| | Identification | Back 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 Properties | Back 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
 | 
 | Hazard Information | Back 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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