LBF20306CV03

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Upper classes: LB LBF



10,11-epoxy Chlorovulone I
LBF20306CV03.png
Structural Information
Systematic Name Methyl- (cis-5,trans-7) -7- [ (2S,3S,4R) -4-chloro-3,4-epoxy-2-hydroxy-2- (cis-2-octenyl) -5-oxo-3-cyclopentanylidene] -5-heptenoic acid
Common Name
  • 10,11-epoxy Chlorovulone I
  • Methyl- (5Z,7E) -7- [ (2S,3S,4R) -4-chloro-3,4-epoxy-2-hydroxy-2- (2Z-octenyl) -5-oxo-3-cyclopentanylidene] -5-heptenoic acid
Symbol
Formula C21H29ClO5
Exact Mass 396.17035174800003
Average Mass 396.90466
SMILES C(C=CCCCCC)[C@]([C@@H]12)(O)C(C(=O)[C@@]1(Cl)O2)=CC=CCCCC(OC)=O
Physicochemical Information
Melting Point
Boiling Point
Density
Optical Rotation [ α ]D -24.1°(C 0.44, CHCl3) IguchiKet al.
Refractive Index
Solubility 10,11-Epoxychlorovulone I is soluble in MeOH, EtOH, CHCl3, or hexane.
Source 10,11-Epoxychlorovulone I was isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard. Iguchi_K et al.
Chemical Synthesis Epoxidation of chlorovulone I with excess 5% aqueous sodium hypochlorite solution in DMF gave 10,11-epoxychlorovulone I. Iguchi_K et al.
Metabolism
Biological Activity 10,11-Epoxychlorovulone I showed the strong antiproliferative and cytotoxic activities in himan promyelocytic leukemia (HL-60) ((IC^{50} 0.04 mu g/ml, cytotoxic effect >0.3 mu g/ml). Honda_A et al. Iguchi_K et al.
Genetic Information
Note
Spectral Information
Mass Spectra HRCIMS m/z 397.1815 (M+1, calcd for C35
21
  ClO5, 397.1780) IguchiKet al.
UV Spectra λ max(EtOH) 300 nm( ε 4300) IguchiKet al.
IR Spectra ν max(CHCl3)3580,1740, and 1625cm-1 IguchiKet al.
NMR Spectra 1H-NMR(400MHz,CDCl3) δ ppm0.88(3H,t,J=7.2Hz),1.80(2H,quint.,J=7.4Hz),1.99(2H,brq,J=7.7Hz),2.33(2H,t,J=7.3Hz),2.39(2H,m),2.72(1H,brd,J=7.3Hz),3.68(3H,s),3.96(1H,s),5.23(1H,m),5.60(1H,m),6.13(1H,tdd,J=7.9,10.9,1.0Hz),6.82(1H,tdd,J=1.6,10.9,12.5Hz),7.54(1H,d,J=12.5Hz). IguchiKet al.
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20306CV03 See above. Honda_A et al. 1988


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