8098/8116/8117/8119):m/e= GC-EI-MS(Me-ester;after reduction and TBDMS)(Ref. 8098): GC-EI-MS(Me-ester; after reduction, hydrogenation and TMS)(Ref. 8080/8098/8099/8105/8116)			Autooxidation of arachidonic acid(Ref. 8080/8097/8105). Oxidation of arachidonic acid by singlet-oxygen(Ref. 8098/8099). Reaction products between arachidonic acid and lipoxygenase from living cells(12-HPETE)(Ref. 8031/8100/8101/8102/8103).				Isomerization of hydroperoxides : Both 5- and 15-hydroperoxide were generated predominantly by autooxidation or singlet-oxygen mediated oxidation(Ref. 8080/8097/8106). However, the proportion of each isomer generated become almost equal by supplementation of hydrogen donor such as tocopherol(Ref. 8041/8080/8106).	[8031] / [8041] / [8080] / [8097] / [8098] / [8099] / [8100] / [8101] / [8102] / [8103] / [8104] / [8105] / [8106] / [8116] / [8117] / [8119]
679			15-Hydroperoxy-5,8,11,13-Eicosatetraenoic Acid/15-Hydroperoxy-5,8,11,13-Eicosatetraenoate	DFA8084	Tetsuyuki Kobayashi		C₂₀H₃₂O₄	336.466		15-HPETE generated by 15-lipoxygenase is enzymatically converted to bioactive compounds such as leukotriene and HETE(Ref. 8100/8101/8103/8104).							UV(Ref. 8099) conjugated diene: lmax=235nm, UV(Me-ester)(Ref. 8098) conjugated diene: lmax=232.5nm, UV(Me-ester; after reduction)(Ref. 8105) conjugated cis, trans diene: lmax=236nm, conjugated trans, trans diene: lmax=232.	IR(Me-ester; after reduction)(Ref. 8105) conjugated cis, trans diene: 985, 950cm^-¹, conjugated trans, trans diene: 989cm^-¹		GC-EI-MS(Me-ester;after reduction and TMS)(Ref. 8080/8098/8115/8116) GC-EI-MS(Me-ester;after reduction and TBDMS)(Ref. 8098), GC-EI-MS(Me-ester;after reduction, hydrogenation and TMS)(Ref. 8080/8098/8099/8105/8115/8120)			Autooxidation of arachidonic acid(Ref. 8080/8097/8105). Oxidation of arachidonic acid by singlet-oxygen(Ref. 8098/8099). Reaction products between arachidonic acid and lipoxygenase from living cells(15-HPETE)(Ref. 8031/8100/8101/8102/8103).				Isomerization of hydroperoxides : Both 5- and 15-hydroperoxide were generated predominantly by autooxidation or singlet-oxygen mediated oxidation(Ref. 8080/8097/8106). However, the proportion of each isomer generated become almost equal by supplementation of hydrogen donor such as tocopherol(Ref. 8041/8080/8106).	[8031] / [8041] / [8080] / [8097] / [8098] / [8099] / [8100] / [8101] / [8102] / [8103] / [8104] / [8105] / [8106] / [8115] / [8116] / [8120]
680			6-Hydroperoxy-4,8,11,14-Eicosatetraenoic Acid/6-Hydroperoxy-4,8,11,14-Eicosatetraenoate	DFA8085	Tetsuyuki Kobayashi		C₂₀H₃₂O₄	336.466												GC-EI-MS(Me-ester; after reduction and TMS)(Ref. 8098): m/e=406[M]; 316[M-HOTMS]; GC-EI-MS(Me-ester; after reduction and TBDMS)(Ref. 8098): m/e=448[M], 391[M-(CH3)3C], GC-EI-MS(Me-ester; after reduction, hydrogenation and TMS)(Ref. 8098/8099): m/e=399[M-CH3]			Oxidation of arachidonic acid by singlet-oxygen(Ref. 8098/8099).				Isomerization of hydroperoxides : Both 5- and 15-hydroperoxide were generated predominantly by autooxidation or singlet-oxygen mediated oxidation(Ref. 8080/8097/8106). However, the proportion of each isomer generated become almost equal by supplementation of hydrogen donor such as tocopherol(Ref. 8041/8080/8106).	[8041] / [8080] / [8097] / [8098] / [8099] / [8106]
681			14-Hydroperoxy-5,8,11,15-Eicosatetraenoic Acid/14-Hydroperoxy-5,8,11,15-Eicosatetraenoate	DFA8086	Tetsuyuki Kobayashi		C₂₀H₃₂O₄	336.466												GC-EI-MS(Me-ester; after reduction and TMS)(Ref. 8098): m/e=406[M]; 316[M-HOTMS]; GC-EI-MS(Me-ester; after reduction and TBMDS)(Ref. 8098): m/e=448[M], 391[M-(CH3)3C], GC-EI-MS(Me-ester; after reduction, hydrogenation and TMS)(114/115): m/e=399[M-CH3]			Oxidation of arachidonic acid by singlet-oxygen(Ref. 8098/8099).				Isomerization of hydroperoxides: Both 5- and 15-hydroperoxide were generated predominantly by autooxidation or singlet-oxygen mediated oxidation(Ref. 8080/8097/8106). However, the proportion of each isomer generated become almost equal by supplementation of hydrogen donor such as tocopherol(Ref. 8041/8080/8106).	[8041] / [8080] / [8097] / [8098] / [8099] / [8106]
682			5,12-Dihydroperoxy-6,8,10,14-Eicosatetraenoic Acid/5,12-Dihydroperoxy-6,8,10,14-Eicosatetraenoate	DFA8087	Tetsuyuki Kobayashi		C₂₀H₃₂O₆	368.464									UV(Me-ester)(Ref. 8098) conjugated triene: 270nm and 281nm	IR(Me-ester)(Ref. 8098) OOH group: 3400cm^-¹	¹H-NMR(Me-ester)(Ref. 8098)OOH: 8.3ppm	GC-EI-MS(Me-ester;after reduction, hydrogenation and TMS-derivatization)(Ref. 8097/8098): m/e=487[M-CH3]; 401[M-(CH2)3COOCH3]; 389[M-(CH2)7CH3]; 311[401- HOTMS]; 299[389-HOTMS]; 215[SMTO=CH(CH2)7CH3]; 203[SMTO=CH(CH2)3COOCH3]			Autooxidation of arachidonic acid(Ref. 8097). In degradation products of 12-hydroperoxides of arachidonic acid in the presence of Fe(III)-ascorbic acid. Oxidation of arachidonic acid by singlet-oxygen(Ref. 8098). It is produced enzymatically from 5- or 12-HPETE in vivo(5,12-DHPETE)(Ref. 8103/8104).					[8097] / [8098] / [8103] / [8104]
683			5,15-Dihydroperoxy-6,8,11,13-Eicosatetraenoic Acid/5,15-Dihydroperoxy-6,8,11,13-Eicosatetraenoate	DFA8088	Tetsuyuki Kobayashi		C₂₀H₃₂O₆	368.464									UV(Me-ester)(Ref. 8098) conjugated diene: 236nm	IR(Me-ester)(Ref. 8098) OOH group: 3400cm^-¹	¹H-NMR(Me-ester)(Ref. 8098) OOH: 8.3ppm	GC-EI-MS(Me-ester;after reduction, hydrogenation and TMS-derivatization)(Ref. 8097/8098): m/e=487[M-CH3]; 431[M-(CH2)4CH3]; 401[M-(CH2)3COOCH3]; 341[431-H OTMS]; 311[401-HOTMS]; 203[SMTO=CH(CH2)3COOCH3]; 173[SMTO=CH(CH2)4CH3]			Autooxidation of arachidonic acid(Ref. 8097). In degradation products of 15-hydroperoxides of arachidonic acid in the presence of Fe(III)-ascorbic acid. Oxidation of arachidonic acid by singlet-oxygen(Ref. 8098). It is produced enzymatically from 15-HPETE in vivo(5,15-DHPETE)(Ref. 8103/8104).					[8097] / [8098] / [8103] / [8104]
684			8,15-Dihydroperoxy-5,9,11,13-Eicosatetraenoic Acid/8,15-Dihydroperoxy-5,9,11,13-Eicosatetraenoate	DFA8089	Tetsuyuki Kobayashi		C₂₀H₃₂O₆	368.464									UV(Me-ester)(Ref. 8098) conjugated triene: 270nm and 281nm	IR(Me-estre)(Ref. 8098)OOH group: 3400cm^-¹, IR(after reduction)(Ref. 8108) trans unsaturation: 968cm^-¹, OH group: 1040, 3540cm^-¹	¹H-NMR(Me-ester)(Ref. 8098) OOH: 8.3ppm, ¹H-NMR(after reduction)(Ref. 8108) C8, C15: 4.2ppm; OH: 6.3ppm	EI-MS(Me-ester; after reduction)(Ref. 8108): m/e=350[M]; 332[M-H2O]; 301[332-OCH3]; 261[332-(CH2)4CH3]; 209[M-CH=CH(CH2)4COOCH3]; 191[209-H2O]; GC-EI-MS(Me-ester; after reduction, hydrogenation and TMS)(Ref. 8097/8098): m/e=487[M-CH3]; 431[M-(CH2)4CH3]; 359[M-(CH2)6COOCH3]			Autooxidation of arachidonic acid(Ref. 8097). In degradation products of 15-hydroperoxides of arachidonic acid in the presence of Fe(III)-ascorbic acid. Oxidation of arachidonic acid by singlet-oxygen(Ref. 8098). It is produced enzymatically from 15-HPETE in vivo(8,15-DHPETE)(Ref. 8103/8104). It is produced from 15-HPETE by soy bean lipoxygenase(Ref. 8108).					[8097] / [8098] / [8103] / [8104] / [8108]
685			7-[3,5-Epidioxy-2-(2-Octenyl)Cyclopentyl]-5-Hydroperoxy-6-Heptenoic Acid/7-[3,5-Epidioxy-2-(2-Octenyl)Cyclopentyl]-5-Hydroperoxy-6-Heptenoate	DFA8090	Tetsuyuki Kobayashi		C₂₀H₃₂O₆	368.464												GC-EI-MS(Me-ester; after reduction and TMS)(Ref. 8080): m/e=569[M-CH3]; 494[M-HOTMS]; 483[M-(CH2)3COOCH3]; 404[M-2xHOTMS]; 378[494-SMTO=CHCH2]; 367[M-SMTOCH=CHCH=OTMS]; 203[SMTO=CH(CH2)3COOCH3]; 191[SMTO=CHOTMS]			Oxidation of arachidonic acid in the presence of hemoglobin, mioglobin(Ref. 8080) or Fe(III)- ascorbic acid(Ref. 8097).					[8080] / [8097]
686			7-[3,5-Epidioxy-2-(3-Hydroperoxy-1-Octenyl)Cycropentyl]-5-Heptenoic Acid/7-[3,5-Epidioxy-2-(3-Hydroperoxy-1-Octenyl)Cycropentyl]-5-Heptenoate	DFA8091	Tetsuyuki Kobayashi		C₂₀H₃₂O₆	368.464												GC-EI-MS(Me-ester; after reduction and TMS)(Ref. 8080): m/e=569[M-CH3]; 513[M-(CH2)4CH3]; 494[M-HOTMS]; 404[M-2xHOTMS]; 378[494-SMTO=CHCH2]; 367[M-SMTOCH=CHCH=OTMS]; 191[SMTO=CHOTMS]; 173[SMTO=CH(CH2)4CH3]; GC-EI-MS(Me-ester; after reduction, hydrogenation and TMS)			Oxidation of arachidonic acid in the presence of hemoglobin, mioglobin(Ref. 8080)or Fe(III)- ascorbic acid(Ref. 8097). It is produced from arachidonic acid by cyclooxygenase in vivo(PGG2)(Ref. 8100/8103/8104).					[8080] / [8097] / [8100] / [8103] / [8104]
687			Methyl 9,11-Epidioxy-12,15-Dihydroperoxy-5,7,13-Eicosatrienoate	DFA8092	Tetsuyuki Kobayashi		C₂₁H₃₄O₈	414.490												GC-EI-MS(after reduction, hydrogenation and TMS-derivatization)(Ref. 8097): m/e=517[M-(CH2)4CH3-HOTMS]; 483[M-CH3-2xHOTMS]; 467[M-OCH3-2xHOTMS]; 431[M-(CH2)7COOCH3-HOTMS]; 427[517-HOTMS]; 341[431-HOTMS]; 375[SMTO=CHCH2CH(OTMS)(CH2)7COOCH3]			In degradation products of 15-hydroperoxides of arachidonic acid in the presence of Fe(III)-ascorbic acid. Oxidation of arachidonic acid in the presence of Fe(III)-ascorbic acid(Ref. 8097).					[8097]
688			Methyl 6,8-Epidioxy-5,15-Dihydroperoxy-9,11,13-Eicosatrienoate	DFA8093	Tetsuyuki Kobayashi		C₂₁H₃₄O₈	414.490												GC-EI-MS(after reduction, hydrogenation and TMS-derivatization)(Ref. 8097): m/e=517[M-(CH2)4CH3-HOTMS]; 427[M-(CH2)4CH3-2xHOTMS]; 385[M-SMTO=CH(CH2)3COOCH3-HOTMS]; 359[SMTO=CH(CH2)6CH(OTMS)(CH2)4CH3]; 337[M-(CH2)4CH3-3xHOTMS]			In degradation products of 15-hydroperoxides of arachidonic acid in the presence of Fe(III)-ascorbic acid. Oxidation of arachidonic acid in the presence of Fe(III)-ascorbic acid(Ref. 8097).					[8097]
689			Methyl 6,8,9,11-Bisepidioxy-5-Hydroperoxy-12,14-Eicosadienoate	DFA8094	Tetsuyuki Kobayashi		C₂₁H₃₄O₈	414.490												GC-EI-MS(after reduction, hydrogenation and TMS-derivatization)<<>>: m/e=473[M-SMTO=CH(CH2)3COOCH3-HOTMS]; 383[M-SMTO=CH(CH2)3COOCH3-2xHOTMS]; 331[SMTO=CHCH2CH(OTMS)CH(OTMS)(CH2)3COOCH3-HOTMS]; 241[SMTO=CHCH2CH(OTMS)CH(OTMS)(CH2)3COOCH3-2xHOTMS]			In degradation products of 11-hydroperoxides of arachidonic acid in the presence of Fe(III)-ascorbic acid.
690			Methyl 4-[2-(2-Formylvinyl)-3-Hydroxy-5-Oxocyclopentanyl]Butanoate	DFA8095	Tetsuyuki Kobayashi		C₁₃H₁₉O₅	255.287										OH group: 3500cm^-¹; five-membered ring ketone: 1740cm^-¹; ester corbonyl: 1730cm^-¹; conjugated aldehyde: 1690cm^-¹; trans unsaturation: 980cm^-¹ (Ref. 8107)		GC-EI-MS(Me-ester; after reduction WITH NaBH4 and TMS-derivatization)(Ref. 8107): m/e=459[M-CH3]; 443[M-OCH3]; 384[M-HOTMS]; 373[M-(CH2)3COOCH3]; 358[459-(CH2)3COOCH3]; 294[M-2xHOTMS]; 255[M-SMTOC3H5OTMS]; 243[SMTOC5H5OTMS]; 191[SMTOCHOTMS]; 167[C6H6OTMS]			It is produced from oxidation of 8-hydroperoxides of arachidonic acid(Ref. 8107).					[8107]
691			5-Hydroperoxy-6,8,11,14,17-Icosapentaenoic Acid/5-Hydroperoxy-6,8,11,14,17-Icosapentaenoate	DFA8096	Tetsuyuki Kobayashi		C₂₀H₃₀O₄	334.450		5-Hydroperoxide derivative of icosapentaenoic acid, which is produced concomitantly with action of 15-lipoxygenase against arachidonate, is further metabolized to hydroxylate and leukotrienes, but their physiological activities remain to be clarified(Ref. 8111/8112/8113).							UV(Me-ester)(Ref. 8109): conjugated diene: lmax=235.5nm; UV(after reduction)(Ref. 8121): conjugated diene: l=max=235nm	IR(Me-ester)(Ref. 8109): OOH group: 3400cm^-¹	¹H-NMR(Ref. 8109): OOH proton: 8.5ppm	GC-EI-MS(Me-ester; after reduction and TMS-derivatization)(Ref. 8109/8118/8119/8121): m/e=404[M]; 389[M-CH3]; 314[M-HOTMS]; 303[M-(CH2)3COOCH3]; 255[M-CH2CH=CH(CH2)3CH3]; 213[303-HOTMS]; 203[SMTO=CH(CH2)3COOCH3]			Autooxidation of icosapentaenoate(Ref. 8109). Oxidation of icosapentaenoate by singlet-oxygen(Ref. 8109). Oxidation of icosapentaenoate in the presence of mioglobin(Ref. 8110). It is produced from icosapentaenoate by 5-lipoxygenate of arachidonic acid(Ref. 8111/8112/8113).				Isomerization of hydroperoxides generated from icosapentaenoete by autooxidation: the proportion of 5-, 18-isomer (outer hydroperoxides) is higher than that of other isomer (8-,9-,11-,12-,14-,15-isomer[inner hydroperoxides])(Ref. 8110).	[8109] / [8110] / [8111] / [8112] / [8113] / [8118] / [8119] / [8121]
692			Methyl 6-Hydroperoxy-4,8,11,14,17-Icosapentaenoate	DFA8097	Tetsuyuki Kobayashi		C₂₁H₃₂O₄	348.476										OOH group: 3400cm^-¹ (Ref. 8109)	¹H-NMR(Ref. 8109): OOH proton: 8.5ppm	GC-EI-MS(after reduction and TMS-derivatization)(Ref. 8109): m/e=404[M]; 389[M-CH3] 314[M-HOTMS], GC-EI-MS(after reduction, hydrogenation, and TMS-derivatization)(Ref. 8109): m/e=399[M-CH3]; 383[M-OCH3]; 367[399-CH3OH]; 299[SMTO=CH(CH2)13CH3]			Oxidation of icosapentaenoate by singlet-oxygen(Ref. 8109).					[8109]
693			Methyl 8-Hydroperoxy-5,9,11,14,17-Icosapentaenoate	DFA8098	Tetsuyuki Kobayashi		C₂₁H₃₂O₄	348.476									conjugated diene: lmax=235.5nm (Ref. 8109)	OOH group: 3400cm^-¹ (Ref. 8109)	¹H-NMR(Ref. 8109): OOH proton: 8.5ppm	GC-EI-MS(after reduction and TMS-derivatization)(Ref. 8109): m/e=404[M]; 389[M-CH3] 314[M-HOTMS], GC-EI-MS(Me-ester: after reduction, hydrogenation and TMS-derivatization)(Ref. 8109): m/e=399[M-CH3]; 383[M-OCH3]; 367[399-CH3OH]; 271[SMTO=CH(CH2)11CH3]			Autooxidation of icosapentaenoate(Ref. 8109). Oxidation of icosapentaenoate by singlet-oxygen(Ref. 8109). Oxidation of icosapentaenoate in the presence of myoglobin(Ref. 8110).				Isomerization of hydroperoxides generated from icosapentaenoete by autooxidation: the proportion of 5-, 18-isomer (outer hydroperoxides) is higher than that of other isomer (8-,9-,11-,12-,14-,15-isomer[inner hydroperoxides])(Ref. 8110).	[8109] / [8110]
