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Olivetolic acid (OA) is a key biosynthetic precursor to olivetolic acid-derived cannabinoids, including
-THC and CBD, serving as a versatile building block for customized cannabinoid synthesis. Its 2,4-dihydroxybenzoate structure allows for specific modifications, particularly at the C2, C4, or side-chain positions, to produce unnatural cannabinoids with varying side chains.
Key Aspects of Olivetolic Acid for Derivatization
- Biosynthesis & Sourcing: OA is produced by the condensation of one hexanoyl-CoA and three malonyl-CoA molecules, catalyzed by olivetol synthase (OLS) and olivetolic acid cyclase (OAC). Microbial engineering (e.g., in E. coli or Y. lipolytica) is used to produce higher titers for synthetic biology applications.
- Derivatization Sites: The structure enables aromatic prenylation (e.g., adding geranyl pyrophosphate to create CBGA) or methylation to modulate pharmacological activity.
- Orthogonal Protection: Techniques include creating methyl ethers or using catalytic oxidative approaches to yield olivetol derivatives.
- Analytical Techniques: The compound can be analyzed via liquid chromatography-mass spectrometry (LC-MS).
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Olivetol Series Products,CBD Derivatives - Qixi Chemicals
qixiolivetol.com
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qixiolivetol.com
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Qixiolivetol.com supplies Olivetol Series, CBD Derivatives and Benzoquinone Compounds. It offers custom synthesis, bulk supply and pharmaceutical ...
Structure of the Cannabis sativa olivetol‐producing enzyme ...
PubMed Central (PMC) (.gov)
https://pmc.ncbi.nlm.nih.gov › articles › PMC7217186
PubMed Central (PMC) (.gov)
https://pmc.ncbi.nlm.nih.gov › articles › PMC7217186
by LJ Kearsey2019Cited by 56 — TKS is a type III polyketide synthase, and the question arises why it is unable to form olivetolic acid directly, but instead forms this unwanted side product.Read more
Application Notes and Protocols for the Derivatization of ...
Benchchem
https://www.benchchem.com › pdf › Application_...
Benchchem
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Olivetol, a resorcinolic lipid, is a key precursor in the biosynthesis of cannabinoids, including tetrahydrocannabinol (THC) and cannabidiol (CBD).Read more
Catalytic Synthesis of Olivetol and Derivatives - Thieme Gruppe
Thieme Group
https://www.thieme.de › thieme-chemistry › synform-n...
Thieme Group
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We report a catalytic oxidative approach to aromatization leading to the synthesis olivetol and olivetolate ester derivatives as well as orthogonally protected ...Read more
Identification and Optimization of more Efficient Olivetolic Acid ...
PubMed Central (PMC) (.gov)
https://pmc.ncbi.nlm.nih.gov › articles › PMC11685297
PubMed Central (PMC) (.gov)
https://pmc.ncbi.nlm.nih.gov › articles › PMC11685297
by Y Yang2024 — Olivetolic acid (OLA) is a key intermediate in cannabidiol (CBD) synthesis, and cannabinoids are important neuroactive drugs.
Development of a Novel Olivetolic Acid Production Platform ...
eScholarship
https://escholarship.org › item
eScholarship
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by I Okorafor2023 — I describe the development of an olivetolic acid platform that represents a new strategy to produce cannabinoid precursors in microbes without relying on plant ...Read more
AU2019242553A1 - Biosynthesis of olivetolic acid
Google Patents
https://patents.google.com › patent
Google Patents
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[0005] Currently, the production of olivetolic acid and its derivatives is primarily through direct extraction from plants. ... derivatization at 70 °C for 1 h.Read more
Complete biosynthesis of cannabinoids and their unnatural ...
ResearchGate
https://www.researchgate.net › ... › Yeasts
ResearchGate
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Mar 21, 2019 — Expression of the genes encoding CsTKS and CsOAC produced olivetolic acid, which was prenylated by CsPT4. The resulting CBGA was transformed to ...Read more
Olivetolic Acid (CAS 491-72-5)
Cayman Chemical
https://www.caymanchem.com › product › olivetolic-acid
Cayman Chemical
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Olivetolic acid (Item No. 26282) is an analytical reference standard categorized as an intermediate in the phytocannabinoid biosynthetic pathway.Read more
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What is the use of olivetolic acid?
Olivetolic acid is a biosynthetic precursor of cannabinol acid (CBGA). Olivetolic acid exhibits a modest anticonvulsant effect in a mouse model of Dravet syndrome. Olivetolic acid can be used for the study of convulsion.
Olivetolic acid | Anticonvulsant Agent - MedchemExpress.com
MedchemExpress.com
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MedchemExpress.com
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What is the biosynthesis of olivetolic acid?
Olivetolic acid (OLA) biosynthesis involves the condensation of one hexanoyl-CoA with three malonyl-CoAs by OLA synthase (OLS) to construct a linear tetraketide, which is then converted into OLA by olivetolate cyclase (OAC), both of which are derived from C. sativa.Feb 2, 2025
Efficient Escherichia coli Platform for Cannabinoid Precursor Olivetolic ...
ACS Publications - American Chemical Society
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ACS Publications - American Chemical Society
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Biosynthesis of Nature-Inspired Unnatural Cannabinoids
MDPI
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MDPI
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by KJH Lim2021Cited by 31 — Instead, a cyclase enzyme, olivetolic acid cyclase (OAC), catalyzes the necessary C2 to C7 aldol condensation reaction to produce olivetolic acid (OLA) [24].Read more