LBF20406HO21

From Jcbl.jp
Jump to: navigation, search
LipidBank Top
(トップ)
Fatty acid
(脂肪酸)
Glycerolipid
(グリセロ脂質)
Sphingolipid
(スフィンゴ脂質)
Journals
(雑誌一覧)
How to edit
(ページの書き方)


Upper classes: LB LBF



12S-Hydroxy- (5Z,8E,10Z,14Z) -eicosatetraenoic acid
LBF20406HO21.png
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.
LBF20406HO21FT0001.gif
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



Personal tools