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Fatty acid

(total 755)
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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
MELTING POINT BOILING POINT DENSITY REFRACTIVE INDEX OPTICAL ROTATION SOLUBILITY UV SPECTRA IR SPECTRA NMR SPECTRA MASS SPECTRA OTHER SPECTRA
1
Formic acid
Methanoic acid
DFA0001
Tetsuyuki Kobayashi
Fo
CH2O2 46.025 Download ChemDraw structure fileDownload mol format file
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.
8.4degC
100.5degC
d4-20 1.220
1.3714 at 20degC
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)



2
Acetic acid
Ethanoic acid
DFA0002
Tetsuyuki Kobayashi
Ac
C2H4O2 60.052 Download ChemDraw structure fileDownload mol format file

16.7degC
118.2degC
d4-20 1.049
1.3718 at 20degC
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)



3
Propioic acid
Propanoic acid
DFA0003
Tetsuyuki Kobayashi
Pp
C3H6O2 74.079 Download ChemDraw structure fileDownload mol format file

-22.0degC
141.1degC
d4-20 0.992
1.3874 at 20degC
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)



4
Butyric acid
Butanoic acid
DFA0004
Tetsuyuki Kobayashi
Bt/C4:0
C4H8O2 88.105 Download ChemDraw structure fileDownload mol format file

-7.9degC
163.5degC
d4-20 0.9587
1.33906 at 20degC
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.



5
Valeric acid
Pentanoic acid
DFA0005
Tetsuyuki Kobayashi
Vl/C5:0
C5H10O2 102.132 Download ChemDraw structure fileDownload mol format file

-34.5degC
187.0degC
d4-20 0.942
1.4086 at 20degC
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.



6
Caproic acid
Hexanoic acid
DFA0006
Tetsuyuki Kobayashi
Hxo/C6:0
C6H12O2 116.158 Download ChemDraw structure fileDownload mol format file

-3.4degC
205.8degC
d4-20 0.929
1.41635 at 20degC
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.



7
Heptylic acid / Enanthic acid / Enanthylic acid / Heptoic acid
Heptanoic acid
DFA0007
Tetsuyuki Kobayashi
Hpo / C7:0
C7H14O2 130.185 Download ChemDraw structure fileDownload mol format file

-10.5degC
223.0degC
d4-20 0.92215
1.4230 at 20degC
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.



8
Caprylic acid / Octylic acid
Octanoic acid
DFA0008
Tetsuyuki Kobayashi
Oco / C8:0
C8H16O2 144.211 Download ChemDraw structure fileDownload mol format file

16.7degC
239.7degC
d4-20 0.910
1.4285 at 20degC
very slightly soluble in water (0.068g/100g at 20degC); freely soluble in alcohol, chloroform, ether, carbon disulfide, petroleum ether and glacial acetic acid.(Ref. 0347)




Butterfat;palm-kernel oils




9
Pelargonic acid / Nonylic acid
Nonanoic acid
DFA0009
Tetsuyuki Kobayashi
Nno / C9:0
C9H18O2 158.238 Download ChemDraw structure fileDownload mol format file

12.5degC
255.6degC
d4-20 0.907
1.4322 at 20degC
practically insoluble in water; soluble in alcohol, chloroform and ether.(Ref. 0021)(Ref. 0022)(Ref. 0523)




Butterfat;hair fat




10
Capric acid
Decanoic acid
DFA0010
Tetsuyuki Kobayashi
Dec / Dco / C10:0
C10H20O2 172.265 Download ChemDraw structure fileDownload mol format file

31.6degC
270.0degC
d404 0.8858
1.42855 at 40degC
practically insoluble in water (0.015g/100g at 20degC); also soluble in ethanol, ether, chloroform, benzene and carbon disulfide.(Ref. 0353)(Ref. 0380)(Ref. 0449)




Butterfat;palm-kernel oils




11
Undecylic acid / Hendecanoic acid
Undecanoic acid
DFA0011
Tetsuyuki Kobayashi
Udo / C11:0
C11H22O2 186.291 Download ChemDraw structure fileDownload mol format file

29.3degC
284.0degC
d4-25 0.9905
1.4202 at 70degC
soluble in alcohol, chloroform and ether.(Ref. 0219)(Ref. 0523)




Human-hair fat.




12
Lauric acid
Dodecanoic acid
DFA0012
Tetsuyuki Kobayashi
Lau / C12:0
C12H24O2 200.318 Download ChemDraw structure fileDownload mol format file

44.2degC
225degC at 100 mmHg
d504 0.8690
1.4261 at 60degC
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




13
Tridecylic acid
Tridecanoic acid
DFA0013
Tetsuyuki Kobayashi
C13:0
C13H26O2 214.344 Download ChemDraw structure fileDownload mol format file

41.5degC
236degC at 100 mm Hg
d4-80 0.8458
1.4286 at 60degC
soluble in acetone, alcohol, ether and petroleum ether.<0219>>(Ref. 0305)(Ref. 0445)(Ref. 0523)




Human-hair fat




14
Myristic acid
Tetradecanoic acid
DFA0014
Tetsuyuki Kobayashi
Myr / C14:0
C14H28O2 228.371 Download ChemDraw structure fileDownload mol format file

53.9degC
250degC at 100 mmHg
d544 0.8622
1.4273 at 70degC
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




15
Pentadecylic acid
Pentadecanoic acid
DFA0015
Tetsuyuki Kobayashi
C15:0
C15H30O2 242.398 Download ChemDraw structure fileDownload mol format file

52.3degC
202.5degC at 10 mmHg
d4-80 0.8423
1.4292 at 70degC
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




16
Palmitic acid
Hexadecanoic acid
DFA0016
Tetsuyuki Kobayashi
Pam / C16:0
C16H32O2 256.424 Download ChemDraw structure fileDownload mol format file

63.1degC
268degC at 100 mmHg
d4-70 0.8487
1.4309 at 70degC
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




17
Margaric acid / Heptadecylic acid
Heptadecanoic acid
DFA0017
Tetsuyuki Kobayashi
C17:0
C17H34O2 270.451 Download ChemDraw structure fileDownload mol format file

61.3degC
220degC at 10 mmHg
d604 0.853
1.4324 at 70degC
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




18
Stearic acid
Octadecanoic acid
DFA0018
Tetsuyuki Kobayashi
Ste / C18:0
C18H36O2 284.477 Download ChemDraw structure fileDownload mol format file

69.6degC
213degC at 5 mmHg
d4-80 0.8390
1.4337 at 70degC
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)




19
Nonadecylic acid
Nonadecanoic acid
DFA0019
Tetsuyuki Kobayashi
C19:0
C19H38O2 298.504 Download ChemDraw structure fileDownload mol format file

68.6degC
299degC at 10 mmHg
d4-24 0.8771
1.4512 at 25degC
soluble in acetone, hot alcohol, ether and petroleum ether.(Ref. 0182)(Ref. 0277)(Ref. 0319)(Ref. 0329)(Ref. 0360)(Ref. 0527)




Ox fat




20
Arachidic acid
Icosanoic acid / Eicosanoic acid
DFA0020
Tetsuyuki Kobayashi
Ach / C20:0
C20H40O2 312.530 Download ChemDraw structure fileDownload mol format file

76.5-77.0degC
204degC at 1 mmHg
d1004 0.8240
1.4250 at 100degC
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




21
Heneicosanoic acid / Henicosanoic acid
DFA0021
Tetsuyuki Kobayashi
C21:0
C21H42O2 326.557 Download ChemDraw structure fileDownload mol format file

74.3degC
infinitely soluble in ether, chloroform; very soluble in alcohol.(Ref. 0079)(Ref. 0361)(Ref. 0516)




Japanwax(?);peanut oil(?);synthetic




22
Behenic acid
Docosanoic acid
DFA0022
Tetsuyuki Kobayashi
Beh / C22:0
C22H44O2 340.584 Download ChemDraw structure fileDownload mol format file

81.5degC
306degC at 60 mmHg
d1004 0.8221
1.4270 at 100degC
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




23
Tricosanoic acid
DFA0023
Tetsuyuki Kobayashi
C23:0
C23H46O2 354.610 Download ChemDraw structure fileDownload mol format file

79.1degC
203-205degC at 1 mmHg
1.4252 at 70degC
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




24
Lignoceric acid
Tetracosanoic acid
DFA0024
Tetsuyuki Kobayashi
Lig / C24:0
C24H48O2 368.637 Download ChemDraw structure fileDownload mol format file

87.5-88.0degC
272degC at 10 mmHg
d1004 0.8207
1.4373 at 70degC
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




25
Pentacosanoic acid
DFA0025
Tetsuyuki Kobayashi
C25:0
C25H50O2 382.663 Download ChemDraw structure fileDownload mol format file

84-85.0degC
1.4292 at 70degC
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




26
Cerotic acid
Hexacosanoic acid
DFA0026
Tetsuyuki Kobayashi
C26:0 / Crt
C26H52O2 396.690 Download ChemDraw structure fileDownload mol format file

87.7-88.5degC
d1004 0.8198
1.4313 at 100degC
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




27
Carboceric acid
Heptacosanoic acid
DFA0027
Tetsuyuki Kobayashi
C27:0
C27H54O2 410.716 Download ChemDraw structure fileDownload mol format file

87.6degC
1.4324at 70degC




Synthetic,from 1-hexacosanol




28
Montanic acid
Octacosanoic acid
DFA0028
Tetsuyuki Kobayashi
C28:0 / Mon
C28H56O2 424.743 Download ChemDraw structure fileDownload mol format file

90.0-90.9degC
d1004 0.8191
1.4313at 100degC
soluble in hot acetic acid, hot benzene and hot methyl alcohol.(Ref. 0368)(Ref. 0369)(Ref. 0522)(Ref. 0523)




Insect,leaf and montan waxes




29
Nonacosanoic acid
DFA0029
Tetsuyuki Kobayashi
C29:0
C29H58O2 438.770 Download ChemDraw structure fileDownload mol format file

90.3-90.5degC




Montan wax;bitumen from peat




30
Melissic acid
Triacontanoic acid
DFA0030
Tetsuyuki Kobayashi
C30:0
C30H60O2 452.796 Download ChemDraw structure fileDownload mol format file

93.6degC
1.4323 at 100degC
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




31
Hentriacontanoic acid
DFA0031
Tetsuyuki Kobayashi
C31:0
C31H62O2 466.823 Download ChemDraw structure fileDownload mol format file

soluble in chloroform and hot methanol.(Ref. 0390/0420)




Peat wax and montan wax (?).
synthetic.



32
Lacceroic acid
Dotriacontanoic acid
DFA0032
Tetsuyuki Kobayashi
C32:0
C32H64O2 480.849 Download ChemDraw structure fileDownload mol format file

96.2degC
Soluble in hot acetone, hot benzene and chloroform.(Ref. 0180/0183/0191/0390/0420/0472)




Stick-lac wax.




33
Psyllic acid / Ceromelissic cid
Tritriacontanoic acid
DFA0033
Tetsuyuki Kobayashi
C33:0
C33H66O2 494.876 Download ChemDraw structure fileDownload mol format file





Ceroplastes ceriferous and C. rubens.(Ref. 0300/0302/0471)




34
Gheddic acid / Geddic acid
Tetoratriacontanoic acid
DFA0034
Tetsuyuki Kobayashi
C34:0
C34H68O2 508.903 Download ChemDraw structure fileDownload mol format file

98.4degC
Soluble in hot acetone, hot benzene and chloroform.(Ref. 0184/0472)




Ghedda wax.
Synthesized by oxidation of 1-tetratriacontanol with the nitrile method.



35
Ceroplastic acid
Pentatriacontanoic acid
DFA0035
Tetsuyuki Kobayashi
C35:0
C35H70O2 522.929 Download ChemDraw structure fileDownload mol format file

98.4degC
Soluble in hot acetone, hot benzene and chloroform.(Ref. 0079/0183/0230/0302/0404/0471)




Ceroplasters rubens wax.




36
Hexatriacontanoic acid
DFA0036
Tetsuyuki Kobayashi
C36:0
C36H72O2 536.956 Download ChemDraw structure fileDownload mol format file




Milk and milk products.
Synthetic wax; melting point, 99.9degC.(Ref. 0302/0390/0404)



37
Heptariacontanoic acid
DFA0037
Tetsuyuki Kobayashi
C37:0
C37H74O2 550.982 Download ChemDraw structure fileDownload mol format file





Synthetic wax.(Ref. 0183/0300/0302/0404/0471)



38
Octatriacontanoic acid
DFA0038
Tetsuyuki Kobayashi
C38:0
C38H76O2 565.009 Download ChemDraw structure fileDownload mol format file






Synthetic wax; melting point, 101.6degC.(Ref. 0180/0184/0191/0390/0417)



39
Hexatetracontanoic acid
DFA0039
Tetsuyuki Kobayashi
C46:0
C46H92O2 677.221 Download ChemDraw structure fileDownload mol format file






Synthetic wax; melting point, 106.8degC.(Ref. 0061/0180/0184/0390/0472/0521)



40
Acrylic acid
2-Propenoic acid
DFA0040
Tetsuyuki Kobayashi
C3:1
C3H4O2 72.063 Download ChemDraw structure fileDownload mol format file

12.3degC/13degC
141.9degC(Ref. 0001)
d4-16 1.0621
1.4224 at 20degC
Soluble in acetone, alcohol, toluene and water.(Ref. 0184/0472)





Synthesized by oxidation of acrolein.



