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Eicosanoid


DATA No : XPR1901 INFORMANT : Shouzo Yamamoto

NAME : 7-[2(R)-(3(S)-Hydroxy-1(E)-octenyl)-3-oxo-4-cyclopenten-1(R)-yl]-5(Z)-heptenoic acid

COMMON NAME: PROSTAGLANDIN J2
SYMBOL: PGJ2
FORMULA: C20H30O4 MOL.WT (average) : 334.450


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BIOLOGICAL ACTIVITY
The anti-tumor and anti-viral activities of prostaglandin J2 are attributed to D12-prostaglandin J2 which is a degradation product of prostagladnin J2 and is characteristic of its alkylidene cyclopentenone structure (Ref. 0010).
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:ACETONITRILE(Ref. 1048)CHLOROFORM, ETHANOL (Ref. 1049)
SPECTRAL DATA
UV SPECTRA:l MeOHmax = 305(e 1200), 216(e 9900)nm (Ref. 1049)

IR SPECTRA:n 3400, 3200, 2660, 1710, 1085, 970 cm-1 (Ref. 1049)

NMR SPECTRA:1H-NMR(CDCl3) : d 7.75-7.55(m, 1H, 9-CH), 6.30-6.10(m, 1H, 10-CH), 5.90(brs, 2H, OH), 5.75-5.35(m, 4H), 4.30-3.95(m, 1H, 15-CH) (Ref. 1049)

MASS SPECTRA:TMS ETHER ; M+ 478.2934 (Ref. 1049)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE

CHEMICAL SYNTHESIS
(Ref. 1049)
[Table 0001]
METABOLISM
In aqueous solution prostaglandin D2 undergoes non-enzymatic dehydration and is converted to prostaglandin J2 (Ref. 0010).
GENETIC INFORMATION

NOTE

REFERENCES
[0010]
AUTHOR:Fukushima, M.
TITLE:Biological activities and mechanisms of action of PGJ2 and related compounds: an update PubMed ID:1438462
JOURNAL:Prostaglandins Leukot Essent Fatty Acids.
VOL:47 PAGE : 1-12 (1992)
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[1048]
AUTHOR:Mubarik Ali,S., Chapeleo,C.B., Finch,M.A.W., Roberts,S.M., Woolley,G.T., Cave,R.J., and Newton,R.F.
TITLE:Preparation and Some Reactions of 2-Oxatricyclo[3.3.0.04.6]oct-7-en-3-one: Synthesis of 9-Deoxa-9,10-dehydroprostaglandin D2.
JOURNAL:J. Chem. Soc. Perkin I
VOL: PAGE : 2093 -2097 (1980)
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[1049]
AUTHOR:Bundy,G.L., Morton,D.R., Peterson,D.C., Nishizawa,E.E., and Miller,W.L.
TITLE:Synthesis and Platetet Aggregation Inhibiting Activity of Prostaglanin D Analogues. PubMed ID:6854581
JOURNAL:J. Med. Chem.
VOL:26 PAGE : 790 -799 (1983)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.