15(R)-Prostaglandin F

Cayman Chemical Item Number 16740

15-epi PGF (CAS 37658-84-7)

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Description

15(R)-PGF is the C-15 epimer of the naturally occurring mammalian autacoid PGF. It has only 25% of the potency of PGF in hamster antifertility studies,1 which may be due to reduced affinity for FP receptors. Compared to PGF, 15(R)-PGF has a binding affinity of 6.7% to ovine luteal cell receptors.2 Similarly, the binding affinity to rat vascular smooth muscle cells is negligible as compared to PGF.3

1. Miller, W.L., and Sutton, M.J. Relative biological activity of certain prostaglandins and their enantiomers. Prostaglandins 11 77-84 (1976).

2. Balapure, A.K., Rexroad, C.E., Kawada, K., et al. Structural requirements for prostaglandin analog interaction with the ovine corpus luteum prostaglandin F receptor. Biochem Pharmacol 38 2375-2381 (1989).

3. Hanasaki, K., Kishi, M., and Arita, H. Phorbol ester-induced expression of the common, low-affinity binding site for primary prostanoids in vascular smooth muscle cells. J Biol Chem 265 4871-4875 (1990).

Synonyms
  • 15-epi PGF
Formal Name 9α,​11α,​15R-​trihydroxy-​prosta-​5Z,​13E-​dien-​1-​oic acid
CAS Number 37658-84-7
Molecular Formula C20H34O5
Formula Weight 354.5
Formulation A solution in methyl acetate
Purity ≥98%
Stability 1 year
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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O[C@@H]​1[C@H]​(C/C=C\CCCC(O)​=O)​[C@@H]​(/C=C/[C@H]​(O)​CCCCC)​[C@H]​(O)​C1
InCHI Code
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​1S/C20H34O5/c1-2-3-6-9-15(21)​12-13-17-16(18(22)​14-19(17)​23)​10-7-4-5-8-11-20(24)​25/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)​/b7-4-,13-12+/t15-,16-,17-,18+,19-/m1/s1
InCHI Key
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PXGPLTODNUVGFL-CKXCCYAOSA-N

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15(R)-Prostaglandin F is available in the following screening libraries:

Size Price Quantity Subtotal
500 µg $45.00 $0.00
1 mg $77.00 $0.00
5 mg $360.00 $0.00
10 mg $630.00 $0.00
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