2-Palmitoylglycerol - CAS 23470-00-0
Category: Inhibitor
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Molecular Formula:
C19H38O4
Molecular Weight:
330.51
COA:
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Targets:
Cannabinoid Receptor
Description:
2-Palmitoylglycerol is an endogenous fatty acid glycerol ester that enhances activity of 2-arachidonylglycerol. It is an endogenous agonist of the CB1 and CB2 cannabinoid receptors. 2-Palmitoylglycerol 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.
Synonyms:
2-Hydroxy-1-(hydroxymethyl)ethyl hexadecanoic acid ester; 2-Monohexadecanoylglycerol; 2-Monopalmitin; 2-Monopalmitoyl-sn-glycerol; 2-Monopalmitoylglycerol; 2-Palmitoylglycerol; Glycerol-β-palmitate; Palmitic Acid β-monoglyceride; β-Monopalmitin
Storage:
Store in a cool and dry place (or refer to the Certificate of Analysis).
MSDS:
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InChIKey:
BBNYCLAREVXOSG-UHFFFAOYSA-N
InChI:
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
Canonical SMILES:
CCCCCCCCCCCCCCCC(=O)OC(CO)CO
1.2-Arachidonoylglycerol as a possible treatment for anorexia nervosa in animal model in mice.
Avraham Y;Paturski I;Magen I;Vorobiev L;Berry EM Brain Res. 2017 Sep 1;1670:185-190. doi: 10.1016/j.brainres.2017.06.003. Epub 2017 Jun 9.
We have investigated the effects of 0.001mg/kg 2-arachidonoylglycerol (2-AG) administered in combination with compounds present in the body alongside 2-AG like 2-palmitoylglycerol and 2-linoleylglycerol (also termed "entourage"), on cognitive function,food intake, and neurotransmitter levels in the hippocampus and hypothalamus of mice under diet restriction. Young female Sabra mice were treated with vehicle, 2-AG, 2-AG+entourage, 2-AG+entourage+5-(4-Chlorophenyl)-1-(2,4-dichloro-phenyl)- 4-methyl-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide (SR141716A, a CB;1; antagonist) and SR141716A. The mice were fed for 2.5h a day for 14days. Cognitive function was evaluated by the eight arm maze test, and neurotransmitter (norepinephrine, dopamine, L-DOPA and serotonin) levels were measured in the hippocampus and hypothalamus by high-performance liquid chromatography-electrochemical detection. Food intake was increased by 2-AG and, to an even greater extent, by 2-AG+entourage. SR141716A reversed the effect of 2-AG+entourage. The administration of 2-AG+entourage improved cognitive function compared to the vehicle mice, and this improvement was blocked by SR141716A. 2-AG+entourage-treated mice showed an increase in norepinephrine (NE), dopamine and L-DOPA levels in the hippocampus.
2.Highly selective synthesis of 1,3-oleoyl-2-palmitoylglycerol by lipase catalysis.
Schmid U;Bornscheuer UT;Soumanou MM;McNeill GP;Schmid RD Biotechnol Bioeng. 1999 Sep 20;64(6):678-84.
1,3-Oleoyl-2-palmitoylglycerol (OPO), an important structured triglyceride in infant nutrition, was synthesized by a two-step process in high yields and purity using sn1,3-regiospecific lipases. In the first step, tripalmitin (TP) was subjected to an alcoholysis reaction in an organic solvent catalyzed by sn1,3-regiospecific lipases yielding the corresponding 2-monopalmitin (2-MP). The 2-MP was isolated in up to 85% yield and >95% purity by crystallization and esterified in the second step with oleic acid using the same lipases to form the structured triglyceride OPO in up to 78% yield containing 96% palmitic acid in the sn2-position. Water activity, solvent, as well as carrier for lipase immobilization strongly influenced the yield and purity of products in both steps. The best results were achieved with lipases from Rhizomucor miehei and Rhizopus delemar immobilized on EP 100 and equilibrated to a water activity of 0.43. Special emphasis was given to develop this process in solvents that are allowed to be used in foodstuffs and to perform the second step in a solvent-free system.
3.The effect of triglyceride positional distribution on fatty acid absorption in rats.
Lien EL;Boyle FG;Yuhas R;Tomarelli RM;Quinlan P J Pediatr Gastroenterol Nutr. 1997 Aug;25(2):167-74.
BACKGROUND: ;Human milk contains palmitic acid predominantly in the triglyceride sn-2 position, and differs from the palmitic acid positional distribution found in most infant formulas (predominantly positions sn-1 and sn-3). Following lipolysis by pancreatic lipase, 2-monoglycerides and free fatty acids are produced. All 2-monoglycerides are well absorbed, including 2-monopalmitin, thus providing one reason for the efficient absorption of palmitic acid in breast-fed infants. If infants are fed fat blends with palmitic acid located in the sn-1 and sn-3 positions, the resulting free fatty acids may form poorly absorbed calcium soaps. Therefore, many infant formulas contain only modest levels of palmitic acid.;METHODS: ;Fat absorption studies were conducted in rats with preparations containing various amounts of palmitic acid in the triglyceride sn-2 position. Determining total fat absorption, specific fatty acid absorption, and the presence of calcium-fatty acid soaps.;RESULTS: ;Betapol, a new triacylglycerol, similar to human milk in its palmitic acid content and positional distribution, demonstrated excellent absorption characteristics compared to fat blends derived from either palm olein or oleo (similar in fatty acid profile to Betapol, but with most palmitic acid in the sn-1 and sn-3 positions).
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CAS 23470-00-0 2-Palmitoylglycerol

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