41
Isocrotonic acid
cis-2-Butenoic acid
DFA0041
Tetsuyuki Kobayashi
C4:1
C4H6O2 86.089 Download ChemDraw structure fileDownload mol format file

14.4-14.6degC
171.9degC/169.3degC (decomposes)
d15.54 1.0312
1.4457 at 20degC
Soluble in alcohol, CS2, ether, petroleum ether. Slightly soluble in water.(Ref. 0286/0447/0451)




Reported in the seed oil of Croton tiglium.




42
Crotonic acid
trans-2-Butenoic acid
DFA0042
Tetsuyuki Kobayashi
C4:1
C4H6O2 86.089 Download ChemDraw structure fileDownload mol format file

72.0degC
189degC
d4-20 1.018
1.4228 at 79.7degC
Soluble in acetone, alcohol, petroleum ether, toluene and water.(Ref. 0286/0447/0451)




Reported in the seed oil of Croton tiglium.
Synthetic.



43
Vinylacetic acid
3-Butenoic acid
DFA0043
Tetsuyuki Kobayashi
C4:1
C4H6O2 86.089 Download ChemDraw structure fileDownload mol format file

-39degC
163degC
d4-15 1.013
1.4257 at 15degC
Soluble in alcohol, benzene, ether. Slightly soluble in water.(Ref. 0300/0302/0347/0471)





Synthetic.



44
bEthylacrylic acid
2-Pentenoic acid
DFA0044
Tetsuyuki Kobayashi
C5:1
C5H8O2 100.116 Download ChemDraw structure fileDownload mol format file

8degC
200degC at 17mmHg
d4-15 0.9921
1.450 at 15degC
Soluble in alcohol and ether. (Ref. 0347)





Synthesized by reaction of 2-bromovaleic acid with quinoline.



45
bPenteic acid / bPentenoic acid
3-Pentenoic acid
DFA0045
Tetsuyuki Kobayashi
C5:1
C5H8O2 100.116 Download ChemDraw structure fileDownload mol format file

193degC at 760mmHg
Soluble in benzene, chloroform and ether. (Ref. 0347)





Synthesized by decarboxylation of the reaction product of propionaldehyde and malonic acid.



46
Allylacetic acid
4-Pentenoic acid
DFA0046
Tetsuyuki Kobayashi
C5:1
C5H8O2 100.116 Download ChemDraw structure fileDownload mol format file

-18degC
189degC at 760mmHg
d4-18 0.9843
1.4341 at 7.5degC
Soluble in benzene, chloroform and ether. (Ref. 0347)





Synthetic.



47
Isohydrosorbic acid / b-propylacrylic acid
2-Hexenoic acid
DFA0047
Tetsuyuki Kobayashi
C6:1
C6H10O2 114.142 Download ChemDraw structure fileDownload mol format file

32degC
217degC at 760mmHg
d4-20 0.965
1.4460 at 40degC
Soluble in alcohol, benzene, chloroform, CS2 and ether. Slightly soluble in water.(Ref. 0347)




Japanese peppermint oil.
Synthesized from n-capronic acid.



48
Hydrosorbic acid
3-Hexenoic acid
DFA0048
Tetsuyuki Kobayashi
C6:1
C6H10O2 114.142 Download ChemDraw structure fileDownload mol format file

12degC
208degC at 760mmHg
d4-22 0.9610
1.4355
Soluble in benzene and petroleum ether. (Ref. 0347)





Synthetic.



49
g -Hexenoic acid
4-Hexenoic acid
DFA0049
Tetsuyuki Kobayashi
C6:1
C6H10O2 114.142 Download ChemDraw structure fileDownload mol format file

10degC
206.5degC at 760mmHg
d4-20 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.



50
d -Hexenoic acid
5-Hexenoic acid
DFA0050
Tetsuyuki Kobayashi
C6:1
C6H10O2 114.142 Download ChemDraw structure fileDownload mol format file

203degC at 121mmHg
d194 0.9639
1.4343 at 20degC
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.



51
a -Heptenoic acid
2-Heptenoic acid
DFA0051
Tetsuyuki Kobayashi
C7:1
C7H12O2 128.169 Download ChemDraw structure fileDownload mol format file

120-121degC at 11mmHg
d4-20 0.9575
1.4488 at 20degC
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.



52
b -Heptenoic acid
3-Heptenoic acid
DFA0052
Tetsuyuki Kobayashi
C7:1
C7H12O2 128.169 Download ChemDraw structure fileDownload mol format file

-12degC
226-228degC at 760mmHg
Soluble in alcohol, ether and petroleum ether. (Ref. 0347)





Synthesized from n-valeraldehyde by the malonic acid method.



53
g -Heptenoic acid
4-Heptenoic acid
DFA0053
Tetsuyuki Kobayashi
C7:1
C7H12O2 128.169 Download ChemDraw structure fileDownload mol format file

98-100degC at 5mmHg
d4-15 0.949
1.4418 at 15degC
Soluble in acetone, ether, and methanol. (Ref. 0263)





Synthetic.



54
d -Heptenoic acid
5-Heptenoic acid
DFA0054
Tetsuyuki Kobayashi
C7:1
C7H12O2 128.169 Download ChemDraw structure fileDownload mol format file

117degC at 11mmHg
d4-20 0.9496
1.4444 at 20degC
Soluble in alcohol, chloroform, ether, and petroleum ether. (Ref. 0098/0398)





Synthesized by the reaction of 4-chlorobutiric acid and K or Na acetoacetate.



55
e -Heptenoic acid
6-Heptenoic acid
DFA0055
Tetsuyuki Kobayashi
C7:1
C7H12O2 128.169 Download ChemDraw structure fileDownload mol format file

-6.5degC
125degC at 15mmHg
d14.94 0.9515
1.4404 at 14.9degC
Soluble in acetone and methanol. (Ref. 0192)





Synthesized by the reaction of 7-aminoheptanoic acid and HNO2.



56
3-n-Amylacrylic acid / cis-a-octenoic acid
cis-2-Octenoic acid
DFA0056
Tetsuyuki Kobayashi
C8:1
C8H14O2 142.196 Download ChemDraw structure fileDownload mol format file

154degC at 22mmHg
d4-20 0.9807
1.4587 at 20degC





Synthesized by condensation of caprylic aldehyde with malonic acid in the presence of pyridine.



57
trans-a-Octenoic acid
trans-2-Octenoic acid
DFA0057
Tetsuyuki Kobayashi
C8:1
C8H14O2 142.196 Download ChemDraw structure fileDownload mol format file

143degC at 15mmHg
d4-15 0.945
1.462





Synthetic.



58
cis-b-Octenoic acid
cis-3-Octenoic acid
DFA0058
Tetsuyuki Kobayashi
C8:1
C8H14O2 142.196 Download ChemDraw structure fileDownload mol format file

-25degC
150degC at 19mmHg
d4-20 0.9352
1.4433 at 20 degC





Synthetic.



59
trans-b-Octenoic acid
trans-3-Octenoic acid
DFA0059
Tetsuyuki Kobayashi
C8:1
C8H14O2 142.196 Download ChemDraw structure fileDownload mol format file

1degC
142degC at 19mmHg
d4-20 0.942
1.4456 at 20 degC





Synthetic.



60
g-Octenoic acid
cis-4-Octenoic acid
DFA0060
Tetsuyuki Kobayashi
C8:1
C8H14O2 142.196 Download ChemDraw structure fileDownload mol format file

-35degC
96degC at 0.8mmHg
d4-20 0.9301
1.4417 at 20 degC





Synthetic.



61
cis-d-Octenoic acid
cis-5-Octenoic acid
DFA0061
Tetsuyuki Kobayashi
C8:1
C8H14O2 142.196 Download ChemDraw structure fileDownload mol format file






Synthetic



62
trans-d-Octenoic acid
trans-5-Octenoic acid
DFA0062
Tetsuyuki Kobayashi
C8:1
C8H14O2 142.196 Download ChemDraw structure fileDownload mol format file






Synthetic



63
cis-e-Octenoic acid
cis-6-Octenoic acid
DFA0063
Tetsuyuki Kobayashi
C8:1
C8H14O2 142.196 Download ChemDraw structure fileDownload mol format file

-17degC
88degC at 0.8 mmHg
d4 0.9378
1.4441 at 20degC





Synthetic



64
trans-e-Octenoic acid
trans-6-Octenoic acid
DFA0064
Tetsuyuki Kobayashi
C8:1
C8H14O2 142.196 Download ChemDraw structure fileDownload mol format file

6degC
90degC at 1.2 mm Hg
d4 0.9422
1.4454 at 20degC





Synthetic



65
a-Nonylenic acid
cis-2-Nonenoic acid
DFA0065
Tetsuyuki Kobayashi
C9:1
C9H16O2 156.222 Download ChemDraw structure fileDownload mol format file

4degC
90degC at 20 mmHg
d4-15 0.9316
1.4587 at 20degC





Synthetic



66
b-Nonylenic acid / 3-nonylenic acid
3-Nonenoic acid
DFA0066
Tetsuyuki Kobayashi
C9:1
Download ChemDraw structure fileDownload mol format file

106degC at 1 mmHg
d4-20 0.9290
1.4484 at 20degC





Synthetic



67
8-Nonylenic acid
8-Nonenoic acid
DFA0067
Tetsuyuki Kobayashi
C9:1
C9H16O2 156.222 Download ChemDraw structure fileDownload mol format file

5degC
116-118degC at 1 mmHg
d4-16 0.9146
1.4492









68
2-Decylenic acid
2-Decenoic acid
DFA0068
Tetsuyuki Kobayashi
C10:1
C10H18O2 170.249 Download ChemDraw structure fileDownload mol format file

12degC
165degC at 15 mmHg
d4-15 0.9280
1.46161 at 20degC





Synthetic by condensation of caprylic aldehyde with malonic acid in presence of pyridene.



69
3-Decylenic acid
3-Decenoic acid
DFA0069
Tetsuyuki Kobayashi
C10:1
C10H18O2 170.249 Download ChemDraw structure fileDownload mol format file

18degC
154-163degC at 11 mmHg
d4-15 0.914
1.4510 at 18degC





Synthetic by distillation of hexyl paraconic acid.



70
Obtusilic acid
4-Decenoic acid
DFA0070
Tetsuyuki Kobayashi
C10:1
C10H18O2 170.249 Download ChemDraw structure fileDownload mol format file

148-150degC at 13 mmHg
d4-20 0.9197
1.4497 at 20degC
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)



71
Isodecenoic acid
8-Decenoic acid
DFA0071
Tetsuyuki Kobayashi
C10:1
C10H18O2 170.249 Download ChemDraw structure fileDownload mol format file

155-157degC at 14 mmHg
d4-15 0.930




Butterfat and milk of man, goat, and Indian buffalo.




72
9-Decylenic acid / caproleic acid
9-Decenoic acid
DFA0072
Tetsuyuki Kobayashi
C10:1
C10H18O2 170.249 Download ChemDraw structure fileDownload mol format file

158-163degC at 21 mmHg
d4-15 0.9238
1.4485 at 21degC
soluble in ethanol and ether.(Ref. 0493)




Mild fats of most animals.




73
2-Hendecenoic acid
2-Undecenoic acid
DFA0073
Tetsuyuki Kobayashi
C11:1
C11H20O2 184.275 Download ChemDraw structure fileDownload mol format file










74
9-Hendecenoic acid / 9-undecylenic acid
9-Undecenoic acid
DFA0074
Tetsuyuki Kobayashi
C11:1
C11H20O2 184.275 Download ChemDraw structure fileDownload mol format file

11.4degC
129degC at 1 mmHg





Synthetic by debromination of 9-bromo-9undecenoic acid with (i)Na in ethanol,or (ii)Zn and propionic acid.



75
10-Hendecenoic acid / 10-undecylenic acid
10-Undecenoic acid
DFA0075
Tetsuyuki Kobayashi
C11:1
C11H20O2 184.275 Download ChemDraw structure fileDownload mol format file

24.5degC
275degC at 25 mmHg
d4-25 0.9075
1.4464 at 20degC
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 400deg under a pressure of 50 mm produced a distillate composed of about 40% heptaldehyde and 20% undecylenic acid.



76
2-Lauroleic acid
2-Dodecenoic acid
DFA0076
Tetsuyuki Kobayashi
C12:1
C12H22O2 198.302 Download ChemDraw structure fileDownload mol format file

17degC
172-174degC at 8 mmHg
d4-20 0.9130
1.4639 at 20degC





Synthetic by reation of decanaldehyde with malonic acid in presence of pyridene.



77
Linderic acid
4-Dodecenoic acid
DFA0077
Tetsuyuki Kobayashi
C12:1
C12H22O2 198.302 Download ChemDraw structure fileDownload mol format file

1-1.3degC
170-172degC at 13 mmHg
d4-15 0.9106
1.4545 at 15degC
soluble in benzene,chloroform and ether.(Ref. 0298)(Ref. 0492)




Seed oils or Lindera obtusiloba and various Formosan plants.




78
6-Lauroleic acid
6-Dodecenoic acid
DFA0078
Tetsuyuki Kobayashi
C12:1
C12H22O2 198.302 Download ChemDraw structure fileDownload mol format file










79
7-Lauroleic acid
7-Dodecenoic acid
DFA0079
Tetsuyuki Kobayashi
C12:1
C12H22O2 198.302 Download ChemDraw structure fileDownload mol format file

Oil
1.4486 at 27.5degC









80
9-Lauroleic acid
9-Dodecenoic acid
DFA0080
Tetsuyuki Kobayashi
C12:1
C12H22O2 198.302 Download ChemDraw structure fileDownload mol format file

142degC at 4 mmHg
soluble in benzene, chloroform and ether.(Ref. 0301)




Milk fats;cochineal wax;wax of Tachardina theae.




