LBF17307HO02: Difference between revisions

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Upper classes: LB LBF

(S) , (Z,E,E) -12-Hydroxy-5,8,10-heptadecatrienoic acid

Structural Information
	(S) , (Z,E,E) -12-Hydroxy-5,8,10-heptadecatrienoic acid
	(S) , (Z,E,E) -12-Hydroxy-5,8,10-heptadecatrienoic acid
	HHT
Formula	C17H28O3
Exact Mass	280.203844762
Average Mass	280.40242
SMILES	`CCCCC[C@H](O)C=CC=CCC=CCCCC(O)=O`
Physicochemical Information



	METHYL ESTER ; [ α ]25 D =+7.5°(C=0.2, CHLOROFORM) Nicolaou_KC et al.

	DIETHYL ETHER Hamberg_Met al.

	Nicolaou_KC et al.
	When prostaglandin H2 reacts with thromboxane A synthase and the endoperoxide moiety is cleaved, the production of thromboxane A2 is accompanied by the formation of 12(S)-hydroxy-5,8,10-heptadecatrienoic acid in an almost equimolar amount liberating malondialdehyde Hamberg_M et al.. This compound is also a product of non-enxymatic degradation of prostaglandin H2 Nugteren_DH et al..
	The compound stimulates chemotactic and chemokinetic activities of human polymorphonuclear leukocytes Goetzl_EJ et al..


Spectral Information
Mass Spectra	METHYL ESTER TMS ETHER ; m/e 366(M⁺), 335, 295, 276, 225, 173, (128) Hamberg_Met al. METHYL ESTER ; 298(M⁺), 224 Nicolaou_KC et al.
UV Spectra	METHYL ESTER ; ETHANOL : 232nm( ε 33,400) Hamberg_Met al.. METHANOL : 240nm Nicolaou_KC et al.
IR Spectra
NMR Spectra	METHYL ESTER ; ¹H-NMR(CDCl₃) : δ 6.17(dd, J=15.11, 10.36Hz, 1H, 10-CH), 6.04(dd, J=15,05, 10.52Hz, 1H, 9-CH), 5.66(dt, J=15.16, 6.48Hz, 1H), 5.60(dd, J=17.17, 7.04Hz, 1H, 11-CH), 5.42(m, 2H, 5-CH, 6-CH), 4.1(m, 1H, 12-CH), 3.66(s, 3H, COOCH₃), 2.81(m, 2H, 7-CH), 2.36(t, J=7.51Hz, 2H, 2-CH), 2.1-0.85(m, 16H, CH₂ and CH₃) Nicolaou_KC et al.
Other Spectra
Chromatograms

Reported Metabolites, References

Biospecies	ID	Compound Name	Reference
n.a.	LBF17307HO02	See above.	Goetzl_EJ et al. 1978
n.a.	LBF17307HO02	See above.	Hamberg_M et al. 1974
n.a.	LBF17307HO02	See above.	Hamberg_M et al. 1974
n.a.	LBF17307HO02	See above.	Hamberg_M et al. 1974
n.a.	LBF17307HO02	See above.	Nicolaou_KC et al. 1989
n.a.	LBF17307HO02	See above.	Nugteren_DH et al. 1973

@@ Line 8: / Line 8: @@
 |SysName= (S) , (Z,E,E) -12-Hydroxy-5,8,10-heptadecatrienoic acid
 |Common Name=&&(S) , (Z,E,E) -12-Hydroxy-5,8,10-heptadecatrienoic acid&&
-|Optical=METHYL ESTER ; [ alpha ]X^{25}_D  =+7.5°(C=0.2, CHLOROFORM) [[Reference:Nicolaou_KC:Stylianides_NA:Ramphal_JY:,J. Chem. Soc. Perkin Trans. I,1989,,2131|{{RelationTable/GetFirstAuthor|Reference:Nicolaou_KC:Stylianides_NA:Ramphal_JY:,J. Chem. Soc. Perkin Trans. I,1989,,2131}}]]
+|Optical=METHYL ESTER ; [ alpha ]^{25}_D  =+7.5°(C=0.2, CHLOROFORM) [[Reference:Nicolaou_KC:Stylianides_NA:Ramphal_JY:,J. Chem. Soc. Perkin Trans. I,1989,,2131|{{RelationTable/GetFirstAuthor|Reference:Nicolaou_KC:Stylianides_NA:Ramphal_JY:,J. Chem. Soc. Perkin Trans. I,1989,,2131}}]]
 |Solubility=DIETHYL ETHER [[Reference:Hamberg_M:Samuelsson_B:,Proc. Natl. Acad. Sci. U. S. A.,1974,71,3400|{{RelationTable/GetFirstAuthor|Reference:Hamberg_M:Samuelsson_B:,Proc. Natl. Acad. Sci. U. S. A.,1974,71,3400}}]]
 |Mass Spectra=METHYL ESTER TMS ETHER ; m/e 366(M^+ ), 335, 295, 276, 225, 173, (128)[[Reference:Hamberg_M:Svensson_J:Wakabayashi_T:Samuelsson_B:,Proc. Nat. Acad. Sci. USA,1974,71,345|{{RelationTable/GetFirstAuthor|Reference:Hamberg_M:Svensson_J:Wakabayashi_T:Samuelsson_B:,Proc. Nat. Acad. Sci. USA,1974,71,345}}]] METHYL ESTER ; 298(M^+ ), 224 [[Reference:Nicolaou_KC:Stylianides_NA:Ramphal_JY:,J. Chem. Soc. Perkin Trans. I,1989,,2131|{{RelationTable/GetFirstAuthor|Reference:Nicolaou_KC:Stylianides_NA:Ramphal_JY:,J. Chem. Soc. Perkin Trans. I,1989,,2131}}]]

IDs and Links
LipidBank	XPR6201
LipidMaps	-
CAS
KEGG	{{{KEGG}}}
KNApSAcK	{{{KNApSAcK}}}

mol	LBF17307HO02

LBF17307HO02: Difference between revisions

Revision as of 16:20, 26 February 2010

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