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23470-00-0

23470-00-0 Structure

23470-00-0 Structure
IdentificationBack Directory
[Name]

2-MONOPALMITIN
[CAS]

23470-00-0
[Synonyms]

2-MONOOLEIN
2-O-Palmitoylglycerol
2-Hexadecanoylglycerol
2-Monopalmitoylglycerol
Glyceryl 2-monopalmitate
2-Palmitoyl-rac-glycerol
2-O-Palmitoyl-L-glycerol
2-O-Hexadecanoylglycerol
2-Monohexadecanoylglycerol
2-monopalmitoylglycerol (C16:0)
1,3-Dihydroxypropan-2-yl palmitate
Palmitic acid 2-hydroxy-1-(hydroxymethyl)ethyl ester
Hexadecanoic acid [2-hydroxy-1-(hydroxymethyl)ethyl] ester
2-(1,3-dihydroxypropan-2-yl)hexadecanoic acid compound with 1,3-dihydroxypropan-2-yl palmitate (1:1)
[Molecular Formula]

C19H38O4
[MDL Number]

MFCD00273078
[MOL File]

23470-00-0.mol
[Molecular Weight]

330.5
Chemical PropertiesBack Directory
[Melting point ]

68-70°C
[Boiling point ]

387.92°C (rough estimate)
[density ]

0.9708 (rough estimate)
[refractive index ]

1.4434 (estimate)
[storage temp. ]

−20°C
[solubility ]

Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
[form ]

neat
[pka]

13.54±0.10(Predicted)
[color ]

White to Off-White
[biological source]

synthetic
[BRN ]

1796692
[Major Application]

food and beverages
[InChI]

1S/C19H38O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(22)23-18(16-20)17-21/h18,20-21H,2-17H2,1H3
[InChIKey]

BBNYCLAREVXOSG-UHFFFAOYSA-N
[SMILES]

O=C(CCCCCCCCCCCCCCC)OC(CO)CO
Safety DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

43
[Safety Statements ]

36/37
[WGK Germany ]

3
[Storage Class]

11 - Combustible Solids
Hazard InformationBack Directory
[Description]

2-Arachidonoyl glycerol (2-AG; ) is an endogenous agonist of the CB1 and CB2 cannabinoid receptors. 2-Palmitoyl glycerol is a fatty acid ester that does not bind directly to cannabinoid receptors, nor inhibit adenylyl cyclase, but rather potentiates the activity of 2-AG (and other endocannabinoids) to bind to CB1 and CB2 and inhibit adenylyl cyclase. This “entourage” effect has been attributed to blockade of the breakdown and reuptake pathways that normally function to reduce endocannabinoid levels rapidly upon release. 2-Palmitoyl glycerol and related endogenous fatty acid derivatives have been shown to interact with endocannabinoids in the modulation of pain sensitivity.
[Chemical Properties]

White Solid
[Uses]

A biomarker of metabolic responses to hepatotoxicants and carcinogens.
[Definition]

ChEBI: A 2-monoglyceride where the acyl group is hexadecanoyl (palmitoyl).
[Biological Activity]

Endogenous fatty acid glycerol ester that enhances activity of 2-arachidonylglycerol ((5Z,8Z,11Z,14Z)-5,8,11,14-Eicosatetraenoic acid,2-hydroxy-1-(hydroxymethyl)ethyl ester ). Does not bind to CB 1 or CB 2 cannabinoid receptors, but potentiates the apparent binding of 2-AG and increases its ability to inhibit adenylyl cyclase. Enhances in vivo cannabinoid effects of 2-AG following combined administration with 2-linoleoylglycerol.牋.
[References]

[1] SHIMON BEN-SHABAT . An entourage effect: inactive endogenous fatty acid glycerol esters enhance 2-arachidonoyl-glycerol cannabinoid activity[J]. European journal of pharmacology, 1998, 353 1: Pages 23-31. DOI: 10.1016/s0014-2999(98)00392-6
[2] J.MICHAEL WALKER. Endocannabinoids and related fatty acid derivatives in pain modulation[J]. Chemistry and Physics of Lipids, 2002, 121 1: Pages 159-172. DOI: 10.1016/s0009-3084(02)00152-4
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