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Join us! · InformexUSA 2012 · New Orleans, Louisiana · February 14-17, 2012 · Booth 2514

Arachidonoyl-1-thio-Glycerol Exclusive

Cayman Chemical Item Number 10007904

1-S-Arachidonoyl-1-mercapto-2,3-propanediol

Arachidonoyl-1-thio-Glycerol

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Description

2-Arachidonoyl glycerol (2-AG) is an endogenous agonist of the central cannabinoid (CB1) receptor.1,2 It is present at relatively high levels in the central nervous system and is the most abundant molecular species of monoacylglycerol found in rat brain.2,3 Monoacylglycerol lipase (MGL) hydrolyzes 2-AG to arachidonic acid and glycerol, thereby terminating its biological actions.4 Arachidonoyl-1-thio-glycerol is a thioester substrate analog of 2-AG that can be utilized for the measurement of MGL activity.5 Hydrolysis of the thioester bond by MGL generates a free thiol that reacts rapidly with the chromogenic reagent DTNB (Ellman’s reagent) resulting a yellow product with an absorbance maximum at 412 nm.

1 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).

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

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 Cox, J.W., and Horrocks, L.A. Preparation of thioester substrates and development of continuous spectrophotometric assays for phospholipase A1 and monoacylglycerol lipase. J Lipid Res 22 496-505 (1981).

Synonyms
  • 1-S-Arachidonoyl-1-mercapto-2,3-propanediol
Formal Name 5Z,​8Z,​11Z,​14Z-​eicosatetraenyl,​1-​thio glycerol
Molecular Formula C23H38O3S
Formula Weight 394.6
Formulation A solution in acetonitrile
Purity >98%
λmax 233 nm
Stability 6 months
Storage -80°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES
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CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)​SCC(O)​CO

Background Reading

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).

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).

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

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).

Cox, J.W., and Horrocks, L.A. Preparation of thioester substrates and development of continuous spectrophotometric assays for phospholipase A1 and monoacylglycerol lipase. J Lipid Res 22 496-505 (1981).

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Arachidonoyl-1-thio-Glycerol is available in the following screening library:

Size Price Quantity Subtotal
1 mg $22.00 $0.00
5 mg $99.00 $0.00
10 mg $176.00 $0.00
25 mg $385.00 $0.00
Bulk Contact
Cart Total $0.00

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

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Pricing updated 2012-02-12. 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.

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