2-OG.2-oleoylglycerol

2-Oleoylglycerol is a monounsaturated 2-monoacylglycerol, a congener of 2-AG, whose established pharmacology is intestinal rather than cannabinoid. Released into the lumen of the small intestine by pancreatic lipase, it activates GPR119 on enteroendocrine cells, at micromolar concentrations in cell systems, and triggers GLP-1 and GIP secretion; jejunal administration in healthy volunteers reproduced that response (Hansen 2011), and a controlled nutrition study concluded that the 2-monoacylglycerol fraction of olive oil was enough to account for the release of GLP-1, PYY and neurotensin (Mandøe 2015). On the endocannabinoid side, the available demonstration concerns CB1 and is negative: no inhibition of neurotransmission via CB1, no modulation of cyclic AMP, ERK or β-arrestin recruitment by that receptor (Murataeva 2016). The old entourage-effect hypothesis, in which this inactive lipid would reinforce 2-AG, has not been confirmed: in autaptic neurons it behaved as a functional CB1 antagonist and interfered with receptor internalisation. Human data are limited to a few short physiological studies of incretin secretion; no clinical efficacy, no long-term safety and no pattern of use are established, and nothing indicates a validated therapeutic benefit.

Source

An endogenous mammalian molecule and a normal product of intestinal lipolysis: it appears in the lumen of the small intestine at every fatty meal, and it has been found in brain tissue, spleen and the digestive tract alongside 2-AG. It does not belong to the hemp phytocomplex and is not a plant cannabinoid. Its technical form, monoolein, is among the synonyms of the food additive E471 and is used as an emulsifier.

2-oleoylglycerol arises from the digestion of fats: pancreatic lipase hydrolyses the sn-1 and sn-3 positions of triglycerides rich in oleic acid, those of olive oil for example, and leaves a 2-monoacylglycerol that retains the oleoyl chain in the central position. A second pathway, common to endogenous 2-acylglycerols, proceeds through the hydrolysis of membrane diacylglycerols, which explains the presence of this lipid in tissues alongside 2-AG. Cannabis does not produce it: the origin is dietary and endogenous.

European Union

No classification at European level: the substance appears neither in the international narcotics conventions monitored by the UNODC and the INCB, nor in the lists of new psychoactive substances monitored by the EUDA. It is, on the other hand, regulated as a component of the mono- and diglycerides of fatty acids (E471), of which monoolein is a synonym within the meaning of Regulation (EU) No 231/2012; the re-evaluation published by EFSA in 2017 concluded that no numerical acceptable daily intake was necessary and that this additive raised no concern at the reported uses and use levels. No specific authorisation is documented for isolated use as an active ingredient in a food supplement.

France

No French text classifies 2-oleoylglycerol. The decree of 22 February 1990, annex IV, covers "Tetrahydrocannabinols, their esters, ethers, salts as well as the salts of the aforementioned derivatives": this generic clause covers only tetrahydrocannabinol derivatives, whereas the molecule is an ester of oleic acid and glycerol, with no tetrahydrocannabinol ring. It is therefore neither named by the ANSM nor caught by the clause, and remains unclassified. It is, moreover, an endogenous compound and a normal product of the digestion of fats, present in everyday food; its technical form, monoolein, falls under the food-additives regulations.

Sources: EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA. Our method.

Family

Endocannabinoid or related mediator › Endocannabinoidome

Verification

Every fact on this entry was checked against its primary sources on 20 October 2026.

Wikipedia (English)

2-Oleoylglycerol (new tab)

Article paired by the molecule's structure (InChIKey), revision read on 19 October 2026. Read as a second opinion, never cited as a source.

1. 1Hansen KB et al., 2-Oleoyl glycerol is a GPR119 agonist and signals GLP-1 release in humans, J Clin Endocrinol Metab, 2011 (new tab)PMID 21778222
2. 2Murataeva N et al., Where's my entourage? The curious case of 2-oleoylglycerol, 2-linolenoylglycerol, and 2-palmitoylglycerol, Pharmacol Res, 2016 (new tab)PMID 27117667
3. 3Mandøe MJ et al., The 2-monoacylglycerol moiety of dietary fat appears to be responsible for the fat-induced release of GLP-1 in humans, Am J Clin Nutr, 2015 (new tab)PMID 26178726
4. 4Ben-Shabat S et al., An entourage effect: inactive endogenous fatty acid glycerol esters enhance 2-arachidonoyl-glycerol cannabinoid activity, Eur J Pharmacol, 1998 (new tab)PMID 9721036
5. 5EFSA ANS Panel, Re-evaluation of mono- and di-glycerides of fatty acids (E 471) as food additives, EFSA Journal, 2017 (new tab)
6. 6Order of 22 February 1990 setting the list of substances classified as narcotics, Annex IV (Légifrance) (new tab)
7. 7PubChem, 2-Oleoylglycerol, CID 5319879 (new tab)

SMILES

CCCCCCCC/C=C\CCCCCCCC(=O)OC(CO)CO

Machine-readable entry (JSON)

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