694			Methyl 9-Hydroperoxy-5,7,11,14,17-Icosapentaenoate	DFA8099	Tetsuyuki Kobayashi		C₂₁H₃₂O₄	348.476									conjugated diene: lmax=235.5nm (Ref. 8109)	OOH group: 3400cm^-¹ (Ref. 8109)	¹H-NMR(Ref. 8109): OOH proton: 8.5ppm	GC-EI-MS(after reduction and TMS-derivatization)(Ref. 8109): m/e=404[M]; 389[M-CH3] 314[M-HOTMS], GC-EI-MS(Me-ester: after reduction, hydrogenation and TMS-derivatization) (125): m/e=399[M-CH3]; 383[M-OCH3]; 367[399-CH3OH]			Autooxidation of icosapentaenoate(Ref. 8109). Oxidation of icosapentaenoate by singlet-oxygen(Ref. 8109). Oxidation of icosapentaenoate in the presence of myoglobin(Ref. 8110).				Isomerization of hydroperoxides generated from icosapentaenoete by autooxidation: the proportion of 5-, 18-isomer (outer hydroperoxides) is higher than that of other isomer (8-,9-,11-,12-,14-,15-isomer[inner hydroperoxides])(Ref. 8110).	[8109] / [8110]
695			Methyl 11-Hydroperoxy-5,8,12,14,17-Icosapentaenoate	DFA8100	Tetsuyuki Kobayashi		C₂₁H₃₂O₄	348.476									conjugated diene: lmax=235.5nm (Ref. 8109)	OOH group: 3400cm^-¹ (Ref. 8109)	¹H-NMR(Ref. 8109): OOH proton: 8.5ppm	GC-EI-MS(after reduction and TMS-derivatization)(Ref. 8109): m/e=404[M]; 389[M-CH3] 314[M-HOTMS], GC-EI-MS(Me-ester: after reduction, hydrogenation and TMS-derivatization) (Ref. 8109): m/e=399[M-CH3]; 383[M-OCH3]; 367[399-CH3OH]			Autooxidation of icosapentaenoate(Ref. 8109). Oxidation of icosapentaenoate by singlet-oxygen(Ref. 8109). Oxidation of icosapentaenoate in the presence of myoglobin(Ref. 8110).				Isomerization of hydroperoxides generated from icosapentaenoete by autooxidation: the proportion of 5-, 18-isomer (outer hydroperoxides) is higher than that of other isomer (8-,9-,11-,12-,14-,15-isomer[inner hydroperoxides])(Ref. 8110).	[8109] / [8110]
696		Cucurbic acid	3-Hydroxy-2-(2-pentenyl)-cyclopentane 1-acetic acid	DFA8101	Tetsuyuki Kobayashi		C₁₂H₂₀O₃	212.285		At concentrations above 10 ^-⁶ M, cucurbic acid exhibits strong tuber-inducing activity in single-node segments of etiolated potato shoots(Ref. 8127).													Cucurbic acid is a naturally occurring metabolite of 7-epi jasmonic acid which acts as a plant growth regulator.					[8127]
697			5S,6R-dihydroxy-7E,9E,11Z,14Z-eicosatetraenoic acid	DFA8102	Tetsuyuki Kobayashi	5(S),6(R)-DiHETE	C₂₀H₃₂O₄	336.466		5(S),6(R)-DiHETE is a weak LTD 4 receptor agonist in guinea pig lung membranes(Ref. 8129). It induces guinea pig ileum contraction with an ED value of 1.3 mM.						Soluble in ethanol.	lmax:273nm e:40,000						5S,6R-DiHETE is a dihydroxy polyunsaturated fatty acid and a nonenzymatic hydrolysis product of leukotriene A 4 .		Mouse liver cytosolic epoxide hydrolase catalyzes the conversion of LTA to 5,6-DiHETE(Ref. 8128).			[8128] / [8129]
698			5S,6S-dihydroxy-7E,9E,11Z,14Z-eicosatetraenoic acid	DFA8103	Tetsuyuki Kobayashi	5(S),6(S)-DiHETE	C₂₀H₃₂O₄	336.466		5(S),6(S)-DiHETE does not have a significant leukotriene-like activity(Ref. 8130).							lmax:273nm e:40,000						5(S),6(S)-DiHETE is a dihydroxy polyunsaturated fatty acid and a nonenzymatic hydrolysis product of leukotriene A 4 .					[8130]
699			5S,15S-dihydroxy-6E,8Z,10Z,13E-eicosatetraenoic acid	DFA8104	Tetsuyuki Kobayashi	5(S),15(S)-DiHETE	C₂₀H₃₂O₄	336.466		5(S),15(S)-DiHETE potentiates the degranulation of human polymorphonuclear leukocytes in response to platelet activating factor, but not f-Met-Leu-Phe, calcium ionophore A23187, or Leukotriene B 4 (Ref. 8132). 5(S),15(S)-DiHETE is chemotactic for eosinophils with an ED₅₀ of 0.3 mM(Ref. 8133).							lmax: 243nm e: 33,500						5(S),15(S)-DiHETE is synthesized by 15-lipoxygenase from 5(S)-HETE (Ref. 8131).					[8131] / [8132] / [8133]
700			8S,15S-dihydroxy-5Z,9E,11Z,13E-eicosatetraenoic acid	DFA8105	Tetsuyuki Kobayashi	8(S),15(S)-DiHETE	C₂₀H₃₂O₄	336.466		8(S),15(S)-diHETE causes chemotaxis of human eosinophils with an ED ₅₀ of 1.5 mM but is not chemotactic for neutrophils (Ref. 8133). 8(S),15(S)-diHETE exhibits hypoalgesic activity by antagonizing the hyperalgesic activity of 8(R),15(S)-diHETE and LTB 4 when measuring nociceptive activity in the rat hindpaw model of pain <<>8134>.							lmax: 269 nm e: 40,000						8(S),15(S)-DiHETE is formed when15(S)-HETE is subjected to further oxidation by 15-lipoxygenase (Ref. 8133).					[8133]
701			()5, 6-dihydroxy-8Z,11Z,14Z-eicosatrienoic acid	DFA8106	Tetsuyuki Kobayashi	()5,6-DiHETrE	C₂₀H₃₄O₄	338.482																	Epoxide hydrolases convert the EpETrEs into vicinal diols(Ref. 8130), with the concurrent loss of much of their biological activity. ()5,6-DiHETrE is a substrate for sheep seminal vesicle cyclooxygenase, producing 5,6-dihydroxy PGE1 and F1 metabolites in vitro(Ref. 8134).			[8130] / [8134]
702			()8,9-dihydroxy-5Z,11Z,14Z-eicosatrienoic acid	DFA8107	Tetsuyuki Kobayashi	()8,9-DiHETrE	C₂₀H₃₄O₄	338.482		Epoxide hydrolases convert the EpETrEs into vicinal diols(Ref. 8130), with the concurrent loss of much of their biological activity. The 8(S),9(R)-EpETrE isomer is metabolized by platelet cyclooxygenase to form 8(S),9(R)-THETA, a trihydroxy fatty acid which may act as a renal vasoconstrictor(Ref. 8135).																		[8130] / [8135]
703			()11,12-dihydroxy-5Z,8Z,14Z-eicosatrienoic acid	DFA8108	Tetsuyuki Kobayashi	()11,12-DiHETrE	C₂₀H₃₄O₄	338.482																	Epoxide hydrolases convert the EpETrEs into vicinal diols(Ref. 8130), with the concurrent loss of much of their biological activity.			[8130]
704			()14,15-dihydroxy-5Z,8Z,11Z-eicosatrienoic acid	DFA8109	Tetsuyuki Kobayashi	()14,15-DiHETrE	C₂₀H₃₄O₄	338.482																	Epoxide hydrolases convert the EpETrEs into vicinal diols(Ref. 8130), with the concurrent loss of much of their biological activity. ()14,15-DiHETrE is the urinary metabolite of ()14(15)-EpETrE which has been documented by GC/MS to be elevated in pregnancy induced hypertension (Ref. 8136).			[8130] / [8136]
705			()5(6)-epoxy-8Z,11Z,14Z-eicosatrienoic acid	DFA8110	Tetsuyuki Kobayashi	()5(6)-EpETrE	C₂₀H₃₂O₃	320.466		In neuroendocrine cells such as the anterior pituitary and pancreatic islet, ()5(6)-EpETrE has been implicated in the mobilization of Ca ²⁺ and hormone secretion (Ref. 8138/8139).													()5(6)-EpETrE is biosynthesized in rat and rabbit liver microsomes by cytochrome P450 (Ref. 8130/8137).					[8130] / [8137] / [8138] / [8139]
706			()8(9)-epoxy-5Z,11Z,14Z-eicosatrienoic acid	DFA8111	Tetsuyuki Kobayashi	()8(9)-EpETrE	C₂₀H₃₂O₃	320.466		()8(9)-EpETrE reduces the glomerular filtration rate (GFR) through cyclooxygenase-dependent preglomerular vasoconstriction (Ref. 8140)>.()8(9)-EpETrE has been shown to play a role in the recovery of depleted Ca²⁺ pools in cultured smooth muscle cells (Ref. 8141).													()8(9)-EpETrE is biosynthesized in rat and rabbit liver microsomes by cytochrome P450 (Ref. 8130/8137). ()8(9)-EpETrE is a major P450 metabolite in the renal cortex (Ref. 8135).					[8130] / [8135] / [8137] / [8140] / [8141]
707			()11(12)-epoxy-5Z,8Z,14Z-eicosatrienoic acid	DFA8112	Tetsuyuki Kobayashi	()11(12)-EpETrE	C₂₀H₃₂O₃	320.466		()11(12)-EpETrE has been shown, along with ()8(9)-EpETrE, to play a role in the recovery of depleted Ca²⁺ pools in cultured smooth muscle cells (Ref. 8141).													()11(12)-EpETrE is biosynthesized in rat and rabbit liver microsomes by cytochrome P450 (Ref. 8130/8137).					[8130] / [8137] / [8141]
708			()14(15)-epoxy-5Z,8Z,11Z-eicosatrienoic acid	DFA8113	Tetsuyuki Kobayashi	()14(15)-EpETrE	C₂₀H₃₂O₃	320.466															()14(15)-EpETrE is biosynthesized in rat and rabbit liver microsomes by cytochrome P450 (Ref. 8130/8137).		Dramatic increases in urinary ()14,15-DiHETrE, a ()14(15)-EpETrE metabolite, have been documented by GC/MS in pregnancy induced hypertension (Ref. 8136).			[8130] / [8136] / [8137]
709			11R-hydroxy-12E,14Z-eicosadienoic acid	DFA8114	Tetsuyuki Kobayashi	11(R)-HEDE	C₂₀H₃₆O₃	324.498									lmax: 234nm e: 23,000						11(R)-HEDE is produced from 11Z,14Z-eicosadienoic acid by cyclooxygenase in a lipoxygenase-type reaction (Ref. 8142).					[8142]
710			11S-hydroxy-12E,14Z-eicosadienoic acid	DFA8115	Tetsuyuki Kobayashi	11(S)-HEDE	C₂₀H₃₆O₃	324.498									lmax: 234nm e: 23,000
711			15R-hydroxy-11Z-13E-eicosadienoic acid	DFA8116	Tetsuyuki Kobayashi	15(R)-HEDE	C₂₀H₃₆O₃	324.498									lmax: 234nm e: 23,000
712			15S-hydroxy-11Z,13E-eicosadienoic acid	DFA8117	Tetsuyuki Kobayashi	15(S)-HEDE	C₂₀H₃₆O₃	324.498		15(S)-HEDE is an inhibitor of RBL-1 cell 5-lipoxygenase with an IC₅₀ of 26 mM(Ref. 8143).							lmax: 234nm e: 23,000											[8143]
713			5S-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid	DFA8118	Tetsuyuki Kobayashi	5(S)-HEPE	C₂₀H₃₀O₃	318.450									lmax: 236nm e: 23,000						The synthesis of 5(S)-HEPE from EPA by tissue homogenates has been demonstrated (Ref. 8144/8145).					[8144] / [8145]
714			()-8-hydroxy-5Z,9E,11Z,14Z,17Z-Eicosapentaenoic acid	DFA8119	Tetsuyuki Kobayashi	()8-HEPE	C₂₀H₃₀O₃	318.450		()8-HEPE causes barnacle eggs to hatch with an IC₅₀ = 2.4 x 10^-⁶ M (Ref. 8147). Reports conflict as to whether the barnacle hatching activity is a result of the 8(R)-or the 8(S)-enantiomer (Ref. 8146/8147/8148). Apparently, only the 8(R)-HEPE induces oocyte maturation in the starfish (Ref. 8147).							lmax: 236nm e: 23,000						()8-HEPE is the major eicosanoid extract from the barnacle, E. modestus. (Ref. 8146).					[8146] / [8147] / [8148]
715			8S-hydroxy-5Z,9E,11Z,14Z,17Z-Eicosapentaenoic acid	DFA8120	Tetsuyuki Kobayashi	8(S)-HEPE	C₂₀H₃₀O₃	318.450		At a 10 nM concentration, 8(S)-HEPE causes the eggs of the barnacle, E. modestus to hatch (Ref. 8146). ()8-HETE, derived from arachidonic acid, was ineffective in egg hatching (Ref. 8146).							lmax: 236nm e: 23,000											[8146]
716			9S-hydroxy-5Z,7E,11Z,14Z,17Z-Eicosapentaenoic acid	DFA8121	Tetsuyuki Kobayashi	9(S)-HEPE	C₂₀H₃₀O₃	318.450		Almost all hydroxy-polyunsaturated fatty acids have been implicated in inflammatory reactions in humans. However, there have not been reports specifying the biological activity of 9(S)-HEPE.							lmax: 235nm e: 23,000
717			11R-hydroxy-5Z,8Z,12E,14Z,17Z-Eicosapentaenoic acid	DFA8122	Tetsuyuki Kobayashi	11(R)-HEPE	C₂₀H₃₀O₃	318.450									lmax: 236nm e: 23,000
718			11S-hydroxy-5Z,8Z,12E,14Z,17Z-Eicosapentaenoic acid	DFA8123	Tetsuyuki Kobayashi	11(S)-HEPE	C₂₀H₃₀O₃	318.450		Almost all hydroxy-polyunsaturated fatty acids have been implicated in inflammatory reactions in humans. However, there have not been reports specifying the biological activity of 11(S)-HEPE.							lmax: 236nm e: 23,000
719			12R-hydroxy-5Z,8Z,12E,14Z,17Z-Eicosapentaenoic acid	DFA8124	Tetsuyuki Kobayashi	12(R)-HEPE	C₂₀H₃₀O₃	318.450		The biological activity of 12(R)-HEPE has not been extensively documented, but may be similar to that of 12(R)-HETE (Ref. 8149/8150).							lmax: 237nm e: 23,000						12(R)-HEPE is a monohydroxy fatty acid synthesized from EPA by the eggs of the sea urchin S. purpuratus (Ref. 8204).					[8149] / [8150] / [8204]
720			12S-hydroxy-5Z,8Z,10E,14Z,17Z-eicosapentaenoic acid	DFA8125	Tetsuyuki Kobayashi	12(S)-HEPE	C₂₀H₃₀O₃	318.450									lmax: 237nm e: 23,000						12(S)-HEPE is a monohydroxy fatty acid synthesized from EPA by the action of 12-lipoxygenase.
721			15S-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid	DFA8126	Tetsuyuki Kobayashi	15(S)-HEPE	C₂₀H₃₀O₃	318.450		15(S)-HEPE generated by soybean lipoxygenation of EPA inhibits RBL-1 cell 5-lipoxygenase with an IC₅₀ of 28 mM(Ref. 8151).							lmax: 236nm e: 23,000						The biosynthesis of 15-HEPE from EPA in guinea pig epidermal enzyme preparations has been documented (Ref. 8151).					[8151]
722			3R-hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid	DFA8127	Tetsuyuki Kobayashi	3(R)-HETE	C₂₀H₃₂O₃	320.466		3(R)-HETE enhances the formation of platelet activating factor and release of arachidonic acid from human nutrophils (Ref. 8152).																		[8152]
723			5R-hydroxy-6E,8Z,11Z,14Z-eicosatetraenoic acid	DFA8128	Tetsuyuki Kobayashi	5(R)-HETE	C₂₀H₃₂O₃	320.466		5(R)-HETE is a potent chemotactic agent. 5(R)-HETE induces human neutrophil migration across cellular and noncellular barriers in a dose- and time-dependent fashion, whereas 5(S)-HETE is inactive. (Ref. 8153).							lmax: 236nm e: 27,000						5(R)-HETE is a monohydroxy polyunsaturated fatty acid produced by the nonenzymatic oxidation of arachidonic acid.					[8153]
724			5S-hydroxy-6E,8Z,11Z,14Z-eicosatetraenoic acid	DFA8129	Tetsuyuki Kobayashi	5(S)-HETE	C₂₀H₃₂O₃	320.466		5(S)-HETE is incorporated specifically into phosphatidylcholine and glycerol esters causing the inhibition of prostaglandin I₂ and E₂ synthesis in histamine or arachidonic acid stimulated human endothelial cells (Ref. 8154).							lmax: 236nm e: 27,000						5(S)-HETE is a monohydroxy polyunsaturated fatty acid produced by the action of 5-lipoxygenase on arachidonic acid.		5(S)-HETE is metabolized to 5-OxoETE by a 5-hydroxyeicosanoid dehydrogenase present in intact human polymorphonuclear leukocytes (Ref. 8155).			[8154] / [8155]
