LBF20407HO07: Difference between revisions

Revision as of 21:00, 6 January 2010

Upper classes: LB LBF

15 (S) -Hydroxy-5,8,11,13- (Z,Z,Z,E) -eicosatetraenoic acid

Structural Information
	15 (S) -Hydroxy-5,8,11,13- (Z,Z,Z,E) -eicosatetraenoic acid
	15 (S) -Hydroxy-5,8,11,13- (Z,Z,Z,E) -eicosatetraenoic acid
	15(S)-HETE
Formula	C20H32O3
Exact Mass	320.23514489
Average Mass	320.46628
SMILES	`C(CC[C@@H](C=CC=CCC=CCC=CCCCC(O)=O)O)CC`
Physicochemical Information





	DIETHYL ETHER Baldwin_JE et al.

	Baldwin_JE et al.
	When arachidonic acid is oxygenated by 15-lipoxygenase, 15(S)-hydroperoxy-5,8,11,13-(Z,Z,Z,E)-eicosatetraenoic acid is produced Bryant_RW et al.. The latter compound is reduced to a corresponding 15(S)-hydroxy acid with whole cells or crude enzyme preparations.
	In connection with biological activities of 15-hydroxyeicosatetraenoic acid, there are reports for pain response of skin, mucus secretion in airway, histamine hypersensitivity, prolactin secretion, and regulation of protein phosporylation and cell signalling Kuhn_H et al..


Spectral Information
Mass Spectra	METHYL ESTER TMS ETHER ; m/e 406(M⁺), 391, 335, 316, 305, 225, 173 Baldwin_JE et al.
UV Spectra	METHYL ESTER ; l (ISOOCTANE) = 236nm(e 27200) Baldwin_JE et al.
IR Spectra
NMR Spectra	METHYL ESTER ; ¹H-NMR(90MHz) : d 6.56(dd, J=11, 14.5Hz, 1H, 13-CH), 6.02(dd, J=11,11Hz, 1H, 12-CH), 5.7(dd, J=6.8, 14.5Hz, 1H,14-CH), 5.51(dd, J=6,11Hz, 1H, 11-CH), 4.16(dd, J=6.8, 6.8Hz, 1H, 15-CH), 3.69(s, 3H, OCH₃), 2.98(2H, 10-CH), 2.84(2H, 7-CH), 2.35(2H, 2-CH), 2.08(2H, 4-CH), 1.47(2H, 16-CH), 2.3-0.9(11H) Baldwin_JE et al.
Other Spectra
Chromatograms

Reported Metabolites, References

Biospecies	ID	Compound Name	Reference
n.a.	LBF20407HO07	See above.	Baldwin_JE et al. 1979
n.a.	LBF20407HO07	See above.	Bryant_RW et al. 1982
n.a.	LBF20407HO07	See above.	Kuhn_H et al. 1995

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 |Chemical Synthesis=[[Reference:Baldwin_JE:Davies_DI:Hughes_L:Gutterridge_NJA:,J. Chem. Soc. Perkin I,1979,,115|{{RelationTable/GetFirstAuthor|Reference:Baldwin_JE:Davies_DI:Hughes_L:Gutterridge_NJA:,J. Chem. Soc. Perkin I,1979,,115}}]] {{Image200|LBF20407HO07FT0001.gif}}
 |Metabolism=When arachidonic acid is oxygenated by 15-lipoxygenase, 15(S)-hydroperoxy-5,8,11,13-(Z,Z,Z,E)-eicosatetraenoic acid is produced [[Reference:Bryant_RW:Bailey_JM:Schewe_T:Rapoport_SM:,J. Biol. Chem.,1982,257,6050|{{RelationTable/GetFirstAuthor|Reference:Bryant_RW:Bailey_JM:Schewe_T:Rapoport_SM:,J. Biol. Chem.,1982,257,6050}}]]. The latter compound is reduced to a corresponding 15(S)-hydroxy acid with whole cells or crude enzyme preparations.
+|Symbol=15(S)-HETE
+|Biological Activity=In connection with biological activities of 15-hydroxyeicosatetraenoic acid, there are reports for pain response of skin, mucus secretion in airway, histamine hypersensitivity, prolactin secretion, and regulation of protein phosporylation and cell signalling [[Reference:Kuhn_H:Thiele_BJ:,J. Lipid Mediat. Cell Signal.,1995,12,157|{{RelationTable/GetFirstAuthor|Reference:Kuhn_H:Thiele_BJ:,J. Lipid Mediat. Cell Signal.,1995,12,157}}]].
 }}
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