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{{chembox
{{chembox
| Watchedfields = changed
| Watchedfields = changed
| verifiedrevid = 451300133
| verifiedrevid = 452062592
|ImageFile=2-Oleoylglycerol.svg
| ImageFile = 2-Oleoylglycerol.svg
|ImageSize=
| ImageSize =
|IUPACName=1,3-dihydroxypropan-2-yl (''Z'')-octadec-9-enoate
| IUPACName = 2-''O''-[(9''Z'')-Octadec-9-enoyl]glycerol
| SystematicName = 1,3-Dihydroxypropan-2-yl (9''Z'')-octadec-9-enoate
|OtherNames=2-Monoolein
| OtherNames = 2-Monoolein
|Section1= {{Chembox Identifiers
|Section1={{Chembox Identifiers
⚫
| CASNo=3443-84-3
| IUPHAR_ligand = 5112
⚫
| PubChem=5319879
| UNII_Ref = {{fdacite|correct|FDA}}
| CASNo_Ref = {{cascite|correct|??}}
⚫
| CASNo=3443-84-3
⚫
| PubChem=5319879
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 9A2389K694
| UNII = 9A2389K694
| SMILES=CCCCCCCCC=CCCCCCCCC(=O)OC(CO)CO
| SMILES = CCCCCCCCC=CCCCCCCCC(=O)OC(CO)CO
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4478086
| ChemSpiderID = 4478086
| 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-
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
⚫
| InChIKey = UPWGQKDVAURUGE-KTKRTIGZBO
| StdInChI = 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-
| StdInChI = 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-
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = UPWGQKDVAURUGE-KTKRTIGZSA-N
⚫
| StdInChIKey = UPWGQKDVAURUGE-KTKRTIGZSA-N
}}
}}
|Section2= {{Chembox Properties
|Section2={{Chembox Properties
| C=21 | H=40 | O=4
| Formula=C<sub>21</sub>H<sub>40</sub>O<sub>4</sub>
⚫
| Appearance =
| MolarMass=356.5399
⚫
| Density = 0.958 g/cm<sup>3</sup>
⚫
| Appearance=
⚫
| MeltingPt =
⚫
| Density=0.958 g/cm<sup>3</sup>
⚫
| BoilingPt =
⚫
| MeltingPt=
⚫
| Solubility =
⚫
| BoilingPt=
⚫
| Solubility=
}}
}}
|Section3= {{Chembox Hazards
|Section3={{Chembox Hazards
| MainHazards=
| MainHazards =
| FlashPt= >113.0° C
| FlashPt = >
| FlashPtC = 113.0
| Autoignition=
| AutoignitionPt =
}}
}}
}}
}}

'''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).<ref>{{cite pmid|12136125}}</ref> In 2011, 2OG was found to be an endogenous ligand to [[GPR119]].<ref name=hansen2011>{{cite pmid|21778222}}</ref> 2OG has been shown to increase [[Glucagon-like peptide-1]] (GLP-1) and [[Gastric inhibitory polypeptide]] (GIP) levels following administration to the [[small intestine]].<ref name=hansen2011/>
'''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).<ref>{{Cite journal
| last1 = Dinh | first1 = T. P.
| last2 = Carpenter | first2 = D.
| last3 = Leslie | first3 = F. M.
| last4 = Freund | first4 = T. F.
| last5 = Katona | first5 = I.
| last6 = Sensi | first6 = S. L.
| last7 = Kathuria | first7 = S.
| last8 = Piomelli | first8 = D.
| title = Brain monoglyceride lipase participating in endocannabinoid inactivation
| doi = 10.1073/pnas.152334899
| journal = Proceedings of the National Academy of Sciences
| volume = 99
| issue = 16
| pages = 10819–10824
| pmc = 125056
| year = 2002
| pmid = 12136125
| bibcode = 2002PNAS...9910819D
| doi-access = free
}}</ref> In 2011, 2OG was found to be an endogenous ligand to [[GPR119]].<ref name=hansen2011>{{Cite journal
| last1 = Hansen | first1 = K. B.
| last2 = Rosenkilde | first2 = M. M.
| last3 = Knop | first3 = F. K.
| last4 = Wellner | first4 = N.
| last5 = Diep | first5 = T. A.
| last6 = Rehfeld | first6 = J. F.
| last7 = Andersen | first7 = U. B.
| last8 = Holst | first8 = J. J.
| last9 = Hansen | first9 = H. S.
| doi = 10.1210/jc.2011-0647
| title = 2-Oleoyl Glycerol is a GPR119 Agonist and Signals GLP-1 Release in Humans
| journal = Journal of Clinical Endocrinology & Metabolism
| volume = 96
| issue = 9
| pages = E1409–E1417
| year = 2011
| pmid = 21778222
| doi-access = free
}}</ref> 2OG has been shown to increase [[glucagon-like peptide-1]] (GLP-1) and [[gastric inhibitory polypeptide]] (GIP) levels following administration to the [[small intestine]].<ref name=hansen2011/> 2OG has also been discovered to potentiate G protein and not β-arrestin signaling via allosteric binding of the 5-HT<small>2A</small> receptor.<ref>{{Cite journal |last=Cao |first=Dongmei |last2=Yu |first2=Jing |last3=Wang |first3=Huan |last4=Luo |first4=Zhipu |last5=Liu |first5=Xinyu |last6=He |first6=Licong |last7=Qi |first7=Jianzhong |last8=Fan |first8=Luyu |last9=Tang |first9=Lingjie |last10=Chen |first10=Zhangcheng |last11=Li |first11=Jinsong |last12=Cheng |first12=Jianjun |last13=Wang |first13=Sheng |date=2022-01-28 |title=Structure-based discovery of nonhallucinogenic psychedelic analogs |url=https://www.science.org/doi/10.1126/science.abl8615 |journal=Science |language=en |volume=375 |issue=6579 |pages=403–411 |doi=10.1126/science.abl8615 |issn=0036-8075}}</ref>


==See also==
==See also==
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{{Reflist}}
{{Reflist}}



⚫
[[Category:Carboxylate esters]]
{{Neurotransmitters}}
{{Cannabinoidergics}}

{{DEFAULTSORT:Oleoylglycerol, 2-}}

⚫
[[Category:Fatty acid esters]]
[[Category:Lipids]]
[[Category:Lipids]]
[[Category:Endocannabinoids]]
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