725			8R-hydroxy-5Z,9E,11Z,14Z-eicosatetraenoic acid	DFA8130	Tetsuyuki Kobayashi	8(R)-HETE	C₂₀H₃₂O₃	320.466		8(R)-HETE induces maturation of starfish oocytes at a concentration of 0.071mM (Ref. 8156). This activity if neglible in the 8(S)-enantiomer (Ref. 8156).							lmax: 237nm e: 27,000						8(R)-HETE is a metabolite of arachidonic acid by the 8-lipoxygenase pathway in marine organisms (Ref. 8156/8157).		The precursor of 8(R)-HETE, 8(R)-HpETE, is the putative intermediate in the biosynthesis of marine prostaglandins via the allene oxide synthase pathway.(Ref. 8157).			[8156] / [8157]
726			8S-hydroxy-5Z,9E,11Z,14Z-eicosatetraenoic acid	DFA8131	Tetsuyuki Kobayashi	8(S)-HETE	C₂₀H₃₂O₃	320.466		Both 8(S)- and 8(R)-HETEs activate mouse skin protein kinase C at a dose of 100mM(Ref. 8158). It activates mouse keratinocyte protein kinase C with an IC₅₀ of 100mM (Ref. 8159). 8(S)-HETE also activates PPARa selectively at concentrations as low as 0.3mM (Ref. 8160).							lmax: 237nm e: 27,000						8(S)-HETE is a major lipoxygenase product in PMA-treated mouse epidermis (Ref. 8158).		8(S)-HETE is synthesized from arachidonic acid by a 8(S)-lipoxygenase present in phorbol ester-treated mouse skin (Ref. 8158).			[8158] / [8159] / [8160]
727			9R-hydroxy-5Z,7E,11Z,14Z-eicosatetraenoic acid	DFA8132	Tetsuyuki Kobayashi	9(R)-HETE	C₂₀H₃₂O₃	320.466									lmax: 235nm e: 27,000
728			9S-hydroxy-5Z,7E,11Z,14Z-eicosatetraenoic acid	DFA8133	Tetsuyuki Kobayashi	9(S)-HETE	C₂₀H₃₂O₃	320.466									lmax: 235nm e: 27,000
729			11R-hydroxy-5Z,8Z,12E,14Z-eicosatetraenoic acid	DFA8134	Tetsuyuki Kobayashi	11(R)-HETE	C₂₀H₃₂O₃	320.466		11(R)-HETE has been associated with sea urchin fertilization and/or maturation, as well as hydroid tentacle regeneration (Ref. 8161/8162).							lmax: 235nm e: 27,000						11(R)-HETE is synthesized from arachidonic acid by novel 11(R)-lipoxygenases present in the sea urchin eggs, S.purpuratus, and the freshwater hydrozoan, H. vulgaris (Ref. 8161/8162).					[8161] / [8162]
730			11S-hydroxy-5Z,8Z,12E,14Z-eicosatetraenoic acid	DFA8135	Tetsuyuki Kobayashi	11(S)-HETE	C₂₀H₃₂O₃	320.466									lmax: 236nm e: 27,000						The synthesis of 11-HETE by rat polymorphonuclear neutrophils has been reported (Ref. 8163), but the stereochemistry of the 11-HETE produced was not defined.					[8163]
731			12R-hydroxy-5Z,8Z,10E,14Z-eicosatetraenoic acid	DFA8136	Tetsuyuki Kobayashi	12(R)-HETE	C₂₀H₃₂O₃	320.466		12(R)-HETE is the primary lipoxygenase product in invertebrates such as the sea urchin where it plays a role in reproduction physiology (Ref. 8161).1 12(R)-HETE has been isolated from several tissues in mammals, but it is controversial whether it is derived from cytochrome P450 or 12(R)-lipoxygenase metabolism, in some cases. 12(R)-HETE is a potent chemotactic factor exhibiting dose-dependent neutrophil chemotaxis with significant responses observed at doses as low as 10 ^-¹¹ M (Ref. 8164). It produces neovascularization in rabbit corneas at 0.5							lmax: 237nm e: 27,000						12(R)-HETE is produced by the action of 12(R)-lipoxygenase on arachidonic acid (Ref. 8161).		12(R)-HETE is the predominant stereoisomer produced by psoriatic skin scales and rat liver microsomal cytochrome P-450 (Ref. 8165/8166).			[8161] / [8164] / [8165] / [8166] / [8167] / [8168]
732			8R-hydroxy-4Z,6E,10Z-hexadecatrienoic acid	DFA8137	Tetsuyuki Kobayashi	8(R)-HHxTrE/2,3,4,5-tetranor 12(R)-HETE	C₁₆H₂₆O₃	266.376									lmax: 234nm e: 23,000								Metabolism of 12(R)-HETE in corneal tissue produces predominantly the compound resulting from the loss of four carbon atoms through b-oxidation from C-1 (Ref. 8169). This metabolite is 8(R)-hydroxy hexadecatrienoic acid (8(R)-HHxTrE) or 2,3,4,5-tetranor 12(R)-HETE.			[8169]
733			12-hydroxy-5Z,8Z,10E,14Z-eicosatetraenoic acid	DFA8138	Tetsuyuki Kobayashi	12(S)-HETE	C₂₀H₃₂O₃	320.466		12(S)-HETE enhances tumor cell adhesion to endothelial cells, subendothelial matrix, and fibronectin but not to type IV collagen at the concentration of 0.01mM to 0.1mM (Ref. 8171/8172).							lmax: 237nm e: 27,000								12(S)-HETE is a metabolite of arachidonic acid via the 12-lipoxygenase pathway (Ref. 8170).			[8170] / [8171] / [8172]
734			15R-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid	DFA8139	Tetsuyuki Kobayashi	15(R)-HETE	C₂₀H₃₂O₃	320.466									lmax: 236nm e: 27,000								()15-HETE, an autoxidation product of arachidonic acid, is comprised of an equal mixture of 15(R)- and 15(S)-HETE. Aspirin-inactivated human recombinant and ovine COX-2 metabolizes arachidonic acid to 15(R)-HETE (Ref. 8173/8174).			[8173] / [8174]
735			15S-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid	DFA8140	Tetsuyuki Kobayashi	15(S)-HETE	C₂₀H₃₂O₃	320.466		15(S)-HETE is a potent inflammatory mediator and agonist of tracheal mucus secretions (Ref. 8175). 15(S)-HETE also evokes contractions in a variety of blood vessels, and these responses are sensitive to thromboxane A2 receptor antagonists (Ref. 8176).							lmax: 236nm e: 27,000						15(S)-HETE is the metabolite of arachidonic acid from the 15-lipoxygenase pathway.					[8175] / [8176]
736			20-hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid	DFA8141	Tetsuyuki Kobayashi	20-HETE	C₂₀H₃₂O₃	320.466																	20-HETE is a cytochrome P metabolite of arachidonic acid (Ref. 8177). 20-HETE can be further metabolized to 20-hydroxy prostaglandin G2 and 20-hydroxy prostaglandin H2 (Ref. 8178).			[8177] / [8178]
737			5S-hydroxy-6E,8Z,11Z-eicosatrienoic acid	DFA8142	Tetsuyuki Kobayashi	5(S)-HETrE	C₂₀H₃₄O₃	322.482									lmax: 235nm e: 23,000						5(S)-HETrE is produced by the action of 5-lipoxygenase when mead acid is the substrate (Ref. 8179/8180).					[8179] / [8180]
738			8S-hydroxy-9E,11Z,14Z-eicosatrienoic acid	DFA8143	Tetsuyuki Kobayashi	8(S)-HETrE	C₂₀H₃₄O₃	322.482									lmax: 235nm e: 23,000						8(S)-HETrE is a monohydroxy polyunsaturated fatty acid produced by rabbit neutrophil lipoxygenase when dihomo-g-linolenic acid is used as a substrate (Ref. 8183).					[8183]
739			15S-hydroxy-8Z,11Z,13E-eicosatrienoic acid	DFA8144	Tetsuyuki Kobayashi	15(S)-HETrE	C₂₀H₃₄O₃	322.482		Compared to a series of hydroxypolyenoic fatty acids, 15(S)-HETrE is a more potent inhibitor of human 5-lipoxygenase from polymorphonuclear leukocytes having an IC₅₀ of 4.6mM at an arachidonic acid concentration of 5 mM (Ref. 8181). In rat basophilic leukemia cell lysates, 15(S)-HETrE inhibits 5-lypoxygenase with an IC₅₀ of 77mM (arachidonic acid concentration of 60mM) <<>8182>. 15(S)-HETrE is 10- to 20-fold less potent than 15(S)-HETE and 15(S)-HpETE under these experimental conditions (Ref. 8182).							lmax: 235nm e: 23,000						15(S)-HETrE is a hydroxy fatty acid derived from dihomo-g-linolenic acid.					[8181] / [8182]
740			12S-hydroxy-5Z,8E,10E-heptadecatrienoic acid	DFA8145	Tetsuyuki Kobayashi	12(S)-HHTrE	C₁₇H₂₈O₃	280.402		At a concentration of 0.5mM 12(S)-HHTrE stimulates prostacyclin production in human endothelial cells (Ref. 8185).							lmax: 232nm e: 33,400						12(S)-HHTrE is produced either enzymatically by thromboxane A2 synthase on thromboxane A2 or by a nonenzymatic, heme-mediated decomposition of PGH (Ref. 8184).		12(S)-HHTrE is an excellent substrate for porcine kidney 15-hydroxyprostaglandin dehydrogenase with a K value of 0.8mM (Ref. 8186). Porcine kidney 15-hydroxyprostaglandin dehydrogenase converts 12(S)-HHTrE to 12-OxoHTrE (Ref. 8186).			[8184] / [8185] / [8186]
741			13S-hydroxy-6Z,9Z,11E-octadecatrienoic acid	DFA8146	Tetsuyuki Kobayashi	13(S)-HOTrE(g)	C₁₈H₃₀O₃	294.429									lmax: 235nm e: 23,000						13(S)-HOTrE(g) is the 15-lipoxygenase product of g-linolenic acid. It is synthesized in human platelets.
742			15S-hydroperoxy-11Z,13E-eicosadienoic acid	DFA8147	Tetsuyuki Kobayashi	15(S)-HpEDE	C₂₀H₃₆O₄	340.497		Although the biological activities of 15(S)-HpEDE have not been well characterized, it is expected to behave similarly to 15(S)-HpETE.							lmax: 234nm e: 23,000						15(S)-HpEDE is a monohydroperoxy polyunsaturated fatty acid produced by the action of 15-lipoxygenase on eicosadienoic acid.
743			5S-hydroperoxy-6E,8Z,11Z,14Z,17Z-eicosadienoic acid	DFA8148	Tetsuyuki Kobayashi	5(S)-HpEPE	C₂₀H₃₀O₄	334.450									lmax: 236nm e: 23,000						5(S)-HpEPE is formed by the action of 5-lipoxygenase on eicosapentaenoic acid (Ref. 8144). Production of 5(S)-HpEPE is the committing step in the formation of 5(S)-HpEPE and the 5-series leukotrienes.					[8144]
744			12S-hydroperoxy-5Z,8Z,10E,14Z,17Z-eicosadienoic acid	DFA8149	Tetsuyuki Kobayashi	12(S)-HpEPE	C₂₀H₃₀O₄	334.450									lmax: 237nm e: 23,000
745			15S-hydroperoxy-5Z,8Z,11Z,13E,17Z-eicosadienoic acid	DFA8150	Tetsuyuki Kobayashi	15(S)-HpEPE	C₂₀H₃₀O₄	334.450									lmax: 236nm e: 23,000
746			13S-hydroperoxy-6Z,9Z,11E-octadecatrienoic acid	DFA8151	Tetsuyuki Kobayashi	13(S)-HpOTrE(g)	C₁₈H₃₀O₄	310.428									lmax: 235nm e: 23,000						13(S)-HpOTrE(g) is produced from g-linolenic acid by soybean 15-lipoxygenase (Ref. 8187).					[8187]
747			12(s)-hydroxy-16-Heptadecynoic acid	DFA8152	Tetsuyuki Kobayashi		C₁₇H₃₀O₃	282.418		12(S)-hydroxy-16-heptadecynoic acid inhibits prostaglandin w-hydroxylase with a K_i of 1.8mM (Ref. 8188).																		[8188]
748		lipoxin A₄	5S,6R,15S-trihydroxy-7E,9E,11Z,13E-eicosatetraenoic acid	DFA8153	Tetsuyuki Kobayashi	LXA4	C₂₀H₃₂O₅	352.465		LXA is equipotent to LTB in inducing superoxide generation in human neutrophils (0.1mM) (Ref. 8190). LXA4 is associated with several other biological functions including leukocyte activation, chemotaxis promotion, natural killer cell inhibition, and monocyte migration and adhesion (Ref. 8190/8191/8192).							lmax: 302nm e: 50,000						LXA4 is formed in vitro by a number of mechanisms from arachidonic acid, 15-HpETE, and leukotriene A4 (LTA4 ) (Ref. 8189/8190).					[8189] / [8190] / [8191] / [8192]
749		lipoxin B₄	5S,14R,15S-trihydroxy-6E,8Z,10E,12E-eicosatetraenoic acid	DFA8154	Tetsuyuki Kobayashi	LXB4	C₂₀H₃₂O₅	352.465		It is associated with several biological functions including leukocyte activation, natural killer cell inhibition, and monocyte migration and adhesion (Ref. 8191/8192).							lmax: 302nm e: 50,000						LXB4 is a trihydroxy fatty acid containing a conjugated tetraene, isolated when arachidonic acid is incubated with A23187-stimulated mixtures of human platelets and granulocytes (Ref. 8189).					[8189] / [8191] / [8192]
750			15-oxo-11Z,13E-eicosadienoic acid	DFA8155	Tetsuyuki Kobayashi	15-OxoEDE/15-KEDE	C₂₀H₃₄O₃	322.482		15-OxoEDE is produced by the oxidation of 15-HEDE. Some other oxo-eicosanoids have been shown to be biosynthesized and to have potent inflammatory activity (Ref. 8193).							lmax: 279nm e: 23,000											[8193]
751			5-oxo-6E,8Z,11Z,14Z-eicosatetraenoic acid	DFA8156	Tetsuyuki Kobayashi	5-OxoETE/5-KETE	C₂₀H₃₀O₃	318.450		It stimulates cytosolic calcium levels in neutrophils with an EC of 2 nM (Ref. 8194). 5-OxoETE selectively stimulates the migration and degranulation of eosinophils and activates the MAPK pathway in stimulated neutrophils (Ref. 8195/8196).							lmax: 279nm e: 22,100						5-OxoETE is a polyunsaturated keto acid formed by the oxidation of 5-HETE in human neutrophils (Ref. 8193).					[8193] / [8194] / [8195] / [8196]
752			12-oxo-5Z,8Z,10E,14Z-eicosatetraenoic acid	DFA8157	Tetsuyuki Kobayashi	12-OxoETE/12-KETE	C₂₀H₃₀O₃	318.450		12-OxoETE induces a rapid, dose related increase of cytoplasmic free calcium via a leukotriene B4 receptor or a common activation sequence (Ref. 8200).							lmax: 280nm e: 30,000						12-OxoETE is synthesized by human platelets and Aplaysia nervous tissue after incubation with arachidonic acid (Ref. 8197/8198). Microsomal fractions of various tissues will reduce 12-oxoETE to 12(S)-HETE or a mixture of 12(S)- and 12(R)-HETE (Ref. 8197/8199).					[8197] / [8198] / [8199] / [8200]
753			15-oxo-5Z,8Z,11Z,13E-eicosatetraenoic acid	DFA8158	Tetsuyuki Kobayashi	15-OxoETE/15-KETE	C₂₀H₃₀O₃	318.450									lmax: 279nm e: 22,000
754		12-oxo-phytodienoic acid	4-oxo-5b-(2Z-pentenyl)-2-cyclopentene-1b-octanoic acid	DFA8159	Tetsuyuki Kobayashi	12-oxo PDA	C₁₈H₂₈O₃	292.413		12-oxo PDA is the precursor of the biologically active 7-epi jasmonic acid which is a plant growth inhibitor and senescence inducer (Ref. 8201/8202).													12-oxo PDA is present in seedlings of sunflower and corn plants.					[8201] / [8202]
755		traumatic acid/trans-2-dodecenedioic acid	2E-dodecenedioic acid	DFA8160	Tetsuyuki Kobayashi		C₁₂H₂₀O₄	228.285		Traumatic acid is a wound-healing agent that stimulates cell division near a wound site to form a protective callus (Ref. 8203).													Traumatic acid is a product of the hydroperoxide lyase pathway in plants.					[8203]

