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870450O

Avanti

2-AG

Avanti Research™ - A Croda Brand 870450O

Synonyme(s) :

2-arachidonoyl glycerol

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About This Item

Formule empirique (notation de Hill):
C23H38O4
Numéro CAS:
53847-30-6
Poids moléculaire :
378.55
Code UNSPSC :
12352211
Nomenclature NACRES :
NA.25

Forme

liquid

Conditionnement

pkg of 1 × 5 mg (with screw cap/argon/foil bag (870450O-5mg))

Fabricant/nom de marque

Avanti Research™ - A Croda Brand 870450O

Type de lipide

bioactive lipids
phosphoglycerides

Conditions d'expédition

dry ice

Température de stockage

−70°C

Chaîne SMILES 

[H]C(CO)(OC(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O)CO

InChI

1S/C23H38O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(26)27-22(20-24)21-25/h6-7,9-10,12-13,15-16,22,24-25H,2-5,8,11,14,17-21H2,1H3/b7-6-,10-9-,13-12-,16-15-

Clé InChI

RCRCTBLIHCHWDZ-DOFZRALJSA-N

Catégories apparentées

Description générale

2-Arachidonoylglycerol (2-AG), is an endocannabinoid, an endogenous agonist of the CB1 receptor. 2-AG, unlike anandamide, is present at relatively high levels in the central nervous system; it is the most abundant molecular species of monoacylglycerol found in mouse and rat brain (~5-10 nmol/g tissue). Detection of 2-AG in brain tissue is complicated by the relative ease of its isomerization to 1-AG during standard lipid extraction conditions. Unlike anandamide, formation of 2-AG is calcium-dependent and is mediated by the activities of phospholipase C (PLC) and diacylglycerol lipase (DAGL). 2-AG acts as a full agonist at the CB1 receptor. At a concentration of 0.3nM, 2-AG induces a rapid, transient increase in intracellular free calcium in NG108-15 neuroblastoma X glioma cells through a CB1 receptor-dependent mechanism. 2-AG is hydrolyzed in vitro by monoacylglycerol lipase (MAGL), fatty acid amide hydrolase (FAAH), and the uncharacterized serine hydrolase enzymes ABHD6 and ABHD12.

Conditionnement

5 mL PTFE Vial with Screw Cap/Argon/Foil Bag (870450O-5mg)

Informations légales

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Code de la classe de stockage

12 - Non Combustible Liquids

Classe de danger pour l'eau (WGK)

WGK 3

Certificats d'analyse (COA)

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Stearoyl ethanolamide ≥98%, crystalline

Sigma-Aldrich

S8439

Stearoyl ethanolamide

Palmitoylethanolamide

Sigma-Aldrich

P0359

Palmitoylethanolamide

2-OG Avanti Research™ - A Croda Brand 870451O

Avanti

870451O

2-OG

AM630 ≥90% (HPLC)

Sigma-Aldrich

SML0327

AM630

Acide arachidonique >95.0% (GC)

Sigma-Aldrich

10931

Acide arachidonique

Acide arachidonique from non-animal source, ≥98.5% (GC)

Sigma-Aldrich

A3611

Acide arachidonique

Jonathan Z Long et al.
Nature chemical biology, 5(1), 37-44 (2008-11-26)
2-Arachidonoylglycerol (2-AG) and anandamide are endocannabinoids that activate the cannabinoid receptors CB1 and CB2. Endocannabinoid signaling is terminated by enzymatic hydrolysis, a process that for anandamide is mediated by fatty acid amide hydrolase (FAAH), and for 2-AG is thought to
Erik Keimpema et al.
Scientific reports, 3, 2093-2093 (2013-06-29)
Endocannabinoids are small signaling lipids, with 2-arachidonoylglycerol (2-AG) implicated in modulating axonal growth and synaptic plasticity. The concept of short-range extracellular signaling by endocannabinoids is supported by the lack of trans-synaptic 2-AG signaling in mice lacking sn-1-diacylglycerol lipases (DAGLs), synthesizing
Kwang-Mook Jung et al.
Cell metabolism, 15(3), 299-310 (2012-03-13)
The endocannabinoid system plays a critical role in the control of energy homeostasis, but the identity and localization of the endocannabinoid signal involved remain unknown. In the present study, we developed transgenic mice that overexpress in forebrain neurons the presynaptic
T P Dinh et al.
Proceedings of the National Academy of Sciences of the United States of America, 99(16), 10819-10824 (2002-07-24)
The endogenous cannabinoids (endocannabinoids) are lipid molecules that may mediate retrograde signaling at central synapses and other forms of short-range neuronal communication. The monoglyceride 2-arachidonoylglycerol (2-AG) meets several criteria of an endocannabinoid substance: (i) it activates cannabinoid receptors; (ii) it
S Kondo et al.
FEBS letters, 429(2), 152-156 (1998-07-03)
The molecular species compositions of monoacylglycerols obtained from various rat tissues were examined by reverse-phase high-performance liquid chromatography (HPLC) and gas chromatography-mass spectrometry (GC-MS) analyses. We confirmed that 2-arachidonoylglycerol, an endogenous cannabinoid receptor agonist, is one of the most abundant
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