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olivetolic acid

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CAS:491-72-5
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  • Olivetolic acid
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  • CAS:491-72-5
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  • CAS:491-72-5
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olivetolic acid Basic information
Product Name:olivetolic acid
Synonyms:olivetolic acid;2,4-Dihydroxy-6-pentylbenzoic acid;Olivetolcarboxylic acid;139400;olivanic acid powder 98%;Benzoic acid, 2,4-dihydroxy-6-pentyl-;Olivetolic acid 1000 μg/mL in Methanol;Olivetolic acid in Methanol
CAS:491-72-5
MF:C12H16O4
MW:224.25
EINECS:
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Mol File:491-72-5.mol
olivetolic acid Structure
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)
form Solid
pka3.41±0.34(Predicted)
color Light Beige to Light Brown
Stability:Hygroscopic
InChIInChI=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)
InChIKeySXFKFRRXJUJGSS-UHFFFAOYSA-N
SMILESC(O)(=O)C1=C(CCCCC)C=C(O)C=C1O
Safety Information
MSDS Information
olivetolic acid Usage And Synthesis
UsesOlivetolic Acid is a precursor in the synthesis of primin and tetrahydrocannabinol.
DefinitionChEBI: 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.
BiosynthesisOlivetolic 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).
olivetolic acid Preparation Products And Raw materials
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