Olivetolic Acid (CAS No.491-72-5) is a polyketide compound with significant biological and industrial applications. Below is a detailed overview of its properties and uses.
Name :
Olivetolic acidCAS No. :
491-72-5MF :
C₁₂H₁₆O₄MW :
224.25Purity :
98%Appearance :
Off white powderStorage Condition :
Sealed in dry, Room TemperatureChemical Properties
|
Formal Name |
2,4-Dihydroxy-6-pentylbenzoic acid |
|
Synonyms |
OA;OLA;Olivetolate;Olivetolcarboxylic Acid;Allazetolcarboxylic acid |
|
CAS Number |
491-72-5 |
|
Molecular Formula |
C₁₂H₁₆O₄ |
|
Formula Weight |
224.25 g/mol |
Structure:
A benzoic acid derivative with hydroxyl (-OH) and pentyl (-C₅H₁₁) substituents at the 2nd and 4th positions, respectively.
Physical Characteristics:
Appearance: Off white powder
Melting point:143 °C
Boiling Point: 403.9±25.0 °C(Predicted)
Density: 1.237±0.06 g/cm3(Predicted)
Solubility: DMSO (Slightly), Methanol (Slightly)
Biological Activities
Precursor in Cannabinoid Synthesis:Olivetolic Acid is the psychoactive component of Cannabis sativa.It condenses with geranyl pyrophosphate to form cannabigerolic acid (CBGA), the precursor to other cannabinoids
Antimicrobial and Antioxidant Properties:Exhibits antimicrobial activity against certain bacterial strains and antioxidant effects, contributing to its potential in pharmaceutical formulations
Anti-Inflammatory and Neuroprotective Effects:Emerging research highlights its role in reducing inflammation and protecting neuronal cells, suggesting applications in neurodegenerative diseases.
Biosynthesis
Pathway: Produced via a polyketide synthase (PKS) pathway in Cannabis sativa:
Condensation: Hexanoyl-CoA and three malonyl-CoA units are combined by tetraketide synthase (CsOLS).
Cyclization: Olivetolic acid cyclase (CsOAC) forms the aromatic ring structure
Microbial Production: Engineered Yarrowia lipolyticaand E. colistrains have achieved trace OA synthesis by optimizing acyl-CoA synthesis and carbon flux redirection
Applications
Pharmaceuticals:
Core Cannabinoid Synthesis:Precursor in Cannabinoid Synthesis.Olivetolic Acid is the psychoactive component of Cannabis sativa.It condenses with geranyl pyrophosphate to form cannabigerolic acid (CBGA), the precursor to other cannabinoids.
Drug Discovery Scaffold:PPARγ Agonists;Anti-Inflammatory Agents;Neuroprotectants
Cosmetics: Anti-Aging Formulations;Skin Brightening;Acne Treatments
Biotechnology & Metabolic Engineering:Cannabinoid Pathway Optimization;Biosensor Design
Agriculture: Plant Defense Elicitor;Eco-Friendly Pesticides
Research Tools:Analytical Reference Standard;Metabolic Pathway Studies
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Shipment Guidelines
Labeling: Include hazard symbols CAS number, and "Keep Away from Heat/Incompatible Substances" warnings.
Air Freight: Preferred for urgent shipments; ensure packages meet IATA Dangerous Goods Regulations (DGR) for organic peroxides.
Shipping Modes:
Expedited: 3–5 business days (e.g., DHL Express) for time-sensitive research projects.
Standard: 7–14 days via sea freight, cost-effective for bulk orders.
Storage Conditions:
Pre-Shipment: Store at 2–8°C if light-sensitive; avoid freezing to prevent crystallization.
In Transit: Maintain ambient temperature (15–25°C) with humidity <60%. Use data loggers for real-time monitoring.
Risk Mitigation: Include desiccants and oxygen absorbers in packaging. Avoid prolonged exposure to sunlight or electromagnetic fields.
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