Olivetol

Olivetol (5-pentylresorcinol) is the alkylresorcinol that forms the aromatic core of the cannabinoids. In Cannabis sativa the pathway starts with a tetraketide synthase that assembles a linear intermediate; olivetolic acid cyclase, identified in 2012, closes it into olivetolic acid, the precursor of cannabigerolic acid. Without this cyclase the same reaction gives olivetol by decarboxylation, which explains why an enzyme cloned in 2009 was first named olivetol synthase. Olivetol is therefore not a cannabinoid but a side product of their biosynthesis and a classic intermediate of their chemical synthesis. At the human CB1 receptor, a 2022 study reports partial displacement of the radioligand (estimated Ki of 17 nM) with no measurable agonist activity.

Source

A simple alkylresorcinol. In hemp it forms as a side product of the cannabinoid pathway, by decarboxylation of the precursor of olivetolic acid. It is not a cannabinoid: it is the phenolic half from which cannabinoids are built.

Biosynthetic pathway: the hemp tetraketide synthase, a type III polyketide synthase, assembles a linear tetraketide intermediate. In the presence of olivetolic acid cyclase, a C2 to C7 aldol condensation with carboxylate retention gives olivetolic acid, the first intermediate of the cannabinoid pathway. In the absence of this cyclase, a non-enzymatic decarboxylative aldol condensation gives olivetol, a side product of the reaction. Olivetolic acid is then prenylated into cannabigerolic acid, from which THCA, CBDA and CBCA derive.

European Union

No control measure of its own at European Union level. The molecule appears in no schedule of the 1961 Convention on Narcotic Drugs or of the 1971 Convention on Psychotropic Substances. It holds no marketing authorisation and no novel food authorisation under Regulation (EU) 2015/2283: it circulates only as a chemical or reference standard intended for research.

France

Unscheduled substance. Olivetol is named in no annex of the order of 22 February 1990 and falls under no generic clause: it is neither a tetrahydrocannabinol nor a derivative of the benzo[c]chromene nucleus targeted by the ANSM decision of 22 May 2024. It is a laboratory chemical, with no status as a food or cosmetic ingredient.

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

1. 1Gagne et coll., identification de la cyclase de l'acide olivétolique de Cannabis sativa, PNAS 2012 (new tab)PMID 22802619
2. 2Taura et coll., caractérisation de l'olivétol synthase, polykétide synthase de la voie de biosynthèse des cannabinoïdes, FEBS Letters 2009 (new tab)PMID 19454282
3. 3Kearsey et coll., structure de l'enzyme productrice d'olivétol de Cannabis sativa et plasticité de cyclisation des polykétide synthases de type III, FEBS Journal 2020 (new tab)PMID 31605668
4. 4Zagzoog et coll., modulation de l'activité du récepteur cannabinoïde de type 1 par des sous-produits cannabinoïdes de Cannabis sativa et des phytomolécules non cannabiques, Frontiers in Pharmacology 2022 (new tab)PMID 36091813
5. 5Légifrance, annexe IV de l'arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants (new tab)
6. 6PubChem CID 10377 : olivétol (identifiants) (new tab)

SMILES

CCCCCC1=CC(=CC(=C1)O)O

InChIKey

IRMPFYJSHJGOPE-UHFFFAOYSA-N

Machine-readable entry (JSON)

LLM ingestion format: a structured superset of the entry (identifiers, binding, versioned legal status). Full corpus.