| Identification | Back Directory | [Name]
(5Z,8Z,11Z,14Z)-20-hydroxy-N-(2-hydroxyethyl)icosa-5,8,11,14-tetraenamide | [CAS]
942069-11-6 | [Synonyms]
20-hydroxy-5(Z),8(Z),11(Z),14(Z)-eicosatetraenoyl ethanolamide
20-hydroxy-N-(2-hydroxyethyl)-5(Z),8(Z),11(Z),14(Z)-eicosatetraenamide
(5Z,8Z,11Z,14Z)-20-hydroxy-N-(2-hydroxyethyl)icosa-5,8,11,14-tetraenamide | [Molecular Formula]
C22H37NO3 | [MOL File]
942069-11-6.mol | [Molecular Weight]
363.53 |
| Chemical Properties | Back Directory | [Boiling point ]
563.6±50.0 °C(Predicted) | [density ]
0.990±0.06 g/cm3(Predicted) | [solubility ]
DMF: 10 mg/ml; DMSO: 10 mg/ml; Ethanol: 50 mg/ml; Ethanol:PBS (pH 7.2) (1:2): 5 mg/ml; PBS (pH 7.2): 0.1 mg/ml | [pka]
14.48±0.10(Predicted) |
| Hazard Information | Back Directory | [Description]
Arachidonoyl ethanolamide (AEA) is an endogenous lipid neurotransmitter with cannabinergic activity, binding both the central cannabinoid (CB1) and peripheral cannabinoid (CB2) receptors. Fatty acid amide hydrolase (FAAH) is the enzyme responsible for the hydrolysis and inactivation of AEA. Metabolism of AEA by cyclooxygenase-2, leading to formation of prostaglandin ethanolamides, and by lipoxygenases has also been documented. 20-HETE ethanolamide is a potential cytochrome P450 metabolite of arachidonoyl ethanolamide, which may be particularly relevant under conditions of fatty acid amide hydrolase inhibition. Evidence for the formation of 20-HETE ethanolamide in vivo has not been documented. | [Uses]
20-HETE Ethanolamide is a metabolite of endocannabinoid Anandamide. 20-HETE Ethanolamide binds to the rat brain cannabinoid CB1 receptor with a Ki of 985 nM[1][2]. | [Definition]
ChEBI:N-(20-hydroxyarachidonoyl)ethanolamine is an N-(polyunsaturated fatty acyl)ethanolamine that is anandamide in which one of the methyl hydrogens at position 20 has been replaced by a hydroxy group. It has a role as a human xenobiotic metabolite. It is a N-(long-chain-acyl)ethanolamine, a N-(polyunsaturated fatty acyl)ethanolamine, an endocannabinoid and an oxidized N-(fatty acyl)-ethanolamine. It is functionally related to an anandamide and a 20-HETE. | [References]
[1] Sridar C, et al. Anandamide oxidation by wild-type and polymorphically expressed CYP2B6 and CYP2D6. Drug Metab Dispos. 2011;39(5):782-788. DOI:10.1124/dmd.110.036707
[2] Snider NT, et al. Anandamide metabolism by human liver and kidney microsomal cytochrome p450 enzymes to form hydroxyeicosatetraenoic and epoxyeicosatrienoic acid ethanolamides. J Pharmacol Exp Ther. 2007;321(2):590-597. DOI:10.1124/jpet.107.119321 |
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Enzo Biochem Inc
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