LBF20406CV02

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Upper classes: LB LBF



Clavulolactone III
LBF20406CV02.png
Structural Information
Systematic Name 4R- { (trans-1,cis-3) -3- [2S-Acetoxy-2- (cis-2-octenyl) -5-oxo-3-cyclopentenylidene] -1-propenyl} -4-butanolide
Common Name
  • Clavulolactone III
  • 4R- { (1E,3Z) -3- [2S-Acetoxy-2- (2Z-octenyl) -5-oxo-3-cyclopentenylidene] -1-propenyl} -4-butanolide
Symbol
Formula C22H28O5
Exact Mass 372.193674006
Average Mass 372.45472000000007
SMILES CC(=O)O[C@@](CC=CCCCCC)(C=2)C(C(C2)=O)=CC=C[C@H](O1)CCC(=O)1
Physicochemical Information
Melting Point
Boiling Point
Density
Optical Rotation [ α ]D -7.3°(C 0.21, CHCl3) IguchiKet al.
Refractive Index
Solubility
Source Clavulolactones were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard. Iwashima_M et al. Iguchi_K et al.
Chemical Synthesis Clavulolactone III was converted from clavulone III. Iguchi_K et al.
Metabolism
Biological Activity
Genetic Information
Note
Spectral Information
Mass Spectra EIMS m/z 372 (M+). HREIMS m/z 372.1961 for C22}H_{28O5, calcd 372.1937. IguchiKet al.
UV Spectra λ EtOH
max
   293 nm( ε 15500),229 nm( ε 17900) IguchiKet al.
IR Spectra ν film
max
  1778,1742, 1698, 1643, and 1232cm-1 IguchiKet al.
NMR Spectra 1H-NMR(400MHz,CDCl3) δ ppm0.88(3H,t,J=7.1Hz),1.22-1.33(6H,m),1.97(2H,brq,J=7.2Hz),2.03(3H,s),2.05(1H,m),2.47(1H,m),2.58(2H,dd,J=6.9,9.3Hz),2.65(1H,brdd,J=7.6,14.3Hz),2.84(1H,brdd,J=7.3,14.3Hz),5.10(1H,brdd,J=7.3,7.9Hz),5.22(1H,m),5.54(1H,m),6.08(1H,dd,J=7.3,15.6Hz),6.38(1H,d,J=6.1Hz),6.53(1H,d,J=11.3Hz),7.49(1H,d,J=6.1Hz),7.82(1H,brdd,J=11.3,15.6Hz). IguchiKet al. 13C-NMR(100MHz,CDCl3) δ ppm14.0,21.6,22.5,27.4,28.6,28.6,29.0,31.4,35.7,80.0,85.0,121.1,127.6,132.4,135.0,136.6,139.8,139.8,156.3,169.6,176.5,194.0. IguchiKet al.
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20406CV02 See above. Iguchi_K et al. 1995
n.a. LBF20406CV02 See above. Iwashima_M et al. 1999


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