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

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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	:	84.5-85.5C (Ref. 1113)

BOILING POINT	:

REFRACTIVE INDEX	:

OPTICAL ROTATION	:	[a]=-48.9(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)

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[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)

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[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)

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[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)

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[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)

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[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)

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[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)

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