LBF20406CV14

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Upper classes: LB LBF



Chlorovulone III
LBF20406CV14.png
Structural Information
Systematic Name Methyl- (trans-5,cis-7) -7- [ 4R-chloro-2-hydroxy-2- (cis-2-octenyl) -5-oxo-3-cyclopentenylidene ] -5-heptenoic acid
Common Name
  • Chlorovulone III
  • Methyl- (5E,7Z) -7- [ 4R-chloro-2-hydroxy-2- [(2Z-octenyl) -5-oxo-3-cyclopentenylidene ] -5-heptenoic acid
Symbol
Formula C21H29ClO4
Exact Mass 380.175437126
Average Mass 380.90525999999994
SMILES C(C(=O)1)(Cl)=C[C@](CC=CCCCCC)(C(=CC=CCCCC(OC)=O)1)O
Physicochemical Information
Melting Point
Boiling Point
Density
Optical Rotation [ α ]D +27.3°(C 0.033, CHCl3) IguchiKet al.
Refractive Index
Solubility Chlorovulones are soluble in MeOH, EtOH, CHCl3, or hexane.
Source Chlorovulones were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard. Iguchi_K et al. Nagaoka_H et al.
Chemical Synthesis Photoisomerization of chlorovulone I (fluoresent lamp, benzene, 40 hr) gave a mixture of chlorovulones I, II and III. Iguchi_K et al.
Metabolism
Biological Activity
Genetic Information
Note
Spectral Information
Mass Spectra
UV Spectra λ max(EtOH) 238 nm( ε 13200),315 nm( ε 11900) IguchiKet al.
IR Spectra ν max(CHCl3)1725,1700, and 1630cm-1(Yamada Yasuji)
NMR Spectra 1H-NMR(400MHz,CDCl3) δ ppm0.88(3H,t,J=7.1Hz),1.30(6H,m),1.81(2H,quint.,J=7.5Hz),2.00(2H,brq,J=6.9Hz),2.30(2H,brq,J=7.5Hz),2.35(2H,t,J=7.5Hz),2.55(1H,brdd,J=7.6,14.4Hz),2.67(1H,brdd,J=8.3,14.4Hz),3.68(3H,s),5.29(1H,ttd,J=1.7,7.6,10.9Hz),5.38(1H,brtd,J=7.4,10.9Hz),6.19(1H,td,J=7.1,15.7Hz),6.68(1H,d,J=11.4Hz),7.15(1H,s),7.56(1H,tdd,J=1.4,11.4,15.7Hz). IguchiKet al.
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20406CV14 See above. Iguchi_K et al. 1985
n.a. LBF20406CV14 See above. Nagaoka_H et al. 1986


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