2-Oleoylglycerol

2-Oleoylglycerol (2OG) is a monoacylglycerol that is found in biologic tissues. Its synthesis is derived from diacylglycerol precursors. It is metabolized to oleic acid and glycerol primarily by the enzyme monoacylglycerol lipase (MAGL).[1] In 2011, 2OG was found to be an endogenous ligand to GPR119.[2] 2OG has been shown to increase glucagon-like peptide-1 (GLP-1) and gastric inhibitory polypeptide (GIP) levels following administration to the small intestine.[2]

2-Oleoylglycerol

Names
IUPAC name 1,3-dihydroxypropan-2-yl (Z)-octadec-9-enoate
Other names 2-Monoolein
Identifiers
CAS Number	3443-84-3^Y
3D model (JSmol)	Interactive image
ChemSpider	4478086^Y
IUPHAR/BPS	5112
PubChem CID	5319879
UNII	9A2389K694^Y
CompTox Dashboard (EPA)	DTXSID8058661
InChI InChI=1S/C21H40O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(24)25-20(18-22)19-23/h9-10,20,22-23H,2-8,11-19H2,1H3/b10-9-^Y Key: UPWGQKDVAURUGE-KTKRTIGZSA-N^Y InChI=1/C21H40O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(24)25-20(18-22)19-23/h9-10,20,22-23H,2-8,11-19H2,1H3/b10-9- Key: UPWGQKDVAURUGE-KTKRTIGZBO
SMILES CCCCCCCCC=CCCCCCCCC(=O)OC(CO)CO
Properties
Chemical formula	C21H40O4
Molar mass	356.547 g·mol^−1
Density	0.958 g/cm^3
Hazards
Flash point	>113.0 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

See also

• 2-Arachidonoylglycerol
• JZL184

References

1. Dinh, T. P.; Carpenter, D.; Leslie, F. M.; Freund, T. F.; Katona, I.; Sensi, S. L.; Kathuria, S.; Piomelli, D. (2002). "Brain monoglyceride lipase participating in endocannabinoid inactivation". Proceedings of the National Academy of Sciences. 99 (16): 10819–10824. doi:10.1073/pnas.152334899. PMC 125056. PMID 12136125.
2. Hansen, K. B.; Rosenkilde, M. M.; Knop, F. K.; Wellner, N.; Diep, T. A.; Rehfeld, J. F.; Andersen, U. B.; Holst, J. J.; Hansen, H. S. (2011). "2-Oleoyl Glycerol is a GPR119 Agonist and Signals GLP-1 Release in Humans". Journal of Clinical Endocrinology & Metabolism. 96 (9): E1409–E1417. doi:10.1210/jc.2011-0647. PMID 21778222.