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Olivetol (5-Pentylresorcinol, CAS No. 500-66-3) is a naturally occurring phenolic compound with significant biological and chemical properties.

1. Chemical Structure and Properties

• Molecular Formula: C₁₁H₁₆O₂
• Molecular Weight: 180.24 g/mol
• Physical State: Solid, appearing as off-white to light-brown powder.
• Melting Point: 46–48°C.
• Solubility: Soluble in DMSO (dimethyl sulfoxide), with limited solubility in chloroform and methanol.
• Storage: Should be stored at -20°C under nitrogen to maintain stability and avoid degradation.

2. Natural Sources and Biological Activity

• Occurrence: Found in lichens and produced by certain insects.
• Biological Roles:
  • Cannabinoid Receptor Modulation: Acts as a competitive inhibitor of cannabinoid receptors CB1 and CB2, with IC₅₀ values of 15.3 μM (CB1) and 7.21 μM (CB2).
  • CYP450 Enzyme Inhibition: Inhibits CYP2C19 and CYP2D6 enzymes, with IC₅₀ values of 15.3 μM and 7.21 μM, respectively.
  • Antioxidant and Anti-inflammatory Properties: Demonstrates strong antioxidant activity, making it valuable in therapeutic applications.

3. Synthetic and Pharmaceutical Applications

• Synthetic Precursor: Used as a key intermediate in the synthesis of tetrahydrocannabinol (THC) and other cannabinoids.
• Therapeutic Potential:
  • Antioxidant Effects: Helps mitigate oxidative stress and associated diseases.
  • Anti-inflammatory Activity: Reduces inflammation by modulating enzyme activity and receptor interactions.
  • Metabolic Regulation: Inhibits enzymes involved in drug metabolism, such as CYP2C19 and CYP2D6, affecting the pharmacokinetics of co-administered drugs.

4. Safety and Usage Guidelines

• Purity and Handling: Available in high-purity grades (≥98%) for research purposes.
• Experimental Use: Intended for in vitro and in vivo studies only; not for human consumption.
• Safety Precautions:
  • Wear appropriate protective equipment (lab coat, gloves) to avoid skin and eye contact.
  • Avoid inhalation or ingestion; handle in a fume hood if working with volatile derivatives.
  • Store in a cool, dry place away from light to prevent degradation.

5. Research and Market Availability

• Research Focus: Ongoing studies explore its role in neuroprotection, obesity management, and cancer therapy.
• Suppliers: Available from chemical vendors  in various quantities and purities for research purposes.

6. Regulatory and Ethical Considerations

• Prohibited for Human Use: All products containing olivetol are strictly for scientific research or drug development.
• Ethical Compliance: Researchers must adhere to institutional guidelines and ethical standards when using olivetol in experiments.