2-Palmitoylglycerol
Basic information
- CAS
23470-00-0- Standard SMILES
CCCCCCCCCCCCCCCC(=O)OC(CO)CO- InChIKey
BBNYCLAREVXOSG-UHFFFAOYSA-N- Molecular formula
- C19H38O4
- Average molar mass
- 330.5 g/mol
- Monoisotopic mass
- 330.27700969
Overview
2-palmitoylglycerol is a 2-monoglyceride where the acyl group is hexadecanoyl (palmitoyl). It has a role as an algal metabolite. It is functionally related to a hexadecanoic acid.
Names & identifiers
- Preferred name
- 2-Palmitoylglycerol
- IUPAC
- 1,3-dihydroxypropan-2-yl hexadecanoate
- English name
- 2-MONOPALMITIN
- Molecular formula
- C19H38O4
- Molecular weight
- 330.5
Names & synonyms
2-Palmitoylglycerol2-Monopalmitin23470-00-01,3-dihydroxypropan-2-yl hexadecanoate2-Monopalmitoylglycerol2-Hexadecanoyl glycerol2-palmitoyl-glycerolGlycerol, 2-palmitatePalmitin, 2-monoGlyceryl 2-palmitateHexadecanoic acid, 2-hydroxy-1-(hydroxymethyl)ethyl ester21I29V2935
Show more names
2-MONOOLEIN2-O-Palmitoylglycerol2-HexadecanoylglycerolGlyceryl 2-monopalmitate2-O-Hexadecanoylglycerol2-O-Palmitoyl-L-glycerol2-Monohexadecanoylglycerol
CHEBI:75455DTXSID301780242-Palm-GlRefChem:910191DTXCID601005152-Palmitoyl-rac-glycerol1,3-dihydroxypropan-2-yl palmitatePalmitin, 2-mono-
Database identifiers
- CAS
23470-00-0- PubChem CID
- 123409
- DTXSID
DTXSID30178024- ChEMBL
CHEMBL1317070- ChEBI
CHEBI:75455- UNII
- 21I29V2935
- Nikkaji
- J103.626B
Properties
Computed structural properties
- XLogP
- 6.1
- Topological polar surface area
- 66.8 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 18
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 252
Experimental & physicochemical properties
LipidsLipids -> Glycerolipids [GL] -> Monoradylglycerols [GL01] -> Monoacylglycerols [GL0101]
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 68 · 68-70°C
- Boiling point
- 387.92 °C · 387.92°C (rough estimate)
- Density
- 0.9708 · 0.9708 (rough estimate)
- refractive index
- 1.4434 · 1.4434 (estimate)
- storage temp.
- 20 °C · −20°C
- solubility
- Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
- pka
- 13.54 · 13.54±0.10(Predicted)
- form
- Solid
- color
- White to Off-White
- biological source
- synthetic
- BRN
- 1796692 · 1796692
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- risk_code
- 43
- hazard_code
- Xi
- safety_code
- 36/37
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Pharmacology
Tissue LocationsAll Tissues
Cellular LocationsExtracellular
Metabolite PathwaysD-glyceric acidura
Applications
Description2-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.
UsesA biomarker of metabolic responses to hepatotoxicants and carcinogens.
Additional notes
DefinitionChEBI: A 2-monoglyceride where the acyl group is hexadecanoyl (palmitoyl).
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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