From Wikipedia, the free encyclopedia
2-Oleoylglycerol
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Names
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IUPAC name
2-O-[(9Z)-Octadec-9-enoyl]glycerol
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Systematic IUPAC name
1,3-Dihydroxypropan-2-yl (9Z)-octadec-9-enoate
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Other names
2-Monoolein
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Identifiers
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ChemSpider
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UNII
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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- YKey: UPWGQKDVAURUGE-KTKRTIGZSA-N Y
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CCCCCCCCC=CCCCCCCCC(=O)OC(CO)CO
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Properties
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C21H40O4
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Molar mass
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356.547 g·mol−1
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Density
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0.958 g/cm3
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Hazards
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Flash point
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> 113.0 °C (235.4 °F; 386.1 K)
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Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound
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]
See also
References
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^ 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.
- ^
a
b 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.
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Receptor (
ligands) |
CB1Tooltip Cannabinoid receptor type 1 | Agonists (abridged,
full list) | |
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Inverse agonists | |
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Antagonists | |
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CB2Tooltip Cannabinoid receptor type 2 | Agonists |
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2-AG
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2-AGE (noladin ether)
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3,3'-Diindolylmethane
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4-O-Methylhonokiol
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α-Amyrin · β-Amyrin
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A-796,260
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A-834,735
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A-836,339
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AM-1172
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AM-1221
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AM-1235
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AM-1241
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AM-2232
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Anandamide
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AZ-11713908
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Cannabinol
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Caryophyllene
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CB-13
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CBS-0550
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CP 55,940
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GW-405,833 (L-768,242)
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GW-842,166X
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HU-308
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JTE 7-31
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JWH-007
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JWH-015
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JWH-018
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JWH-73
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JWH-133
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L-759,633
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L-759,656
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Lenabasum (anabasum)
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Magnolol
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MDA-19
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Nabitan
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NADA
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Olorinab (APD-371)
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PF-03550096
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S-444,823
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SER-601
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Serinolamide A
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UR-144
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Tedalinab
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THC (dronabinol)
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THCV
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Tetrahydromagnolol
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Virodhamine
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Antagonists | |
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NAGly (
GPR18) | |
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GPR55 | |
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GPR119 | |
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Transporter (
modulators) |
eCBTsTooltip Endocannabinoid transporter | |
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Enzyme (
modulators) | |
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Others |
- Others:
2-PG (directly potentiates activity of 2-AG at CB1 receptor)
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ARN-272 (FAAH-like anandamide transporter inhibitor)
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