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Eicosanoid


DATA No : XPR1500 INFORMANT : Shouzo Yamamoto

NAME : 7-[3(R),5(S)-Dihydroxy-2(R)-(3(S)-hydroxy-1(E)-octenyl)cyclopentan-1(R)-yl]-heptanoic acid / (8R,9S,11R,13E,15S)-9,11,15-Trihydroxyprost-13-enoic acid

COMMON NAME: PROSTAGLANDIN F1a
SYMBOL: PGF1a
FORMULA: C20H36O5 MOL.WT (average) : 356.497


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BIOLOGICAL ACTIVITY
In terms of contraction of gastrointestinal smooth muscles, prostaglandin F1a was repoprted to be about 10 times less active than prostaglandin F2a (Ref. 0082). Reference (Ref. 0002) contains a table for comparison of biological activities of various prostaglandins including F1a.
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:102-103degC (Ref. 1110)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]d-25=+30deg(ETHANOL) (Ref. 1005)

DENSITY:

SOLUBILITY:DIETHYL ETHER, ETHYL ACETATE, METHANOL (Ref. 1110), ETHANOL (Ref. 1005)
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:d,l-PGF1a ; KBr : n 3330, 1716, 967 cm-1 (Ref. 1111)

NMR SPECTRA:1H-NMR(ACETONE-d6, TMS) : d 5.50(2H, 13-,14-CH), 3.75-4.3(m, 3H), 0.88(t, 3H) (Ref. 1102)1H-NMR(CD3OD, TMS, 300MHz):d4.10(1H, 9-CH), 3.81(1H, 11-CH), 2.36(1H, 10b-CH), 1.57(1H, 10a-CH)(Ref. 1112)

MASS SPECTRA:m/e 356(M+), 338, 320 (Ref. 1102)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Prostaglandin F1a is contained in human seminal plasma in an amount of 3.6 microgram/ml (Ref. 0001), and is detected in ovine seminal plasma and seminal vesicle, human amniotic fluid, umbilical cord, placental vessels and decidua, frog spinal cord and intestine, and rat adrenal (Ref. 0084).
CHEMICAL SYNTHESIS
(Ref. 1111)
[Table 0001]
METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0001]
AUTHOR:Bergstrom, S.
TITLE:Prostaglandins: members of a new hormonal system. These physiologically very potent compounds of ubiquitous occurrence are formed from essential fatty acids PubMed ID:4291104
JOURNAL:Science.
VOL:157 PAGE : 382-391 (1967)
[TOP]

[0002]
AUTHOR:Bergstrom, S., Carlson, L. A., and Weeks, J. R.
TITLE:The prostaglandins: a family of biologically active lipids PubMed ID:4873508
JOURNAL:Pharmacol Rev.
VOL:20 PAGE : 1-48 (1968)
[TOP]

[0082]
AUTHOR:Horton, E. W.
TITLE:Hypotheses on physiological roles of prostaglandins PubMed ID:4302663
JOURNAL:Physiol Rev.
VOL:49 PAGE : 122-161 (1969)
[TOP]

[0084]
AUTHOR:Horton, E. W.
TITLE:Biological activities of pure prostaglandins PubMed ID:5318739
JOURNAL:Experientia.
VOL:21 PAGE : 113-118 (1965)
[TOP]

[1005]
AUTHOR:Pike, J.E., Lincoln,F.H., and Schneider,W.P.
TITLE:Prostanoic Acid Chemistry.
JOURNAL:J. Org. Chem.
VOL:34 PAGE : 3552 -3557 (1969)
[TOP]

[1102]
AUTHOR:Ramwell,P.W., Shaw,J.E., Clarke,G.B., Grostic,M.F., Kaiser,D.G. and Pike, J.E.
TITLE:Prostaglandins (Review).
JOURNAL:Progr. Chem. Fats Other Lipids
VOL:9 PAGE : 233 -273 (1968)
[TOP]

[1110]
AUTHOR:Bergströ$m,S. and Sjö$vall
TITLE:The Isolation of Prostaglandin F from Sheep Prostate Glands. PubMed ID:12336881
JOURNAL:Acta Chem. Scand.
VOL:14 PAGE : 1693 -1700 (1960)
[TOP]

[1111]
AUTHOR:Miyano, M., Dorn, C. R., and Mueller, R. A.
TITLE:Prostaglandins. IV. A synthesis of F-type prostaglandins. A total synthesis of prostaglandin F 1 PubMed ID:5037449
JOURNAL:J Org Chem.
VOL:37 PAGE : 1810-1818 (1972)
[TOP]

[1112]
AUTHOR:De Clercq, P., Samson, M., Tavernier, D., Van Haver, D., and Vandewalle, M.
TITLE:Conformational analysis of prostaglandins F1 based on proton nuclear magnetic resonance spectral data PubMed ID:894396
JOURNAL:J Org Chem.
VOL:42 PAGE : 3140-3144 (1977)
[TOP]

Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.