81
10-Lauroleic acid
10-Dodecenoic acid
DFA0081
Tetsuyuki Kobayashi
C12:1
C12H22O2 198.302 Download ChemDraw structure fileDownload mol format file

18degC
166-168degC at 9 mmHg









82
11-Lauroleic acid
11-Dodecenoic acid
DFA0082
Tetsuyuki Kobayashi
C12:1
C12H22O2 198.302 Download ChemDraw structure fileDownload mol format file

20degC
171-172degC at 13 mmHg
d4-20 0.9030
1.4510 at 20degC





Synthetic by conversion (i) from 10-undecenoic acid and (ii) of 1-bromo-10-decene to 11-dodecenenitrile, followed by hydrolysis.



83
3-n-Decylacrylic acid
2-Tridecenoic acid
DFA0083
Tetsuyuki Kobayashi
C13:1
C13H24O2 212.328 Download ChemDraw structure fileDownload mol format file

38-39degC
167-171degC at 2 mmHg
d304 0.8995
1.46121 at 20degC





Synthetic by rection of undecanaldehyde with malonic acid in presence of pyrideine.



84
Isotridecenoic acid
11-Tridecenoic acid
DFA0084
Tetsuyuki Kobayashi
C13:1
C13H24O2 212.328 Download ChemDraw structure fileDownload mol format file

28-29degC
183-185degC at 13.5 mm Hg





Synthetic by reaction of undecanaodehyde with malonic acid in presence of pyridine.



85
12-Tridecenoic acid
DFA0085
Tetsuyuki Kobayashi
C13:1
C13H24O2 212.328 Download ChemDraw structure fileDownload mol format file

38-39degC
192degC at 20 mmHg





Synthetic by (i) reaction of 1-bromo-10-undecene ethyl malonate and Na and (ii) conversion of 10-undecenoic acid to 11-dodecenoic acid.



86
2-Tetradecenoic acid
DFA0086
Tetsuyuki Kobayashi
C14:1
C14H26O2 226.355 Download ChemDraw structure fileDownload mol format file

33degC/50-53degC
186-188degC at 8 mmHg





Synthetic by rection of lauric aldehyde with malonic acid in presence of pyridine.



87
Tsuzuic acid
4-Tetradecenoic acid
DFA0087
Tetsuyuki Kobayashi
C14:1
C14H26O2 226.355 Download ChemDraw structure fileDownload mol format file

18-18.5degC
185degC at 13 mmHg
d4-20 0.9024
1.4559 at 20degC
soluble in benzene,petroleum and ether.(Ref. 0298)




Seed oils of Lindera obtusiloba Litsea sp.,Tetradenia glauca and related plants.




88
Physeteric acid / 5-myristoleic acid
5-Tetradecenoic acid
DFA0088
Tetsuyuki Kobayashi
C14:1
C14H26O2 226.355 Download ChemDraw structure fileDownload mol format file

20degC
190-195degC at 15 mmHg
d4-20 0.9046
1.4552 at 20degC
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.




89
cis-8-Tetradecenoic acid
DFA0089
Tetsuyuki Kobayashi
C14:1
C14H26O2 226.355 Download ChemDraw structure fileDownload mol format file

Oil
1.4569 at 17degC
soluble in benzene, ether and petroleum ether.(Ref. 0023)(Ref. 0033)(Ref. 0429)




Lipids of all eubacteria investigated.




90
Myristoleic acid
cis-9-Tetradecenoic acid
DFA0090
Tetsuyuki Kobayashi
C14:1
C14H26O2 226.355 Download ChemDraw structure fileDownload mol format file

-4degC
d4 0.9018
1.4519 at 20degC
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.




91
2-Pentadecenoic acid
DFA0091
Tetsuyuki Kobayashi
C15:1
C15H28O2 240.382 Download ChemDraw structure fileDownload mol format file

4.5degC





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.



92
14-Pentadecenoic acid
DFA0092
Tetsuyuki Kobayashi
C15:1
C15H28O2 240.382 Download ChemDraw structure fileDownload mol format file

198degC at 8 mmHg





Synthetic, by the malonic acid method form 1-bromo-12-tridecene and ethyl malonate in presence of sodium ethoxide.



93
Gaidic acid / 2-Palmitoleic acid
2-Hexadecenoic acid
DFA0093
Tetsuyuki Kobayashi
C16:1
C16H30O2 254.408 Download ChemDraw structure fileDownload mol format file

39degC/45degC
soluble in alcohol and ether(Ref. 0396)(Ref. 0434)





Synthetic, by the action of alcoholic KOH on 2-iodopalmitic acid.



94
7-Palmitoleic acid
7-Hexadecenoic acid
DFA0094
Tetsuyuki Kobayashi
C16:1n-9
C16H30O2 254.408 Download ChemDraw structure fileDownload mol format file

21degC/33degC/32-33degC [a-form]/40-41degC[b-form]
236degC at 15 mmHg value for a-form/180-183degC at 1 mmHg value for b-form
1.4583 at 20degC 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.



95
cis-9-Palmitoleic acid
cis-9-Hexadecenoic acid
DFA0095
Tetsuyuki Kobayashi
DPam / C16:1n-7
C16H30O2 254.408 Download ChemDraw structure fileDownload mol format file

-0.5 to +0.5degC
140-141degC at 5mmHg




Widely distrobuted in animal, vegetable and marine oils




96
trans-9-Palmitoleic acid
trans-9-Hexadecenoic acid
DFA0096
Tetsuyuki Kobayashi
C16:1n-7
C16H30O2 254.408 Download ChemDraw structure fileDownload mol format file

31degC




snade fish , human-hair(Ref. 4001)
Synthetic, by treatment of the cis-form with Se or N oxides.



97
cis-10-Palmitoleic acid
cis-10-Hexadecenoic acid
DFA0097
Tetsuyuki Kobayashi
C16:1
C16H30O2 254.408 Download ChemDraw structure fileDownload mol format file

15-16degC
1.4593 at 20degC



Gas liquid chromatogram
[Chromatogram 0001]
[Chromatogram 0002] (provided by Dr. Akiko Horiuchi).





98
2-Heptadecylenic acid
2-Heptadecenoic acid
DFA0098
Tetsuyuki Kobayashi
C17:1
C17H32O2 268.435 Download ChemDraw structure fileDownload mol format file

57.5degC
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.



99
9-Heptadecylenic acid
cis-9-Heptadecenoic acid
DFA0099
Tetsuyuki Kobayashi
C17:1
C17H32O2 268.435 Download ChemDraw structure fileDownload mol format file

11.4-12.2degC / 14.5degC
175degC at 0.5 mmHg
1.4598 at 20degC
crystals from light petroleum / Li solt crystals from alcohol (Ref. 0120)(Ref. 0221)(Ref. 0443)




Butterfat ; bogy fat Ovibos moschatus subsp.(Canadian musk ox)




100
cis-2-Octadecenoic acid
DFA0100
Tetsuyuki Kobayashi
C18:1
C18H34O2 282.461 Download ChemDraw structure fileDownload mol format file

50.5degC
soluble in benzene, chloroform and ether(Ref. 0371)(Ref. 0372)









101
trans-2-Oleic acid
trans-2-Octadecenoic acid
DFA0101
Tetsuyuki Kobayashi
C18:1
C18H34O2 282.461 Download ChemDraw structure fileDownload mol format file

58.5degC
d904 0.8484




No natural source




102
3-Octadecylenic acid
3-Octadecenoic acid
DFA0102
Tetsuyuki Kobayashi
C18:1
C18H34O2 282.461 Download ChemDraw structure fileDownload mol format file

56-57degC
1.4466 at 65degC




No natural source




103
4-Octadecylenic acid
4-Octadecenoic acid
DFA0103
Tetsuyuki Kobayashi
C18:1
C18H34O2 282.461 Download ChemDraw structure fileDownload mol format file

52-53degC




Only natural source, seed oil of Thalictrum polycarpum
Synthetic in trans-form.



104
5-Octadecylenic acid
trans-5-Octadecenoic acid
DFA0104
Tetsuyuki Kobayashi
C18:1
C18H34O2 282.461 Download ChemDraw structure fileDownload mol format file

43-44degC/47.5degC





Synthetic, by the addition of HI to 5-stearolic acid followed by reduction of the addition product with Zn plus acetic acid.



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 Download ChemDraw structure fileDownload mol format file

33degC
215-217degC at 2-3 mmHg
d354 0.8824
1.4536 at 65degC
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)




106
Petroselaidic acid
trans-6-Octadecenoic acid
DFA0106
Tetsuyuki Kobayashi
C18:1
C18H34O2 282.461 Download ChemDraw structure fileDownload mol format file

54-59degC
1.4408 at 70degC





Synthetic, by partial reduction of natural 6-octadecynoic (tariric) acid which has been synthesized by 2 different method.



107
cis-7-Octadecenoic acid
DFA0107
Tetsuyuki Kobayashi
C18:1
C18H34O2 282.461 Download ChemDraw structure fileDownload mol format file

12.5-13.1degC





synthetic, by the alkyl-acetylene method (also true for other positional isomers up to the 12-cis-isomer).



108
trans-7-Octadecenoic acid
DFA0108
Tetsuyuki Kobayashi
C18:1
C18H34O2 282.461 Download ChemDraw structure fileDownload mol format file

44.2-44.5degC





Synthetic, by addition of HI to 7-stearolic acid, followed by reduction of the addition product with Zn plus acetic acid.



109
cis-8-Oleic acid
cis-8-Octadecenoic acid
DFA0109
Tetsuyuki Kobayashi
C18:1
C18H34O2 282.461 Download ChemDraw structure fileDownload mol format file

13.4degC [a-]/16.3degC [b-]
234degC at 15 mmHg
d4-20 0.898
1.45823 at 20degC




Reported in human-hair fat and olive oil; presence in other fats suspected
Synthetic, by the alkylacetylene method.



110
trans-8-Elaidic acid
trans-8-Octadecenoic acid
DFA0110
Tetsuyuki Kobayashi
C18:1
C18H34O2 282.461 Download ChemDraw structure fileDownload mol format file

52-52.6degC





Synthetic, by isomerization of the cis-isomer with Se.



111
9-Octadecylenic acid / Oleic acid
cis-9-Octadecenoic acid
DFA0111
Tetsuyuki Kobayashi
Ole / C18:1n-9
C18H34O2 282.461 Download ChemDraw structure fileDownload mol format file

12degC [labile] / 16degC [stable]
234degC at 15 mmHg
d4-20 0.898
1.45823 at 20degC
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.


112
9-Elaidic acid
trans-9-Octadecenoic acid
DFA0112
Tetsuyuki Kobayashi
C18:1
C18H34O2 282.461 Download ChemDraw structure fileDownload mol format file

44.5-46.5degC
234degC at 15 mmHg
d4-70 0.8565
1.4405 at 70degC
soluble in alcohol,chloroform, ether and petroleum ether(Ref. 0189)




Fat of ruminants; human-mother's milk (Ref. 4002)




113
cis-10-Oleic acid
cis-10-Octadecenoic acid
DFA0113
Tetsuyuki Kobayashi
C18:1
C18H34O2 282.461 Download ChemDraw structure fileDownload mol format file

22.2-22.8degC




Root nodules of Pinellia ternate




114
trans-10-Octadecenoic acid
DFA0114
Tetsuyuki Kobayashi
C18:1
C18H34O2 282.461 Download ChemDraw structure fileDownload mol format file





Root of nodules of Pinellia




115
cis-Vaccenic acid
cis-11-Octadecenoic acid
DFA0115
Tetsuyuki Kobayashi
cis-Vac / C18:1n-7
C18H34O2 282.461 Download ChemDraw structure fileDownload mol format file

14.5-15.5degC




Found in butterfat and in other animal fats. (Ref. 4004)



116
trans-Vaccenic acid
trans-11-Octadecenoic acid
DFA0116
Tetsuyuki Kobayashi
trans-Vac / C18:1n-7
C18H34O2 282.461 Download ChemDraw structure fileDownload mol format file

44degC
d4-70 0.8563
1.4406 at 70degC
soluble in acetone and mathanol(Ref. 0062)(Ref. 0083)(Ref. 0209)(Ref. 0262)(Ref. 0474)




Small proportion in ox and sheep body fats; butter




117
cis-12-Oleic acid
cis-12-Octadecenoic acid
DFA0117
Tetsuyuki Kobayashi
C18:1
C18H34O2 282.461 Download ChemDraw structure fileDownload mol format file

9.8-10.4 / 26.5-27.5degC
196degC at 1.5 mmHg




Soybean oil




118
trans-12-Elaidic acid
trans-12-Octadecenoic acid
DFA0118
Tetsuyuki Kobayashi
C18:1
C18H34O2 282.461 Download ChemDraw structure fileDownload mol format file

39.7-40.1degC
196degC at 1.5 mmHg









119
trans-15-Octadecenoic acid
DFA0119
Tetsuyuki Kobayashi
C18:1
C18H34O2 282.461 Download ChemDraw structure fileDownload mol format file

61-61.5degC(Ref. 0001)





Synthetic by partial hydrogenation of linolenic acid.



