LBF17307HO02

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Upper classes: LB LBF



12S-Hydroxy- (5Z,8E,10E) -heptadecatrienoic acid
LBF17307HO02.png
Structural Information
Systematic Name 12S-Hydroxy- (cis-5,trans-8,trans-10) -heptadecatrienoic acid
Common Name
  • 12S-Hydroxy- (5Z,8E,10E) -heptadecatrienoic acid
  • (S)- (Z,E,E) -12-Hydroxy-5,8,10-heptadecatrienoic acid
Symbol HHT
Formula C17H28O3
Exact Mass 280.203844762
Average Mass 280.40242
SMILES CCCCC[C@H](O)C=CC=CCC=CCCCC(O)=O
Physicochemical Information
Melting Point
Boiling Point
Density
Optical Rotation METHYL ESTER ; [ α ]25
D
   =+7.5°(C=0.2, CHLOROFORM) Nicolaou_KC et al.
Refractive Index
Solubility DIETHYL ETHER HambergMet al.
Source
Chemical Synthesis Nicolaou_KC et al.
LBF17307HO02FT0001.gif
Metabolism 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..
Biological Activity The compound stimulates chemotactic and chemokinetic activities of human polymorphonuclear leukocytes Goetzl_EJ et al..
Genetic Information
Note
Spectral Information
Mass Spectra METHYL ESTER TMS ETHER ; m/e 366(M+), 335, 295, 276, 225, 173, (128) HambergMet al. METHYL ESTER ; 298(M+), 224 Nicolaou_KC et al.
UV Spectra METHYL ESTER ; ETHANOL : 232nm( ε 33,400) HambergMet 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 Comment
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


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