11β-Prostaglandin F Ethanolamide

Cayman Chemical Item Number 16522

11-epi PGF-EA; 11β-PGF-EA (CAS 714966-38-8)

11β-Prostaglandin F2α Ethanolamide (CAS 714966-38-8)

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Description

11β-Prostaglandin F ethanolamide (11β-PGF-EA) is the theoretical hepatic metabolite of PGD2-EA, produced during COX-2 metabolism of the endogenous cannabinoid AEA which is found in brain, liver, and other mammalian tissues.1 AEA can be used directly by COX-2 and specific PG synthase to produce ethanolamide congeners of the classical PGs.2,3 PGD2-EA is formed in activated RAW 264.7 cells treated with AEA.3

1 Bachur, N.R., Masek, K., Melmon, K.L., et al. Fatty acid amides of ethanolamine in mammalian tissues. J Biol Chem 240 1019-1024 (1965).

2 Yu, M., Ives, D., and Ramesha, C.S. Synthesis of prostaglandin E2 ethanolamide from anandamide by cyclooxygenase-2. J Biol Chem 272 21181-21186 (1997).

3 Kozak, K.R., Crews, B.C., Morrow, J.D., et al. Metabolism of the endocannabinoids, 2-arachidonylgycerol and anandamide, into prostaglandin, thromboxane, and prostacyclin glycerol esters and ethanolamides. J Biol Chem 277(47) 44877-44885 (2002).

Synonyms
  • 11-epi PGF-EA
  • 11β-PGF-EA
Formal Name N-​(2-​hydroxyethyl)-​9α,​11β,​15S-​trihydroxy-​prosta-​5Z,​13E-​dien-​1-​amide
CAS Number 714966-38-8
Molecular Formula C22H39NO5
Formula Weight 397.6
Formulation A solution in ethanol
Purity ≥95%
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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OCCN([H]​)​C(CCC/C=C\C[C@@H]​1[C@@H]​(/C=C/[C@@H]​(O)​CCCCC)​[C@@H]​(O)​C[C@@H]​1O)​=O
InCHI Code
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​1S/C22H39NO5/c1-2-3-6-9-17(25)​12-13-19-18(20(26)​16-21(19)​27)​10-7-4-5-8-11-22(28)​23-14-15-24/h4,7,12-13,17-21,24-27H,2-3,5-6,8-11,14-16H2,1H3,(H,23,28)​/b7-4-,13-12+/t17-,18+,19+,20-,21-/m0/s1
InCHI Key
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XCVCLIRZZCGEMU-WMTHMIERSA-N

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11β-Prostaglandin F2α Ethanolamide is available in the following screening libraries:

Size Price Quantity Subtotal
1 mg $86.00 $0.00
5 mg $387.00 $0.00
10 mg $688.00 $0.00
50 mg $3,010.00 $0.00
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Cart Total $0.00

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Pricing updated 2014-04-20. Prices are subject to change without notice.

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