120
trans-16-Octadecenoic acid
DFA0120
Tetsuyuki Kobayashi
C18:1
C18H34O2 282.461 Download ChemDraw structure fileDownload mol format file

65.6-66.2degC




Hydrolysates of betterfat and of ox and sheep fats




121
cis-17-Octadecenoic acid
DFA0121
Tetsuyuki Kobayashi
C18:1
C18H34O2 282.461 Download ChemDraw structure fileDownload mol format file

55-55.5degC




Kamala-seed oil
Synthetic, by reduction of ethyl undecanoate with LiAlH4 to 10-undecenol, followed by further reactions to cis-17-octadecenoic acid.



122
2-Nonadecenoic acid
DFA0122
Tetsuyuki Kobayashi
C19:1
C19H36O2 296.488 Download ChemDraw structure fileDownload mol format file

66.5degC
297-298degC at 100 mmHg





Synthetic, by dehydrohalogenation of 2-bromononadecanoic acid.



123
cis-Gadoleic acid
cis-9-Eicosenoic acid / cis-9-icosenoic acid
DFA0123
Tetsuyuki Kobayashi
C20:1
C20H38O2 310.515 Download ChemDraw structure fileDownload mol format file

23-23.5degC
170degC at 0.1 mmHg
d4-25 0.882
1.4597 at 25degC
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



124
cis-Gondoic acid
cis-11-Eicosenoic acid / cis-11-icosenoic acid
DFA0124
Tetsuyuki Kobayashi
C20:1
C20H38O2 310.515 Download ChemDraw structure fileDownload mol format file

23-24/50degC
267degC 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




125
trans-Gondoic acid
trans-11-Eicosenoic acid / trans-11-icosenoic acid
DFA0125
Tetsuyuki Kobayashi
C20:1
C20H38O2 310.515 Download ChemDraw structure fileDownload mol format file

52-53degC




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.




126
cis-14-Eicosenoic acid / cis-14-icosenoic acid
DFA0126
Tetsuyuki Kobayashi
C20:1
C20H38O2 310.515 Download ChemDraw structure fileDownload mol format file

42.5degC





Synthetic



127
cis-Cetoleic acid
cis-11-Docosenoic acid
DFA0127
Tetsuyuki Kobayashi
C22:1
C22H42O2 338.568 Download ChemDraw structure fileDownload mol format file

33-33.7degC
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).




128
cis-Erucic acid
cis-13-Docosenoic acid
DFA0128
Tetsuyuki Kobayashi
C22:1
C22H42O2 338.568 Download ChemDraw structure fileDownload mol format file

34.7degC
281degC at 30 mmHg
d4-70 0.85321
1.44438 at 70degC
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



129
trans-Brassidic acid
trans-13-Docosenoic acid
DFA0129
Tetsuyuki Kobayashi
C22:1
C22H42O2 338.568 Download ChemDraw structure fileDownload mol format file

61.9degC
265degC at 15 mmHg
d4-70 0.85002
1.44349 at 70degC
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.



130
22-Tricosenoic acid
DFA0130
Tetsuyuki Kobayashi
C23:1
C23H44O2 352.594 Download ChemDraw structure fileDownload mol format file

75.1-75.2degC





Synthetic, by lengthening the chain of 10-undecenoic acid.



131
Nervonic acid / cis-Selacholeic acid
cis-15-Tetracosenoic acid
DFA0131
Tetsuyuki Kobayashi
C24:1
C24H46O2 366.621 Download ChemDraw structure fileDownload mol format file

42.5-43degC
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.




132
trans-Selacholeic acid
trans-15-Tetracosenoic acid
DFA0132
Tetsuyuki Kobayashi
C24:1
C24H46O2 366.621 Download ChemDraw structure fileDownload mol format file

65.5degC





Synthetic



133
9-Hexacosenoic acid
DFA0133
Tetsuyuki Kobayashi
C26:1
C26H50O2 394.674 Download ChemDraw structure fileDownload mol format file





Reported to be a component of lipids in Spheciospongia vesparia (a sponge)




134
Ximenic acid
cis-17-Hexacosenoic acid
DFA0134
Tetsuyuki Kobayashi
C26:1
C26H50O2 394.674 Download ChemDraw structure fileDownload mol format file

45-45.5degC(?)
soluble in benzene, chloroform, ether and petoleumether (Ref. 0082) (Ref. 0407)




Reported in the seed oil of Ximenia americana (an Indian shrub).




135
cis-19-Octacosenoic acid
DFA0135
Tetsuyuki Kobayashi
C28:1
C28H54O2 422.727 Download ChemDraw structure fileDownload mol format file

57-58degC




Small proportion of South African Ximenia spp.; 4.7-12.2% of seed oils of various Ximenia spp.




136
Lumepueic acid
cis-21-Triacontenoic acid
DFA0136
Tetsuyuki Kobayashi
C30:1
C30H58O2 450.780 Download ChemDraw structure fileDownload mol format file

soluble in benzene, chloroform, ether and petroleumether (Ref. 0082)




Reported to be 3-7% of fatty acids in various African Ximenia oils.




137
cis-Dotriacontenoic acid
DFA0137
Tetsuyuki Kobayashi
C32:1
C32H62O2 478.833 Download ChemDraw structure fileDownload mol format file





Approx. 1% in seed oils of Ximenia americana & X. caffra.




138
b-Vinylacrylic acid
2, 4-Pentadienoic acid
DFA0138
Tetsuyuki Kobayashi
C5:2
C5H6O2 98.100 Download ChemDraw structure fileDownload mol format file

80degC
decomposes, 100degC
very soluble in ethanol and ether / soluble in hot water / slightly soluble in petroleumether (Ref. 0162)





Synthetic



139
Sorbic acid
2, 4-Hexadienoic acid
DFA0139
Tetsuyuki Kobayashi
C6:2
C6H8O2 112.127 Download ChemDraw structure fileDownload mol format file

134.5degC
decomposes, 228degC
soluble in ethanol / slightly solubule in hot water (Ref. 0080) (Ref. 0229) (Ref. 0242)




Berries of mountain ash; unripe sorb apples.




140
cis, cis-Stillingic acid
cis-2, cis-4-Decadienoic acid
DFA0140
Tetsuyuki Kobayashi
C10:2
C10H16O2 168.233 Download ChemDraw structure fileDownload mol format file

1.4896 at 17degC
soluble in acetone, ether and hexane (Ref. 0146)




Stillingia oils.




141
cis-2, trans-4-Decadienoic acid
DFA0141
Tetsuyuki Kobayashi
C10:2
C10H16O2 168.233 Download ChemDraw structure fileDownload mol format file

112-114degC at 0.45 mm Hg
1.5007 at 18degC
soluble in acetone, ether and petroleumether (Ref. 0146)




Sebastiania fruticosa seeds.




142
trans, cis-Stillingic acid
trans-2, cis-4-Decadienoic acid
DFA0142
Tetsuyuki Kobayashi
C10:2
C10H16O2 168.233 Download ChemDraw structure fileDownload mol format file

107degC at 0.2 mm Hg
1.5078 at 18degC




Stillingia oils.




143
trans-2, trans-4-Decadienoic acid
DFA0143
Tetsuyuki Kobayashi
C10:2
C10H16O2 168.233 Download ChemDraw structure fileDownload mol format file

49-50degC
121-124degC at 0.3 mmHg
1.5058 at 31degC





Synthetic



144
cis-2, cis-6-Decadienoic acid
DFA0144
Tetsuyuki Kobayashi
C10:2
C10H16O2 168.233 Download ChemDraw structure fileDownload mol format file

Oil
1.4730 at 17degC





Synthetic



145
trans-2, cis-6-Decadienoic acid
DFA0145
Tetsuyuki Kobayashi
C10:2
C10H16O2 168.233 Download ChemDraw structure fileDownload mol format file





Stillingia oils.




146
trans-2, trans-6-Decadienoic acid
DFA0146
Tetsuyuki Kobayashi
C10:2
C10H16O2 168.233 Download ChemDraw structure fileDownload mol format file

42-43degC





Synthetic



147
trans-4, trans-6-Decadienoic acid
DFA0147
Tetsuyuki Kobayashi
C10:2
C10H16O2 168.233 Download ChemDraw structure fileDownload mol format file






Synthetic



148
9, 12-Hexadecadienoic acid
DFA0148
Tetsuyuki Kobayashi
C16:2
C16H28O2 252.392 Download ChemDraw structure fileDownload mol format file

soluble in acetone, ether and petroleumether (Ref. 0101) (Ref. 0122) (Ref. 0223)




Seed oils of Acacia giraffae, Asclepias syriaca, and Macadamia ternifolia.




149
cis-5, cis-12-Octadecadienoic acid
DFA0149
Tetsuyuki Kobayashi
C18:2
C18H32O2 280.445 Download ChemDraw structure fileDownload mol format file






Synthetic



150
cis-5, trans-12-Octadecadienoic acid
DFA0150
Tetsuyuki Kobayashi
C18:2
C18H32O2 280.445 Download ChemDraw structure fileDownload mol format file

-4 to -2degC
1.4677 at 20degC





Synthetic



151
trans-5, cis12-Octadecadienoic acid
DFA0151
Tetsuyuki Kobayashi
C18:2
C18H32O2 280.445 Download ChemDraw structure fileDownload mol format file

-12degC to -9degC
168degC to 170degC at 0.3mmHg
1.4684 at 20degC









152
trans-5, trans-12-Octadecadienoic acid
DFA0152
Tetsuyuki Kobayashi
C18:2
C18H32O2 280.445 Download ChemDraw structure fileDownload mol format file

16degC to 19degC
175degC to 176degC at 0.4mmHg
1.4671 at 20degC









153
6, 8-Octadecadienoic acid
DFA0153
Tetsuyuki Kobayashi
C18:2
C18H32O2 280.445 Download ChemDraw structure fileDownload mol format file

153degC to 155degC at 0.1mmHg









154
trans-8, trans-10-Octadecadienoic acid
DFA0154
Tetsuyuki Kobayashi
C18:2
C18H32O2 280.445 Download ChemDraw structure fileDownload mol format file

56degC to 56.5degC
d604 0.8808
1.4682 at 60degC









155
cis-8, cis-11-Octadecadienoic acid
DFA0155
Tetsuyuki Kobayashi
C18:2
C18H32O2 280.445 Download ChemDraw structure fileDownload mol format file

-12.5degC to -9.5degC
11.8degC to 20degC at 0.0001mmHg
1.4663 at 25degC









156
cis-9, cis-11-Octadecadienoic acid
DFA0156
Tetsuyuki Kobayashi
C18:2
C18H32O2 280.445 Download ChemDraw structure fileDownload mol format file

42degC to 43.2degC









157
cis-9, trans-11-Octadecadienoic acid
DFA0157
Tetsuyuki Kobayashi
C18:2
C18H32O2 280.445 Download ChemDraw structure fileDownload mol format file

-6degC to -3degC









158
trans-9, trans-11-Octadecadienoic acid
DFA0158
Tetsuyuki Kobayashi
C18:2
C18H32O2 280.445 Download ChemDraw structure fileDownload mol format file

54degC
d774 0.8659
1.4624 at 77degC









159
Linoleic acid
cis-9, cis-12-Octadecadienoic acid
DFA0159
Tetsuyuki Kobayashi
LA / C18:2n-6 / C18:2w6
C18H32O2 280.445 Download ChemDraw structure fileDownload mol format file
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.
-5degC
229degC to 230degC at 16mmHg
d4-20 0.9031
1.4711 at 20degC
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.


160
cis-9, trans-12-Octadecadienoic acid
DFA0160
Tetsuyuki Kobayashi
C18:2
C18H32O2 280.445 Download ChemDraw structure fileDownload mol format file

1degC
1.4650 at 27degC





Synthetic by dehydration of ricinoleic acid or elaidinization of linoleic acid.



161
trans-9, cis-12-Octadecadienoic acid
DFA0161
Tetsuyuki Kobayashi
C18:2
C18H32O2 280.445 Download ChemDraw structure fileDownload mol format file

1degC
1.4690 at 27degC









162
Linolelaidic
trans-9, trans-12-Octadecadienoic acid
DFA0162
Tetsuyuki Kobayashi
C18:2
C18H32O2 280.445 Download ChemDraw structure fileDownload mol format file

28degC to 29degC
179degC to 183degC at 0.8mmHg
1.4641 at 27degC
soluble in alcohol, ether, methyl alcohol and petroleum ether.(Ref. 0127)(Ref. 0193)(Ref. 0275)




Seed fat of Chilopsis linearis.




163
cis-10, cis-12-Octadecadienoic acid
DFA0163
Tetsuyuki Kobayashi
C18:2
C18H32O2 280.445 Download ChemDraw structure fileDownload mol format file

38.2degC to 39degC









164
trans-10, cis-12-Octadecadienoic acid
DFA0164
Tetsuyuki Kobayashi
C18:2
C18H32O2 280.445 Download ChemDraw structure fileDownload mol format file

22.23degC




Seed fat of Chilopsis linearis.




