See personalized New Product recommendations! Get personalized New Product recommendations! Register or Login for personalized New Product recommendations!

Holiday Notification: Cayman Chemical will be closed Monday, May 28, 2012, in observance of the Memorial Day holiday. More…
Please feel free to continue placing orders via our website or via fax at 734-971-3640. You may send an email to customer service at custserv@caymanchem.com , or to technical support at techserv@caymanchem.com which we will respond to the next business day. Cayman will resume regular business hours and shipping schedules on Tuesday, May 29, 2012. Thank you for your patience and understanding.

2-(14,15-Epoxyeicosatrienoyl) Glycerol

Cayman Chemical Item Number 10009962

2-14,15-EG (CAS 848667-56-1)

2-(14,15-Epoxyeicosatrienoyl) Glycerol (CAS 848667-56-1)

See more

Description

2-Arachidonoyl glycerol (2-AG) is 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 liver and kidney 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.

1 Stella, N., Schweitzer, P., and Piomelli, D. A second endogenous cannabinoid that modulates long-term potentiation. Nature 388 773-778 (1997).

2 Sugiura, T., Kodaka, T., Nakane, S., et al. Evidence that the cannabinoid CB1 receptor is a 2-arachidonoylglycerol receptor. Structure-activity relationship of 2-arachidonoylglycerol, ether-linked analogues, and related compounds. J Biol Chem 274 2794-2801 (1999).

3 Kondo, S., Kondo, H., Nakane, S., et al. 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. FEBS Lett 429 152-156 (1998).

4 Dinh, T.P., Carpenter, D., Leslie, F.M., et al. Brain monoglyceride lipase participating in endocannabinoid inactivation. Proc Natl Acad Sci USA 99(16) 10819-10824 (2002).

5 Kozak, K.R., and Marnett, L.J. Oxidative metabolism of endocannabinoids. Prostaglandins Leukot Essent Fatty Acids 66(2&3) 211-220 (2002).

6 Snider, N.T., Kornilov, A.M., Kent, U.M., et al. Anandamide metabolism by human liver and kidney microsomal cytochrome P450 enzymes to form hydroxyeicosatetraenoic and epoxyeicosatrienoic acid ethanolamides. J Pharmacol Exp Ther 321(2) 590-597 (2007).

7 Chen, J., Chen, J., Falck, J.R., et al. Mitogenic activity and signaling mechanism of 2-(14,15-epoxyeicosatrienoyl)glycerol, a novel cytochrome P450 arachidonate metabolite. Mol Cell Biol 27(8) 3023-3034 (2007).

Synonyms
  • 2-14,15-EG
Formal Name 2-​hydroxy-​1-​(hydroxymethyl)ethyl ester-​13-​(3-​pentyloxiranyl)-​5Z,​8Z,​11Z-​tridecatrienoic acid
CAS Number 848667-56-1
Molecular Formula C23H38O5
Formula Weight 394.5
Formulation A solution in acetonitrile
Purity ≥95%
Stability 1 year
Storage -80°C
Shipping Dry ice in continental US; may vary elsewhere
SMILES
Copy SMILES to clipboard
CCCCCC1OC1C/C=C\C/C=C\C/C=C\CCCC(=O)​OC(CO)​CO

Background Reading

Stella, N., Schweitzer, P., and Piomelli, D. A second endogenous cannabinoid that modulates long-term potentiation. Nature 388 773-778 (1997).

Kondo, S., Kondo, H., Nakane, S., et al. 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. FEBS Lett 429 152-156 (1998).

Kozak, K.R., and Marnett, L.J. Oxidative metabolism of endocannabinoids. Prostaglandins Leukot Essent Fatty Acids 66(2&3) 211-220 (2002).

Chen, J., Chen, J., Falck, J.R., et al. Mitogenic activity and signaling mechanism of 2-(14,15-epoxyeicosatrienoyl)glycerol, a novel cytochrome P450 arachidonate metabolite. Mol Cell Biol 27(8) 3023-3034 (2007).

Snider, N.T., Kornilov, A.M., Kent, U.M., et al. Anandamide metabolism by human liver and kidney microsomal cytochrome P450 enzymes to form hydroxyeicosatetraenoic and epoxyeicosatrienoic acid ethanolamides. J Pharmacol Exp Ther 321(2) 590-597 (2007).

Dinh, T.P., Carpenter, D., Leslie, F.M., et al. Brain monoglyceride lipase participating in endocannabinoid inactivation. Proc Natl Acad Sci USA 99(16) 10819-10824 (2002).

Sugiura, T., Kodaka, T., Nakane, S., et al. Evidence that the cannabinoid CB1 receptor is a 2-arachidonoylglycerol receptor. Structure-activity relationship of 2-arachidonoylglycerol, ether-linked analogues, and related compounds. J Biol Chem 274 2794-2801 (1999).

Show all 7 Hide all but first 3
Size Price Quantity Subtotal
25 µg $193.00 $0.00
50 µg $367.00 $0.00
100 µg $695.00 $0.00
500 µg $3,088.00 $0.00
Bulk Contact
Cart Total $0.00

This product is available in custom sizes and/or larger quantities.

Please contact our Sales Department for a quote or to purchase.

Pricing updated 2012-05-25. Prices are subject to change without notice.

To ask for assistance with one of our products please contact a Technical Support Scientist.

Warning This product is not for human or veterinary use.

Related Products

14(15)-EET
14(15)-EET Ethanolamide
2-Arachidonoyl Glycerol

Downloads

Batch-specific Information

Login to access batch-specific information

Cayman Chemical is a manufacturer, supplier and vendor of biochemical reagents, assay kits, antibodies, and proteins.

Other Resources
Management Team Company Profile Company History ChemAssistant Tools FAQs Cayman Europe Cayman Pharma CaBRI Cayman Gear Press Releases Illustrations and Charts Key Research Area Posters Article Library Analysis Tools Conference Schedule Order Terms Browser Recommendation Privacy Statement Site Map

Cayman Chemical Company · 1180 East Ellsworth Road · Ann Arbor, Michigan 48108 · USA

Toll Free: (800) 364-9897 (USA and Canada Only) · Fax: (734) 971-3640

Copyright 2012 Cayman Chemical Company

Lost password?