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2-Arachidonylglycerol
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Name

2-Arachidonylglycerol

 EINECS 200-835-2
CAS No. 53847-30-6 Density 0.992 g/cm3
PSA 66.76000 LogP 5.02850
Solubility N/A Melting Point N/A
Formula C23H38O4 Boiling Point 508.6 °C at 760 mmHg
Molecular Weight 378.552 Flash Point 163 °C
Transport Information N/A Appearance Liquid
Safety 26-36/37 Risk Codes 11-20/21/22-36
Molecular Structure Molecular Structure of 53847-30-6 (2-AG) Hazard Symbols FlammableF,HarmfulXn
Synonyms

5,8,11,14-Eicosatetraenoicacid, 2-hydroxy-1-(hydroxymethyl)ethyl ester, (all-Z)-;2-Arachidonylglycerol;2-Monoarachidonoylglycerol;

Article Data 13

2-Arachidonylglycerol Synthetic route

439146-25-5

2-O-arachidonoyl-1,3-bis-O-(trifluoroacetyl)glycerol

53847-30-6

2-arachidonoyl glycerol

Conditions
ConditionsYield
With pyridine; methanol In dichloromethane; pentane for 3h; from -20 degC to rt;92%
With pyridine; methanol In dichloromethane; pentane at 20℃; for 3h;92%

2-arachidonylglycerol 1,3-phenylboronate ester

53847-30-6

2-arachidonoyl glycerol

Conditions
ConditionsYield
With water In methanol Hydrolysis;86%
1274596-36-9

2-((5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy)propane-1,3-diyl dibutyrate

53847-30-6

2-arachidonoyl glycerol

Conditions
ConditionsYield
With Rhizomucor miehei lipase; ethanol at 20℃; for 24h; Enzymatic reaction; regiospecific reaction;75%
64-17-5

ethanol

1274596-36-9

2-((5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy)propane-1,3-diyl dibutyrate

A

95285-77-1, 1808-26-0

ethyl arachidonate

B

53847-30-6

2-arachidonoyl glycerol

Conditions
ConditionsYield
With immobilized Candida antarctica at 20℃; for 2h; Enzymatic reaction;A 27%
B 67%
With resin-immobilized lipase B from Candida antarctica for 2.33333h; Inert atmosphere; Enzymatic reaction;A n/a
B 54%
223259-26-5

(5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoic acid 2-triisopropylsilanyloxy-1-triisopropylsilanyloxymethyl-ethyl ester

53847-30-6

2-arachidonoyl glycerol

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride; acetic acid In tetrahydrofuran -25 deg C, overnight then r.t., 1 h;59%

2-arachidonylglycerol 1,3-benzylidene acetal

A

1385032-29-0

C30H42O4

B

53847-30-6

2-arachidonoyl glycerol

Conditions
ConditionsYield
Stage #1: 2-arachidonylglycerol 1,3-benzylidene acetal With 2-chloro-1,3,2-benzodioxaborole In dichloromethane at 0℃; for 2.5h; Inert atmosphere; Darkness;
Stage #2: With water In methanol; dichloromethane Inert atmosphere; Darkness;		A 30 mg
B 44%

2-arachidonoyl-1,3-benzylideneglycerol

53847-30-6

2-arachidonoyl glycerol

Conditions
ConditionsYield
With Trimethyl borate; boric acid at 100℃; for 0.333333h; Heating;

2-arachidonoyl-1,3-dibenzylglycerol

A

35474-99-8

2-arachidonyl-glycerol

B

53847-30-6

2-arachidonoyl glycerol

Conditions
ConditionsYield
With 2-chloro-1,3,2-benzodioxaborole In dichloromethane at 20℃; for 2h;
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

53847-30-6

2-arachidonoyl glycerol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 95 percent / 4-(dimethylamino)pyridine; N,N'-dicyclohexylcarbodiimide / CH2Cl2 / 12 h / 20 °C
2: 94 percent / CH2Cl2 / -20 - 20 °C
3: 92 percent / pyridine; methanol / pentane; CH2Cl2 / 3 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: oxalyl chloride / CH2Cl2 / 4 h / 20 °C
1.2: 80 percent / CH2Cl2 / 24 h / 20 °C
2.1: B-chlorocatecholborane / CH2Cl2 / 2 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: 94 percent / dimethylaminopyridine, 1-(3-dimethyl-aminopropyl)-3-ethylcarbodiimide hydrochloride / CH2Cl2 / 24 h / Ambient temperature
2: 59 percent / AcOH, TBAF / tetrahydrofuran / -25 deg C, overnight then r.t., 1 h
View Scheme
439146-24-4

oxiran-2-ylmethyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate

53847-30-6

2-arachidonoyl glycerol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 94 percent / CH2Cl2 / -20 - 20 °C
2: 92 percent / pyridine; methanol / pentane; CH2Cl2 / 3 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: 94 percent / CH2Cl2 / 1 h / 20 °C
2: 92 percent / pyridine; methanol / pentane; CH2Cl2 / 3 h / from -20 degC to rt
View Scheme

2-Arachidonylglycerol Specification

The 2-Arachidonylglycerol, with the CAS registry number 53847-30-6, is also known as 5,8,11,14-Eicosatetraenoic acid, 2-hydroxy-1-(hydroxymethyl)ethyl ester, (5Z,8Z,11Z,14Z)-. It belongs to the product categories of Cannabinoid Receptor; Cannabinoid. This chemical's molecular formula is C23H38O4 and molecular weight is 378.27701. Its IUPAC name is called 1,3-dihydroxypropan-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate. This chemical's classification codes are Endocannabinoids; Hormones; Hormones, Hormone Substitutes, and Hormone Antagonists; Neurotransmitter Agents.

Physical properties of 2-Arachidonylglycerol: (1)ACD/LogP: 6.25; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 6.25; (4)ACD/LogD (pH 7.4): 6.25; (5)ACD/BCF (pH 5.5): 32843.03; (6)ACD/BCF (pH 7.4): 32843; (7)ACD/KOC (pH 5.5): 59491.39; (8)ACD/KOC (pH 7.4): 59491.32; (9)#H bond acceptors: 4; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 20; (12)Index of Refraction: 1.507; (13)Molar Refractivity: 113.63 cm3; (14)Molar Volume: 381.5 cm3; (15)Surface Tension: 38.7 dyne/cm; (16)Density: 0.992 g/cm3; (17)Flash Point: 163 °C; (18)Enthalpy of Vaporization: 89.68 kJ/mol; (19)Boiling Point: 508.6 °C at 760 mmHg; (20)Vapour Pressure: 1.78E-12 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
This chemical may catch fire in contact with air and only need brief contact with an ignition source which has a very low flash point or evolve highly flammable gases in contact with water. Besides, this chemical may cause damage to health. It is harmful by inhalation, in contact with skin and if swallowed. In addition, it is irritating to eyes. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing and gloves.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO)CO
(2)Isomeric SMILES: CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC(CO)CO
(3)InChI: 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-
(4)InChIKey: RCRCTBLIHCHWDZ-DOFZRALJSA-N

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