165
trans-10, trans-12-Octadecadienoic acid
DFA0165
Tetsuyuki Kobayashi
C18:2
C18H32O2 280.445 Download ChemDraw structure fileDownload mol format file

56degC to 57degC
d4-70 0.8686
1.4656 at 70degC
soluble in acetone, cyclohexane and ether.(Ref. 0085)(Ref. 0117)(Ref. 0252)(Ref. 0266)









166
cis-10, cis-13-Octadecadienoic acid
DFA0166
Tetsuyuki Kobayashi
C18:2
C18H32O2 280.445 Download ChemDraw structure fileDownload mol format file

-9degC to -6.5degC
121degC to 128degC at 0.0001mmHg
1.4670 at 25degC









167
cis-11, cis-14-Octadecadienoic acid
DFA0167
Tetsuyuki Kobayashi
C18:2
C18H32O2 280.445 Download ChemDraw structure fileDownload mol format file

6degC to 8degC
112degC to 115degC at 0.0001mmHg
1.4664 at 25degC









168
cis-10, cis-13-Nonadecadienoic acid
DFA0168
Tetsuyuki Kobayashi
C19:2
C19H34O2 294.472 Download ChemDraw structure fileDownload mol format file





Liver oil of Carcharodon carcharias; Cambodiafish oil.




169
11, 14-Eicosadienoic acid / 11, 14-icosadienoic acid
DFA0169
Tetsuyuki Kobayashi
C20:2
C20H36O2 308.499 Download ChemDraw structure fileDownload mol format file

soluble in acetone, ether and petroleum ether.(Ref. 0287)(Ref. 0292)




Herring and menhaden oils; cattle-liver phosphatides; swine brain lipids; shark liver oil.




170
5, 13-Docosadienoic acid
DFA0170
Tetsuyuki Kobayashi
C22:2
C22H40O2 336.552 Download ChemDraw structure fileDownload mol format file





Fish oils.




171
13, 16-Docosadienoic acid
DFA0171
Tetsuyuki Kobayashi
C22:2
C22H40O2 336.552 Download ChemDraw structure fileDownload mol format file

soluble in acetone and ether.(Ref. 0045)(Ref. 0241)









172
17, 20-Hexacosadienoic acid
DFA0172
Tetsuyuki Kobayashi
C26:2
C26H48O2 392.658 Download ChemDraw structure fileDownload mol format file

soluble inether and petroleum ether.(Ref. 0059)




Fish oils; Spheciospongia vesparia (sponge).




173
4, 7, 10-Hexadecatrienoic acid
DFA0173
Tetsuyuki Kobayashi
C16:3
C16H26O2 250.376 Download ChemDraw structure fileDownload mol format file

soluble in alcohol and ether.(Ref. 0295)




Sardine oil.




174
trans-5, trans-8, trans-11-Hexadecatrienoic acid
DFA0174
Tetsuyuki Kobayashi
C16:3
C16H26O2 250.376 Download ChemDraw structure fileDownload mol format file

soluble in methyl alcohol and petroleum ether.(Ref. 0347)









175
6, 9, 12-Hexadecatrienoic acid
DFA0175
Tetsuyuki Kobayashi
C16:3
C16H26O2 250.376 Download ChemDraw structure fileDownload mol format file

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)




176
Hiragonic acid
6,10,14-Hexadecatrienoic acid
DFA0176
Tetsuyuki Kobayashi
C16:3
C16H26O2 250.376 Download ChemDraw structure fileDownload mol format file

180-190degC at 15mmHg
d4-20 0.9296
1.4850 at 50degC
soluble in acetone, ethanol, ether and methylalcohol.(Ref. 0488)(Ref. 0489)




Oil of Sardinops melanosticta.




177
7, 10, 13-Hexadecatrienoic acid
DFA0177
Tetsuyuki Kobayashi
C16:3
C16H26O2 250.376 Download ChemDraw structure fileDownload mol format file

soluble in acetone, ethanol, ether and pentane.(Ref. 0231)(Ref. 0295)(Ref. 0465)




Menhaden oil.




178
9, 12, 15-Hexadecatrienoic acid
DFA0178
Tetsuyuki Kobayashi
C16:3
C16H26O2 250.376 Download ChemDraw structure fileDownload mol format file

very soluble in acetone, ethanol, pentane, and petroleumether.(Ref. 0295)




Jacaranda oils.




179
Calea
trans-3, cis-9, cis-12-Octadecatrienoic acid
DFA0179
Tetsuyuki Kobayashi
C18:3
C18H30O2 278.430 Download ChemDraw structure fileDownload mol format file

61-61.5degC
soluble in acetone, ethanol, ether, and petroleumether.(Ref. 0040)




Linseed, perilla, and hemp oils.




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 Download ChemDraw structure fileDownload mol format file
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 -11degC
125degC at 0.05mmHg
d4-20 0.9164
1.4800 at 20degC
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)


181
6, 10, 14-Octadecatrienoic acid
DFA0181
Tetsuyuki Kobayashi
C18:3
C18H30O2 278.430 Download ChemDraw structure fileDownload mol format file

d4-20 0.9221
1.4794 at 20degC
soluble in ethanol, pentane and petroleum ether.(Ref. 0495)(Ref. 0498)(Ref. 0499)




Trichosanthes oils.




182
cis-8, trans-10, cis-12-Octadecatrienoic acid
DFA0182
Tetsuyuki Kobayashi
C18:3
C18H30O2 278.430 Download ChemDraw structure fileDownload mol format file

43.5-44degC
very soluble in petroleumether and soluble in acetone, ethanol, CS2 and pentane.(Ref. 0125)




Catalpa ovata seed oil; Jacaranda oils.




183
a-Calendic acid
trans-8, trans-10, cis-12-Octadecatrienoic acid
DFA0183
Tetsuyuki Kobayashi
C18:3
C18H30O2 278.430 Download ChemDraw structure fileDownload mol format file

40-40.5degC
soluble in acetone, ethanol, cyclohexane, ether, pentane and petroleum ether.(Ref. 0123)




Neou, po-yak, and tung oils.




184
b-Calendic acid
trans-8, trans-10, trans-12-Octadecatrienoic acid
DFA0184
Tetsuyuki Kobayashi
C18:3
C18H30O2 278.430 Download ChemDraw structure fileDownload mol format file

77-78degC
soluble in ethanol, CS2, ether, heptane, metylalcohol and petroleum ether.(Ref. 0123)(Ref. 0279)




Cattle-liver phosphatides.




185
Punicic acid / trichosanic acid
cis-9, trans-11, cis-13-Octadecatrienoic acid
DFA0185
Tetsuyuki Kobayashi
C18H30O2 278.430 Download ChemDraw structure fileDownload mol format file

43.5-44degC
d504 0.9025
1.5113 at 50degC
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.




186
a-Eleostearic acid
cis-9, trans-11, trans-13-Octadecatrienoic acid
DFA0186
Tetsuyuki Kobayashi
C18:3
C18H30O2 278.430 Download ChemDraw structure fileDownload mol format file

49-49.2degC
235degC at 15 mmHg
d504 0.9028
1.5112 at 50degC
soluble in ethanol, cyclohexane and petroleum ether.(Ref. 0128)




Aleurites spp. (tung) , neou, and po-yak oils; oils of tropical and subtropical species.




187
trans-9, trans-11, trans-13-Octadecatrienoic acid
DFA0187
Tetsuyuki Kobayashi
C18:3
C18H30O2 278.430 Download ChemDraw structure fileDownload mol format file

61.5-62.5degC
soluble in acetone, ethanol, CS2, heptane, methylalcohol and pentane.(Ref. 0131)




Cattle-liver phosphatides.




188
b-Eleostearic acid
trans-9, trans-11, trans-13-Octadecatrienoic acid
DFA0188
Tetsuyuki Kobayashi
C18:3
C18H30O2 278.430 Download ChemDraw structure fileDownload mol format file

71-71.5degC
188degC at 1 mmHg
d4-75 0.8909
1.5011 at 75degC
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.



189
Isomerized punicic acid
trans-9, trans-11, trans-13-Octadecatrienoic acid
DFA0189
Tetsuyuki Kobayashi
C18:3
C18H30O2 278.430 Download ChemDraw structure fileDownload mol format file

70-71degC





Synthetic, by isomerization of the a-acid.



190
9, 12, 14-Octadecatrienoic acid
DFA0190
Tetsuyuki Kobayashi
C18:3
C18H30O2 278.430 Download ChemDraw structure fileDownload mol format file






Synthetic, by isomerization of a-linolenic acid.



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 Download ChemDraw structure fileDownload mol format file
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 -11degC
125degC at 0.05 mmHg
d4-20 0.9164
1.4678 at 50degC
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.


192
Elaidolinoleic acid
trans-9, trans-12, trans-15-Octadecatrienoic acid
DFA0192
Tetsuyuki Kobayashi
C18:3
C18H30O2 278.430 Download ChemDraw structure fileDownload mol format file

29.5-30degC
solubule in methylalcohol and petroleum ether.(Ref. 0279)





Synthetic, by treatment of the ester form of a-linolenic acid with 1% Se at 205-215degC to yield this acid ester (melting point, 29-30degC).



193
10, 12, 14-Octadecatrienoic acid
DFA0193
Tetsuyuki Kobayashi
C18:3
C18H30O2 278.430 Download ChemDraw structure fileDownload mol format file

79degC









194
Pseudoeleostearic acid
trans-10, trans-12, trans-14-Octadecatrienoic acid
DFA0194
Tetsuyuki Kobayashi
C18:3
C18H30O2 278.430 Download ChemDraw structure fileDownload mol format file

77-77.5degC





Synthetic, by alkali isomerization of a-linolenic acid.



195
10, 12 ,15-Octadecatrienoic acid
DFA0195
Tetsuyuki Kobayashi
C18:3
C18H30O2 278.430 Download ChemDraw structure fileDownload mol format file






Synthetic, by alkali isomerization of a-linolenic acid.



196
5, 8, 11-Eicosatrienoic acid / 5, 8, 11-icosatrienoic acid
DFA0196
Tetsuyuki Kobayashi
C20:3
C20H34O2 306.483 Download ChemDraw structure fileDownload mol format file

solubule in CS2, heptane and methylalcohol.(Ref. 0292)




Fish oils; phosphatides of liver and suprarenals of land animals and of brain.




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 Download ChemDraw structure fileDownload mol format file

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).




198
11, 14, 17-Eicosatrienoic acid / 11, 14, 17-icosatrienoic acid
DFA0198
Tetsuyuki Kobayashi
C20:3
C20H34O2 306.483 Download ChemDraw structure fileDownload mol format file





Shark-liver and herring oil.




199
Podocarpric acid
x, y, z-Eicosatrienoic acid/x, y, z-icosatrienoic acid
DFA0199
Tetsuyuki Kobayashi
C20:3
C20H34O2 306.483 Download ChemDraw structure fileDownload mol format file





Podocarpus oil.




200
7, 10, 13-Docosatrienoic acid
DFA0200
Tetsuyuki Kobayashi
C22:3
C22H38O2 334.536 Download ChemDraw structure fileDownload mol format file





Reported in brain and cattle-liver phosphatides.




201
8, 11, 14-Docosatriennoic acid
DFA0201
Tetsuyuki Kobayashi
C22:3
C22H28O2 324.457 Download ChemDraw structure fileDownload mol format file





Reported in liver oil of Carcharodon carcharias (a shark); cattle-suprarenal phosphatides.




202
4, 7, 10, 13-Hexadesatetraenoic acid
DFA0202
Tetsuyuki Kobayashi
C16:4
C16H24O2 248.361 Download ChemDraw structure fileDownload mol format file

soluble in acetone, alcohol, ether and petroleum ether.(Ref. 0448)




South Africa pilchad oil; Japanease sardine oil.




203
4, 7, 11, 14-Hexadesatetraenoic acid
DFA0203
Tetsuyuki Kobayashi
C16:4
C16H24O2 248.361 Download ChemDraw structure fileDownload mol format file

soluble in acetone, alcohol, ether, carbon disuifide and petroleum ether.(Ref. 0510)(Ref. 0511)




Japanease sardine oil.




204
4, 8, 12, 16-Hexadesatetraenoic acid
DFA0204
Tetsuyuki Kobayashi
C16:4
C16H24O2 248.361 Download ChemDraw structure fileDownload mol format file

soluble in acetone, alcohol, ether and petroleum ether.(Ref. 0268)(Ref. 0295)




Japanease sardine oil.




205
6, 9, 12, 15-Hexadesatetraenoic acid
DFA0205
Tetsuyuki Kobayashi
C16:4
C16H24O2 248.361 Download ChemDraw structure fileDownload mol format file

1.4870 at 29degC
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.




206
trans-3, cis-9, cis-12, cis-15-Octadecatetraenoic acid
DFA0206
Tetsuyuki Kobayashi
C18:4
C18H28O2 276.414 Download ChemDraw structure fileDownload mol format file





Seed oil of Stenolobium stans.




207
Moroctic acid / Moritic acid
4, 8, 12, 15-Octadecatetraenoic acid
DFA0207
Tetsuyuki Kobayashi
C18:4
C18H28O2 276.414 Download ChemDraw structure fileDownload mol format file

208-215degC at 15 mmHg
0.9297 at 20degC
1.4911at 20degC
soluble in acetone, alcohol, ether and petroleum ether.(Ref. 0103)(Ref. 0472)(Ref. 0489)(Ref. 0500)




Sardine oil; head oil of the white whale.




208
6, 9, 12, 15-Octadecatetraenoic acid
DFA0208
Tetsuyuki Kobayashi
C18:4
C18H28O2 276.414 Download ChemDraw structure fileDownload mol format file

-57.4 to -56.6degC
14888 at 16degC
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.




209
a-Parinaric acid
9, 11, 13, 15-Octadecatetraenoic acid
DFA0209
Tetsuyuki Kobayashi
C18:4n-3
C18H28O2 276.414 Download ChemDraw structure fileDownload mol format file

85 to 86 degC
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.




