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(±)17(18)-EpETE-Ethanolamide

(±)17(18)-EpETE-Ethanolamide Structure
(±)17(18)-EpETE-Ethanolamide structure
CAS No.
2123491-23-4
Chemical Name:
(±)17(18)-EpETE-Ethanolamide
Synonyms
(±)17(18)-EpETE-Ethanolamide;5,8,11,14-Hexadecatetraenamide, 16-(3-ethyl-2-oxiranyl)-N-(2-hydroxyethyl)-, (5Z,8Z,11Z,14Z)-
CBNumber:
CB66197340
Molecular Formula:
C22H35NO3
Molecular Weight:
361.52
MDL Number:
MOL File:
2123491-23-4.mol
Last updated:2023-05-21 10:59:17
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(±)17(18)-EpETE-Ethanolamide Properties

Boiling point 547.7±50.0 °C(Predicted)
Density 1.000±0.06 g/cm3(Predicted)
storage temp. Store at -20°C
solubility DMF: 30 mg/ml; DMSO: 25 mg/ml; Ethanol: 30 mg/ml
pka 14.48±0.10(Predicted)

(±)17(18)-EpETE-Ethanolamide Chemical Properties,Uses,Production

Description

(±)17(18)-EpETE-Ethanolamide is an ω-3 endocannabinoid epoxide.1 It is formed from the endocannabinoid eicosapentaenoic ethanolamide (EPEA) via cytochrome P450 (CYP) epoxygenases and hydrolyzed by soluble epoxide hydrolase (sEH) and fatty acid amide hydrolase (FAAH). It is endogenously produced in LPS-stimulated BV-2 microglia cells and in BV-2 microglia cells supplemented with EPEA, an effect that can be reduced by the CYP inhibitor ketoconazole. (±)17(18)-EpETE-ethanolamide decreases IL-6 and nitrite production induced by LPS in BV-2 microglia and increases the production of IL-10. It inhibits platelet aggregation induced by arachidonic acid when used at a concentration of 50 μM but not aggregation induced by ADP , collagen, or ristocetin. It also induces relaxation of preconstricted bovine coronary arteries (ED50 = 1.1 μM) and inhibits VEGF-stimulated tubulogenesis in human microvascular endothelial cells (HMVECs). (±)17(18)-EpETE-ethanolamide is the predominant EPEA metabolite found in rat brain, and it has also been found in rat heart, kidney, spleen, and liver, as well as in pig brain. It activates cannabinoid receptor 1 (CB1) and CB2 with EC50 values of 18.5 and 1.4 nM, respectively, in a β-arrestin recruitment assay.

References

1. McDougle, D.R., Watson, J.E., Abdeen, A.A., et al. Anti-inflammatory ω-3 endocannabinoid epoxides Proc. Natl. Acad. Sci. USA 114(30),E6034-E6043(2017).

(±)17(18)-EpETE-Ethanolamide Preparation Products And Raw materials

Raw materials

Preparation Products

(±)17(18)-EpETE-Ethanolamide Suppliers

Global( 5)Suppliers
Supplier Tel Email Country ProdList Advantage
Shanghai Hongye Biotechnology Co. Ltd 400-9205774 sales@glpbio.cn China 6870 58
ChemeGen(Shanghai) Biotechnology Co.,Ltd. 18818260767 sales@chemegen.com China 11289 58
Shanghai Yifei Biotechnology Co. , Ltd. 021-65675885 18964387627 customer_service@efebio.com China 11975 58
TargetMol Chemicals Inc. 15002134094 marketing@targetmol.cn China 18470 58
Supplier Advantage
Shanghai Hongye Biotechnology Co. Ltd 58
ChemeGen(Shanghai) Biotechnology Co.,Ltd. 58
Shanghai Yifei Biotechnology Co. , Ltd. 58
TargetMol Chemicals Inc. 58
(±)17(18)-EpETE-Ethanolamide 5,8,11,14-Hexadecatetraenamide, 16-(3-ethyl-2-oxiranyl)-N-(2-hydroxyethyl)-, (5Z,8Z,11Z,14Z)- 2123491-23-4