GenetixBayEST. 2009
Glossary · Cannabinoids and terpenes

Olivetolic acid

Olivetolic acid is the phenolic building block of cannabinoids; joined to geranyl pyrophosphate it forms CBGA, and its five-carbon chain becomes the pentyl tail of THC and CBD.

Also written OAolivetolateolivetolic

EstablishedDraft: awaiting expert reviewUpdated

Olivetolic acid is a polyketide made in trichome secretory cells from hexanoyl-CoA and three malonyl-CoA units. Two enzymes do the work: a polyketide synthase (often called olivetol synthase or tetraketide synthase) and olivetolic acid cyclase. The product is the aromatic ring and five-carbon (pentyl) side chain that every "regular" cannabinoid carries.

In practice

Growers never see olivetolic acid on a COA; it is consumed as fast as it is made. Its relevance is conceptual. The side-chain length is set here: when the plant starts from a shorter precursor it makes divarinic acid instead, and the whole downstream chain shifts to the propyl "varin" cannabinoids (CBGVA, THCVA, CBDVA). That is why THCV-rich plants tend to be lower in THC, not higher. Researchers producing cannabinoids in yeast also have to rebuild this step.

Don't confuse with

  • Olivetol: the decarboxylated form, used in chemical synthesis; not the natural plant substrate.
  • Geranyl pyrophosphate: the terpene-derived partner that joins olivetolic acid to make CBGA.
  • CBGA: the product, the first true cannabinoid in the pathway.

Related terms

Sources

  1. Gülck T, Møller BL. 2020. Phytocannabinoids: origins and biosynthesis. Trends in Plant Science 25(10):985-1004..
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