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Eicosanoid


DATA No : XPR8044 INFORMANT : Yasuji Yamada

NAME : (Z)-2-[(R)-2-acetoxy-2-[(Z)-2-octenyl]-5-oxo-3-cyclopentenylidene]acetaldehyde

COMMON NAME: clavirin I (Ref. 8043)
SYMBOL:
FORMULA: C17H22O4 MOL.WT (average) : 290.354


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BIOLOGICAL ACTIVITY
Clavirins showed growth-inhibitory activity toward Hela S3 at 1 mg/ml.(Ref. 8043)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]D -17.1deg(C 0.48, CHCl3)(Ref. 8043)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nfilmmax1735,1714,1682, and 1227cm-1(Ref. 8043)

NMR SPECTRA:1H-NMR(500MHz,CDCl3)dppm0.88(3H,t,J=7.1Hz),1.20-1.36(6H,m),1.96(2H,brq,J=7.1Hz),2.05(3H,s),2.68(1H,dd,J=7.7,14.6Hz),2.77(1H,dd,J=7.4,14.6Hz),5.23(1H,dt,J=7.1,10.9Hz),5.59(1H,ddd,J=7.4,7.7,10.9Hz),6.21(1H,d,J=7.6Hz),6.49(1H,d,J=6.2Hz),7.56(1H,d,J=6.2Hz),10.79(1H,d,J=7.6Hz).(Ref. 8043) 13C-NMR(125MHz,CDCl3)dppm14.0,21.3,22.5,27.4,29.0,31.4,36.0,83.5,120.1,129.9,136.0,136.1,150.2,169.5,11.7,192.9.(Ref. 8043)

MASS SPECTRA:HREIMS m/z 230.1298 for C15H18O2 (M+-CH3CO2H), calcd 230.1307.(Ref. 8043)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Clavirins were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8043)
CHEMICAL SYNTHESIS
Clavirin I and II were synthesized from 4-alkoxy-2-cyclopentenone.(Ref. 8043)
METABOLISM
Clavirins may possibly be biosynthesized from clavulone.(Ref. 8043)
GENETIC INFORMATION

NOTE

REFERENCES
[8043]
AUTHOR:Iwashima, M., Okamoto, K., and Iguchi, K.
TITLE:Clavirins, a New Type of Marine Oxylipins with Growth-inhibitory Activity from the Okinawan Soft Coral, Clavularia viridis.
JOURNAL:Tetrahedron Lett.
VOL:40 PAGE : 6455 -6459 (1999)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.