2-(14,15-Epoxyeicosatrienoyl) Glycerol (CAS 848667-56-1)
QUICK LINKS
An endogenous central cannabinoid (CB1) receptor agonist that is present at relatively high levels in the central nervous system.1,2,3 2-AG is hydrolyzed by the enzyme monoacylglycerol lipase, terminating its biological activity, and metabolism by cyclooxygenase-2 and lipoxygenases has been documented.4,5 The related endocannabinoid, 2-arachidonoyl ethanolamide (AEA), can be metabolized by cytochrome P450 (CYP450) enzymes in human kidney and liver to a number of epoxy-ethanolamide derivatives.6 2-14,15-EG is a novel CYP450 metabolite of 2-AG in the kidney.7 2-14,15-EG is a potent mitogen for renal epithelial cells, increasing DNA synthesis in LLCPKcl4 cells at concentrations as low as 100 nM and doubling cell proliferation rates at 1 µM.7 In these cells, 2-14,15-EG activates the metalloprotease ADAM17, which cleaves proTGF-α and releases TGF-α as a ligand that initiates the EGFR-ERK signalling pathway.
2-(14,15-Epoxyeicosatrienoyl) Glycerol (CAS 848667-56-1) References
- Oxidative metabolism of endocannabinoids. | Kozak, KR. and Marnett, LJ. 2002. Prostaglandins Leukot Essent Fatty Acids. 66: 211-20. PMID: 12052037
- Brain monoglyceride lipase participating in endocannabinoid inactivation. | Dinh, TP., et al. 2002. Proc Natl Acad Sci U S A. 99: 10819-24. PMID: 12136125
- 14,15-Dihydroxyeicosatrienoic acid activates peroxisome proliferator-activated receptor-alpha. | Fang, X., et al. 2006. Am J Physiol Heart Circ Physiol. 290: H55-63. PMID: 16113065
- Anandamide metabolism by human liver and kidney microsomal cytochrome p450 enzymes to form hydroxyeicosatetraenoic and epoxyeicosatrienoic acid ethanolamides. | Snider, NT., et al. 2007. J Pharmacol Exp Ther. 321: 590-7. PMID: 17272674
- Mitogenic activity and signaling mechanism of 2-(14,15- epoxyeicosatrienoyl)glycerol, a novel cytochrome p450 arachidonate metabolite. | Chen, J., et al. 2007. Mol Cell Biol. 27: 3023-34. PMID: 17283047
- EDHF function in the ductus arteriosus: evidence against involvement of epoxyeicosatrienoic acids and 12S-hydroxyeicosatetraenoic acid. | Baragatti, B., et al. 2009. Am J Physiol Heart Circ Physiol. 297: H2161-8. PMID: 19801493
- Endocannabinoid oxygenation by cyclooxygenases, lipoxygenases, and cytochromes P450: cross-talk between the eicosanoid and endocannabinoid signaling pathways. | Rouzer, CA. and Marnett, LJ. 2011. Chem Rev. 111: 5899-921. PMID: 21923193
- Endocannabinoids anandamide and 2-arachidonoylglycerol are substrates for human CYP2J2 epoxygenase. | McDougle, DR., et al. 2014. J Pharmacol Exp Ther. 351: 616-27. PMID: 25277139
- Detection of urine metabolites in polycystic ovary syndrome by UPLC triple-TOF-MS. | Wang, W., et al. 2015. Clin Chim Acta. 448: 39-47. PMID: 26093338
- Integration analysis of metabolome and transcriptome profiles revealed the age-dependent dynamic change in chicken meat. | Li, J., et al. 2022. Food Res Int. 156: 111171. PMID: 35651035
- A second endogenous cannabinoid that modulates long-term potentiation. | Stella, N., et al. 1997. Nature. 388: 773-8. PMID: 9285589
- 2-Arachidonoylglycerol, an endogenous cannabinoid receptor agonist: identification as one of the major species of monoacylglycerols in various rat tissues, and evidence for its generation through CA2+-dependent and -independent mechanisms. | Kondo, S., et al. 1998. FEBS Lett. 429: 152-6. PMID: 9650580
- Evidence that the cannabinoid CB1 receptor is a 2-arachidonoylglycerol receptor. Structure-activity relationship of 2-arachidonoylglycerol, ether-linked analogues, and related compounds. | Sugiura, T., et al. 1999. J Biol Chem. 274: 2794-801. PMID: 9915812
Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
2-(14,15-Epoxyeicosatrienoyl) Glycerol, 25 µg | sc-205073 | 25 µg | $399.00 | |||
2-(14,15-Epoxyeicosatrienoyl) Glycerol, 50 µg | sc-205073A | 50 µg | $748.00 |