Product Name

  • Name

    2-AG

  • EINECS 200-835-2
  • CAS No. 53847-30-6
  • Article Data13
  • CAS DataBase
  • Density 0.992 g/cm3
  • Solubility
  • Melting Point
  • Formula C23H38O4
  • Boiling Point 508.6 °C at 760 mmHg
  • Molecular Weight 378.552
  • Flash Point 163 °C
  • Transport Information
  • 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;
  • PSA 66.76000
  • LogP 5.02850

Synthetic route

2-O-arachidonoyl-1,3-bis-O-(trifluoroacetyl)glycerol
439146-25-5

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

2-arachidonoyl 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

2-arachidonylglycerol 1,3-phenylboronate ester

2-arachidonoyl glycerol
53847-30-6

2-arachidonoyl glycerol

Conditions
ConditionsYield
With water In methanol Hydrolysis;86%
2-((5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy)propane-1,3-diyl dibutyrate
1274596-36-9

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

2-arachidonoyl glycerol
53847-30-6

2-arachidonoyl glycerol

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

ethanol

2-((5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy)propane-1,3-diyl dibutyrate
1274596-36-9

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

A

ethyl arachidonate
95285-77-1, 1808-26-0

ethyl arachidonate

B

2-arachidonoyl glycerol
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%
...Expand
(5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoic acid 2-triisopropylsilanyloxy-1-triisopropylsilanyloxymethyl-ethyl ester
223259-26-5

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

2-arachidonoyl glycerol
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

2-arachidonylglycerol 1,3-benzylidene acetal

A

C30H42O4
1385032-29-0

C30H42O4

B

2-arachidonoyl glycerol
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

2-arachidonoyl-1,3-benzylideneglycerol

2-arachidonoyl glycerol
53847-30-6

2-arachidonoyl glycerol

Conditions
ConditionsYield
With Trimethyl borate; boric acid at 100℃; for 0.333333h; Heating;
2-arachidonoyl-1,3-dibenzylglycerol

2-arachidonoyl-1,3-dibenzylglycerol

A

2-arachidonyl-glycerol
35474-99-8

2-arachidonyl-glycerol

B

2-arachidonoyl glycerol
53847-30-6

2-arachidonoyl glycerol

Conditions
ConditionsYield
With 2-chloro-1,3,2-benzodioxaborole In dichloromethane at 20℃; for 2h;
all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

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

2-arachidonoyl glycerol
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
oxiran-2-ylmethyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
439146-24-4

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

2-arachidonoyl glycerol
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
all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

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

A

C30H42O4
1385032-29-0

C30H42O4

B

2-arachidonoyl glycerol
53847-30-6

2-arachidonoyl glycerol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere
2.1: pyridine / dichloromethane / 0.5 h / -72 - 20 °C / Inert atmosphere
3.1: 2-chloro-1,3,2-benzodioxaborole / dichloromethane / 2.5 h / 0 °C / Inert atmosphere; Darkness
3.2: Inert atmosphere; Darkness
View Scheme
1-stearoyl-2-arachidonoyl-sn-glycerol
65914-84-3

1-stearoyl-2-arachidonoyl-sn-glycerol

2-arachidonoyl glycerol
53847-30-6

2-arachidonoyl glycerol

Conditions
ConditionsYield
With diacylglycerol lipase Enzymatic reaction;
C37H51NO6

C37H51NO6

A

7-diethylamino-4-(dihydroxym,ethyl)-2-oxo-2H-chromen

7-diethylamino-4-(dihydroxym,ethyl)-2-oxo-2H-chromen

B

7-(diethylamino)-2-oxo-2H-1-benzopyran-4-carboxaldehyde
54711-39-6

7-(diethylamino)-2-oxo-2H-1-benzopyran-4-carboxaldehyde

C

2-arachidonoyl glycerol
53847-30-6

2-arachidonoyl glycerol

Conditions
ConditionsYield
With water for 0.0333333h; Mechanism; Time; UV-irradiation;
...Expand
benzoyl chloride
98-88-4

benzoyl chloride

2-arachidonoyl glycerol
53847-30-6

2-arachidonoyl glycerol

1,3-di-O-benzoyl-2-O-arachidonoylglycerol

1,3-di-O-benzoyl-2-O-arachidonoylglycerol

Conditions
ConditionsYield
With pyridine In dichloromethane at -20 - 20℃;86%
2-arachidonoyl glycerol
53847-30-6

2-arachidonoyl glycerol

A

all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

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

B

2-arachidonyl-glycerol
35474-99-8

2-arachidonyl-glycerol

Conditions
ConditionsYield
With mouse brain extracts containing membrane bound monoacrylglycerol lipase (MAGL) for 0.5h; pH=7.4; buffer; Enzymatic reaction;
2-arachidonoyl glycerol
53847-30-6

