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2-Oleoylglycerol

From Wikipedia, the free encyclopedia
2-Oleoylglycerol
Names
IUPAC name
2-O-[(9Z)-Octadec-9-enoyl]glycerol
Systematic IUPAC name
1,3-Dihydroxypropan-2-yl (9Z)-octadec-9-enoate
Other names
2-Monoolein
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • 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- checkY
    Key: UPWGQKDVAURUGE-KTKRTIGZSA-N checkY
  • CCCCCCCCC=CCCCCCCCC(=O)OC(CO)CO
Properties
C21H40O4
Molar mass356.547 g·mol−1
Density0.958 g/cm3
Hazards
Flash point> 113.0 °C (235.4 °F; 386.1 K)
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Chemical compound

2-Oleoylglycerol (2OG) is amonoacylglycerol that is found in biologic tissues. Its synthesis is derived fromdiacylglycerol precursors. It is metabolized tooleic acid andglycerol primarily by the enzymemonoacylglycerol lipase (MAGL).[1] In 2011, 2OG was found to be an endogenous ligand toGPR119.[2] 2OG has been shown to increaseglucagon-like peptide-1 (GLP-1) andgastric inhibitory polypeptide (GIP) levels following administration to thesmall intestine.[2] 2OG has also been discovered to potentiate G protein and not β-arrestin signaling via allosteric binding of the 5-HT2A receptor.[3]

See also

[edit]

References

[edit]
  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. ^abHansen, 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.


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CB1Tooltip Cannabinoid receptor type 1
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CB2Tooltip Cannabinoid receptor type 2
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NAGly
(
GPR18)
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eCBTsTooltip Endocannabinoid transporter
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  • Others:2-PG(directly potentiates activity of 2-AG at CB1 receptor)
  • ARN-272(FAAH-like anandamide transporter inhibitor)
See also
Receptor/signaling modulators
Cannabinoids (cannabinoids by structure)
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