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2-Oleoylglycerol

Names
IUPAC name 2-O-glycerol
Systematic IUPAC name 1,3-Dihydroxypropan-2-yl (9Z)-octadec-9-enoate
Other names 2-Monoolein
Identifiers
CAS Number	3443-84-3
3D model (JSmol)	Interactive image
ChemSpider	4478086
IUPHAR/BPS	5112
PubChem CID	5319879
UNII	9A2389K694
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-Key: UPWGQKDVAURUGE-KTKRTIGZSA-N
SMILES CCCCCCCCC=CCCCCCCCC(=O)OC(CO)CO
Properties
Chemical formula	C21H40O4
Molar mass	356.547 g·mol
Density	0.958 g/cm
Hazards
Flash point	> 113.0 °C (235.4 °F; 386.1 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Y verify (what is  ?) Infobox references

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). In 2011, 2OG was found to be an endogenous ligand to GPR119. 2OG has been shown to increase glucagon-like peptide-1 (GLP-1) and gastric inhibitory polypeptide (GIP) levels following administration to the small intestine. 2OG has also been discovered to potentiate G protein and not β-arrestin signaling via allosteric binding of the 5-HT2A receptor.

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. Bibcode:2002PNAS...9910819D. 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.
3. Cao, Dongmei; Yu, Jing; Wang, Huan; Luo, Zhipu; Liu, Xinyu; He, Licong; Qi, Jianzhong; Fan, Luyu; Tang, Lingjie; Chen, Zhangcheng; Li, Jinsong; Cheng, Jianjun; Wang, Sheng (2022-01-28). "Structure-based discovery of nonhallucinogenic psychedelic analogs". Science. 375 (6579): 403–411. doi:10.1126/science.abl8615. ISSN 0036-8075.

• Fatty acid esters
• Lipids
• Endocannabinoids