LBF20306HX04

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Upper classes: LB LBF



Hepoxilin B3
LBF20306HX04.png
Structural Information
Systematic Name 10-Hydroxy- (11R,12S)-epoxy- (cis-5,cis-8,cis-14) -eicosatrienoic acid
Common Name
  • Hepoxilin B3
  • 10-Hydroxy- (11R,12S)-epoxy- (5Z,8Z,14Z) -eicosatrienoic acid
  • 10-Hydroxy-11 (R) ,12 (S) -epoxyeicosa-5,8,14 (Z,Z,Z) -trienoic acid
Symbol HxB3
Formula C20H32O4
Exact Mass 336.23005951199997
Average Mass 336.46567999999996
SMILES C(CC=CC[C@@H]([C@@H](C(O)C=CCC=CCCCC(O)=O)1)O1)CCC
Physicochemical Information
Melting Point
Boiling Point
Density
Optical Rotation ACETATE, METHYL ESTER ; [ α ]X23
D
   =-10.9°(C=0.11, CHLOROFORM) Moghaddam_MF et al.
Refractive Index
Solubility DIETHYL ETHER Pace-Asciak_CR et al.
Source Hepoxilin B3 together with hepoxilin A3 is produced from arachidonic acid or more directly from 12(S)-hydroperoxy-5,8,10,14-eicosatetraenoic acid in various animal tissues including brain, pineal gland, pancreas and skin Pace-Asciak_CR .
Chemical Synthesis Corey_EJ et al.
LBF20306HX04FT0001.gif
Metabolism The presence of hepoxilin synthase was suggested by a finding that intact cells (skin) and tissue slices (brain hippocampus and pineal gland) transformed 12(S)-hydroperoxy-5,8,10,14-eicosatetraenoic acid to hepoxilins A3 and B3, but tissue boiling inhibited the hepoxilin production Pace-Asciak_CR et al..
Biological Activity Little has been described about the biological actvity of hepoxilin B3 except for its poteniation of glucose-dependent insulin secretion Pace-Asciak_CR and of bradykinin-induced increase of vascular permeability .
Genetic Information
Note
Spectral Information
Mass Spectra METHYL ESTER TMS ETHER ; m/e 311, 282, 269(base peak) Moghaddam_MF et al.
UV Spectra
IR Spectra ACETATE METHYL ESTER ; ν (CHLOROFORM) 2956, 1743, 1550, 1372, 1234, 1033, 999cm-1 Moghaddam_MF et al.
NMR Spectra ACETATE METHYL ESTER ; 1H-NMR(C6D6) : δ 5.67(dd, J=9.2, 6.4Hz, 1H, 10-CH), 5.52, 5.46, 5.42, 5.35, 5.32, 3.36(s, 3H, OCH3), 2.95(m, 2H, 7-CH), 2.92(m, 1H, 11-CH), 2.86(ddd, J=7.4, 7.4, 2.1Hz, 1H, 12-CH), 2.30(ddd, J=14.8, 7.4, 7.4Hz, 1H, 13-CH), 2.18(ddd, J=14.8, 7.4, 7.4Hz, 1H, 13-CH), 2.12(t, J=7.4Hz, 2H, 2-CH), 1.98(dt, J=7.4, 7.4Hz, 2H, 4-CH), 1.92(dt, J=8.8, 8.8Hz, 2H, 16-CH), 1.65(s, 3H, COCH3), 1.60(tt, J=7.4, 7.4Hz, 2H, 3-CH), 1.25(m, 6H), 0.88(t, J=7.0Hz, 3H, 20-CH). Moghaddam_MF et al. 13NMR(C6D6) : 134.22, 133.35, 130.17, 127.74, 124.31, 123.37, 70.86, 58.30, 55.71, 50.94, 33.30, 31.71, 29.66, 29.52, 27.59, 26.73, 25.00, 22.88, 20.53, 14.23 Moghaddam_MF et al.
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20306HX04 See above. Corey_EJ et al. 1983
n.a. LBF20306HX04 See above. Moghaddam_MF et al. 1990
n.a. LBF20306HX04 See above. Pace-Asciak_CR 1994
n.a. LBF20306HX04 See above. Pace-Asciak_CR et al. 1983
n.a. LBF20306HX04 See above. Pace-Asciak_CR et al. 1995


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