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AUTHOR	:	Gupta, S. S., Hilditch, T. P., Paul ,J. and Shrivastava, R. K.
TITLE	:	The Constitution of Vaccenic Acid.
JOURNAL	:	J. Chem. Soc. London
VOL	:	PAGE : 3484-3490 (1950)

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AUTHOR	:	Hale, J. B., et al.
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JOURNAL	:	J. Amer. Chem. Soc.
VOL	:	32 PAGE : 4536- (1930)

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AUTHOR	:	Hancox, N. C. Hatt, H. H.
TITLE	:
JOURNAL	:	Queensl. J. Agr. Sci.
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AUTHOR	:	Handford, W. E., et al.
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JOURNAL	:	U. S. Pat.
VOL	:	2 PAGE : 340745- (1944)

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[0213]

AUTHOR	:	Hansen, R. P.
TITLE	:	Occurrence of trans-Octadec-16-enoic Acid in Sheep and Ox Perinephric Fats
JOURNAL	:	Nature (London)
VOL	:	198 PAGE : 995-995 (1963)

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AUTHOR	:	Hansen, R. P., and Cooke, N. J.
TITLE	:	The isolation and characterization of trans-octadec-16-enoic acid from butterfat PubMed ID:13904440
JOURNAL	:	Biochem J.
VOL	:	81 PAGE : 233-237 (1961)

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AUTHOR	:	Hansen, R. P., and Shorland, F. B.
TITLE	:	The branched-chain fatty acids of butterfat. I. The isolation from butterfat of branched-chain fatty acids with special reference to the C17 acids PubMed ID:14904394
JOURNAL	:	Biochem J.
VOL	:	50 PAGE : 207-210 (1951)

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AUTHOR	:	Hansen, R. P., et al.
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JOURNAL	:	Chem. Ind. (London)
VOL	:	PAGE : 839-839 (1951)

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[0217]

AUTHOR	:	Hansen, R. P., Shorland, F. B., and Cooke, N. J.
TITLE	:	The branched-chain fatty acids of butterfat. IV. The isolation of (+)-12-methyltetradecanoic acid and of 13-methyltetradecanoic acid PubMed ID:13172183
JOURNAL	:	Biochem J.
VOL	:	57 PAGE : 297-301 (1954)

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[0218]

AUTHOR	:	Hansen, R. P., Shorland, F. B., and Cooke, N. J.
TITLE	:	The branched-chain fatty acids of ox fat. 2. The isolation of 15-methylhexadecanoic acid PubMed ID:13260188
JOURNAL	:	Biochem J.
VOL	:	61 PAGE : 141-143 (1955)

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[0219]

AUTHOR	:	Hansen, R. P., et al.
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JOURNAL	:	Chem. Ind. (London)
VOL	:	PAGE : 92- (1955)

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[0220]

AUTHOR	:	Hansen, F. P., et al.
TITLE	:	Occurrence of n-Nonadecanoic Acid in Ox Perinephric Fat
JOURNAL	:	Nature (London)
VOL	:	176 PAGE : 882-882 (1955)

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AUTHOR	:	Hansen, R. P., et al.
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JOURNAL	:	Biochem. J.
VOL	:	77 PAGE : 64- (1960)

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[0222]

AUTHOR	:	Hansen, R. P., et al.
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JOURNAL	:	Helv. Chem. Acta
VOL	:	34 PAGE : 2343- (1951)

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AUTHOR	:	Harrison, G. S., and Hawke, F.
TITLE	:
JOURNAL	:	J. S. Afr. Chem. Inst.
VOL	:	5 PAGE : 23- (1952)

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[0224]

AUTHOR	:	Hartley, P.
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JOURNAL	:	J. Physiol. (London)
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[0225]

AUTHOR	:	Hartley, P.
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JOURNAL	:	J. Physiol. (London)
VOL	:	38 PAGE : 353-353 (1909)

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[0226]

AUTHOR	:	Hata, T.
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JOURNAL	:	Nippon Kagaku Kaishi
VOL	:	60 PAGE : 122-125 (1939)

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AUTHOR	:	Hatt, H. H. and Redcliffe, A.H.
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JOURNAL	:	Aust. J. Chem.
VOL	:	14 PAGE : 321-125 (1961)

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[0228]

AUTHOR	:	Hawke, F.
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JOURNAL	:	J. S. Afr. Chem. Inst.
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AUTHOR	:	Hegenmeyer, H. J., Jr.
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VOL	:	41 PAGE : 765- (1919)

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[0230]

AUTHOR	:	Hell, C., and Hermanns, O.
TITLE	:
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VOL	:	13 PAGE : 1713- (1880)

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[0231]

AUTHOR	:	Heyes, J. K., and Shorland, F. B.
TITLE	:	The constitution of hexadecatrienoic acid from the glycerides of rape (Brassica napus L) leaf PubMed ID:14886315
JOURNAL	:	Biochem J.
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AUTHOR	:	Hicks, C. S.
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JOURNAL	:	J. Chem. Soc. London Trans.
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AUTHOR	:	Hilditch, T. P.
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JOURNAL	:	J. Oil Colour Chem. Ass.
VOL	:	32 PAGE : 5- (1949)

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[0234]

AUTHOR	:	Hileditch, T. P. and Houlbrooke, A.
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JOURNAL	:	Analyst (London)
VOL	:	53 PAGE : 246- (1928)

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[0235]

AUTHOR	:	Hilditch, T. P. and Meara, M. L.
TITLE	:	The Seed Fat of the Annual Nasturtium(Tropaeolum var.).
JOURNAL	:	J. Chem. Soc. London
VOL	:	PAGE : 1608-1610 (1938)

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AUTHOR	:	Hilditch, T. P. and Vidyarthi, N. L.
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VOL	:	46 PAGE : 172- (1927)

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AUTHOR	:	Hilditch, T. P., and Vidyarthi, N. L.
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VOL	:	47 PAGE : 35- (1928)

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AUTHOR	:	Hilditch, T. P., and Vidyarthi, N. L.
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AUTHOR	:	Hilditch, T. P., et al.
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VOL	:	60 PAGE : 198-198 (1941)

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AUTHOR	:	Hilditch, T. P., et al.
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VOL	:	63 PAGE : 112-112 (1944)

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AUTHOR	:	Hilditch, T. P., et al.
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AUTHOR	:	Hofmann, A. W.
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AUTHOR	:	Hofmann, K.
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AUTHOR	:	Hofmann, K. and Lucas. R. A.
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VOL	:	72 PAGE : 4328-4328 (1950)

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AUTHOR	:	Hofmann, K., and Sax, S. M.
TITLE	:	The chemical nature of the fatty acids of Lactobacillus casei PubMed ID:13117883
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AUTHOR	:	Hofmann, K., Lucas, R. A., and Sax, S. M.
TITLE	:	The chemical nature of the fatty acids of Lactobacillus arabinosus PubMed ID:14946156
JOURNAL	:	J Biol Chem.
VOL	:	195 PAGE : 473-485 (1952)

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AUTHOR	:	Hopff, H. and Rapp, W.
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JOURNAL	:	Chem. Abstr.
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AUTHOR	:	Hopkins, C. Y.
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AUTHOR	:	Hopkens, C. Y. and Chisholm, M. J.
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AUTHOR	:	Hopkins, C. Y. and Chisholm. M. J.
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AUTHOR	:	Hopkins, C. Y. and Chisholm. M. J.
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AUTHOR	:	Hopkins, C. Y. and Chisholm. M. J.
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AUTHOR	:	Hopkens, C. Y. and Swingle, S.
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AUTHOR	:	Hopkens, C. Y., et al.
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AUTHOR	:	Horn, D. J. S. and Pretorius. Y. Y.
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AUTHOR	:	Horn, D. J. S. et al.
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AUTHOR	:	Hounston, D. F.
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AUTHOR	:	Howard, J. W., and Fraser, W. A.
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AUTHOR	:	Howton,D.R.,and Davis,R.H.
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AUTHOR	:	Huang,P.T.,et al.
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AUTHOR	:	Huber,W.F.
TITLE	:	A Study of n-Octadecenoic Acid. I. Synthesis of cis-and trans-7-through 12-and of 17-Octadenoic Acids
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AUTHOR	:	Hunsdiecker,H.
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AUTHOR	:	Irvine,J.C.
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AUTHOR	:	Ito,S., and K.Fukuzumi.
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AUTHOR	:	Jackson,J.D., et al.
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AUTHOR	:	James, A. T., and Martin, A. J.
TITLE	:	Gas-liquid chromatography: the separation and identification of the methyl esters of saturated and unsaturated acids from formic acid to n-octadecanoic acid PubMed ID:13315260
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AUTHOR	:	Jangaard,P.M.
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AUTHOR	:	Jangaard,P.M., and R.G.Ackman.
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AUTHOR	:	Jeger, O., et al
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JOURNAL	:	Helv. Chim. Acta
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[0271]

AUTHOR	:	Jegrow, J.
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JOURNAL	:	Chem. Zentralbl
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AUTHOR	:	Jelinek, V. C., and Upson, F. W.
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[0273]

AUTHOR	:	Jensen, W.
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AUTHOR	:	Karrer,P., and H.Koenig.
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AUTHOR	:	Kass,J.P., and G.O.Burr.
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AUTHOR	:	Kass,J.P., and G.O.Burr.
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AUTHOR	:	Kass,J.P.,and Keyser,L.S.
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AUTHOR	:	Kass, J. P., and Miller, E. S.
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AUTHOR	:	Kass, J .P., et al.
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AUTHOR	:	Kaufmann, H. P.
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JOURNAL	:	Chem. Ber.
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[0281]

AUTHOR	:	Kaufmann, H. P., and Keller, M.
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JOURNAL	:	Chem. Ber.
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AUTHOR	:	Keller, E. H.
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AUTHOR	:	Kendall, E. C., and McKenzie, B. M.
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JOURNAL	:	Org. Syn.
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AUTHOR	:	Kendall, V. G., et al.
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JOURNAL	:	Chem. Ind. (London)
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AUTHOR	:	Kerchbaum, M.
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JOURNAL	:	Ber. Deut. Chem. Ges.
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AUTHOR	:	Kirk, R. E., and Othmer, D. F., ed. 1947-60. Encyclopedia of Chemical Technology. Interscience, New York. v.1-15, suppl. 1 and 2.
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AUTHOR	:	Kishimoto, Y., and Radin, N. S.
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AUTHOR	:	Klein, A., and Stigol, M.
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AUTHOR	:	Klenk, E.
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AUTHOR	:	Klenk, E.
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AUTHOR	:	Klenk, E.
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AUTHOR	:	Klenk, E., and Bongard, W.
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AUTHOR	:	Klenk, E., and Ebarhagen, D.
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AUTHOR	:	Klenk, E., and Lindlar, F.
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AUTHOR	:	Klenk, E., and Steinbach, H.
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AUTHOR	:	Klenk, E., and Tomuschat, H. J.
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AUTHOR	:	Knight, J. A., and Diamond, J. H.
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AUTHOR	:	Komori, S., and Ueno, S.
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AUTHOR	:	Kono, M., and Maruyama, R.
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AUTHOR	:	Koyama, R.
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AUTHOR	:	Koyama, Y., and Toyama, Y.
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AUTHOR	:	Koyama, Y., and Toyama, Y.
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AUTHOR	:	Krafft, F.
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AUTHOR	:	Krafft, F.
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AUTHOR	:	Krafft, F.
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AUTHOR	:	Kuhn, R., and Michel, J.
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AUTHOR	:	Le Sueur, H. R.
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AUTHOR	:	Shukoff, A. A., and Schestakoff, P. J.
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AUTHOR	:	Skogh, M.
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AUTHOR	:	Steger, A. and van Loon, J.
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AUTHOR	:	Steger, A., and van Loon, J.
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AUTHOR	:	Stoll, M., and Gardner, R. E.
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AUTHOR	:	Stoll, M., and Rouvé, A.
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AUTHOR	:	Stoll, M., and Rouvé, A.
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AUTHOR	:	Taverne, H. J.
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AUTHOR	:	Taylor, W. R., and Strong, F. M.
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AUTHOR	:	Toyama, Y.
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AUTHOR	:	Toyama, Y.
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AUTHOR	:	Toyama, Y.
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AUTHOR	:	Toyama, Y., and Ishikawa, T.
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AUTHOR	:	Toyama, Y., and Tsuchiya, T.
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AUTHOR	:	Toyama, Y., and Tsuchiya, T.
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AUTHOR	:	Toyama, Y., and Tsuchiya, T.
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AUTHOR	:	Toyama, Y., and Tsuchiya, T.
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AUTHOR	:	Toyama, Y., and Tamamoto, T.
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AUTHOR	:	Toyama, Y., and Yamamoto, T.
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AUTHOR	:	Tropsch, H., and Kreutzer, A.
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AUTHOR	:	Tsujimoto, M.
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AUTHOR	:	Tsujimoto, M.
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AUTHOR	:	Tsujimoto, M.
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AUTHOR	:	Tsujimoto, M., and Koyanagi, H.
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AUTHOR	:	Vongerichten, E., and Koehler, H.
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AUTHOR	:	Weitzel, G., and Wojahn, J.
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AUTHOR	:	Yumoto, T., and Ishikawa, Y.
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AUTHOR	:	Zaar, B.
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AUTHOR	:	Zetsche, F., and Sonderegger, G.
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AUTHOR	:	Bowman, R.E.
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AUTHOR	:	Bhattacharyya, Sourirajan
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AUTHOR	:	Mckusick and Hoover (1960) U.S.pats.,2, 940, 913, and 2,940,914, to du Pont
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AUTHOR	:	Faith, Keyes and Clark's Industrial Chemicals 4th ed. (Lowenheim,F.A.,Moran,M.K. eds.), pp8-15, Wiley-Interscience, New York
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AUTHOR	:	(1978), in F.S.Wagner in Kirk-Othmer Encyclopedia of Chemical Technology vol.1 3rd ed., pp124-147, Wiley-Interscience, New York
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AUTHOR	:	Shoda, R., Matsueda, K., Yamato, S., and Umeda, N.
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AUTHOR	:	Galliard,T. (1973) Phospholipid Methabolism in Photosynthetic Plants in Form and Function of Phospholipid, (Ansell,G.B., Dawson,R.M.C., and Hawthorne,J.N. eds), pp.253-288, Elsevier Scientific Publising Company.
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AUTHOR	:	Kates,M. (1970) Plant Phospholipids and Glycolipids in ADV. in Lipid Res. Vol.8, (Paoletti,R., and Kritchevsky,D., eds), pp.225-265, Academic Press.
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AUTHOR	:	Hayashi, A., and Matsubara, T.
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AUTHOR	:	Happ,G.P.,and Stewart,D.W.
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AUTHOR	:	Miller,A.L.,Cook,N.C.,and Whitmore,F.C.
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AUTHOR	:	Milburn,A.H.,and Truter,E.V.
TITLE	:	The Components of Wool Wax Part Ii. Synthesis of The Acids and Alcohols of The Iso- and The (+)-Anteiso-Series
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AUTHOR	:	Guertin,D.L.,Wiberley,S.E.,and Bauer,W.H.
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AUTHOR	:	Guertin,D.L.,Wiberley,S.E.,Bauer,W.H.,and Golderson,J.
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AUTHOR	:	Harple,W.W.,Wiberley,S.E.,and Bauer,W.H.
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AUTHOR	:	Sobotka,H.,and Stynler,E.
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AUTHOR	:	Freeman,N.K.
TITLE	:	Infrared Spectra of Branched Long-Chain Fatty Acids
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AUTHOR	:	Cason,J.,and Sumrell,G.
TITLE	:	Branched-Chain Fatty Acids. Xviii. Ultraviolet Absorption Spectra of Saturated Branched-Chain Acids
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AUTHOR	:	Cason,J.,and Kalm,M.J.
TITLE	:	Branched-Chain Fatty Acids XXXI. Assignment of Geometric Configuration in The 2-Methyl-2-Alkenoic Acids
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TITLE	:	The Ultravaiolet Absorption Spectra of Acrylic Acids and Esters
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AUTHOR	:	Kwart,H.,and Miller,R.K.
TITLE	:	Allylic Rearrangement in The Reaction of 1-Chloro-3-Methyl-2-Butene ; An Attempt At Total Synthesis of Geraniol
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AUTHOR	:	Semenow,D.,Shih,C.-H.,and Young,G.
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AUTHOR	:	Ishimaru,H
TITLE	:	Study of Unsaturated Fatty Acids
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AUTHOR	:	Jocelyn,P.C.,and Polgar,N.
TITLE	:	Methyl-Substituted, $Beta$-Unsaturated Acid
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AUTHOR	:	Cason,J.,Allinger,N.L.,and Sumrell,G.
TITLE	:	Branched-Chain Fatty Acids XXV. Methods of Synthesis of 2-Alkenoic Acid
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AUTHOR	:	Freeman,N.K.
TITLE	:	Infrared Spectra of Some Long-Chain 2-Alkenoic Acids and Their Bearing on The Structure of C27-Phthienoic Acid
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AUTHOR	:	Cason,J.,Allinger,N.L.,and Williams,D.E.
TITLE	:	Branched-Chain Fatty Acids XXIV. Synthesis of 2-Methyl-2-Dodecenoic Acid and of 2-Methylene-Dodecanoic Acid
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AUTHOR	:	Cason,J.,Allinger,N.L.,and Allen,C.F.
TITLE	:	Branched-Chain Fatty Acids XXVI. Synthesis of Optically Active Acids of Use in The Study of The Structure of C27-Phthienoic Acid. Rartial Thermal Racemization of (-)5-Methyl-2-Tridecenoic Acid
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AUTHOR	:	Bruhl,J.W.
TITLE	:	Die Chemische Constitution Organischer Korpor in Beziehung Zu Deren Dichte Und Ihren Vermogen Das Licht Fortzupflanzen
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AUTHOR	:	Kennyon,J., and Ross,W.A.
TITLE	:	The Mechanism of The Decarboxylation of Substituted Malonic Acid Derivativies
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AUTHOR	:	Weisenborn,F.L.,Bolger,J.W.,Rosen,D.B.,Mann,L.T.Jr.,Johnson,L., and Holmes,H.L.
TITLE	:	Synthetic Hypotensive Esters from Germine
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AUTHOR	:	Hancock,K.,Watson,G.M.,and Gilby,R.F.
TITLE	:	Heats of Combustion of The Five Carbon Fatty Acids and Their Methyl and Ethyl Esters
JOURNAL	:	J. Phys. Chem.
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AUTHOR	:	Dolgow,
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AUTHOR	:	Hill,C.M., and Hill,M.E.
TITLE	:	Low Temperature Hydrogenation and Several Properties of Methyl and N-Butylkerene Dimers
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AUTHOR	:	Levene,P.A., and Marker,R.E.
TITLE	:	On Walden Inversion XV.
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VOL	:	91 PAGE : 77-99 (1931)