210
b-Parinaric acid
trans-9, trans-11, trans-13, trans-15-Octadecatetraenoic acid
DFA0210
Tetsuyuki Kobayashi
C18:4
C18H28O2 276.414 Download ChemDraw structure fileDownload mol format file

95 to 96 degC
soluble in ether and petroleum ether.(Ref. 0509)





Synthetic by isomerization of a-acid.



211
9, 12, 15, 18-Octadecatetraenoic acid
DFA0211
Tetsuyuki Kobayashi
C18:4
C18H28O2 276.414 Download ChemDraw structure fileDownload mol format file

soluble in carbon disulfide and methyl alcohol.(Ref. 0347)









212
4, 8, 12, 16-Eicosatetraenoic acid / 4, 8, 12, 16-icosatetraenoic acid
DFA0212
Tetsuyuki Kobayashi
C20:4
C20H32O2 304.467 Download ChemDraw structure fileDownload mol format file

217 to 220 degC at 20 mmHg
0.9263 at 20 degC
1.4915 at 20 degC
soluble in acetone, methyl alcohol, ether and petroleum ether.(Ref. 0442)(Ref. 0489)(Ref. 0496)




Brain phosphatides; sardine oil; whale oils; swine liver.




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 Download ChemDraw structure fileDownload mol format file
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 degC
163 degC at 1 mmHg
0.9082 at 20 degC
1.4824 at 20 degC
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.


214
6, 10, 14, 18-Eicosatetraenoic acid / 6, 10, 14, 18-icosatetraenoic acid
DFA0214
Tetsuyuki Kobayashi
C20:4
C20H32O2 304.467 Download ChemDraw structure fileDownload mol format file

0.9263 at 20 degC
1.4935 at 20 degC
soluble in acetone, methyl alcohol, ether and petroleum ether.(Ref. 0267)




Fish and whale oils.




215
8, 11, 14, 17-Eicosatetraenoic acid / 8, 11, 14, 17-icosatetraenoic acid
DFA0215
Tetsuyuki Kobayashi
C20:4
C20H32O2 304.467 Download ChemDraw structure fileDownload mol format file

soluble in acetone, methyl alcohol and petroleum ether.(Ref. 0464)(Ref. 0465)




Sardine oil.




216
4, 7, 10, 13-Docosatetraenoic acid
DFA0216
Tetsuyuki Kobayashi
C22:4
C22H36O2 332.520 Download ChemDraw structure fileDownload mol format file

soluble in acetone, methyl alcohol and petroleum ether.(Ref. 0292)(Ref. 0294)




Brain phosphatides.




217
7, 10, 13, 16-Docosatetraenoic acid
DFA0217
Tetsuyuki Kobayashi
C22:4
C22H36O2 332.520 Download ChemDraw structure fileDownload mol format file

soluble in carbon disulfide, heptane and methyl alcohol.(Ref. 0292)(Ref. 0294)




Brain and cattle-liver phosphatides.




218
Stearidonic acid
8, 12, 16, 19 (20)-Docosatetraenoic acid
DFA0218
Tetsuyuki Kobayashi
C22:4
C22H36O2 332.520 Download ChemDraw structure fileDownload mol format file

soluble in acetone, methyl alcohol and petroleum ether.(Ref. 0050)(Ref. 0051)




Liver oil of Carcharodon carcharias (a shark).




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 Download ChemDraw structure fileDownload mol format file

0.9399 at 15 degC
1.5109 at 15 degC
soluble in benzene, chloroform, ether and petroleum ether.(Ref. 0489)




Sardine and bonito oils.




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 Download ChemDraw structure fileDownload mol format file
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 degC
1.4977 at 23 degC
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.


221
4, 7, 10, 13, 16-Docosapentaenoic acid
DFA0221
Tetsuyuki Kobayashi
C22:5n-6 / C22:5w6
C22H34O2 330.504 Download ChemDraw structure fileDownload mol format file

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.


222
Clupanodonic acid
4, 8, 12, 15, 19-Docosapentaenoic acid
DFA0222
Tetsuyuki Kobayashi
C22:5
C22H34O2 330.504 Download ChemDraw structure fileDownload mol format file

-78 degC
207 to 212 at 2 mmHg
0.9356 at 20 degC
1.5014 at 20 degC
soluble in acetone, ether and petroleum ether.(Ref. 0470)(Ref. 0501)(Ref. 0502)(Ref. 0505)




Marine oils; body oils of teleost fish.




223
7, 10, 13, 16, 19-Docosapentaenoic acid
DFA0223
Tetsuyuki Kobayashi
C22:5n-3 / C22:5w3
C22H34O2 330.504 Download ChemDraw structure fileDownload mol format file

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.




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 Download ChemDraw structure fileDownload mol format file
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 degC
1.5017 at 26 degC
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.


225
4, 8, 12, 15, 19, 21-Tetracosahexaenoic acid
DFA0225
Tetsuyuki Kobayashi
C24:6
C24H36O2 356.541 Download ChemDraw structure fileDownload mol format file

0.9452 at 20 degC
1.5122 at 20 degC
soluble in benzene, chloroform, methyl alcohol, ether and petroleum ether.(Ref. 0004)




Japanese sardine, fish-liver and whale oils.




226
Isovaleric acid
3-Methylbutanoic acid
DFA0226
Tetsuyuki Kobayashi
C5H10O2 102.132 Download ChemDraw structure fileDownload mol format file

-37.6degC
176.7degC at 760mmHg
d4-150.937
1.40178 at 22.4degC
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.




227
6-Methylcaprylic acid
d-6-Methyloctanoic acid
DFA0227
Tetsuyuki Kobayashi
C9H18O2 158.238 Download ChemDraw structure fileDownload mol format file

soluble in acetone , ether , methyl alcohol and petroleum ether.(Ref. 0110)(Ref. 0147)(Ref. 0325)(Ref. 0326)




Degradation product of polymycins; wool grease.




228
7-Methylcaprylic acid
7-Methyloctanoic acid
DFA0228
Tetsuyuki Kobayashi
C9H18O2 158.238 Download ChemDraw structure fileDownload mol format file

-18.5degC




Minor constituent of wool grease (degras).




229
Isolauric acid
10-Methylhendecanoic acid
DFA0229
Tetsuyuki Kobayashi
C12H24O2 200.318 Download ChemDraw structure fileDownload mol format file

41.2degC
140-145degC 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.




230
d-10-Methyldodecanoic acid
DFA0230
Tetsuyuki Kobayashi
C13H26O2 214.344 Download ChemDraw structure fileDownload mol format file

6.2-6.5degC
178-180degC at 10 mmHg
1.4424 at 25degC
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.



231
Isoundecylic acid / 11-methyllauric acid
11-Methyldodecanoic acid
DFA0231
Tetsuyuki Kobayashi
C13H26O2 214.344 Download ChemDraw structure fileDownload mol format file

39.4-40degC
1.4293at 60degC
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.




232
Isomyristic acid / 12-methyltridecylic acid
(+)-12-Methyltridecanoic acid
DFA0232
Tetsuyuki Kobayashi
C14H28O2 228.371 Download ChemDraw structure fileDownload mol format file

53.6degC
soluble in acetone , methyl alcohol and petroleum ether.(Ref. 0216)(Ref. 6061)




Wool grease; butterfat.




233
12-methylmyristic acid
(+)-12-Methyltetradecanoic acid
DFA0233
Tetsuyuki Kobayashi
C15H30O2 242.398 Download ChemDraw structure fileDownload mol format file

25.8degC
0.4327 at 59degC
soluble in chloroform , ether , methyl alcohol and petroleum ether.(Ref. 0357)




Wool grease; sheep tallow ; butterfat.




234
Isopentadecylic acid / 13-methylmyristic acid
13-Methyltetradecanoic acid
DFA0234
Tetsuyuki Kobayashi
C15H30O2 242.398 Download ChemDraw structure fileDownload mol format file

52.2degC
1.4312 at 59degC
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 170degC in vacuo.



235
Isopalmitic acid / 14-methylpentadecylic acid
14-Methypentadecanoic acid
DFA0235
Tetsuyuki Kobayashi
C16H32O2 256.424 Download ChemDraw structure fileDownload mol format file

62.4degC
d1.012
1.4293 at 70degC
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.



236
14-methylpalmitic acid
(+)-14-Methylhexadecanoic acid
DFA0236
Tetsuyuki Kobayashi
C17H34O2 270.451 Download ChemDraw structure fileDownload mol format file

38.0degC
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.



237
15-methylpalmitic acid
15-Methylhexadecanoic acid
DFA0237
Tetsuyuki Kobayashi
C17H34O2 270.451 Download ChemDraw structure fileDownload mol format file

60.5degC
1.4315 at 70degC
soluble in acetone , ether and petroleum ether.(Ref. 0218)(Ref. 6067)(Ref. 6068)




Wool grease; cattle tallow.




238
10-Methylheptadecanoic acid
DFA0238
Tetsuyuki Kobayashi
C18H36O2 284.477 Download ChemDraw structure fileDownload mol format file

33.5degC
soluble in acetone and glacial acetic acid(Ref. 0459)(Ref. 0525)




Butter fat.




239
Isostearic acid / 16-Methylmargaric acid
(+)-16-Methylheptadecanoic acid
DFA0239
Tetsuyuki Kobayashi
C18H36O2 284.477 Download ChemDraw structure fileDownload mol format file

69.5degC
soluble in acetone , ether , petroleum ether.(Ref. 0179)(Ref. 6070)(Ref. 6009)
Isopropyl : Doublet in 1360-1380cm-1




Wool grease.




240
Tuberculostearic acid / 10-methylstearic acid
l-(+)-10-Methyloctadecanoic acid
DFA0240
Tetsuyuki Kobayashi
C19H38O2 298.504 Download ChemDraw structure fileDownload mol format file

13.2degC
175-178degC at 760mmHg
d4-250.887
1.4512 at 25degC
soluble in acetone , ethanol , methyl alcohol and pentane.(Ref. 0407)(Ref. 0430)(Ref. 0459)(Ref. 0524)




Lipids of human tubercle bacilli.
Synthetic.



241
16-methylstearic acid
(+)-16-Methyloctadecanoic acid
DFA0241
Tetsuyuki Kobayashi
C19H38O2 298.504 Download ChemDraw structure fileDownload mol format file

49.9-50.7degC
1.4342 at 70degC
soluble in acetone , methyl alcohol and petroleum ether.(Ref. 0110)


[Spectrum 0001] (provided by Dr. Takeshi Kasama).


Wool grease.




242
Isoarachidic acid
18-Methylnonadecanoic acid
DFA0242
Tetsuyuki Kobayashi
C20H40O2 312.530 Download ChemDraw structure fileDownload mol format file

75.3degC
soluble in ethanol , ether and petroleum ether.(Ref. 0357)




Wool grease.




243
(+)-18-Methyleicosanoic acid / (+)-18-Methylicosanoic acid
DFA0243
Tetsuyuki Kobayashi
C21H42O2 326.557 Download ChemDraw structure fileDownload mol format file

55.6degC
soluble in acetone , chloroform and petroleum ether.(Ref. 0357)


[Spectrum 0001] (provided by Dr. Takeshi Kasama).


Wool grease.




244
Isobehenic acid
20-Methylheneicosanoic acid / 20-Methylhenicosanoic acid
DFA0244
Tetsuyuki Kobayashi
C22H44O2 340.584 Download ChemDraw structure fileDownload mol format file

79.5degC
soluble in chloroform , ether , methyl alcohol and petroleum ether.(Ref. 0357)




Wool grease.




245
(+)-20-Methyldocosanoic acid
DFA0245
Tetsuyuki Kobayashi
C23H46O2 354.610 Download ChemDraw structure fileDownload mol format file

62.1degC
soluble in acetone , chloroform , ether , and petroleum ether.(Ref. 0357)




Wool grease.




246
22-Methyltricosanoic acid
DFA0246
Tetsuyuki Kobayashi
C24H48O2 368.637 Download ChemDraw structure fileDownload mol format file

83.1degC
soluble in acetone , chloroform and petroleum ether.(Ref. 0027)




Wool grease.




247
3, 13, 19-Trimethyltricosanoic acid
DFA0247
Tetsuyuki Kobayashi
C26H52O2 396.690 Download ChemDraw structure fileDownload mol format file

-8degC
208degC at 760mmHg




Fatty acids in the tubercle bacilli.




248
Isopentacosanoic acid
(+)-23-Methyltetracosanoic acid
DFA0248
Tetsuyuki Kobayashi
C25H50O2 382.663 Download ChemDraw structure fileDownload mol format file

82.4-82.6degC
soluble in ethanol , benzene , chloroform and petroleum ether.(Ref. 0027)




Wool grease.




249
Isocerotic acid
24-Methylpentacosanoic acid
DFA0249
Tetsuyuki Kobayashi
C26H52O2 396.690 Download ChemDraw structure fileDownload mol format file

86.9degC
soluble in acetone , chloroform and glacial acetic acid.(Ref. 0027)




Wool grease.




250
(+)-24-Methylhexacosanoic acid
DFA0250
Tetsuyuki Kobayashi
C27H54O2 410.716 Download ChemDraw structure fileDownload mol format file

72.9degC
soluble in benzene, chloroform , glacial acetic acid and petroleum ether.(Ref. 0357)




Wool grease.




251
Isomontanic acid
26-methylheptacosanoic acid
DFA0251
Tetsuyuki Kobayashi
C28H56O2 424.743 Download ChemDraw structure fileDownload mol format file

89.3 degC
soluble in benzene, chloroform, glacial acetic acid and petroleum ether.(Ref. 0357)




Wool grease.




