15(R),19(R)-hydroxy Prostaglandin F1α

15(R),19(R)-hydroxy Prostaglandin F_1α

Cayman Chemical Item Number 15920

15(R),19(R)-hydroxy PGF_1α

Description

19(R)-Hydroxylated prostaglandins occur in µg/ml concentrations in the semen of certain mammalian species, especially primates. In the case of humans, the compounds are primarily of the PGE series, and the hydroxyl stereochemistry is 15(S),19(R).¹ 19(R)-Hydroxylated prostaglandins are also found in the seminal plasma of marsupials, where F-type compounds of the 1 and 2-series predominate.² The 15(R)-hydroxy epimer of these 19-hydroxylated prostaglandins is the inverse or “unnatural” isomer at C-15. The biological role of 19(R)-hydroxylated prostaglandins is not well established. In the F-series, 19(R)-hydroxylation is associated with a significant loss of receptor-mediated biological activity in some assays.³

1 Cooper, I., and Kelly, R.W. The measurement of E and 19-hydroxy E prostaglandins in human seminal plasma. Prostaglandins 10 507-514 (1975).

2 Marley, P.B., Rodger, J.C., White, I.G., et al. 19-Hydroxylated prostaglandins in the semen of the marsupial Trichosurus vulpecula (brush-tailed possum). Comp Biochem Physiol 70B 619-621 (1981).

3 Woodward, D.F., Protzman, C.E., Krauss, A.H.P., et al. Identification of 19(R)-OH prostaglandin E₂ as a selective prostanoid EP₂-receptor agonist. Prostaglandins 46 371-383 (1993).

Synonyms

15(R),19(R)-hydroxy PGF1α

Formal Name

9α,11α,15R,19R-tetrahydroxy-prost-13E-en-1-oic acid

Molecular Formula

C₂₀H₃₆O₆

Formula Weight

372.5

Formulation

A solution in ethanol

Purity

>98%

Stability

1 year

Storage

-20°C

Shipping

Room temperature in continental US; may vary elsewhere

SMILES

Copy SMILES to clipboard

O[C@@H]1[C@H](CCCCCCC(O)=O)[C@@H](/C=C/[C@H](O)CCC[C@H](O)C)[C@H](O)C1

Background Reading

Woodward, D.F., Protzman, C.E., Krauss, A.H.P., et al. Identification of 19(R)-OH prostaglandin E₂ as a selective prostanoid EP₂-receptor agonist. Prostaglandins 46 371-383 (1993).

Marley, P.B., Rodger, J.C., White, I.G., et al. 19-Hydroxylated prostaglandins in the semen of the marsupial Trichosurus vulpecula (brush-tailed possum). Comp Biochem Physiol 70B 619-621 (1981).

Cooper, I., and Kelly, R.W. The measurement of E and 19-hydroxy E prostaglandins in human seminal plasma. Prostaglandins 10 507-514 (1975).

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50 µg 
$28.00

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100 µg 
$53.00

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500 µg 
$224.00

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5 mg 
$1,680.00

$0.00

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15(R),19(R)-hydroxy Prostaglandin F_1α