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8-iso Prostaglandin F2α Ethanolamide
Cayman Chemical Item Number 10005764
Description
It has been reported that anandamide (AEA) can be used directly by cyclooxygenase-2 and specific prostaglandin H2 (PGH2) isomerases to produce ethanolamide congeners of the classical PGs, including PGF2α.1↗ PGF2α ethanolamide has also been reported to be biosynthesized by this mechanism when AEA was infused into the lung and liver of fatty acid amide hydrolase-deficient mice.2↗ However, the accumulation of AEA can also lead to isoprostane-type peroxidative decomposition. 8-iso PGF2α ethanolamide is a standard that allows one to distinguish these non-enzymatic decomposition products from “prostamides” that could be of enzymatic origin.
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 Weber, A., Ni, J., Ling, K.J., et al. Formation of prostamides from anandamide in FAAH knockout mice analyzed by HPLC with tandem mass spectrometry. J Lipid Res 45 757-763 (2004).
Synonyms iPF2α-III Ethanolamide
8-iso PGF2α Ethanolamide
8-epi PGF2α Ethanolamide
8-Isoprostane Ethanolamide
Formal Name N-(2-hydroxyethyl)-9α,11α,15S-trihydroxy-(8β)-prosta-5Z,13E-dien-1-amide
Molecular Formula C22H39NO5
Formula Weight 397.5
Formulation A solution in ethanol
Purity >98%
Stability 1 year
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES O[C@@H]1[C@@H](C/C=C\CCCC(N([H])CCO)=O)[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C1
InCHI Code 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 XCVCLIRZZCGEMU-JJPTUHNDSA-N |