252
Mycoceranic acid / Mycocerosic acid
2,4,6-(D)-Trimethyloctacosanoic acid
DFA0252
Tetsuyuki Kobayashi
C31H62O2 466.823 Download ChemDraw structure fileDownload mol format file

27-28 degC
soluble in chloroform and petroleum ether.(Ref. 0113)




Lipids of tubercle bacilli.
Synthetic.



253
(+)-28-Methyltriacontanoic acid
DFA0253
Tetsuyuki Kobayashi
C31H62O2 466.823 Download ChemDraw structure fileDownload mol format file

80.7 degC
soluble in benzene, chloroform, glacial acetic acid and petroleum ether.(Ref. 0357)




Wool grease.




254
Angelic acid / a-Methylisocrotonic acid
2-Methyl-cis-2-butenoic acid
DFA0254
Tetsuyuki Kobayashi
C5H8O2 100.116 Download ChemDraw structure fileDownload mol format file

45 degC
185 degC at 760 mm Hg / 88-90 degC at 12 mmHg
d4740.983
1.4434 at 47 degC
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.




255
Tiglic acid / a,b-Dimethylacrylic acid
2-Methyl-trans-2-butenoic acid
DFA0255
Tetsuyuki Kobayashi
C5H8O2 100.116 Download ChemDraw structure fileDownload mol format file

65.5-66.5 degC
198.5 degC at 760 mm Hg / 95-96 degC at 12 mmHg
d4-760.9641
1.4342 at 81 degC / 1.4330 at 76 degC
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.




256
Pyroterebic acid
4-Methyl-3-pentenoic acid
DFA0256
Tetsuyuki Kobayashi
C6H10O2 114.142 Download ChemDraw structure fileDownload mol format file

Oil
207 degC / 99 degC at 10 mm Hg / 103-106 degC 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.



257
C27-Phthienoic acid / Mycolipenic acid
(+)-2, 4(l), 6(l)-Trimethyl-trans-2-tetracosenoic acid
DFA0257
Tetsuyuki Kobayashi
C27H52O2 408.701 Download ChemDraw structure fileDownload mol format file

39.5-41 degC
1.4598 at 25 degC
soluble in acetone, chloroform, methyl alcohol and petroleum ether ; rosettes from acetone at - 8 degC.(Ref. 0358)




Mixture of acids of the tubercle bacilli known as ""phthioic acid"".




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 Download ChemDraw structure fileDownload mol format file

Liquid
97-98 degC 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.




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 Download ChemDraw structure fileDownload mol format file

Liquid




In small proportion in seed oils of Hydnocarpus wightiana and Hydnocarpus anthelmintica.




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 Download ChemDraw structure fileDownload mol format file

12.0 degC
soluble in acetone, ether and petroleum ether.(Ref. 0140)(Ref. 0141)(Ref. 0142)




Oil of Hydnocarpus anthelmintica and Hydnocarpus wightiana.




261
Sterculic acid
w-(2-n-Octylcycloprop-1-enyl)octanoic acid
DFA0261
Tetsuyuki Kobayashi
C19H34O2 294.472 Download ChemDraw structure fileDownload mol format file

18 degC
soluble in ether.(Ref. 0239)(Ref. 0240)




Sterculia foetida ; usually in small proportion in a variety of oils together with malvalic acid.




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 Download ChemDraw structure fileDownload mol format file

48.0 degC
165-168 degC at 1mmHg
soluble in ethanol, ether, methyl alcohol and petroleum ether.(Ref. 0141)




Oil of Hydnocarpus anthelmintica and Hydnocarpus wightiana.




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 Download ChemDraw structure fileDownload mol format file

27.8-28.8 degC
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.).




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 Download ChemDraw structure fileDownload mol format file

60.5 degC
247.5 degC 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.).




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 Download ChemDraw structure fileDownload mol format file

68.5 degC
247.5 degC 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..




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 Download ChemDraw structure fileDownload mol format file

6.0 degC [Liquid]
232.5 degC
d4-250.9436
1.4782 at 25 degC
soluble in hot ethanol.(Ref. 0048)(Ref. 0107)(Ref. 0401)(Ref. 0402)




Glycerides of Oncoba echinata; several Hydnocarpus oils.




267
Glycolic acid
Hydroxyacetic acid
DFA0267
Tetsuyuki Kobayashi
C2H4O3 76.051 Download ChemDraw structure fileDownload mol format file

80 degC
Decomposes at 100 degC
d4-251.49
very soluble in ether and water ; soluble in ethanol.(Ref. 0282)




Cane-sugar juice; unripe grapes.




268
Lactic acid
2-Hydroxypropionic acid
DFA0268
Tetsuyuki Kobayashi
C3H6O3 90.078 Download ChemDraw structure fileDownload mol format file

52.8 degC [ L(+)- and D(-)- ] ; 18 degC [ DL- ]
122 degC at 15 mmHg
d4-251.2060
1.43915 at 20 degC (Value for the DL-form)
very soluble in acetone, ethanol, ether and water.(Ref. 0264)




Widely distributed in nature.




269
b-Lactic acid / Hydracrylic acid
3-Hydroxypropionic acid
DFA0269
Tetsuyuki Kobayashi
C3H6O3 90.078 Download ChemDraw structure fileDownload mol format file

Syrup
very soluble in ethanol, ether and water.(Ref. 0283)(Ref. 0411)




Juice of muscular tissue; bile.




270
dl-2-Hydroxybutyric acid
DFA0270
Tetsuyuki Kobayashi
C4H8O3 104.105 Download ChemDraw structure fileDownload mol format file

43-44 degC
very soluble in ethanol, ether and water.(Ref. 0256)




Fermentation of molasses, starch.




271
b-Hydroxybutyric acid
D(-)-3-Hydroxybutyric acid
DFA0271
Tetsuyuki Kobayashi
C4H8O3 104.105 Download ChemDraw structure fileDownload mol format file

49-50 degC
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.



272
4-Hydroxybutyric acid
DFA0272
Tetsuyuki Kobayashi
C4H8O3 104.105 Download ChemDraw structure fileDownload mol format file

Liquid at -17 degC
130 degC




Urine of diabetics.




273
2-Hydroxyvaleric acid
DL-2-Hydroxypentanoic acid
DFA0273
Tetsuyuki Kobayashi
C5H10O3 118.131 Download ChemDraw structure fileDownload mol format file

34 degC
187 degC
d4-200.942
1.4086 at 20 degC
soluble in ethanol and water.(Ref. 0322)





Synthetic, through corresponding a-harogen or cyanohydrin.



274
3-Hydroxyvaleric acid / 3-Ethylhydracrylic acid
3-Hydroxypentanoic acid
DFA0274
Tetsuyuki Kobayashi
C5H10O3 118.131 Download ChemDraw structure fileDownload mol format file

Liquid at -32 degC
soluble in ethanol, benzene, chloroform and ether.(Ref. 0327)





Synthetic, from butene-1-chlorohydrin.



275
4-Hydroxyvaleric acid
4-Hydroxypentanoic acid
DFA0275
Tetsuyuki Kobayashi
C5H10O3 118.131 Download ChemDraw structure fileDownload mol format file

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).



276
5-Hydroxyvaleric acid / d-hydroxyvaleric acid
5-Hydroxypentanoic acid
DFA0276
Tetsuyuki Kobayashi
C5H10O3 118.131 Download ChemDraw structure fileDownload mol format file

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.



277
2-Hydroxycaproic acid
DL-2-Hydroxyhexanoic acid
DFA0277
Tetsuyuki Kobayashi
C6H12O3 132.158 Download ChemDraw structure fileDownload mol format file

60 degC
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.



278
3-Hydroxycaproic acid
DL-3-Hydroxyhexanoic acid
DFA0278
Tetsuyuki Kobayashi
C6H12O3 132.158 Download ChemDraw structure fileDownload mol format file

13 degC
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.



279
4-Hydroxycaproic acid
DL-4-Hydroxyhexanoic acid
DFA0279
Tetsuyuki Kobayashi
C6H12O3 132.158 Download ChemDraw structure fileDownload mol format file

Reverts to lactone





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.



280
5-Hydroxycaproic acid
5-Hydroxyhexanoic acid
DFA0280
Tetsuyuki Kobayashi
C6H12O3 132.158 Download ChemDraw structure fileDownload mol format file

Reverts to lactone





Synthetic, by (1) debromination of the corresponding bromo acid or (2) reduction of 5-keto-n-caproic acid (see entry 400) with NaHg.



281
6-Hydroxycaproic acid
6-Hydroxyhexanoic acid
DFA0281
Tetsuyuki Kobayashi
C6H12O3 132.158 Download ChemDraw structure fileDownload mol format file






Synthetic, but difficult to prepare in the free state.



282
2-Hydroxyenanthoic acid
2-Hydroxyheptanoic acid
DFA0282
Tetsuyuki Kobayashi
C7H14O3 146.184 Download ChemDraw structure fileDownload mol format file

65 degC
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.



283
4-Hydroxyenanthoic acid
4-Hydroxyheptanoic acid
DFA0283
Tetsuyuki Kobayashi
C7H14O3 146.184 Download ChemDraw structure fileDownload mol format file

Reverts to g-lactone





Synthetic, by (1) heating 4-bromoheptanoic acid with H2O, or (2) decomposition of g-propyl-paraconic acid.



284
d-Hydroxyenanthoic acid
5-Hydroxyheptanoic acid
DFA0284
Tetsuyuki Kobayashi
C7H14O3 146.184 Download ChemDraw structure fileDownload mol format file

Syrupy liquid





Synthetic, by debromination of 5-bromoheptanoic acid with H2O.



285
w-Hydroxyenanthoic acid
7-Hydroxyheptanoic acid
DFA0285
Tetsuyuki Kobayashi
C7H14O3 146.184 Download ChemDraw structure fileDownload mol format file






Synthetic, by reduction of pimelic acid.



286
2-Hydroxycaprylic acid
2-Hydroxyoctanoic acid
DFA0286
Tetsuyuki Kobayashi
C8H16O3 160.211 Download ChemDraw structure fileDownload mol format file

69.5 degC
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.



287
3-Hydroxycaprylic acid
3-Hydroxyoctanoic acid
DFA0287
Tetsuyuki Kobayashi
C8H16O3 160.211 Download ChemDraw structure fileDownload mol format file

48-51 degC





Synthetic.



288
6-Hydroxycaprylic acid
6-Hydroxyoctanoic acid
DFA0288
Tetsuyuki Kobayashi
C8H16O3 160.211 Download ChemDraw structure fileDownload mol format file

Viscous liquid





Synthetic, by reduction of 6-keto-n-caprylic acid (see entry 410) with Zn and KOH.



289
8-Hydroxycaprylic acid
8-Hydroxyoctanoic acid
DFA0289
Tetsuyuki Kobayashi
C8H16O3 160.211 Download ChemDraw structure fileDownload mol format file

58 degC
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.



290
2-Hydroxypelargonic acid
2-Hydroxynonanoic acid
DFA0290
Tetsuyuki Kobayashi
C9H18O3 174.237 Download ChemDraw structure fileDownload mol format file

freezing point , 70 degC
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.



291
3-Hydroxypelargonic acid
(+)-3-Hydroxynonanoic acid
DFA0291
Tetsuyuki Kobayashi
C9H18O3 174.237 Download ChemDraw structure fileDownload mol format file

48-51 degC
freezing point , 48-51 degC
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.



292
4-Hydroxypelargonic acid
4-Hydroxynonanoic acid
DFA0292
Tetsuyuki Kobayashi
C9H18O3 174.237 Download ChemDraw structure fileDownload mol format file

Reverts of g-lactone
117-120 degC at 10 mm Hg , Value for the g-lactone









293
7-Hydroxypelargonic acid
7-Hydroxynonanoic acid
DFA0293
Tetsuyuki Kobayashi
C9H18O3 174.237 Download ChemDraw structure fileDownload mol format file

204 degC at 25 mmHg





Synthetic, by reduction of the corresponding keto acid with Zn and KOH.



294
9-Hydroxypelargonic acid
9-Hydroxynonanoic acid
DFA0294
Tetsuyuki Kobayashi
C9H18O3 174.237 Download ChemDraw structure fileDownload mol format file

51-51.5 degC ; 24-26.5 degC





Synthetic, by partial reduction of potassium methyl azelate with Na in ethanol (also by other methods).



295
2-Hydroxycapric acid
2-Hydroxydecanoic acid
DFA0295
Tetsuyuki Kobayashi
C10H20O3 188.264 Download ChemDraw structure fileDownload mol format file

70.5 degC
decomposes
Crystals from chloroform , petroleum and ether.(Ref. 0037)





Synthetic, by treatment of 2-bromocapric acid with KOH.



296
l-2-Hydroxydecanoic acid
DFA0296
Tetsuyuki Kobayashi
C10H20O3 188.264 Download ChemDraw structure fileDownload mol format file

77.6-78 degC , Reverts to lactone





Synthetic, results with lactone from treatment of 2-bromocapric acid with NaOH.



297
4-Hydroxycapric acid
4-Hydroxydecanoic acid
DFA0297
Tetsuyuki Kobayashi
C10H20O3 188.264 Download ChemDraw structure fileDownload mol format file

Reverts to lactone





Synthetic, reportedly , by action of fuming HCl on the oxime of 9-keto-12-hydroxystearic acid.