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AUTHOR	:	Kogl,F., and Erxleben,H.
TITLE	:	Syntheses Der Auxin-Glutarsaure Und Einiger Isomere
JOURNAL	:	Hopp-Sey. Zeit. Physolog. Chem.
VOL	:	235 PAGE : 190- (1935)

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AUTHOR	:	Hommelen,
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AUTHOR	:	Croxall,W.J. and Van Hook,J.O.
TITLE	:	Transetherification Reactions Preparation and Rearrangment of b-Alloxacrylates
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AUTHOR	:	Holman,R.T., and Edmondson,P.R.
TITLE	:	Near-infrared Spectra of Fatty Acids and Some Related Substances
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VOL	:	28 PAGE : 1533-1538 (1956)

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AUTHOR	:	Gillette,R.H.
TITLE	:	The Effect of Substitution on The Infrared Absorption Spectrum of Acetic Acid
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AUTHOR	:	Adkins,H., and Rosenthal,R.W.
TITLE	:	Carbonylation of Alcohols with Nickel Carbonyl Catalyst
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AUTHOR	:	Berliner,E., and Berliner,F.
TITLE	:	Hyperconjugation IV. The Bromination of Additional Monoalkylbenzenes
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AUTHOR	:	Traynham,J.G., and Battiste,M.A.
TITLE	:	Solvolyses of Some Sterically Hindered Aliphatic Esters
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AUTHOR	:	Weitzel,G.,Fretzdorff,A.M., and Wojahn,J.
TITLE	:	Untersuchungen Uber Die Burzeldrusse Der Vogel III.
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AUTHOR	:	Levene,P.A.,Rothen,A., and Marker,P.E.
TITLE	:	Optical Rotation and Rotatory Didpersions in Homologus Seriese of Aliphatic Nitriles
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AUTHOR	:	Stallberg, and Stenhagen
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AUTHOR	:	Marks,G.S., and Polger,H.
TITLE	:	Mycoceranic Acid Part II.
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AUTHOR	:	Cason,J., and Coad,R.A.
TITLE	:	Branched-Chain Fatty Acid XVI.
JOURNAL	:	J. Am. Chem. Soc.
VOL	:	72 PAGE : 4695-4697 (1950)

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AUTHOR	:	Djerassi,C., and Geller,L.E.
TITLE	:	Optical Rotatory Dispersion Studies XXIV.
JOURNAL	:	J. Am. Chem. Soc.
VOL	:	81 PAGE : 2789-2794 (1959)

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[7048]

AUTHOR	:	Levene,P.A., and Marker,R.E.
TITLE	:
JOURNAL	:	J. Biol. Chem.
VOL	:	91 PAGE : 417- (1931)

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[7049]

AUTHOR	:	Sisido,K.,Kazama,Y.,Kodama,H.,and Hozaki,H.
TITLE	:	Condensation of t-Butyl Ester with Organic Halides in The Presence of Alkali Amides
JOURNAL	:	J. Am. Chem. Soc.
VOL	:	81 PAGE : 5817-5819 (1959)

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[7050]

AUTHOR	:	Sy,
TITLE	:
JOURNAL	:	Compt. Red.
VOL	:	239 PAGE : 1224- (1954)

[TOP]

[7051]

AUTHOR	:	Stdienges, and Kohle,
TITLE	:
JOURNAL	:	U.S.P.
VOL	:	PAGE : 2876241- (1955)

[TOP]

[7052]

AUTHOR	:	Kimura, and Tanaka,
TITLE	:
JOURNAL	:	Chem. Pharm. Bull.
VOL	:	6 PAGE : 9- (1958)

[TOP]

[7053]

AUTHOR	:	Abbott,D.C., and Arcus,C.L.
TITLE	:	The Conversion of Silver +2-Ethyl Hexanoate into +-3-Bromoheptane
JOURNAL	:	J. Chem. Soc.
VOL	:	PAGE : 3195-3197 (1952)

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[7054]

AUTHOR	:	Kullhem,
TITLE	:
JOURNAL	:	Lebigs Ann. Vhem.
VOL	:	173 PAGE : 319- ()

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[7055]

AUTHOR	:	Wotiz,J.H., and Palchak,R.
TITLE	:	The Propargylic Rearrangment III.
JOURNAL	:	J. Am. Chem. Soc.
VOL	:	73 PAGE : 1971-1972 (1951)

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[7056]

AUTHOR	:	Fieser,L.F.
TITLE	:	Naphthoquinone Antimalarials IV. Alkyl Side Chains
JOURNAL	:	J. Am. Chem. Soc.
VOL	:	70 PAGE : 3175-3180 (1948)

[TOP]

[7057]

AUTHOR	:	Levene,P.A., Ana Marker,R.E.
TITLE	:	Maximum Rotations and Correlation of Disubstituted Acetic Acids Containing A Methyl Group
JOURNAL	:	J. Biol. Chem.
VOL	:	98 PAGE : 1-7 (1937)

[TOP]

[7058]

AUTHOR	:	Wilson,C.V.
TITLE	:	The Monomethyldeloic Acids
JOURNAL	:	J. Am. Chem. Soc.
VOL	:	67 PAGE : 2161-2162 (1945)

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[7059]

AUTHOR	:	Ulusoy,E.
TITLE	:	Synthesis of Homologous a, b- and a, b-Methylated Fatty Acids
JOURNAL	:	Rev. Fac. Sci. Istanbul
VOL	:	15 PAGE : 381-389 (1950)

[TOP]

[7061]

AUTHOR	:	Linblad,K., and Stenhagen,E.
TITLE	:	2-Methyl-Tetradecanol-1
JOURNAL	:	J. Am. Chem. Soc.
VOL	:	63 PAGE : 3539-3540 (1941)

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[7062]

AUTHOR	:	Greer,C.M., and Adams,R.
TITLE	:	Preparation and Bactericidial Properties of Certain Pentadecenoic, Heptadecenoic and Nonadecenoic Acids XIX.
JOURNAL	:	J. Am. Chem. Soc.
VOL	:	52 PAGE : 2540-2543 (1930)

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[7065]

AUTHOR	:	Weitzel,G., and Wojahn,J.
TITLE	:	Biochemie Verzweigter Carbonsauren V.
JOURNAL	:	Z. Physiol. Chem.
VOL	:	287 PAGE : 65-89 (1951)

[TOP]

[7068]

AUTHOR	:	Asano, and Azumi,
TITLE	:
JOURNAL	:	J. Pharm. Soc. Japan
VOL	:	55 PAGE : 812- (1935)

[TOP]

[7070]

AUTHOR	:	Cason,J.,Wolfhagen,H.J.,Tarpey,W., and Adams,R.E.
TITLE	:	Branched-Chain Fatty Acids X.
JOURNAL	:	J. Org. Chem.
VOL	:	14 PAGE : 147-154 (1949)

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[7071]

AUTHOR	:	Weitzel,G., and Wojshn,J.
TITLE	:	Biochemie Verzweigter Carbonsauren III.
JOURNAL	:	Z. Physiol. Chem.
VOL	:	285 PAGE : 220-229 (1950)

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[7072]

AUTHOR	:	Abrahamsson,
TITLE	:
JOURNAL	:	Acta Cryat.
VOL	:	12 PAGE : 301- (1959)

[TOP]

[7073]

AUTHOR	:	Weizel,G. and Wojahn,J.
TITLE	:	Biochemie Verzweigter Carbonsauren VII.
JOURNAL	:	Z. Physiol. Chem.
VOL	:	287 PAGE : 296-310 (1951)

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[7074]

AUTHOR	:	Cason,J.
TITLE	:	Branched-Chain Fatty Acids I.
JOURNAL	:	J. Am. Chem. Soc.
VOL	:	64 PAGE : 1106-1110 (1942)

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[7079]

AUTHOR	:	Knight,J., and Waight,E.S.
TITLE	:	Observations on The Ozonolysis of Allylic Compounds
JOURNAL	:	J. Chem. Soc.
VOL	:	PAGE : 2830-2834 (1955)

[TOP]

[7080]

AUTHOR	:	Nasarow,
TITLE	:
JOURNAL	:	Izv. Akad. S.S.S.R. Otd. Chim.
VOL	:	PAGE : 1354- (1958)

[TOP]

[7081]

AUTHOR	:	Allen,F., and Kalm,M.J.
TITLE	:	Trans-2-Methyl-2-Dodecanoic Acid
JOURNAL	:	Org. Synth.
VOL	:	4 PAGE : 608- (1963)

[TOP]

[7082]

AUTHOR	:	Yuan, C., and Bloch, K.
TITLE	:	Synthesis of 3-methyl-3-butenyl-1-pyrophosphate PubMed ID:13846693
JOURNAL	:	J Biol Chem.
VOL	:	234 PAGE : 2605-2608 (1959)

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[7083]

AUTHOR	:	Price,C.C.,Cypher,G.A.,and Krishnamurti,I.V.
TITLE	:	The Thermal Reaction of Formaldehyde with Allyl Cyanide.
JOURNAL	:	J. Am. Chem. Soc.
VOL	:	74 PAGE : 2987-2991 (1952)

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[7084]

AUTHOR	:	Iwakura,Y.,Sato,M.,and Matsuo,Y.
TITLE	:	Studies on 1-Alkenyl Isocyanates V.
JOURNAL	:	J. Chem. Soc. Japan Pure Chem.
VOL	:	80 PAGE : 502-505 (1959)

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[7086]

AUTHOR	:	Rappe,C., and Adestrom,R.
TITLE	:	Favorskii Rearrangemants IV.
JOURNAL	:	Acta Chem. Scand.
VOL	:	19 PAGE : 383-388 (1965)

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[7087]

AUTHOR	:	David,S. and Imer,C.
TITLE	:	Hop Constituents I.
JOURNAL	:	Bull. Chim. Soc. France
VOL	:	PAGE : 634-637 (1951)

[TOP]

[7088]

AUTHOR	:	Mazur,Y. ; Sondheimer,F.
TITLE	:	The Synthesis of Tigogenin and Neotigogenin.
JOURNAL	:	J. Am. Chem. Soc.
VOL	:	81 PAGE : 3161-3162 (1959)

[TOP]

[7089]

AUTHOR	:	Mazur,Y.,Danieli,N.,and Sondheimer,F.
TITLE	:	The Synthesis of The Steroidal Sapogenins.
JOURNAL	:	J. Am. Chem. Soc.
VOL	:	82 PAGE : 5889-5905 (1960)

[TOP]

[7090]

AUTHOR	:	Wagner,R.B.,and Moore,J.A.
TITLE	:	The Rearrangement of a-Dibromoketones.
JOURNAL	:	J. Am. Chem. Soc.
VOL	:	72 PAGE : 974-977 (1950)

[TOP]

[7091]

AUTHOR	:	Cornforth,R.H.
TITLE	:	Stereoselective Reaction of Keton with 3-Chlorobutan-2-one.
JOURNAL	:	J. Chem. Soc.
VOL	:	PAGE : 4052-4058 (1959)

[TOP]

[7092]

AUTHOR	:	Braude,E.A.,and Evans,E.A.
TITLE	:	Alkylation with Lithium Alkenyls Part X.
JOURNAL	:	J. Chem. Soc.
VOL	:	PAGE : 3331-3334 (1955)

[TOP]

[7093]

AUTHOR	:	Eschenmoser,A. and Frey.A.
TITLE	:	Cleavage of Methanesulfonyl Esters of 2-Methyl-2-(Hydroxymethyl)Cyclopentanone with Base
JOURNAL	:	Helv. Chimica Acta.
VOL	:	35 PAGE : 1660-1666 (1952)

[TOP]

[7094]

AUTHOR	:	Newman,D.D.E.,and Owen,L.N.
TITLE	:	Olefinic Acids Part IX.
JOURNAL	:	J. Chem. Soc.
VOL	:	PAGE : 4722-4727 (1952)

[TOP]

[7095]

AUTHOR	:	Brannock,K.C.
TITLE	:	Preparation of Substituted 4-Pentenals.
JOURNAL	:	J. Am. Chem. Soc.
VOL	:	81 PAGE : 3379-3383 (1959)

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[7096]

AUTHOR	:	Adams,R.,and Herz,W.
TITLE	:	Synthesis of Viridifioric Acid.
JOURNAL	:	J. Am. Chem. Soc.
VOL	:	72 PAGE : 155-157 (1950)

[TOP]

[7097]

AUTHOR	:	Morton,A.A., Marsh,F.D., Coombs,R.D., Lyons,A.L., Penner,S.E., Ramsden,H.E., Baker,V.B., Little,E.L.,and Letsinger,R.
TITLE	:	Polymerization XII.
JOURNAL	:	J. Am. Chem. Soc.
VOL	:	72 PAGE : 3785-3792 (1950)

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[7098]

AUTHOR	:	Ansell,M.F.,and Brown,S.S.
TITLE	:	The Synthesis of Some Olefinic Acids Using Tetrahydro-b-Halogeno-Furan and -Pyran Derivatives as Intermediates.
JOURNAL	:	J. Chem. Soc.
VOL	:	PAGE : 1788-1795 (1957)

[TOP]

[7099]

AUTHOR	:	Wiemann,J.,Martineau,L., and Thuan,L.T.
TITLE	:	Isomerization of a-Ethylenic Carbonyl Compounds into Nonconjugated Compounds II.
JOURNAL	:	Bull. Chim. Soc. France
VOL	:	PAGE : 1412-1414 (1959)

[TOP]

[7100]

AUTHOR	:	Bateman,L.,and Cunneen,J.I.
TITLE	:	The Reaction of Oct-1-ene with N-Bromosuccinimide.
JOURNAL	:	J. Chem. Soc.
VOL	:	PAGE : 941-946 (1950)

[TOP]

[7101]

AUTHOR	:	Ishimaru,H.
TITLE	:	Studies on Unsaturated Fatty Acid
JOURNAL	:	J. Chem. Soc. Japan. Pure Chem. Sec.
VOL	:	76 PAGE : 1253-1258 (1955)

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[7102]

AUTHOR	:	Cason,J.,and Rinehart,K.L.
TITLE	:	Pranched-Chain Fatty Acids XXXII.
JOURNAL	:	J. Org. Chem.
VOL	:	20 PAGE : 1591-1606 (1955)

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[7103]

AUTHOR	:	Cason, J., and Allen, C. F.
TITLE	:	Synthesis and properties of L(+)-2,4-dimethyl-2-dodecenoic acid PubMed ID:13117922
JOURNAL	:	J Biol Chem.
VOL	:	205 PAGE : 449-457 (1953)

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[7104]

AUTHOR	:	Bailey,A.S.,Polgar,N.,Tate,F.E.G.,and Wilkinson,A.
TITLE	:	Methyl-Substituted b-Unsaturated Acids. Part II.
JOURNAL	:	J. Chem. Soc.
VOL	:	PAGE : 1547-1551 (1955)

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[7105]

AUTHOR	:	Schulte,K.E.,Weisskopf,W.,and Kirschner,J.
TITLE	:	Information of Branched Fatty Acids.
JOURNAL	:	Z. Physiol. Chem.
VOL	:	288 PAGE : 69-82 (1951)

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[7106]

AUTHOR	:	Cason,J.,and Kalm,M.J.
TITLE	:	Branched-Chain Fatty Acids XXX.
JOURNAL	:	J. Org. Chem.
VOL	:	19 PAGE : 1836-1840 (1954)

[TOP]

[7107]

AUTHOR	:	Willstatter,R.,Mayer,E.W., and Huni,E.
TITLE	:	D3-Phytenic Acid
JOURNAL	:	Liebigs Ann. Der Chem.
VOL	:	378 PAGE : 73-152 (1911)

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[7108]

AUTHOR	:	Akiya,S.,and Nakazawa,Y.
TITLE	:	Studies on The Glycolipide in Oyster III, IV.
JOURNAL	:	J. Pharm. Soc. Japan.
VOL	:	76 PAGE : 1401-1405 (1956)

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[7109]

AUTHOR	:	Lederer,E,.Portelance,V.,and Serck-Hanssen,K.
TITLE	:	Synthesis of Racemic Corynomycolic Acid and of Some Lower and Higher Homologs
JOURNAL	:	Bull. Soc. Chim. France
VOL	:	PAGE : 413-417 (1952)

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[7110]

AUTHOR	:	Asano,M. and Yamakawa,T.
TITLE	:	Antibacterial Action of Fatty Acid III.
JOURNAL	:	J. Pharm. Soc. Japan
VOL	:	70 PAGE : 474-476 (1950)

[TOP]

[7111]

AUTHOR	:	Allen,C.F.,and Kalm,M.J.
TITLE	:	2-Methylenedodecanoic Acid.
JOURNAL	:	Org. Synth. Coll.
VOL	:	4 PAGE : 616-620 (1963)

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[7113]

AUTHOR	:	Auwers,K.V.
TITLE	:	The Olefin Nonocarbonic Acid I.
JOURNAL	:	Liebig's Ann. Chem.
VOL	:	432 PAGE : 46-98 (1923)

[TOP]

[7114]

AUTHOR	:	Kon,G.A.R.,Listead,R.P., and Wright,J.M.
TITLE	:	Investigation of The Olefinic Acid XII.
JOURNAL	:	J. Chem.Soc.
VOL	:	PAGE : 599-604 (1934)

[TOP]

[7115]

AUTHOR	:	Fieser,L.F.,Berliner,E.,Bondhus,F.J.,Chang,F.C.,Dauben,W.G.,and Leffler,M.T.
TITLE	:	Naphthoquinone Antimalarials. Synthesis X.
JOURNAL	:	J. Am. Chem. Soc.
VOL	:	70 PAGE : 3206-3211 (1948)

[TOP]

[7116]

AUTHOR	:	Heilmann,R.,Gaudemaris,G.,and Heindl,R.
TITLE	:	The Willgerodt Reaction in The Aliphatic Series
JOURNAL	:	Compt. Rend.
VOL	:	235 PAGE : 544-546 (1952)

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[7117]

