LBF20406CV03

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Upper classes: LB LBF



4-epi Clavulone II
LBF20406CV03.png
Structural Information
Systematic Name Methyl-4R- (trans-5,trans-7) -4-acetoxy-7- [2R-acetoxy-2- (cis-2-octenyl) -5-oxo-3-cyclopentenylidene] -5-heptenoate
Common Name
  • 4-epi Clavulone II
  • Methyl-4R- (5E,7E) -4-acetoxy-7- [2R-acetoxy-2- (2Z-octenyl) -5-oxo-3-cyclopentenylidene] -5-heptenoate
Symbol
Formula C25H34O7
Exact Mass 446.230453442
Average Mass 446.53326000000004
SMILES O(C(C)=O)[C@@](C1=CC=C[C@H](CCC(OC)=O)OC(C)=O)(CC=CCCCCC)C=CC1=O
Physicochemical Information
Melting Point
Boiling Point
Density
Optical Rotation [ α ]D -18.7°(C 0.30, CHCl3) IwashimaMet al.
Refractive Index
Solubility
Source 4-Epiclavulones were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard. Iwashima_M et al.
Chemical Synthesis 4-Epiclavulone II was synthesized from clavulone II. Iwashima_M et al.
Metabolism
Biological Activity
Genetic Information
Note
Spectral Information
Mass Spectra EIMS m/z 446 (M+). HREIMS m/z 446.2315 for C25}H_{34O7 (M+), calcd 446.2305. IwashimaMet al.
UV Spectra λ EtOH
max
   228 nm(log ε 4.28),291 nm(log ε 4.27) IwashimaMet al.
IR Spectra ν film
max
  1738,1732,1704,1644,and 1232cm-1 IwashimaMet al.
NMR Spectra 1H-NMR(500MHz,CDCl3) δ ppm0.88(3H,t,J=7.2Hz),1.20-1.34(6H,m),1.94(2H,q,J=6.8Hz),1.98-2.06(2H,m),2.03(3H,s),2.09(3H,s),2.37(2H,t,J=7.4Hz),2.71(1H,dd,J=8.4,14.1Hz),2.98(1H,dd,J=7.0,14.1Hz),3.67(3H,s),5.18(1H,ddd,J=7.0,8.4,10.9Hz),5.43(1H,dt,J=6.4,7.0Hz),5.50(1H,dt,J=7.4,10.9Hz),6.07(1H,dd,J=6.4,11.9Hz),6.41(1H,d,J=6.1Hz),6.70(1H,ddd,J=1.0,11.9,15.1Hz),6.88(1H,d,J=15.1Hz),7.48(1H,d,J=6.1Hz). IwashimaMet al. 13C-NMR(125MHz,CDCl3) δ ppm14.0,20.9,21.2,22.5,27.4,29.1,29.2,29.6,31.5,35.9,51.8,72.7,85.3,121.1,126.0,129.4,135.1,135.1,136.7,141.5,157.9,169.2,169.9,172.9,193.4. IwashimaMet al.
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20406CV03 See above. Iwashima_M et al. 1999


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