See personalized New Product recommendations! Get personalized New Product recommendations! Register or Login for personalized New Product recommendations!

Holiday Notification: Cayman Chemical will be closed Monday, May 28, 2012, in observance of the Memorial Day holiday. More…
Please feel free to continue placing orders via our website or via fax at 734-971-3640. You may send an email to customer service at custserv@caymanchem.com , or to technical support at techserv@caymanchem.com which we will respond to the next business day. Cayman will resume regular business hours and shipping schedules on Tuesday, May 29, 2012. Thank you for your patience and understanding.

15(R)-Prostaglandin F2α

Cayman Chemical Item Number 16740

15-epi PGF2α (CAS 37658-84-7)

15(R)-Prostaglandin F2α (CAS 37658-84-7)

See more

Description

15(R)-PGF2α is the C-15 epimer of the naturally occurring mammalian autacoid PGF2α. It has only 25% of the potency of PGF2α in hamster antifertility studies,1 which may be due to reduced affinity for FP receptors. Compared to PGF2α, 15(R)-PGF2α 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 PGF2α.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 F2α 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 PGF2α
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
Copy SMILES to clipboard
CCCCC[C@@H]​(O)​/C=C/[C@H]​1C(O)​CC(O)​C1C/C=C\CCCC(=O)​O

Background Reading

Lepak, N.M., and Serrero, G. Inhibition of adipose differentiation by 9α, 11β-prostaglandins F2α. Prostaglandins 46 511-517 (1993).

Andersen, N.H., Imamoto, S., Subramanian, N., et al. Molecular basis for prostaglandin potency. III. Tests of the significance of the 'hairpin conformation' in biorecognition phenomena. Prostaglandins 22 841-856 (1981).

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

Andersen, N.H., and Lin, B. 500-MHz proton NMR studies of the medium-dependent conformational preference of prostaglandin F2α analogues. Biochemistry 24 2338-2347 (1985).

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).

Balapure, A.K., Rexroad, C.E., Kawada, K., et al. Structural requirements for prostaglandin analog interaction with the ovine corpus luteum prostaglandin F2α receptor. Biochem Pharmacol 38 2375-2381 (1989).

Sun, F.F., Armour, S.B., Bockstanz, V.R., et al. Studies on 15-hydroxyprostaglandin dehydrogenase from monkey lung. Adv Prostaglandin Thromboxane Res 1 163-169 (1976).

Andersen, N.H., and Leovey, E.M.K. Identification and quantitative determination of prostaglandins by high pressure liquid chromatography. Prostaglandins 6 361-374 (1974).

Show all 8 Hide all but first 3

15(R)-Prostaglandin F2α is available in the following screening libraries:

Size Price Quantity Subtotal
1 mg $60.00 $0.00
5 mg $270.00 $0.00
10 mg $480.00 $0.00
50 mg $2,100.00 $0.00
Bulk Contact
Cart Total $0.00

This product is available in custom sizes and/or larger quantities.

Please contact our Sales Department for a quote or to purchase.

Pricing updated 2012-05-26. Prices are subject to change without notice.

To ask for assistance with one of our products please contact a Technical Support Scientist.

Warning This product is not for human or veterinary use.

Related Products

Prostaglandin F2α

Downloads

Batch-specific Information

Login to access batch-specific information

Cayman Chemical is a manufacturer, supplier and vendor of biochemical reagents, assay kits, antibodies, and proteins.

Other Resources
Management Team Company Profile Company History ChemAssistant Tools FAQs Cayman Europe Cayman Pharma CaBRI Cayman Gear Press Releases Illustrations and Charts Key Research Area Posters Article Library Analysis Tools Conference Schedule Order Terms Browser Recommendation Privacy Statement Site Map

Cayman Chemical Company · 1180 East Ellsworth Road · Ann Arbor, Michigan 48108 · USA

Toll Free: (800) 364-9897 (USA and Canada Only) · Fax: (734) 971-3640

Copyright 2012 Cayman Chemical Company

Lost password?