AUTHOR	:	Linstead,R.P.,Shephard,B.R.,Weedon,B.C.L.,and Lunt,J.C.
TITLE	:	Anodic Syntheses Part VIII. New Syntheses of 3:13:19-Trimethyltricosanoic Acid
JOURNAL	:	J. Chem. Soc.
VOL	:	PAGE : 1538-1541 (1953)

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[7119]

AUTHOR	:	Weitzel,G.,and Wojahn,J.
TITLE	:	Biochemistry Branched Carboxylic Acid V.
JOURNAL	:	Z. Physiol. Chem.
VOL	:	287 PAGE : 65-89 (1951)

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[7120]

AUTHOR	:	Paul,R.,and Tchelitcheff,S.
TITLE	:	Synthesis and Some Properties of Trivinylmethane
JOURNAL	:	Compt. Rend.
VOL	:	232 PAGE : 1939-1941 (1951)

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[7121]

AUTHOR	:	Mcelvain,S.M.,and Aldridge,C.L.
TITLE	:	Ketene Acetals XXX. Alkylation of Dimethylketene Dimethyl Acetal
JOURNAL	:	J. Am. Chem. Soc.
VOL	:	75 PAGE : 3987-3993 (1958)

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[7122]

AUTHOR	:	Coffman,D.D.,and Roland,J.R.
TITLE	:	Synthesis of 2,2-Dimethylalkanoic Acids from Ethylene
JOURNAL	:	J. Am. Chem. Soc.
VOL	:	72 PAGE : 3392-3393 (1950)

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[7123]

AUTHOR	:	Hauser,C.R.,and Chambers,W.J.
TITLE	:	The Alkylation of Tertiary Esters of Dialkylacetic Acids by Means of Alkali Amides.
JOURNAL	:	J. Am. Chem. Soc.
VOL	:	78 PAGE : 3837-3841 (1956)

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[7124]

AUTHOR	:	Prout,F.S.,Burachinsky,B.,Brannen,W.T.Jr.,and Young,H.L.
TITLE	:	Unsymmetrical Quaternary Carbon Compounds. III.
JOURNAL	:	J. Org. Chem.
VOL	:	25 PAGE : 835-838 (1960)

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[7125]

AUTHOR	:	Rinehart,K.L.,and Dolby,L.J.
TITLE	:	Olefinic Stability and Tautomeric Equilibria I. Branched-Chain Unsaturated Esters.
JOURNAL	:	J. Org. Chem.
VOL	:	22 PAGE : 13-25 (1957)

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[7126]

AUTHOR	:	Pelton,E.L.,and Holzschuh,A.A.
TITLE	:	Disubstituted Acetic Acids from 2-(Saturated Hydrocarbon-Substituted) Cyclohexanols
JOURNAL	:	U. S. P.
VOL	:	PAGE : 2517708- (1950)

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[7127]

AUTHOR	:	Turner,E.E.,and Turner,L.
TITLE	:	Compounds Containing The 2:2:4-Trimethylhexyl Skeleton Part I
JOURNAL	:	J. Chem. Soc.
VOL	:	PAGE : 2543-2545 (1951)

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[7128]

AUTHOR	:	Prout,F.S.,Dickson,D.E.,and Klimkowski,R.J.
TITLE	:	The Active 12-Methyloctadecanoic Acids
JOURNAL	:	J. Org. Chem.
VOL	:	24 PAGE : 826-829 (1959)

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[7129]

AUTHOR	:	Kimura,K.,and Tanaka,A.
TITLE	:	Anodic Synthesis of Fatty Acids II. The Syntheses of 3,3-Dimethylated Branched Acids
JOURNAL	:	Chem. Pharm. Bl.
VOL	:	6 PAGE : 9-12 (1958)

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[7130]

AUTHOR	:	Linstead,R.P.,Lunt,J.C.,and Weedon,B.C.L.
TITLE	:	Anodic Syntheses Part IV.
JOURNAL	:	J. Chem. Soc.
VOL	:	PAGE : 1130-1132 (1951)

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[7132]

AUTHOR	:	Metzger,A.,and Gawalek,G.
TITLE	:	High-Molecular-Weight Branched-Chain Acids I.
JOURNAL	:	J. Prakt. Chem.
VOL	:	42 PAGE : 168-184 (1955)

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[7133]

AUTHOR	:	Maekawa,E.
TITLE	:	Reactions of Halogens with The Metallic Salts of Fatty Acids V. a-Substituted Carboxylic Acids
JOURNAL	:	Bull. Nagoyainst. Technol.
VOL	:	6 PAGE : 271-274 (1954)

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[7134]

AUTHOR	:	Rapport,H.,and Baldridge Jr.H.D.
TITLE	:	The Carbon Skeleton of Carpaine
JOURNAL	:	J. Am. Chem. Soc.
VOL	:	73 PAGE : 343-346 (1951)

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[7135]

AUTHOR	:	Asano,M.,Takahashi,K.,Murakami,T.,Tsutsumi,Y.,Miura,Y.,and Toyoizumi,Y.
TITLE	:	Synthesis of Several Branched-Chain Fat Acids and Their Antibacterial Actions
JOURNAL	:	J. Pharm. Soc. Jpn.
VOL	:	70 PAGE : 202-209 (1950)

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[7136]

AUTHOR	:	Petrov,A.D.,Nikishin,G.I.,Ogibin,I.N,Nevolin,F.W.,and Tipisova,T.G.
TITLE	:	Synthesis and Surface-Active Properties of Branched-Chain Acids
JOURNAL	:	Fette Seifen Anst.
VOL	:	61 PAGE : 940-946 (1959)

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[7138]

AUTHOR	:	Yamakawa,T.
TITLE	:	The Fate of Branched-Chain Fat Acids in The Animal Body IV
JOURNAL	:	J. Pharm. Soc. Jpn.
VOL	:	70 PAGE : 633-636 (1950)

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AUTHOR	:	Leibnitz,E.,Hager,W.,and Triems,K.
TITLE	:	Products of Paraffin Oxidation III
JOURNAL	:	J. Prkt. Chem.
VOL	:	94 PAGE : 247-257 (1959)

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AUTHOR	:	Rabjohn,N.,and Farmer,H.H.
TITLE	:	Unsymmetrical Tetraalkylmethanes III
JOURNAL	:	J. Org. Chem.
VOL	:	24 PAGE : 359-362 (1959)

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AUTHOR	:	Izawa,M.
TITLE	:	Monolayers of Branched-Chain Fatty Acids I.
JOURNAL	:	Bull. Chem. Soc. Japan
VOL	:	25 PAGE : 182-187 (1952)

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[7143]

AUTHOR	:	Cason,J.,and Winans,W.R.
TITLE	:	Branched-Chain Fatty Acids XIII Preparation of Branched-and Normal Acids For Use in The Study of Melting Points of Binary Mixtures
JOURNAL	:	J. Org. Chem.
VOL	:	15 PAGE : 139-147 (1950)

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[7144]

AUTHOR	:	Kolattukudy, P. E., Bohnet, S., and Rogers, L.
TITLE	:	Disappearance of short chain acids from the preen gland wax of male mallard ducks during eclipse PubMed ID:4045323
JOURNAL	:	J Lipid Res.
VOL	:	26 PAGE : 989-994 (1985)

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AUTHOR	:	Nicolaides, N., and Apon, J. M.
TITLE	:	Further studies of the saturated methyl branched fatty acids of vernix caseosa lipid PubMed ID:994748
JOURNAL	:	Lipids.
VOL	:	11 PAGE : 781-790 (1976)

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AUTHOR	:	Yamazaki, T., Seyama, Y., Otsuka, H., Ogawa, H., and Yamakawa, T.
TITLE	:	Identification of alkyldiacylglycerols containing saturated methyl branched chains in the Harderian gland of guinea pig PubMed ID:7240136
JOURNAL	:	J Biochem (Tokyo).
VOL	:	89 PAGE : 683-691 (1981)

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AUTHOR	:	Abrahamsson,S.,Stallberg-Stenhagen,S., and Stenhagen,E.
TITLE	:	""The Higher Satureated Branched Chain Fatty Acids"
JOURNAL	:
VOL	:	7 PAGE : 110-143 (1963)

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AUTHOR	:	Ishizuka, I. and Niimura, Y. (1979) 5. Lipid. Component of Lipid, in Biochemistry Data Book (The Japanese Biochemical Society ed.), pp811-812, Tokyo Kagaku Dojin, Tokyo
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AUTHOR	:	Chan, H. W., and Levett, G.
TITLE	:	Autoxidation of methyl linoleate. Separation and analysis of isomeric mixtures of methyl linoleate hydroperoxides and methyl hydroxylinoleates PubMed ID:834127
JOURNAL	:	Lipids.
VOL	:	12 PAGE : 99-104 (1977)

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AUTHOR	:	Bolland, J.L., and Koch, H.P.
TITLE	:	The Course of Autoxidation Reactions in Polyisoprenes and Allied Compounds. IX. The Primary Thermal Oxidation Products of Ethyl Linoleate.
JOURNAL	:	J. Chem. Soc.
VOL	:	PAGE : 445-447 (1945)

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AUTHOR	:	Lundberg, W.O., and Chipault, J.R.
TITLE	:	The Oxidation of Methyl Linoleate at Various Temperatures
JOURNAL	:	J. Am. Chem. Soc.
VOL	:	69 PAGE : 833-836 (1947)

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AUTHOR	:	Lundberg, W. O., Chipault, J. R., and Hendrickson, N. J.
TITLE	:	Observation on The Mechanism of The Autoxidation of Methyl Linolate
JOURNAL	:	J. Am. Cil Chem. Soc.
VOL	:	26 PAGE : 109-115 (1949)

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AUTHOR	:	Gardner, H. W., and Weisleder, D.
TITLE	:	Lipoxygenase from Zea Mays: 9-D-Hydroperoxy-trans-10, cis-12-Octadecadienoic Acid
JOURNAL	:	Lipids
VOL	:	5 PAGE : 678-683 (1970)

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AUTHOR	:	Cannon, J. A., Zilch, K. T., Burket, S. C., and Dutton, H. J.
TITLE	:	Analysis of Fat Acid Oxidation Products by Countercurrent Distribution Methods. IV. Methyl Linoleate
JOURNAL	:	J. Am. Oil Chem. Soc.
VOL	:	29 PAGE : 447-452 (1952)

[TOP]

[8007]

AUTHOR	:	Privett, O. S., Lundberg, W. O.,Khan, N. A., Tolberg, W. E., and Wheeler, D. H.
TITLE	:	Structure of Hydroperoxides Obtained from Autoxidized Methyl Linoleate
JOURNAL	:	J. Am. Oil Chem Soc.
VOL	:	30 PAGE : 61-66 (1953)

[TOP]

[8008]

AUTHOR	:	Sephton, H. H., and Sutton, D. A.
TITLE	:	The Chemistry of Polymerized Oils. V. The Autoxidation of Methyl Linoleate
JOURNAL	:	J. Am. Oil Chem Soc.
VOL	:	33 PAGE : 263-272 (1956)

[TOP]

[8009]

AUTHOR	:	Graceland, A.
TITLE	:	Enzymatic Oxidation of Linoleic Acid and Grycerol-1-monolinoleate in Doughs and Flour-Water Suspensions
JOURNAL	:	J. Am. Oil Chem Soc.
VOL	:	47 PAGE : 352-361 (1970)

[TOP]

[8010]

AUTHOR	:	Privett, O. S., Nickell, C., Lundberg, W. O., and Boyer, P. D.
TITLE	:	Products of The Lipoxidase -Catalyzed Oxidation of Sodium Linoleate
JOURNAL	:	J. Am. Oil Chem Soc.
VOL	:	32 PAGE : 505-511 (1955)

[TOP]

[8011]

AUTHOR	:	Gardner, H. W., and Weisleader, D.
TITLE	:	Hydroperoxides from Oxidation of Linoleic and Linolenic Acids by Soybean Lipoxygenase: Proof of The trans-11 Double Bond
JOURNAL	:	Lipids
VOL	:	7 PAGE : 191-193 (1972)

[TOP]

[8012]

AUTHOR	:	Frankel, E. N., Neff, W. E., Rohwedder, W. K., Khambay, B. P., Garwood, R. F., and Weedon, B. C.
TITLE	:	Analysis of autoxidized fats by gas chromatography-mass spectrometry: II. Methyl linoleate PubMed ID:927043
JOURNAL	:	Lipids.
VOL	:	12 PAGE : 908-913 (1977)

[TOP]

[8013]

AUTHOR	:	Gardner, H. W., Kleiman, R., and Weisleder, D.
TITLE	:	Homolytic Decomposition of Linoleic Acid Hydroperoxide: Identification of Fatty Acid Products
JOURNAL	:	Lipids
VOL	:	9 PAGE : 696-706 (1974)

[TOP]

[8014]

AUTHOR	:	Hamberg, M.
TITLE	:	Decomposition of unsaturated fatty acid hydroperoxides by hemoglobin: Structures of major products of 13L-hydroperoxy-9,11-octadecadienoic acid PubMed ID:1167926
JOURNAL	:	Lipids.
VOL	:	10 PAGE : 87-92 (1975)

[TOP]

[8015]

AUTHOR	:	Dolev, A., Rohwedder, W. K., and Dutton, H. J.
TITLE	:	Mechanism of Lipoxidase Reaction. I. Specificity of Hydroperoxidation of Linoleic Acid
JOURNAL	:	Lipids
VOL	:	2 PAGE : 28-32 (1967)

[TOP]

[8016]

AUTHOR	:	Zimmerman, D. C., and Vick, B. A.
TITLE	:	Specificity of flaxseed lipoxidase PubMed ID:5447012
JOURNAL	:	Lipids.
VOL	:	5 PAGE : 392-397 (1970)

[TOP]

[8017]

AUTHOR	:	Neff, W. E., Frankel, E. N., Scholfield, C. R., and Wesleder, D.
TITLE	:	High-Pressure Liquid Chromatgraphy of Autoxidized Lipids: I. Methyl Oleate and Linoleate
JOURNAL	:	Lipids
VOL	:	13 PAGE : 415-421 (1978)

[TOP]

[8018]

AUTHOR	:	Kleiman, R., and Spencer, G. F.
TITLE	:	Gas Chromatgrphy-Mass Spectrometry of Methyl Esters of Unsaturated Oxygenated Fatty Acids
JOURNAL	:	J. Am. Oil Chem Soc.
VOL	:	50 PAGE : 31-38 (1973)

[TOP]

[8019]

AUTHOR	:	Frankel, E. N., Neff, W. E., and Bessler, T. R.
TITLE	:	Analysis of Autoxidized Fats by Gas Chromatgraphy-Mass Spectrometry: V. Photosensitized Oxidation
JOURNAL	:	Lipids
VOL	:	14 PAGE : 961-967 (1979)

[TOP]

[8020]

AUTHOR	:	Chan, H. W.-S.
TITLE	:	Photo-Sensitized Oxidation of Unsaturated Fatty Acids Methyl Esters. The Identification of Different Pathways
JOURNAL	:	J. Am. Oil Chem Soc.
VOL	:	54 PAGE : 100-104 (1977)

[TOP]

[8021]

AUTHOR	:	Frankel, E. N.( 1979 ) Autoxidation, in Fatty Acids ( Pryde, E. H., eds.), pp353-378, American Oil Chemists' Society, Champaign, IL.
TITLE	:
JOURNAL	:
VOL	:	PAGE : - ()

[TOP]

[8022]

AUTHOR	:	Mathusita, S.( 1982 ) Oxidative Products of Unsaturated Fatty Acids, in Nutrition and Foods, pp375-390 (in Japanese)
TITLE	:
JOURNAL	:
VOL	:	PAGE : - ()

[TOP]

[8023]

AUTHOR	:	Matsuo, M. (1985) Synthesis and Degradation of Lipid Peroxides, in Lipid Peroxides in Bodies (Yamauchi, M., Matsuo, M. and Sagai, M., eds.), pp13-44, Center for Academic Publications Japan
TITLE	:
JOURNAL	:
VOL	:	PAGE : - ()

[TOP]

[8024]

AUTHOR	:	Frankel, E. N.
TITLE	:	Lipid oxidation PubMed ID:7232452
JOURNAL	:	Prog Lipid Res.
VOL	:	19 PAGE : 1-22 (1980)

[TOP]

[8025]

AUTHOR	:	Frankel, E. N.
TITLE	:	Volatile lipid oxidation products PubMed ID:6306693
JOURNAL	:	Prog Lipid Res.
VOL	:	22 PAGE : 1-33 (1983)

[TOP]

[8026]

AUTHOR	:	Frankel, E. N.
TITLE	:	Chemistry of free radical and singlet oxidation of lipids PubMed ID:6100997
JOURNAL	:	Prog Lipid Res.
VOL	:	23 PAGE : 197-221 (1984)

[TOP]

[8027]

AUTHOR	:	Frankel, E. N.(1985 ) Chemistry of Autoxidation: Mechanism, products and Flavor Significance, in Flavor Chemistry of Fats and Oils (Min, D. B. and Smouse, T. H.,eds.),pp1-37,American Oil Chemisits' Society, Champaign, IL.
TITLE	:
JOURNAL	:
VOL	:	PAGE : - ()

[TOP]

[8028]

AUTHOR	:	Chan, H. W.-S., Coxon, D. T., Peers, K. E., and Price, K. R.
TITLE	:	Oxidative Reactions of Unsaturated Lipids
JOURNAL	:	Food Chemistry
VOL	:	9 PAGE : 21-34 (1982)

[TOP]

[8029]

AUTHOR	:	Frankel, E. N.(1962 ) Hydroperoxides, in Symposium on Foods: Lipids and Their Oxidation (Shulz, H. W., eds.), pp51-78,Avipubl., Westport, CT.
TITLE	:
JOURNAL	:
VOL	:	PAGE : - ()

[TOP]

[8030]

AUTHOR	:	Miyagawa, T.(1987 ) Oxidative Reactions and Their Priventive Mechanisms, in Foods and Antioxidants ( Ohta, S., eds.), pp1-37, Coference on the Food Materials, Japan
TITLE	:
JOURNAL	:
VOL	:	PAGE : - ()

[TOP]

[8031]