298
5-Hydroxycapric acid
5-Hydroxydecanoic acid
DFA0298
Tetsuyuki Kobayashi
C10H20O3 188.264 Download ChemDraw structure fileDownload mol format file

Reverts to lactone
117-120 degC at 0.02 mm Hg , Value for the lactone.





Synthetic, by partial reduction of various sebacic acid derivatives.



299
10-Hydroxycapric acid
10-Hydroxydecanoic acid
DFA0299
Tetsuyuki Kobayashi
C10H20O3 188.264 Download ChemDraw structure fileDownload mol format file

75.5-76.5 degC
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).



300
2-Hydroxyhendecanoic acid
2-Hydroxyundecanoic acid
DFA0300
Tetsuyuki Kobayashi
C11H22O3 202.291 Download ChemDraw structure fileDownload mol format file

69 degC
freezing point , 69 degC , 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.



301
w-Hydroxyhendecanoic acid
11-Hydroxyundecanoic acid
DFA0301
Tetsuyuki Kobayashi
C11H22O3 202.291 Download ChemDraw structure fileDownload mol format file

71.5degC
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)



302
a-Hydroxylauric acid
2-Hydroxydodecanoic acid
DFA0302
Tetsuyuki Kobayashi
C12H24O3 216.317 Download ChemDraw structure fileDownload mol format file

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



303
b-Hydroxylauric acid
3-Hydroxydodecanoic acid
DFA0303
Tetsuyuki Kobayashi
C12H24O3 216.317 Download ChemDraw structure fileDownload mol format file

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



304
4-Hydroxylauric acid
4-Hydroxydodecanoic acid
DFA0304
Tetsuyuki Kobayashi
C12H24O3 216.317 Download ChemDraw structure fileDownload mol format file

62.3-63.5degC
170-171degC 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



305
12-Hydroxylauric acid
12-Hydroxydodecanoic acid
DFA0305
Tetsuyuki Kobayashi
C12H24O3 216.317 Download ChemDraw structure fileDownload mol format file

84-85degC
164-166degC 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




306
2-Hydroxytridecanoic acid
DFA0306
Tetsuyuki Kobayashi
C13H26O3 230.344 Download ChemDraw structure fileDownload mol format file

78degC
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 Download ChemDraw structure fileDownload mol format file

66-66.5degC
soluble in ethyl alcohol and ether / insoluble in benzene and petroleum ether(Ref. 0134)





Synthetic, by saponification of the g-lactone



308
13-Hydroxytridecanoic acid
DFA0308
Tetsuyuki Kobayashi
C13H26O3 230.344 Download ChemDraw structure fileDownload mol format file

79-79.5degC
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



309
a-Hydroxymyristic acid
2-Hydroxytetradecanoic acid
DFA0309
Tetsuyuki Kobayashi
C14H28O3 244.370 Download ChemDraw structure fileDownload mol format file

51-51.5degC
soluble in ethyl alcohol, chloroform and ether (Ref. 0257)(Ref. 0309)(Ref. 0522)




Beeswax / wool grease
Synthetic, debromination of 2-bromomyristic acid



310
w-Hydroxymyristic acid
14-Hydroxytetradecanoic acid
DFA0310
Tetsuyuki Kobayashi
C14H28O3 244.370 Download ChemDraw structure fileDownload mol format file

54-54.5degC
196-198degC at 10 mmHg





Synthetic, by condensation of dimethyl sodium malonate with 12-bromo-1-dodecanol



311
2-Hydroxypentadecanoic acid
DFA0311
Tetsuyuki Kobayashi
C15H30O3 258.397 Download ChemDraw structure fileDownload mol format file

84.5degC
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 Download ChemDraw structure fileDownload mol format file

63.5-64degC
166degC 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



313
2-Hydroxypalmitic acid
2-Hydroxyhexadecanoic acid
DFA0313
Tetsuyuki Kobayashi
C16h:0
C16H32O3 272.423 Download ChemDraw structure fileDownload mol format file

85.8-86.6degC
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



314
4-Hydroxypalmitic acid
4-Hydroxyhexadecanoic acid
DFA0314
Tetsuyuki Kobayashi
C16H32O3 272.423 Download ChemDraw structure fileDownload mol format file

79-79.6degC
soluble in ethyl acetate(Ref. 0258)




Jalap resin (along with jalaponolic acid) from Vera Cruz and Brazil / Ipomoea and scammony resins




315
11-Hydroxypalmitic acid/builic acid/jalapinoic acid
11-Hydroxyhexadecanoic acid
DFA0315
Tetsuyuki Kobayashi
C16H32O3 272.423 Download ChemDraw structure fileDownload mol format file

68-69degC
183-186degC at 3 mm Hg
soluble in ethyl alcohol and ether(Ref. 0155)(Ref. 0263)(Ref. 0438)




Shellac; root wax of Ipomoea orizabensis (Mexican scammony)




316
14-Hydroxypalmitic acid
14-Hydroxyhexadecanoic acid
DFA0316
Tetsuyuki Kobayashi
C16H32O3 272.423 Download ChemDraw structure fileDownload mol format file

soluble in hot ether / sparingly soluble in coid ether(Ref. 0485)(Ref. 0486)




Juniperus sabina wax




317
Juniperic acid
16-Hydroxyhexadecanoic acid
DFA0317
Tetsuyuki Kobayashi
C16H32O3 272.423 Download ChemDraw structure fileDownload mol format file

95degC
194-196degC 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




318
2-Hydroxyheptadecanoic acid
DFA0318
Tetsuyuki Kobayashi
C17H34O3 286.450 Download ChemDraw structure fileDownload mol format file

89degC



Gas liquid chromatogram
[Chromatogram 0001] (provided by Dr. Etsuko Yasugi).

Synthetic, by the action of KOH on 2-bromomargaric acid



319
17-Hydroxyheptadecanoic acid
DFA0319
Tetsuyuki Kobayashi
C17H34O3 286.450 Download ChemDraw structure fileDownload mol format file

87.5-88degC
210degC at 3 mm Hg





Synthetic, by paratial reduction of heptadecanedioic acid dimethyl ester



320
2-Hydroxystearic acid
DL-2-Hydroxyoctadecanoic acid
DFA0320
Tetsuyuki Kobayashi
C18H36O3 300.477 Download ChemDraw structure fileDownload mol format file

93degC
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



321
3-Hydroxystearic acid
DL-3-Hydroxyoctadecanoic acid
DFA0321
Tetsuyuki Kobayashi
C18H36O3 300.477 Download ChemDraw structure fileDownload mol format file

91degC
soluble in ether / sparingly soluble in hot ethyl alcohol and chloroform(Ref. 0060)(Ref. 0397)





Synthetic



322
4-Hydroxystearic acid
DL-4-Hydroxyoctadecanoic acid
DFA0322
Tetsuyuki Kobayashi
C18H36O3 300.477 Download ChemDraw structure fileDownload mol format file

89degC
soluble in ether / sparingly soluble in hot ethyl alcohol and chloroform(Ref. 0060)(Ref. 0446)





Synthetic



323
5-Hydroxystearic acid
DL-5-Hydroxyoctadecanoic acid
DFA0323
Tetsuyuki Kobayashi
C18H36O3 300.477 Download ChemDraw structure fileDownload mol format file

81.9-82.1degC
soluble in acetone(Ref. 0060)(Ref. 0271)





Synthetic



324
6-Hydroxystearic acid
DL-6-Hydroxyoctadecanoic acid
DFA0324
Tetsuyuki Kobayashi
C18H36O3 300.477 Download ChemDraw structure fileDownload mol format file

83degC
soluble in acetone(Ref. 0060)(Ref. 0087)





Synthetic



325
7-Hydroxystearic acid
DL-7-Hydroxyoctadecanoic acid
DFA0325
Tetsuyuki Kobayashi
C18H36O3 300.477 Download ChemDraw structure fileDownload mol format file

77.6-77.8degC
soluble in petroleum ether(Ref. 0060)(Ref. 0389)





Synthetic, by the Grignard reaction



326
8-Hydroxystearic acid
DL-8-Hydroxyoctadecanoic acid
DFA0326
Tetsuyuki Kobayashi
C18H36O3 300.477 Download ChemDraw structure fileDownload mol format file

81.5-81.7degC
soluble in light petroleum(Ref. 0060)(Ref. 0335)





Synthetic, by the Grignard reaction of 9-aldopelargonic acid with nonylmagnesium btomide



327
9-Hydroxystearic acid
DL-9-Hydroxyoctadecanoic acid
DFA0327
Tetsuyuki Kobayashi
C18H36O3 300.477 Download ChemDraw structure fileDownload mol format file

75.4-75.9degC
212-216degC at 4 mm Hg
soluble in petroleum(Ref. 0016)(Ref. 0043)(Ref. 0060)





Synthetic, by the Grignard reaction



328
10-Hydroxystearic acid/rosilic acid
DL-10-Hydroxyoctadecanoic acid
DFA0328
Tetsuyuki Kobayashi
C18H36O3 300.477 Download ChemDraw structure fileDownload mol format file

84degC
213-217degC 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



329
11-Hydroxystearic acid
DL-11-Hydroxyoctadecanoic acid
DFA0329
Tetsuyuki Kobayashi
C18H36O3 300.477 Download ChemDraw structure fileDownload mol format file

81-82degC
204-206degC 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



330
12-Hydroxystearic acid
DL-12-Hydroxyoctadecanoic acid
DFA0330
Tetsuyuki Kobayashi
C18H36O3 300.477 Download ChemDraw structure fileDownload mol format file

76.6-76.7degC
185-189degC at 2 mm Hg
soluble in petroleum(Ref. 0060)(Ref. 0480)





Synthetic, by the Grignard reaction



331
13-Hydroxystearic acid
DL-13-Hydroxyoctadecanoic acid
DFA0331
Tetsuyuki Kobayashi
C18H36O3 300.477 Download ChemDraw structure fileDownload mol format file

77.2-77.5degC
soluble in light petroleum(Ref. 0060)(Ref. 0469)(Ref. 0480)





synthetic by the Grignard reaction



332
14-Hydroxystearic acid
14-Hydroxyoctadecanoic acid
DFA0332
Tetsuyuki Kobayashi
C18H36O3 300.477 Download ChemDraw structure fileDownload mol format file

76.6-76.8degC
soluble in petroleum and ehtanol(Ref. 0060)(Ref. 0480)





synthetic by the Grignard reaction



333
15-Hydroxystearic acid
15-Hydroxyoctadecanoic acid
DFA0333
Tetsuyuki Kobayashi
C18H36O3 300.477 Download ChemDraw structure fileDownload mol format file

75.3-75.5degC
soluble in petroleum and ehtanol(Ref. 0060)





synthetic by the Grignard reaction



334
16-Hydroxystearic acid
16-Hydroxyoctadecanoic acid
DFA0334
Tetsuyuki Kobayashi
C18H36O3 300.477 Download ChemDraw structure fileDownload mol format file

78.4-78.6degC
soluble in petroleum and ehtanol(Ref. 0060)





synthetic by the Grignard reaction



335
17-Hydroxystearic acid
17-Hydroxyoctadecanoic acid
DFA0335
Tetsuyuki Kobayashi
C18H36O3 300.477 Download ChemDraw structure fileDownload mol format file

76.4-76.6degC
soluble in petroleum and ehtanol(Ref. 0060)





synthetic by the Grignard reaction



336
18-Hydroxystearic acid
18-Hydroxyoctadecanoic acid
DFA0336
Tetsuyuki Kobayashi
C18H36O3 300.477 Download ChemDraw structure fileDownload mol format file

87-88degC (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)



337
2-Hydroxynonadecanoic acid
DFA0337
Tetsuyuki Kobayashi
C19H38O3 314.503 Download ChemDraw structure fileDownload mol format file

83-84degC



Gas liquid chromatogram
[Chromatogram 0001]
[Chromatogram 0002] (provided by Dr. Etsuko Yasugi).

synthetic by treatment of the corresponding bromo acid with KOH



338
19-Hydroxynonadecanoic acid
DFA0338
Tetsuyuki Kobayashi
C19H38O3 314.503 Download ChemDraw structure fileDownload mol format file

91-91.5degC





synthetic by the partial reduction of nonadecanedionic acid dimethyl ester



339
2-Hydroxyeicosanoic acid
DFA0339
Tetsuyuki Kobayashi
C20H40O3 328.530 Download ChemDraw structure fileDownload mol format file

91-92degC





synthetic by heating 2-bromoarachidic acid with ethanolic NaOH



340
3-Hydroxyeicosanoic acid
DFA0340
Tetsuyuki Kobayashi
C20H40O3 328.530 Download ChemDraw structure fileDownload mol format file

93degC









341
20-Hydroxyeicosanoic acid
DFA0341
Tetsuyuki Kobayashi
C20H40O3 328.530 Download ChemDraw structure fileDownload mol format file

97.4-97.8degC (acetyl derivative), 68.5degC (methyl ester)





synthetic by partial reductionof eicosanedioic acid dimethyl ester



342
21-Hydroxyheneicosanoic acid
DFA0342
Tetsuyuki Kobayashi
C21H42O3 342.556 Download ChemDraw structure fileDownload mol format file

92.5-93degC




seed oil of Mallotus philippinensis (kamala)
synthetic by the partial reduction of heneicosanedioic acid dimethyl ester



343
2-Hydroxybehenic
2-Hydroxydocosanoic acid
DFA0343
Tetsuyuki Kobayashi
C22H44O3 356.583 Download ChemDraw structure fileDownload mol format file

99.3-99.6degC