2-arachidonoyl glycerol

2-arachidonyl-glycerol
35474-99-8

2-arachidonyl-glycerol

Conditions
ConditionsYield
for 0.5h; pH=7.4; Buffer;
2-arachidonoyl glycerol
53847-30-6

2-arachidonoyl glycerol

2-hydroxy-1,3,2-dioxaborinan-5-yl (5'Z,8'Z,11'Z,14'Z)-icosa-5',8',11',14'-tetraenoate
1274596-44-9

2-hydroxy-1,3,2-dioxaborinan-5-yl (5'Z,8'Z,11'Z,14'Z)-icosa-5',8',11',14'-tetraenoate

Conditions
ConditionsYield
With boric acid In hexane; water; ethyl acetate Inert atmosphere;
2-arachidonoyl glycerol
53847-30-6

2-arachidonoyl glycerol

cis-14,15-epoxyeicosatrienoic acid
197508-62-6

cis-14,15-epoxyeicosatrienoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: cytochrome P450 reductase; NADPH; Human CYP2J2 epoxygenase / aq. phosphate buffer / 0.08 h / 37 °C / pH 7.4 / Enzymatic reaction
2: potassium hydroxide / methanol; water / 1 h / 50 °C
View Scheme
2-arachidonoyl glycerol
53847-30-6

2-arachidonoyl glycerol

A

19-Hydroxyarachidonic acid
79551-85-2

19-Hydroxyarachidonic acid

B

4-{3-[(2Z,5Z,8Z)-tetradeca-2,5,8-trienyl]oxiran-2-yl}butanoic acid
184488-43-5

4-{3-[(2Z,5Z,8Z)-tetradeca-2,5,8-trienyl]oxiran-2-yl}butanoic acid

C

8,9-epoxyeicosa-5(Z),11(Z),14(Z)-trienoic acid
184488-44-6

8,9-epoxyeicosa-5(Z),11(Z),14(Z)-trienoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: cytochrome P450 reductase; NADPH; Human CYP2J2 epoxygenase / aq. phosphate buffer / 0.08 h / 37 °C / pH 7.4 / Enzymatic reaction
2: cytochrome P450 reductase; NADPH; Human CYP2J2 epoxygenase / aq. phosphate buffer / 0.08 h / 37 °C / pH 7.4 / Enzymatic reaction
View Scheme
...Expand
2-arachidonoyl glycerol
53847-30-6

2-arachidonoyl glycerol

A

all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

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

B

2-11,12-EG

2-11,12-EG

C

2-14,15-EG

2-14,15-EG

D

4-{3-[(2Z,5Z,8Z)-tetradeca-2,5,8-trienyl]oxiran-2-yl}butanoic acid
184488-43-5

4-{3-[(2Z,5Z,8Z)-tetradeca-2,5,8-trienyl]oxiran-2-yl}butanoic acid

E

8,9-epoxyeicosa-5(Z),11(Z),14(Z)-trienoic acid
184488-44-6

8,9-epoxyeicosa-5(Z),11(Z),14(Z)-trienoic acid

F

cis-14,15-epoxyeicosatrienoic acid
197508-62-6

cis-14,15-epoxyeicosatrienoic acid

G

11,12-cis-epoxyeicosatrienoic acid
200960-01-6

11,12-cis-epoxyeicosatrienoic acid

Conditions
ConditionsYield
With cytochrome P450 reductase; Human CYP2J2 epoxygenase; NADPH In aq. phosphate buffer at 37℃; for 0.0833333h; pH=7.4; Kinetics; Enzymatic reaction;
...Expand
2-arachidonoyl glycerol
53847-30-6

2-arachidonoyl glycerol

all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

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

Conditions
ConditionsYield
With abhydrolase domain-containingprotein 12; abhydrolase domain-containingprotein 6; fatty acid amide hydrolase; monoacylglycerol lipase Enzymatic reaction;
With Geobacillus thermocatenulatus lipase C65S/C296S/A193X (X=Cys(Ac-Cys-Phe-Gly-Phe-Gly-Phe-CONH2) connected with Cys-Cys thioether) In ethanol pH=5; Catalytic behavior; Reagent/catalyst; Inert atmosphere; Enzymatic reaction;
With water; esterase from pig liver PLE1 In aq. buffer at 37℃; for 0.166667h; pH=7.4; Reagent/catalyst; Enzymatic reaction;
2-arachidonoyl glycerol
53847-30-6

2-arachidonoyl glycerol

1-Arachidonoyl-sn-glycerol

1-Arachidonoyl-sn-glycerol

Conditions
ConditionsYield
With anandamide In acetonitrile at 37℃; Kinetics; Reagent/catalyst;

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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