AUTHOR	:	Schewe, T., Rapoport, S. M., and Kuhn, H.(1986 ) Enzymology and Physiology of Reticulocyte Lipoxygenase: Comparison with Other Lipoxygenase, in Advancs in Enzymology (Meister, A., eds.), pp191-272, An Interscience, New York
TITLE	:
JOURNAL	:
VOL	:	PAGE : - ()

[TOP]

[8032]

AUTHOR	:	Whitaker, J. R.(1985 ) Mechanism of Oxidoreductases Important in Food Component Modification, in Chemical Changes in Food During Processing ( Richardson, T. and Finley, J. W., eds.), pp121-176, Avipubl, Westport, CT.
TITLE	:
JOURNAL	:
VOL	:	PAGE : - ()

[TOP]

[8033]

AUTHOR	:	Chism, G. W.( 1985 ) Soy Lipoxygenase, in Flavor Chemistry of Fats and Oils ( Min, D. B. and Smouse, T. H., eds.), pp175-188, American Oil Chemists' Sosiety, Champaign, IL.
TITLE	:
JOURNAL	:
VOL	:	PAGE : - ()

[TOP]

[8034]

AUTHOR	:	Mathuo, M.
TITLE	:	Synthesis of Lipid Peroxides and Their Physiological Effects.
JOURNAL	:	Fragrance J. (in Japanese)
VOL	:	76 PAGE : 15-20 (1986)

[TOP]

[8035]

AUTHOR	:	Veldink, G. A., Vligenthart, J. F. G., and Boldingh, J.( 1977 ) Plant Lipoxygenases, in Progress in The Chemistry of Fats and Other Lipids ( Holman, R. T., ed.), pp131-166 (15 ), Pergamon Press, London
TITLE	:
JOURNAL	:
VOL	:	PAGE : - ()

[TOP]

[8036]

AUTHOR	:	Wakabayashi, T.
TITLE	:	Lipoxygenase Reaction of Unsaturated Fatty Acids
JOURNAL	:	Chemistry and Biology (in Japanese)
VOL	:	18 PAGE : 558-564 (1980)

[TOP]

[8037]

AUTHOR	:	Vliegenthart, J. F. G., and Veldink, G. A.(1979 ) Lipoxygenase-Catalized Oxidation of Linoleic Acid, in Autoxidation in Food and Biological Systems ( Simic, M. G., and Karel, M., eds.), pp529-540, Plenum Press, New York
TITLE	:
JOURNAL	:
VOL	:	PAGE : - ()

[TOP]

[8038]

AUTHOR	:	Kurn, H., Schewe, T., and Rapoport, S. M.( 1986 ) The Stereochemistry of The Reactions of Lipoxygenase and Their Metabolites. Proposed Nomenclature of Lipoxygenases and Related Enzymes, in Advances in Enzymology ( Meister, A., ed.), pp273-311, An Interscience, New York
TITLE	:
JOURNAL	:
VOL	:	PAGE : - ()

[TOP]

[8039]

AUTHOR	:	Frankel, E. N.
TITLE	:	Secondary products of lipid oxidation PubMed ID:3311422
JOURNAL	:	Chem Phys Lipids.
VOL	:	44 PAGE : 73-85 (1987)

[TOP]

[8040]

AUTHOR	:	Porter, N. A., Weber, B. A., Weenen, H., and Khan, J. A.
TITLE	:	Autoxidation of Polyunsaturated Lipids. Factors Controlling The Stereo-Chemistry of Product Hydroperoxides
JOURNAL	:	J. Am. Chem. Soc.
VOL	:	102 PAGE : 5597-5601 (1980)

[TOP]

[8041]

AUTHOR	:	Porter, N. A., Lehman, I. S., Weber, B. A. and Smith, K. J.
TITLE	:	Unified Mechanism for Polyunsaturated Fatty Acid Autoxidation. Competition of Radical Hydrogen Atom Abstraction, b-Scission, and Cyclization
JOURNAL	:	J. Am. Chem. Soc.
VOL	:	103 PAGE : 6447-6455 (1981)

[TOP]

[8042]

AUTHOR	:	Porter, N. A., and Wujek, D. G.
TITLE	:	Autoxidation of Polyunsaturated Fatty Acids, An Expanded Mechanistic Study
JOURNAL	:	J. Am. Chem. Soc.
VOL	:	106 PAGE : 2626-2629 (1984)

[TOP]

[8043]

AUTHOR	:	Logani, M. K., and Davies, R. E.
TITLE	:	Lipid oxidation: biologic effects and antioxidants--a review PubMed ID:7401947
JOURNAL	:	Lipids.
VOL	:	15 PAGE : 485-495 (1980)

[TOP]

[8044]

AUTHOR	:	Tappel, A. L.( 1980 ) Free Radicals in Biology ( Pryor, W. A.,ed.),pp1-47 (4 ), Academic Press, New York
TITLE	:
JOURNAL	:
VOL	:	PAGE : - ()

[TOP]

[8045]

AUTHOR	:	Miyazawa, Y (1985 ) II Hydroperoxides and Physiological Factor; 1-2: Foods, in Hydroperoxides and Body ( Uthiyama, M., Mathuo, M., and Sagano, M.,eds.), pp98-122, Press Center of Societies, Japan
TITLE	:
JOURNAL	:
VOL	:	PAGE : - ()

[TOP]

[8046]

AUTHOR	:	Sevanian, A., and Hochstein, P.
TITLE	:	Mechanisms and consequences of lipid peroxidation in biological systems PubMed ID:2992549
JOURNAL	:	Annu Rev Nutr.
VOL	:	5 PAGE : 365-390 (1985)

[TOP]

[8047]

AUTHOR	:	Fujimoto, K.
TITLE	:	Toxicity and Safety of Lipid Peroxidates
JOURNAL	:	Fragrance J. (in Japanese)
VOL	:	76 PAGE : 21-25 (1986)

[TOP]

[8048]

AUTHOR	:	Halliwell, B., and Gutteridge, J. M. C. (1988 ) Free Radical and Bodies ( Translated by Matsuo, M., Sagai, M., and Yoshikawa, T.), pp151-203, Center for Academic Publications Japan
TITLE	:
JOURNAL	:
VOL	:	PAGE : - ()

[TOP]

[8049]

AUTHOR	:	Miyazawa, T., Fujimoto, K., and Kaneda, T.( 1988 ) Lipid Peroxidation in Biological Systems ( Sevanian, A., ed.) pp1, American Oil Chemists' Society, Chanpaign, IL.
TITLE	:
JOURNAL	:
VOL	:	PAGE : - ()

[TOP]

[8050]

AUTHOR	:	Haslbeck, F., Grosch, W., and Firl, J.
TITLE	:	Formation of hydroperoxides with unconjugated diene systems during autoxidation and enzymic oxygenation of linoleic acid PubMed ID:6402025
JOURNAL	:	Biochim Biophys Acta.
VOL	:	750 PAGE : 185-193 (1983)

[TOP]

[8051]

AUTHOR	:	Haslbeck, F., and Grosch, W.
TITLE	:	Autoxidation of Phenyl Linoleate and Phenyl Oleate: HPLC Analysis of The Major and Minor Monohydroperoxides as Phenyl Hydroxystearates
JOURNAL	:	Lipids
VOL	:	18 PAGE : 706-713 (1983)

[TOP]

[8052]

AUTHOR	:	Gardner, H. W., Weisleder, D.,and Kleiman, R.
TITLE	:	Formation Of Trans-12,13-Epoxy-9-Hydroperoxy-trans-10-Octadecenoic Acid from 13-L- Hydroperoxy-cis-9, trans-11-Octadecadienoic Acid Catalyzed by Either A Soybean Extract or Cysteine-Fec13
JOURNAL	:	Lipids
VOL	:	13 PAGE : 246-252 (1978)

[TOP]

[8053]

AUTHOR	:	Gardner, H. W., and Kleiman, R.
TITLE	:	A Soy Extract Catalyzes Formation of 9- Oxo-trans-12,13-Epoxy-trans-10-Ocatdecenoic Acid from 13- Hydroperoxy-cis-9, trans-11-Octadecanoic Acid
JOURNAL	:	Lipids
VOL	:	12 PAGE : 941-944 (1977)

[TOP]

[8054]

AUTHOR	:	Hamberg, M.
TITLE	:	A novel transformation of 13-LS-hydroperoxy-9,11-octadecadienoic acid PubMed ID:6860694
JOURNAL	:	Biochim Biophys Acta.
VOL	:	752 PAGE : 191-197 (1983)

[TOP]

[8055]

AUTHOR	:	Hamberg, M.
TITLE	:	Autoxidation of Linoleic Acid. Isolation and Structure of Four Dihydroxy-Octadecadienoic Acids
JOURNAL	:	Biochim. Biophys. Acta
VOL	:	752 PAGE : 353-356 (1983)

[TOP]

[8056]

AUTHOR	:	Schieberle, P., Tsoukalas, B., and Grosch, W.
TITLE	:	Decomposition of Linoleic Acid Hydroperoxides by Radicals I. Structures of Products of Methyl 13-Hydroperoxy-cis, trans-9,11-Octadecadienoate
JOURNAL	:	Z. Lebensm. Unters. Forsch.
VOL	:	168 PAGE : 448-456 (1979)

[TOP]

[8057]

AUTHOR	:	Schieberle, P., and Grosch, W.
TITLE	:	Decomposition of Linoleic Acid Hydroperoxides II. Breakdown of Methyl 13-Hydroperoxy-cis-9-trans-11-Octadecadienoate by Radicals or Copper II Ions
JOURNAL	:	Z. Lebensm. Unters. Forsch.
VOL	:	173 PAGE : 192-198 (1981)

[TOP]

[8058]

AUTHOR	:	Yamamoto, Y., Saeki, N., Haga, S., Niki, E., and Kamiya. Y.
TITLE	:	Oxidation of Lipids. IX. Decomposition of Methyl Linoleate and Methyl Linolenate Hydroperoxydes in Solution
JOURNAL	:	Bull. Chem. Soc. Jpn.
VOL	:	57 PAGE : 3177-3181 (1984)

[TOP]

[8059]

AUTHOR	:	Streckert, G., and Stan, H. J.
TITLE	:	Conversion of linoleic acid hydroperoxide by soybean lipoxygenase in the presence of guaiacol: identification of the reaction products PubMed ID:813080
JOURNAL	:	Lipids.
VOL	:	10 PAGE : 847-854 (1975)

[TOP]

[8060]

AUTHOR	:	Garssen, G. J., Veldink, G. A., Vliegenthart, J. F., and Boldingh, J.
TITLE	:	The formation of threo-11-hydroxy-trans-12: 13-epoxy-9-cis-octadecenoic acid by enzymic isomerisation of 13-L-hydroperoxy-9-cis, 11-transoctadecadienoic acid by soybean lipoxygenase-1 PubMed ID:814001
JOURNAL	:	Eur J Biochem.
VOL	:	62 PAGE : 33-36 (1976)

[TOP]

[8061]

AUTHOR	:	Tokita, M., and Morita, M.
TITLE	:	Methyl 9-(2-(2,5-Dihydro-5-Pentylfuryl))-Nonanoate in The Copper- Catalyzed Decomposition Products of Methyl Linoleate Hydroperoxides and Some Other Products
JOURNAL	:	Agric. Biol. Chem.
VOL	:	51 PAGE : 309-313 (1987)

[TOP]

[8062]

AUTHOR	:	Wu, G. S., Stein, R. A., and Mead, J. F.
TITLE	:	Autoxidation of fatty acid monolayers adsorbed on silica gel: II. Rates and products PubMed ID:200817
JOURNAL	:	Lipids.
VOL	:	12 PAGE : 971-978 (1977)

[TOP]

[8063]

AUTHOR	:	Gardner, H. W., and Kleiman, R.
TITLE	:	Degradation of linoleic acid hydroperoxides by a cysteine. FeCl3 catalyst as a model for similar biochemical reactions. II. Specificity in formation of fatty acid epoxides PubMed ID:7284409
JOURNAL	:	Biochim Biophys Acta.
VOL	:	665 PAGE : 113-124 (1981)

[TOP]

[8064]

AUTHOR	:	Christophersen, B. O.
TITLE	:	Formation of monohydroxy-polyenic fatty acids from lipid peroxides by a glutathione peroxidase PubMed ID:5680294
JOURNAL	:	Biochim Biophys Acta.
VOL	:	164 PAGE : 35-46 (1968)

[TOP]

[8065]

AUTHOR	:	Hamberg, M., and Samuelsson, B.
TITLE	:	On The Specificity of The Oxygenation of Unsaturated Fatty Acids Catalyzed by Soybean Lipoxidase. PubMed ID:6070850
JOURNAL	:	J. Biol. Chem.
VOL	:	242 PAGE : 5329-5335 (1967)

[TOP]

[8066]

AUTHOR	:	Galliard, T., Phillips, D. R., and Matthew, J. A.
TITLE	:	Enzymic reactions of fatty acid hydroperoxides in extracts of potato tuber. II. Conversion of 9- and 13-hydroperoxy-octadecadienoic acids to monohydroxydienoic acid, epoxyhydroxy- and trihydroxymonoenoic acid derivatives PubMed ID:63
JOURNAL	:	Biochim Biophys Acta.
VOL	:	409 PAGE : 157-171 (1975)

[TOP]

[8067]

AUTHOR	:	Gardner, W. H.
TITLE	:	Sequential enzymes of linoleic acid oxidation in corn germ: lipoxygenase and linoleate hydroperoxide isomerase PubMed ID:5459662
JOURNAL	:	J Lipid Res.
VOL	:	11 PAGE : 311-321 (1970)

[TOP]

[8068]

AUTHOR	:	Gardner, H. W., and Kleiman, R.
TITLE	:	Lack Of Regioselectivity in Formation of Oxohydroxyocatadecenoic Acids from The 9- or 13- Hydroperoxide of Linoleic Acid
JOURNAL	:	Lipids
VOL	:	14 PAGE : 848-851 (1979)

[TOP]

[8069]

AUTHOR	:	Gardner, H. W., Nelson, E. C., Tjarks, L. W., and England, R. E.
TITLE	:	Acid-Catalyzed Transformation of 13(S)- Hydroperoxylinoleic Acid into Epoxyhydroxyoctadecenoic and Trihydroxyoctadecenoic Acids
JOURNAL	:	Chem. Phys. Lipids
VOL	:	35 PAGE : 87-101 (1984)

[TOP]

[8070]

AUTHOR	:	Gardner, H. W., Weisleder, D., and Nelson, E. C.
TITLE	:	Acid Catalysis of A Linoleic Acid Hydroperoxide: Formation of Epoxides by An Intramolecular Cyclization of The Hydroperoxide Group
JOURNAL	:	J. Org. Chem.
VOL	:	49 PAGE : 508-515 (1984)

[TOP]

[8071]

AUTHOR	:	Sessa, D. J., Gardner, H. W., Kleiman, R., and Weisleder, D.
TITLE	:	Oxygenated fatty acid constituents of soybean phosphatidylcholines PubMed ID:561287
JOURNAL	:	Lipids.
VOL	:	12 PAGE : 613-619 (1977)

[TOP]

[8072]

AUTHOR	:	Kato, T., Yamaguthi, H., Uehara, T., and Namai, T.
TITLE	:	Tolerance to Race blast and Oxidized Unsaturated Fatty Acids
JOURNAL	:	Chemistry and Biology (in Japanese)
VOL	:	24 PAGE : 183-188 (1986)

[TOP]

[8073]

AUTHOR	:	Gardner, H. W.
TITLE	:	Decomposition of linoleic acid hydroperoxides. Enzymic reactions compared with nonenzymic PubMed ID:805802
JOURNAL	:	J Agric Food Chem.
VOL	:	23 PAGE : 129-136 (1975)

[TOP]

[8074]

AUTHOR	:	Gardner, H. W. (1985) Oxidation Of Lipids in Biological Tissue and Its Significance, in Chemical Changes in Food during Processing ( Richardson,T., and Finley, J. W.,Eds.), pp177-203, Avi. Publ., Westport, Ct.
TITLE	:
JOURNAL	:
VOL	:	PAGE : - ()

[TOP]

[8075]

AUTHOR	:	Garssen, G. J., Vliegenthart, J. F., and Boldingh, J.
TITLE	:	An anaerobic reaction between lipoxygenase, linoleic acid and its hydroperoxides PubMed ID:5165730
JOURNAL	:	Biochem J.
VOL	:	122 PAGE : 327-332 (1971)

[TOP]

[8076]

AUTHOR	:	Chan, H. W. - S.,And Levett, G.
TITLE	:	Autoxidation of Methyl Linolenate: Analysis of Methyl Hydroxylinolenate Isomers by High Performance Liquid Chromatography.
JOURNAL	:	Lipids
VOL	:	12 PAGE : 837-840 (1977)

[TOP]

[8077]

AUTHOR	:	Frankel, E. N., Neff, W. E., Rohwedder, W. K., Khambay, B. P. S., Garwood, R. F., and Weedon, B. C. L.
TITLE	:	Analysis of Autoxidized Fats By Gas Chromatography- Mass Spectrometry: III. Methyl Linolenate.
JOURNAL	:	Lipids
VOL	:	12 PAGE : 1055-1061 (1977)

[TOP]

[8078]

AUTHOR	:	Toyoda, I., Terao, J.,And Matsushita, S.
TITLE	:	Hydroperoxides Formed by Ferrous Ion- Catalyzed Oxidation of Methyl Linolenate
JOURNAL	:	Lipids
VOL	:	17 PAGE : 84-90 (1982)

[TOP]

[8079]

AUTHOR	:	Terao, J., Inoue, T., Yamagata, S., Murakami, H., and Matsushita, S.
TITLE	:	Gas Chromatography Mass Spectrometric Analysis of Monohydroperoxide Isomers and Their Secondary Oxidation Products of Methyl Linoleate and Methyl Linolenate
JOURNAL	:	Agric. Biol. Chem.
VOL	:	48 PAGE : 1735-1743 (1984)

[TOP]

[8080]

AUTHOR	:	Terao, J., and Matsushita, S.
TITLE	:	Analysis of Hemoprotein Catalyzed Peroxidation Products of Arachidonic Acid by Gas Chromatography- Mass Spectrometry
JOURNAL	:	Agric. Biol. Chem.
VOL	:	45 PAGE : 595-599 (1981)

