Eicosanoid

DATA No : XPR1101 INFORMANT : Shouzo Yamamoto

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

COMMON NAME	:	PROSTAGLANDIN B2
SYMBOL	:	PGB2
FORMULA	:	C₂₀H₃₀O₄ MOL.WT (average) : 334.450

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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES

MELTING POINT	:

BOILING POINT	:

REFRACTIVE INDEX	:

OPTICAL ROTATION	:

DENSITY	:

SOLUBILITY	:

SPECTRAL DATA

UV SPECTRA	:	MeOH: 278 nm (e 26000) (Ref. 1045)

IR SPECTRA	:

NMR SPECTRA	:	METHYL ESTER ; ¹H-NMR : d 6.9(d, J=16Hz, 1H, 13-CH), 6.3(dd, J=5.5, 16Hz, 1H,14-CH), 5.7-5.1(m, 2H), 4.5-4.1(m, 1H, 15-CH), 3.65(S, 3H, OCH3), 3.15-2.85(m, 2H, 7-CH) (Ref. 1046)

MASS SPECTRA	:	METHYL ESTER; m/e 348(M⁺), 317, 249, 247, 245, 217, 215, 133, 119, 109 (Ref. 1046)

OTHER SPECTRA	:

CHROMATOGRAM DATA

SOURCE

Prostaglandin B2 was found in human seminal plasma in an amout of 50 micrograms per ml as measured in combination with prostaglandins A1,A2 and B1 (Ref. 0001).

CHEMICAL SYNTHESIS

METABOLISM

Prostaglandin E2 is converted to prostaglandin B2 non-enzymatically at alkaline condition (Ref. 0039). Huma serum contains a dehydrase converting prostaglandin E2 to A2, an isomerase converting prostaglandin A2 to C2, and another isomerase converting prostaglandin C2 to B2 (Ref. 0040).

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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[0039]

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)

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[0040]

AUTHOR	:	Polet, H., and Levine, L.
TITLE	:	Metabolism of prostaglandins E, A, and C in serum PubMed ID:234423
JOURNAL	:	J Biol Chem.
VOL	:	250 PAGE : 351-357 (1975)

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[1045]

AUTHOR	:	Floyd,M.B., Schaub,R.E., Siuta,G.J., Skotnicki,J.S., Grudzinskas,C.V., Weiss,M.J., Dessy,F., and VanHumbeeck,L.
TITLE	:	Prostaglandins and Congeners. 22. Synthesis of 11-Substituted Derivatives of 11-Deoxyprostaglandins E1 and E2. Potential Bronchodilators. PubMed ID:7401116
JOURNAL	:	J. Med. Chem.
VOL	:	23 PAGE : 903 -913 (1980)

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[1046]

AUTHOR	:	Kelly,R.C., Schletter,I, Jones,R.L.
TITLE	:	Total Synthesis of PGC2 Methyl Ester. Comparison with Enzymatically Produced Material. PubMed ID:7401116
JOURNAL	:	Prostaglandins
VOL	:	4 PAGE : 653 -660 (1973)

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