LBF20406HO21

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Upper classes: LB LBF

IDs and Links
LipidBank	XPR6102
LipidMaps	-
CAS
KEGG	{{{KEGG}}}
KNApSAcK	{{{KNApSAcK}}}
mol	LBF20406HO21

12S-Hydroxy- (5Z,8E,10Z,14Z) -eicosatetraenoic acid
Structural Information
Systematic Name	12S-Hydroxy- (cis-5,trans-8,cis-10,cis-14) -eicosatetraenoic acid
Common Name	12S-Hydroxy- (5Z,8E,10Z,14Z) -eicosatetraenoic acid
Symbol	12S-HETE
Formula	C20H32O3
Exact Mass	320.23514489
Average Mass	320.46628
SMILES	C(CC=CC[C@@H](C=CC=CCC=CCCCC(O)=O)O)CCC
Physicochemical Information
Melting Point
Boiling Point
Density
Optical Rotation	METHYL ESTER ; [ α ]25 D   =+1.50°(C=0.2, CHLOROFORM) Corey_EJ et al., [ α ]22 D   =+13°(C=1.5, ACETONE) LeblancYet al.
Refractive Index
Solubility	DIETHYL ETHER , ACETONE , BENZENE LeblancYet al.
Source
Chemical Synthesis	Corey_EJ et al.
Metabolism	When arachidonic acid is oxygenated by 12-lipoxygenase, 12(S)-hydroperoxy-5,8,10,14-(Z,Z,E,Z)-eicosatetraenoic acid is produced Yamamoto_S et al.. The latter compound is reduced to a corresponding 12(S)-hydroxy acid with whole cells or crude enzyme preparations.
Biological Activity	There are reports for various biological activities of 12(S)-hydroxy acid such as rat hypothalamic secretion of LH-RH, stimulated chemotactic activity of human eosinophils and neutrophils, stimulated migration of epidermal tumor cells and rat aortic smooth muscle cells, involvement in angiotension II-mediated aldosterone biosynthesis in human adrenal glomerulosa, and expression or activation of GpIIb/IIIa in tumor cells, but a general theory has not been established Yamamoto_S et al. Yoshimoto_T et al..
Genetic Information
Note
Spectral Information
Mass Spectra	METHYL ESTER ; m/e 316, 303, 223, 191, 141, 107(base peak) JustGet al.
UV Spectra	METHYL ESTER ; λ MeOH max     = 234nm JustGet al.METHYL ESTER ; λ EtOH max     = 237nm( ε 30500) HambergMet al.
IR Spectra	NEAT : ν 3480b, 1710, 1460, 1400cm-1 LeblancYet al.
NMR Spectra	1H-NMR(250MHz, ACETONE-D6) ; δ 6.58(dd, J=15.3, 11.0Hz, 1H, 10-CH), 5.97(t, J=11.0Hz, 1H, 9-CH), 5.72(dd, J=15.3, 6.2 Hz, 1H, 11-CH), 5.29(m, 5H, 5,6,8,14,15-CH), 4.16(q, J=6.3Hz, 1H, 12-CH), 2.94(t, J=6.1Hz, 2H, 7-CH), 2.27(t,J= 7.4Hz, 2H,2-CH), 2.22(m, 2H, 13-CH), 1.66 and 2.14(m, 2H, 4-and 16-CH), 0.87(t, J=6.3Hz, 3H, 20-CH) LeblancYet al.. 13NMR(C6D6) : 174.3, 137.77, 132.02, 129.98, 129.62, 128.88, 128.69, 125.96, 124.44 LeblancYet al.
Other Spectra
Chromatograms

Reported Metabolites, References
Biospecies ID Compound Name Reference Comment n.a. LBF20406HO21 See above. Corey_EJ et al. 1978 n.a. LBF20406HO21 See above. Hamberg_M et al. 1974 n.a. LBF20406HO21 See above. Just_G et al. 1986 n.a. LBF20406HO21 See above. Leblanc_Y et al. 1986 n.a. LBF20406HO21 See above. Yamamoto_S et al. 1997 n.a. LBF20406HO21 See above. Yoshimoto_T et al. 1995