Back to HOME

Eicosanoid


DATA No : XPR1402 INFORMANT : Shouzo Yamamoto

NAME : 7-[3(R)-Hydroxy-2(R)-(3(S)-hydroxyocta-1(E),5(Z)-dienyl)-5-oxocyclopentan-1(R)-yl]-5(Z)-heptenoic acid / (5Z,8R,11R,12R,13E,15S,17Z)-11,15-Dihydroxy-9-oxo-5,13,17-prostatrienoic acid

COMMON NAME: PROSTAGLANDIN E3
SYMBOL: PGE3
FORMULA: C20H30O5 MOL.WT (average) : 350.449


Download ChemDraw structure data
BIOLOGICAL ACTIVITY
As presented in Table 1 of reference (Ref. 0002), prostaglandin E3 is 1/10-1/2 as active as prostaglandin E2.
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:84.5-85.5degC (Ref. 1113)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]d-24=-48.9deg(C=1.2, TETRAHYDROFURAN) (Ref. 1114)

DENSITY:

SOLUBILITY:TETRAHYDROFURAN (Ref. 1114)
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:

NMR SPECTRA:METHYL ESTER ; 1H-NMR(CDCl3) : d 5.8-5.5(m, 2H,13, 14-CH), 5.5-5.2(m, 4H, 5,6,17,18-CH), 4.4-3.8(m, 2H, 11,15-CH), 0.95(t, 3H, 20-CH) (Ref. 1115)

MASS SPECTRA:METHYL ESTER ; m/e 346(M-18), 328(M-18x2), 315, 297, 277, 259, 188 (Ref. 1116)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Prostaglandin E3 is contained in human seminal plasma in an amount of 5.5 micrograms/ml (Ref. 0001), and also found in ovine seminal vesicle and plasma (Ref. 0083).
CHEMICAL SYNTHESIS
(Ref. 1114)
[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]

[0083]
AUTHOR:Speroff, L., and Ramwell, P. W.
TITLE:Prostaglandins in reproductive physiology PubMed ID:4914185
JOURNAL:Am J Obstet Gynecol.
VOL:107 PAGE : 1111-1130 (1970)
[TOP]

[1113]
AUTHOR:Okamoto,S., Kobayashi,Y. and Sato,F.
TITLE:A Highly Efficient Synthesis of Natural PGE3 and 5,6-Dihydro PGE3 via Two-component Coupling Process.
JOURNAL:Tetrah. Lett.
VOL:30 PAGE : 4379 -4382 (1989)
[TOP]

[1114]
AUTHOR:Corey, E. J., Shirahama, H., Yamamoto, H., Terashima, S., Venkateswarlu, A., and Schaaf, T. K.
TITLE:Stereospecific total synthesis of prostaglandins E3 and F3 alpha PubMed ID:5548346
JOURNAL:J Am Chem Soc.
VOL:93 PAGE : 1490-1491 (1971)
[TOP]

[1115]
AUTHOR:Samuelsson,B.
TITLE:Prostaglandins and Related Factors. 17. The Structure of Prostaglandin E3.
JOURNAL:J. Am. Chem. Soc.
VOL:85 PAGE : 1878 -1879 (1963)
[TOP]

[1116]
AUTHOR:Bergströ$m,S., Dressler,F., Ryhage,R., Samuelsson,B. and Sjö$vall
TITLE:The Isolation of Two Further Prostaglandins from Sheep Prostate Glands. Prostaglndin and Related Factors 8.
JOURNAL:Ark. Kemi.
VOL:19 PAGE : 563 -567 (1962)
[TOP]

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