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Eicosanoid


DATA No : XPR8010 INFORMANT : Yasuji Yamada

NAME : methyl (5E,7Z)-7-[(R)-4-chloro-2-hydroxy-2-[(Z)-2-octenyl]-5-oxo-3-cyclopentenylidene]-5-heptenoate

COMMON NAME: chlorovulone III (Ref. 8025/8026)
SYMBOL:
FORMULA: C21H29O4Cl MOL.WT (average) : 380.905


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]D +27.3deg(C 0.033, CHCl3)(Ref. 8025)

DENSITY:

SOLUBILITY:Chlorovulones are soluble in MeOH, EtOH, CHCl3, or hexane.
SPECTRAL DATA
UV SPECTRA:lmax(EtOH) 238 nm(e13200),315 nm(e11900)(Ref. 8025)

IR SPECTRA:nmax(CHCl3)1725,1700, and 1630cm-1(Yamada Yasuji)

NMR SPECTRA:1H-NMR(400MHz,CDCl3)dppm0.88(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).(Ref. 8025)

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Chlorovulones were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8025/8026)
CHEMICAL SYNTHESIS
Photoisomerization of chlorovulone I (fluoresent lamp, benzene, 40 hr) gave a mixture of chlorovulones I, II and III.(Ref. 8025)
METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[8025]
AUTHOR:Iguchi,K., Kaneta,S., Mori,K., Yamada,Y., Honda,A., and Mori,Y.
TITLE:Chlorovulones, New Halogenated Marine Prostanoids with Antitumor Activity from the Stolonifer Clavularia viridis Quoy and Gaimard.
JOURNAL:Tetrahedron Lett.
VOL:26 PAGE : 5787 -5790 (1985)
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[8026]
AUTHOR:Nagaoka,H., Iguchi,K., Miyakoshi,T., Yamada,N., and Yamada,Y.
TITLE:Determination of Absolute Configuration of Chlorovulones by CD Measurement and by Enantioselective Synthesis of (-)-Chlorovulone II.
JOURNAL:Tetrahedron Lett.
VOL:27 PAGE : 223 -226 (1986)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.