[TOP]

[8081]

AUTHOR	:	Neff, W. E., Frankel, E. N., and Weisleder, D.
TITLE	:	High Pressure Liquid Chromatography of Autoxidized Lipids: II. Hydroperoxycyclic Peroxides and Other Secondary Products from Methyl Linolenate
JOURNAL	:	Lipids
VOL	:	16 PAGE : 439-448 (1981)

[TOP]

[8082]

AUTHOR	:	Nakamura, T.
TITLE	:	Prostaglandin- Like Substances Formed during Autoxidation of Methyl Linoleate
JOURNAL	:	Lipids
VOL	:	21 PAGE : 553-557 (1986)

[TOP]

[8083]

AUTHOR	:	Coxon, D. T., Price, K. R., and Chan, H. W. - S.
TITLE	:	Formation, Isolation and Structure Determination of Methyl Linolenate Diperoxides
JOURNAL	:	Chem. Phys. Lipids
VOL	:	28 PAGE : 365-378 (1981)

[TOP]

[8084]

AUTHOR	:	Neff, W. E., Frankel, E. N., and Weisleder, D.
TITLE	:	Photosensitized Oxidation of Methyl Linolenate. Secondary Products
JOURNAL	:	Lipids
VOL	:	17 PAGE : 780-790 (1982)

[TOP]

[8085]

AUTHOR	:	Neff, W. E., and Frankel, E. N.
TITLE	:	Photosensitized Oxidation of Methyl Linolenate Monohydroperoxides: Hydro-Peroxy Cyclic Peroxides, Dihydroperoxides and Hydroperoxy Bis- Cyclic Peroxides
JOURNAL	:	Lipids
VOL	:	19 PAGE : 952-957 (1984)

[TOP]

[8086]

AUTHOR	:	O'connor, D. E., Mihelich, E. D., and Coleman, M. C.
TITLE	:	Stereochemical Course of The Autoxidative Cyclization of Lipid Hydroperoxides to Prostaglandin-Like Bicyclo Endoperoxides
JOURNAL	:	J. Am. Chem. Soc.
VOL	:	106 PAGE : 3577-3584 (1984)

[TOP]

[8087]

AUTHOR	:	O'connor, D. E., Mihelich, E. D., and Coleman, M. C.
TITLE	:	Isolation and Characterization of Bicyclo Endoperoxides Derived from Methyllinolenate
JOURNAL	:	J. Am. Chem. Soc.
VOL	:	103 PAGE : 223-224 (1981)

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AUTHOR	:	Chan, H. W. - S., Matthew, J. A., and Coxon, D. T.
TITLE	:	A Hydoperoxy- Epidioxide from The Autoxidation of A Hydroperoxide of Methyl Linolenate
JOURNAL	:	J. Chem. Soc. Chem. Commun.
VOL	:	PAGE : 235-236 (1980)

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AUTHOR	:	Frankel, E. N., Neff, W. E., and Plattner, R. D.
TITLE	:	Chemichal Ionization- Mass Spectrometry of Secondary Oxidation Products from Methyl Linoleate and Linolenate
JOURNAL	:	Lipids
VOL	:	21 PAGE : 333-337 (1986)

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[8090]

AUTHOR	:	Terao, J., and Matsushita, S.
TITLE	:	Products Formed by Photosensitized Oxidation of Unsaturated Fatty Acid Esters
JOURNAL	:	J. Am. Oil Chem. Soc.
VOL	:	54 PAGE : 234-238 (1977)

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AUTHOR	:	Thomas, M. J., and Pryor, W. A.
TITLE	:	Singlet Oxygen Oxidation of Methyl Linoleate: Isolation and Characterization of The Nabh4- Reduced Products
JOURNAL	:	Lipids
VOL	:	15 PAGE : 544-548 (1980)

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AUTHOR	:	Terao, J., and Matsushita, S.
TITLE	:	Further Oxygenated Compounds Produced from Methyl Linoleate MonohydroperOxides at The Process of Autoxidation
JOURNAL	:	Agric. Biol. Chem.
VOL	:	39 PAGE : 2027-2033 (1975)

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AUTHOR	:	Hamberg, M., and Gotthammar, B.
TITLE	:	A New Reaction of Unsaturated Fatty Acid Hydroperoxides: Formation of 11-Hydroxy-12,13- Epoxy-9- Octadecenoic Acid from 13- Hydroperoxy-9,11- Octadecadienoic Acid
JOURNAL	:	Lipids
VOL	:	8 PAGE : 737-744 (1973)

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AUTHOR	:	Peers, K. E., Coxon, D. T., and Chan, H. W. - S.
TITLE	:	Autoxidation of Methyl Linolenate. The Effect of Antioxidants on Product Distribution
JOURNAL	:	J. Sci. Food Agric.
VOL	:	35 PAGE : 813-817 (1984)

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AUTHOR	:	Terao, J., and Matsushita, S.
TITLE	:	The Peroxidizing Effect of a- Tocopherol on Autoxidation of Methyl Linoleate in Bulk Phase
JOURNAL	:	Lipids
VOL	:	21 PAGE : 255-260 (1986)

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AUTHOR	:	Fujimoto, K., Neff, W. E., and Frankel, E. N.
TITLE	:	The reaction of DNA with lipid oxidation products, metals and reducing agents PubMed ID:6466690
JOURNAL	:	Biochim Biophys Acta.
VOL	:	795 PAGE : 100-107 (1984)

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AUTHOR	:	Yamagata, S., Murakami, H., Terao, J., and Matsushita, S.
TITLE	:	Nonenzymatic Oxidation Products of Methyl Arachidonate
JOURNAL	:	Agric. Biol. Chem.
VOL	:	47 PAGE : 2791-2799 (1983)

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AUTHOR	:	Terao, J.,And Matsushita, S.
TITLE	:	The Isomeric Compositions of Hydroperoxides Produced by Oxidation of Arachidonic Acid with Singlet Oxygen
JOURNAL	:	Agric. Biol. Chem.
VOL	:	45 PAGE : 587-593 (1981)

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AUTHOR	:	Porter, N. A., Logan, J., and Kontoyiannidou, V.
TITLE	:	Preparation and Purification of Arachidonic Acid Hydroperoxides of Biological Importance
JOURNAL	:	J. Org. Chem.
VOL	:	44 PAGE : 3177-3181 (1979)

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AUTHOR	:	Murota, S.(1982) An Outline of Prostaglandins, in Biochemistry of Prosatglandins (Murota, S., ed.), pp3-26, Tokyo Kagaku Dojin, Japan (in Japanese)
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AUTHOR	:	Spector, A. A., Gordon, J. A., and Moore, S. A.
TITLE	:	Hydroxyeicosatetraenoic acids (HETEs) PubMed ID:3076240
JOURNAL	:	Prog Lipid Res.
VOL	:	27 PAGE : 271-323 (1988)

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AUTHOR	:	Pace- Asciak, C. R., and Smith, W. L.(1983) Enzymes in The Biosynthesis and Catabolism of The Eicosanoids: Prostaglandins, Thromboxanes, Leukotriens and Hydroxy Fatty Acids, In The Enzymes (Boyer, P. D., Ed.), Vol.16, pp543-603, Academic Press New York
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AUTHOR	:	Shimizu, T.
TITLE	:	A Recent Advance in Studies on Leukotriens (in Japanese)
JOURNAL	:	Taisha
VOL	:	24 PAGE : 203-214 (1987)

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AUTHOR	:	Yamamoto, N.(1987) 1. A New Advance in Study on Prostaglandins, 2. Chemistry and Biochemistry, in An Advance in Recent Study on Prostaglandins, pp.1-86, Kodansha Scientific, Tokyo, Japan (in Japanese)
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AUTHOR	:	Porter, N. A., Wolf, R. A., Yarbro, E. M., and Weenen, H.
TITLE	:	The autoxidation of arachidonic acid: formation of the proposed SRS-A intermediate PubMed ID:496937
JOURNAL	:	Biochem Biophys Res Commun.
VOL	:	89 PAGE : 1058-1064 (1979)

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AUTHOR	:	Peers, K. E., and Coxon, D. T.
TITLE	:	Controlled Synthesis of Monohydroperoxides by a- Tocopherol Inhibited Autoxidation of Polyunsaturated Lipids
JOURNAL	:	Chem. Phys. Lipids
VOL	:	32 PAGE : 49-56 (1983)

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AUTHOR	:	Nakamura, T., and Hara, Y.
TITLE	:	Prostaglandin-Like Substances, Precursors of Red Pigment, Formed during Autoxidation of Methyl Arachidonate
JOURNAL	:	J. Agric. Food Chem.
VOL	:	36 PAGE : 15-18 (1988)

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AUTHOR	:	Bild, G. S., Ramadoss, C. S., Lim, S., and Axelrod, B.
TITLE	:	Double dioxygenation of arachidonic acid by soybean lipoxygenase--1 PubMed ID:402916
JOURNAL	:	Biochem Biophys Res Commun.
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AUTHOR	:	Yamauchi, R., Yamada, T., Kato, K., and Ueno, Y.
TITLE	:	Monohydroperoxides Formed by Autoxidation and Photosensitized Oxidation of Methyl Eicosapentaenoate
JOURNAL	:	Agric. Biol. Chem.
VOL	:	47 PAGE : 2897-2902 (1983)

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AUTHOR	:	Yamauchi, R., Yamada, T., Kato, K., and Ueno, Y.
TITLE	:	Myoglobin-Catalyzed Peroxidation Products of Methyl Eicosapentaenoate
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VOL	:	49 PAGE : 3311-3313 (1985)

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AUTHOR	:	Katori, S. (1987) 18. Eicosapentaenoic acid, in An Advance in Recent Study on Prostaglandins, (Murota, S., and Yamanoto, K., eds.), pp.421-438, Kodansha Scientific, Tokyo, Japan (in Japanese)
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AUTHOR	:	Murota, S., and Morita, I. (1988) 10. Eicosapentaenoic Acid, in An Advance in Recent Study on Prostaglandins, (Murota, S., and Yamanoto, K., eds.), pp.137-177, Kodansha Scientific, Tokyo, Japan (in Japanese)
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AUTHOR	:	Lee, T. H., Drazen, J. M., Lewis, R. A., and Austen, K. F.
TITLE	:	Substrate and regulatory functions of eicosapentaenoic and docosahexaenoic acids for the 5-lipoxygenase pathway. Implications for pulmonary responses PubMed ID:2581266
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TITLE	:	Transformation of Arachidonic Acid and Homo-g- Linolenic Acid by Rabbit Polymorphonuclear Leukocytes. PubMed ID:826538
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AUTHOR	:	Narumiya, S., Salmon, J. A., Cottee, F. H., Weatherley, B. C., and Flower, R. J.
TITLE	:	Arachidonic acid 15-lipoxygenase from rabbit peritoneal polymorphonuclear leukocytes. Partial purification and properties PubMed ID:6793572
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AUTHOR	:	Rabinovitch, H., Durand, J., Rigaud, M., Mendy, F., and Breton, J. C.
TITLE	:	Transformation of arachidonic acid into monohydroxy-eicosatetraenoic acids by mouse peritoneal macrophages PubMed ID:7278513
JOURNAL	:	Lipids.
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AUTHOR	:	Koshihara, Y., Mizumura, M., and Murota, S.
TITLE	:	Predominant synthesis of 5-hydroxyeicosatetraenoic acid by a cloned mastocytoma P-815 line, 2-E-6 cells PubMed ID:6810946
JOURNAL	:	Biochim Biophys Acta.
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AUTHOR	:	Ochi, K., Yoshimoto, T., Yamamoto, S., Taniguchi, K., and Miyamoto, T.
TITLE	:	Arachidonate 5-lipoxygenase of guinea pig peritoneal polymorphonuclear leukocytes. Activation by adenosine 5'-triphosphate PubMed ID:6406506
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AUTHOR	:	Furukawa, M., Yoshimoto, T., Ochi, K., and Yamamoto, S.
TITLE	:	Studies on arachidonate 5-lipoxygenase of rat basophilic leukemia cells PubMed ID:6089906
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AUTHOR	:	Mayer, B., Moser, R., Gleispach, H., and Kukovetz, W. R.
TITLE	:	Possible inhibitory function of endogenous 15-hydroperoxyeicosatetraenoic acid on prostacyclin formation in bovine aortic endothelial cells PubMed ID:3081039
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TITLE	:	Stereospecific elimination of hydrogen at C-10 in eicosapentaenoic acid during the conversion to leukotriene C5 PubMed ID:6296095
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AUTHOR	:	Yamagata, S., Murakami, H., Terao, J., and Matsushita, S.
TITLE	:	Decomposition Products of Methyl Arachidonate Monohydroperoxides
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AUTHOR	:	Oliw, E. H., and Sprecher, H.
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AUTHOR	:	Porter, N. A., and Wujek, D. G.
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AUTHOR	:	Haeggstrom, J., Wetterholm, A., Hamberg, M., Meijer, J., Zipkin, R., and Radmark, O.
TITLE	:	Enzymatic formation of 5,6-dihydroxy-7,9,11,14-eicosatetraenoic acid: kinetics of the reaction and stereochemistry of the product PubMed ID:2829972
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AUTHOR	:	Muller, A., Rechencq, E., Kugel, C., Lellouche, J. P., Beaucourt, J. P., Niel, G., Girard, J. P., Rossi, J. C., and Bonne, C.
TITLE	:	Comparative biological activities of the four synthetic (5,6)-dihete isomers PubMed ID:2633210
JOURNAL	:	Prostaglandins.
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AUTHOR	:	Oliw, E.H., Guengerich, F.P., and Oates, J.A.
TITLE	:	Oxygenation of arachidonic acid by hepatic monooxygenases. Isolation and metabolism of four epoxide intermediates. PubMed ID:6801052
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AUTHOR	:	Green, F. A.
TITLE	:	Transformations of 5-HETE by activated keratinocyte 15-lipoxygenase and the activation mechanism PubMed ID:2127820
JOURNAL	:	Lipids.
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AUTHOR	:	O'Flaherty, J. T., and Thomas, M. J.
TITLE	:	Effect of 15-lipoxygenase-derived arachidonate metabolites on human neutrophil degranulation PubMed ID:3920680
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AUTHOR	:	Morita, E., Schroder, J. M., and Christophers, E.
TITLE	:	Identification of a novel and highly potent eosinophil chemotactic lipid in human eosinophils treated with arachidonic acid PubMed ID:2155268
JOURNAL	:	J Immunol.
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AUTHOR	:	Oliw, E. H.
TITLE	:	Biosynthesis of 5,6-dihydroxyprostaglandin E1 and F1 alpha from 5,6-dihydroxyeicosatrienoic acid by ram seminal vesicles PubMed ID:6548162
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AUTHOR	:	Zhang, J. Y., Prakash, C., Yamashita, K., and Blair, I. A.
TITLE	:	Regiospecific and enantioselective metabolism of 8,9-epoxyeicosatrienoic acid by cyclooxygenase PubMed ID:1543485
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AUTHOR	:	Catella, F., Lawson, J. A., Fitzgerald, D. J., and FitzGerald, G. A.
TITLE	:	Endogenous biosynthesis of arachidonic acid epoxides in humans: increased formation in pregnancy-induced hypertension PubMed ID:2198572
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AUTHOR	:	Chacos, N., Falck, J.R., Wixtrom, C., et al.
TITLE	:	Novel epoxides formed during the liver cytochrome P-450 oxidation of arachidonic acid. PubMed ID:6803794
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AUTHOR	:	Snyder, G., Lattanzio, F., Yadagiri, P., Falck, J. R., and Capdevila, J.
TITLE	:	5,6-Epoxyeicosatrienoic acid mobilizes Ca2+ in anterior pituitary cells PubMed ID:3533073
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AUTHOR	:	Falck, J. R., Manna, S., Moltz, J., Chacos, N., and Capdevila, J.
TITLE	:	Epoxyeicosatrienoic acids stimulate glucagon and insulin release from isolated rat pancreatic islets PubMed ID:6411091
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AUTHOR	:	Katoh, T., Takahashi, K., Capdevila, J., Karara, A., Falck, J. R., Jacobson, H. R., and Badr, K. F.
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AUTHOR	:	Haviv, F., Ratajczyk, J.D., DeNet, R.W., et al.
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AUTHOR	:	Kulkarni, P.S., Kaufman, P.L., and Srinivasan, B.D.
TITLE	:	Eicosapentaenoic acid metabolism in cynomolgus and rhesus conjunctiva and eyelid. PubMed ID:2846724
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AUTHOR	:	Kulkarni, P. S., and Srinivasan, B. D.
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JOURNAL	:	Prostaglandins.
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AUTHOR	:	Hill, E.M., Holland, D.L., Gibson, K.H., et al.
TITLE	:	Identification and hatching factor activity of monohydroxyeicosapentaenoic acid in homogenates of the barnacle Elminius modestus.
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AUTHOR	:	Shing, T.K.M., Gibson, K.H., Wiley, J.R., et al.
TITLE	:	First total synthesis of a barnacle hatching factor 8(R)-hydroxy-eicosa-5(Z),9(E),11(Z)-pentaenoic acid.
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AUTHOR	:	Hill, E. M., and Holland, D. L.
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AUTHOR	:	Masferrer, J. L., Dunn, M. W., and Schwartzman, M. L.
TITLE	:	12(R)-hydroxyeicosatetraenoic acid, an endogenous corneal arachidonate metabolite, lowers intraocular pressure in rabbits PubMed ID:2318592
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AUTHOR	:	Conners, M. S., Schwartzman, M. L., Quan, X., Heilman, E., Chauhan, K., Falck, J. R., and Godfrey, H. P.
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AUTHOR	:	Miller, C., Yamaguchi, R. Y., and Ziboh, V. A.
TITLE	:	Guinea pig epidermis generates putative anti-inflammatory metabolites from fish oil polyunsaturated fatty acids PubMed ID:2559281
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AUTHOR	:	Bittleman, D. B., and Casale, T. B.
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AUTHOR	:	Hawkins, D.J. and Brash, A.R.
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