| Identification | More | [Name]
2-AG | [CAS]
53847-30-6 | [Synonyms]
2-AG
NOLADIN
2-Ara-gl
2-ARACHIDONYLGLYCEROL
2-ARACHIDONOYLGLYCEROL
2-Monoarachidonoylglycerol
2-Arachidonyl Glycerol (90%)
2-Arachidonyl Glycerol (~70%)
2-Hydroxy-1-(hydroxymethyl)ethylester
2-Arachidonylglycerol (acetonitrile solution)
(5Z,8Z,11Z,14Z)-5,8,11,14-Eicosatetraenoicacid
2-Arachidonyl glycerol solution in acetonitrile
5Z,8Z,11Z,14Z-EICOSATETRAENOIC ACID, 2-GLYCERYL ESTER
1,3-dihydroxypropan-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
(5Z,8Z,11Z,14Z)-1,3-Dihydroxypropan-2-yl icosa-5,8,11,14-tetraenoate
(all-Z)-5,8,11,14-Eicosatetraenoic Acid 2-Hydroxy-1-(hydroxyMethyl)ethyl Ester
5,8,11,14-Eicosatetraenoic acid, 2-hydroxy-1-(hydroxymethyl)ethyl ester, (all-Z)-
(5Z,8Z,11Z,14Z)-5,8,11,14-EICOSATETRAENOIC ACID, 2-HYDROXY-1-(HYDROXYMETHYL)ETHYL ESTER
5,8,11,14-Eicosatetraenoic acid, 2-hydroxy-1-(hydroxymethyl)ethyl ester, (5Z,8Z,11Z,14Z)- | [EINECS(EC#)]
200-835-2 | [Molecular Formula]
C23H38O4 | [MDL Number]
MFCD01862600 | [Molecular Weight]
378.55 | [MOL File]
53847-30-6.mol |
| Chemical Properties | Back Directory | [Boiling point ]
508.6±50.0 °C(Predicted) | [density ]
0.992±0.06 g/cm3(Predicted) | [Fp ]
2 °C | [storage temp. ]
−20°C
| [solubility ]
DMSO: 10 mg/ml; Ethanol: Miscible; PBS (pH 7.2): ~150 μg/ml | [form ]
acetonitrile solution
| [pka]
13.54±0.10(Predicted) | [color ]
Colorless to light yellow | [CAS DataBase Reference]
53847-30-6(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
F,Xn | [Risk Statements ]
R11:Highly Flammable.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36:Irritating to the eyes. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37:Wear suitable protective clothing and gloves . | [RIDADR ]
UN 1648 3/PG 2
| [WGK Germany ]
2
|
| Hazard Information | Back Directory | [Uses]
2-Arachidonoylglycerol is a major endocannabinoid, which can inhibit synaptic transmission by presynaptic cannabinoid CB1 receptors. It plays an inhibitory role in the bombesin-induced activation of central adrenomedullary outflow in rats. | [Definition]
ChEBI: An endocannabinoid and an endogenous agonist of the cannabinoid receptors (CB1 and CB2). It is an ester formed from omega-6-arachidonic acid and glycerol. | [General Description]
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. | [Biological Activity]
Endogenous cannabinoid ligand that acts as a potent agonist at GPR55 (EC 50 values are 3, 519 and 618 nM at GPR55, CB 1 and CB 2 respectively; K i values are 472 and 1400 nM at CB 1 and CB 2 respectively). Found in the brain at concentrations 1000-fold higher than that of anandamide. | [Biochem/physiol Actions]
Endogenous cannabinoid receptor agonist. | [Enzyme inhibitor]
This potent endocannabinoid (FW = 378.30 g/mol; CAS 53847-30-6; Symbol: 2-AG), also known as 1,3-dihydroxy-2-propanyl (5Z,8Z,11Z,14Z)- 5,8,11,14-eicosatetraenoate, is an endogenous agonist of the CB1, the G- protein-coupled Cannabinoid receptor type-1 found primarily in the central and peripheral nervous system. 2-AG is found at highest concentrations in the CNS, where it exerts its cannabinoid-like neuromodulatory effects. Found in milk, 2-AG plays a role in sustaining infant suckling, and the selective CB1 receptor antagonist SR141617A (N-(piperidin-1-yl)-5-(4- chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3- carboxamide) permanently prevents milk ingestion in a dose-dependent manner, when administered to mouse pups, within 1 day of birth. 2-AG is formed by phospholipase C (PLC) and diacylglycerol lipase (DAGL) from arachidonic acid-containing diacylglycerol (DAG). In the CNS, three serine-hydrolases, monoacylglycerol lipase (MAGL), a,b-hydrolase- domain-6 (ABHD6) and a,b-hydrolase-domain 12 (ABHD12) are responsible for inactivation of the primary 2-arachidonoylglycerol. Irreversible ABHD6 inhibitors show exceptional potency and selectivity in cells (<5 nM) and, at equivalent doses in mice (1 mg/kg), acting as systemic and peripherally restricted inhibitors, respectively. Indeed, selective knockdown of ABHD6 in metabolic tissues protects mice from high-fat-diet-induced obesity, hepatic steatosis, and systemic insulin resistance. | [storage]
Store at -80°C |
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