The inverse isomer of a 19-hydroxylated prostaglandin
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15(R),19(R)-hydroxy Prostaglandin E1

Item No. 13920

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9-oxo-11α,15R,19R-trihydroxy-prost-13E-en-1-oic acid
Synonyms
  • 15(R),19(R)-hydroxy PGE1
Molecular Formula
C20H34O6
Formula Weight
370.5
Purity
≥98%
Formulation (Request formulation change)
A 500 µg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: >100 mg/mlDMSO: >50 mg/mlEthanol: >50 mg/mlPBS (pH 7.2): >1.67 mg/ml
SMILES
O=C1[C@H](CCCCCCC(O)=O)[C@@H](/C=C/[C@H](O)CCC[C@H](O)C)[C@H](O)C1
InChi Code
InChI=1S/C20H34O6/c1-14(21)7-6-8-15(22)11-12-17-16(18(23)13-19(17)24)9-4-2-3-5-10-20(25)26/h11-12,14-17,19,21-22,24H,2-10,13H2,1H3,(H,25,26)/b12-11+/t14-,15-,16-,17-,19-/m1/s1
InChi Key
QVVXWHIDRKRPMO-HESWFPMQSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    50 µg

    $41

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    100 µg

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    500 µg

    $312

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    Product 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 E-series, 19(R)-hydroxylation has been identified with EP2 receptor subtype selectivity.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Cooper, I., and Kelly, R.W. The measurement of E and 19-hydroxy E prostaglandins in human seminal plasma. Prostaglandins 10(3), 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. B Biochem. Mol. Biol. 70(3), 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(4), 371-383 (1993).