LBF20406CV01

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Upper classes: LB LBF



Clavulolactone II
LBF20406CV01.png
Structural Information
Systematic Name 4R- { (trans-1,trans-3) -3- [2S-Acetoxy-2- (cis-2-octenyl) -5-oxo-3-cyclopentenylidene] -1-propenyl} -4-butanolide
Common Name
  • Clavulolactone II
  • 4R- { (1E,3E) -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 -25.6°(C 0.26, 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 II was converted from clavulone II. Iguchi_K et al.
Metabolism
Biological Activity
Genetic Information
Note
Spectral Information
Mass Spectra EIMS m/z 372 (M+). HREIMS m/z 372.1920 for C22}H_{28O5, calcd 372.1937. IguchiKet al.
UV Spectra λ EtOH
max
   292 nm( ε 16500),231 nm( ε 12500) IguchiKet al.
IR Spectra ν film
max
  1778,1745, 1704, 1644, and 1231cm-1 IguchiKet al.
NMR Spectra 1H-NMR(400MHz,CDCl3) δ ppm0.87(3H,t,J=7.2Hz),1.20-1.34(6H,m),1.94(2H,brq,J=6.3Hz),2.02(3H,s),2.04(1H,m),2.52(1H,m),2.55(2H,m),2.71(1H,brdd,J=8.1,14.2Hz),2.91(1H,brdd,J=7.1,14.2Hz),5.15(1H,m),5.15(1H,m),5.52(1H,m),6.17(1H,dd,J=4.9,14.7Hz),6.42(1H,d,J=6.1Hz),6.82(1H,ddd,J=1.5,12.0,14.7Hz),6.91(1H,brd,J=12.0Hz),7.50(1H,brd,J=6.1Hz). IguchiKet al. 13C-NMR(100MHz,CDCl3) δ ppm14.0,21.2,22.5,27.4,27.7,28.2,29.0,31.5,35.8,78.6,85.2,121.0,124.9,128.9,135.06,135.14,137.2,140.8,158.0,169.3,176.2,193.3. IguchiKet al.
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20406CV01 See above. Iguchi_K et al. 1995
n.a. LBF20406CV01 See above. Iwashima_M et al. 1999


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