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Eicosanoid


DATA No : XPR1811 INFORMANT : Shouzo Yamamoto

NAME : 7-[3(R),5(S)-Dihydroxy-2(R)-(3(S)-hydroxy-1(E)-octenyl)cyclopentan-1(R)-yl]-6-oxoheptanoic acid

COMMON NAME: 6-KETOPROSTAGLANDIN F1a
SYMBOL: 6-KETO-PGF1a
FORMULA: C20H36O6 MOL.WT (average) : 372.496


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BIOLOGICAL ACTIVITY
Degradation of prostaglandin I2 to 6-keto-prostaglandin F1a brings about the loss of biological activities. For example, the hypotensive effect of prostaglandin I2 is at least 100 times mor active than 6-keto-prostaglandin F1a (Ref. 0013).
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]d-21= -9.6deg (C=1.04 METHANOL) (Ref. 1053)

DENSITY:

SOLUBILITY:DIETHYL ETHER(Ref. 1052)METHANOL, ACETONE, ETHYL ACETATE (Ref. 1053)
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:NEAT: n 3400, 1715, 1245, 1045, 975, 915, 875, 845, 800, 730 cm-1 (Ref. 1053)

NMR SPECTRA:1H-NMR(ACETONE-D6) : d 6.1-5.4(bs, 4H), 5.5-5.2(m, 2H), 4.7-3.5(m, 3H), 2.5-1.1 (m, 22H), 0.86(t, 3H) (Ref. 1053)

MASS SPECTRA:METHYL ESTER ; 366(M+-18), 348, 335, 330, 323, 319, 279, 265, 223, 196, 195, 164, 143, 121, 111, 99, 95, 71 (Ref. 1053). DIRECT EXPOSURE AMMONIA CI POSITIVE : 370, 353, 244, 163, 153, 136. NEGATIVE : 368, 351, 334, 316, 225, 219, 166, 135, 127 (Ref. 1054)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
When prostaglandin I2 is produced in animal tissues, it is unstable in aqueous solution, especially at acidic pH, and readily decomposed to 6-keto-prostaglandin F1a (Ref. 0013). Therefore, 6-keto-prostaglandin F1a is detected where prostaglandin I2 is produced.
CHEMICAL SYNTHESIS
(Ref. 1053)
[Table 0001]
METABOLISM
6-Keto-prostaglandin F1a is subjected to b-oxidation, and converted to 2,3-dinor-6-keto-prostaglandin F1a which appears in urine as a major metabolite (Ref. 0017).
GENETIC INFORMATION

NOTE

REFERENCES
[0013]
AUTHOR:Moncada, S., and Vane, J. R.
TITLE:Pharmacology and endogenous roles of prostaglandin endoperoxides, thromboxane A2, and prostacyclin PubMed ID:116251
JOURNAL:Pharmacol Rev.
VOL:30 PAGE : 293-331 (1978)
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[0017]
AUTHOR:Needleman, P., Turk, J., Jakschik, B. A., Morrison, A. R., and Lefkowith, J. B.
TITLE:Arachidonic acid metabolism PubMed ID:3017195
JOURNAL:Annu Rev Biochem.
VOL:55 PAGE : 69-102 (1986)
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[1052]
AUTHOR:Pace-Asciak,C.
TITLE:Isolation, Structure, and Biosynthesis of 6-Ketoprostaglandin F1a in the Rat Stomach. PubMed ID:1254872
JOURNAL:J. Am. Chem. Soc.
VOL:98 PAGE : 2348 -2349 (1976)
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[1053]
AUTHOR:Tanaka,T., Hazato,A., Bannai,K., Okamura,N., Sugiura,S., Manabe,K., Toru,T., Kurozumi,S., Suzuki,M., Kawagishi,T., et al
TITLE:Nitro-Olefin Trapping Reaction of Enolates In Situ Generated by Conjugate Addition Reaction: Short Synthesis of PGE1, 6-Oxo-PGE1, 6-Oxo-PGF1a, and PGI2.
JOURNAL:Tetrahedron
VOL:43 PAGE : 813 -824 (1987)
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[1054]
AUTHOR:Cepa, S. R., Hall, E. R., and Venton, D. L.
TITLE:Positive-negative, chemical-ionization, direct exposure mass spectrometry of underivatized prostaglandins PubMed ID:6547237
JOURNAL:Prostaglandins.
VOL:27 PAGE : 645-652 (1984)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.