olivetolic acid Chemical Properties

Melting point:

143 °C

Boiling point:

403.9±25.0 °C(Predicted)

Density 

1.237±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

3.41±0.34(Predicted)

form 

Solid

color 

Light Beige to Light Brown

Stability:

Hygroscopic

InChI

InChI=1S/C12H16O4/c1-2-3-4-5-8-6-9(13)7-10(14)11(8)12(15)16/h6-7,13-14H,2-5H2,1H3,(H,15,16)

InChIKey

SXFKFRRXJUJGSS-UHFFFAOYSA-N

SMILES

C(O)(=O)C1=C(CCCCC)C=C(O)C=C1O

olivetolic acid Usage And Synthesis

Uses

Olivetolic Acid is a precursor in the synthesis of primin and tetrahydrocannabinol.

Definition

ChEBI: A member of the class of benzoic acids that is salicylic acid in which the hydrogens ortho- and para- to the carboxy group are replaced by a pentyl and a hydroxy group, respectively.

Biosynthesis

Olivetolic acid (OLA) biosynthesis involves the condensation of one hexanoyl-CoA with three malonyl-CoAs by a type III PKS (tetraketide synthase) OLA synthase (C. sativa OLS; CsOLS) and an OLA cyclase (CsOAC), both enzymes were derived from the Cannabis species (C. sativa). Studies have achieved trace amount of OLA production in both E. coli and S. cerevisia[1]. Ma et al. find that Pseudomonas sp LvaE encoding a short-chain acyl-CoA synthetase can efficiently convert hexanoic acid to hexanoyl-CoA. The co-expression of the acetyl-CoA carboxylase, the pyruvate dehydrogenase bypass, the NADPH-generating malic enzyme, as well as the activation of peroxisomal β-oxidation pathway and ATP export pathway are effective strategies to redirect carbon flux toward OLA synthesis.

References

[1] Ma, J, Y. Gu, and P. Xu . "Biosynthesis of cannabinoid precursor olivetolic acid by overcoming rate-limiting steps in genetically engineered Yarrowia lipolytica." Cold Spring Harbor Laboratory(2021).