Olivetol
[CAS# 500-66-3]

Identification

• Classification: Natural product >> Natural phenols
• Name: Olivetol
• Synonyms: 3,5-Dihydroxyamylbenzene; 5-Pentyl-1,3-benzenediol; 5-Pentylresorcinol
• Molecular Formula: C₁₁H₁₆O₂
• Molecular Weight: 180.25
• CAS Registry Number: 500-66-3
• EC Number: 207-908-8
• SMILES: CCCCCC1=CC(=CC(=C1)O)O

Properties

• Density: 1.1±0.1 g/cm³ Calc.^*
• Melting point: 46 - 48 °C (Expl.)
• Boiling point: 313.3±12.0 °C 760 mmHg (Calc.)^*, 539.5 - 543 °C (Expl.)
• Flash point: 148.8±14.2 °C (Calc.)^*, 113 °C (Expl.)
• Index of refraction: 1.547 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

Olivetol, chemically known as 5-pentylresorcinol or 5-pentyl-1,3-benzenediol, is a naturally occurring phenolic compound classified as an alkylresorcinol. It possesses a benzene ring substituted with two hydroxyl groups in the meta position (1,3) and a linear pentyl side chain. This simple yet structurally significant molecule is found in certain species of lichen and other plant sources and is notable for its role in the biosynthesis of cannabinoids.

The molecular formula of olivetol is C₁₁H₁₆O₂, and it appears as a pale yellow crystalline solid. Its structure features a hydrophobic pentyl chain and hydrophilic phenolic hydroxyls, imparting amphipathic properties that influence its solubility and interaction with biological membranes.

Olivetol has drawn scientific interest primarily for its relevance in cannabinoid chemistry. It serves as a biosynthetic precursor to tetrahydrocannabinol (THC) in *Cannabis sativa*, where it condenses with geranyl pyrophosphate in an enzyme-catalyzed reaction to form cannabigerolic acid (CBGA), the central intermediate to various cannabinoids. This key reaction represents a rare natural polyketide-terpenoid coupling.

In synthetic chemistry, olivetol is used to produce THC analogs under controlled conditions. When reacted with monoterpenes or their derivatives under acidic or Lewis acid catalysis, it can yield synthetic cannabinoids, including ∆⁹-THC, which exhibit biological activities such as analgesia, antiemesis, and psychoactivity. This route, while of academic interest, is tightly regulated due to the legal status of cannabinoids in many jurisdictions.

Beyond its cannabinoid-related significance, olivetol has demonstrated potential antioxidant and antimicrobial properties in vitro. Its two phenolic groups can act as hydrogen donors, quenching reactive oxygen species and stabilizing free radicals. This suggests possible utility in oxidative stress research or as a natural antioxidant in formulations. Moreover, alkylresorcinols like olivetol have been reported to inhibit the growth of certain bacteria and fungi, likely due to their membrane-disruptive activity.

Despite these bioactivities, olivetol itself is not widely used in pharmaceutical applications. It is more commonly encountered as a research chemical and a synthetic intermediate. Its commercial availability and structural simplicity make it a useful model compound for studying phenolic lipids and their biophysical properties.

Toxicological data on olivetol remain limited, but it is generally considered to have low acute toxicity. Nevertheless, as with many phenolic compounds, high doses may lead to irritation or adverse effects on cells due to oxidative or membrane-disruptive actions.

In conclusion, olivetol is a small but chemically and biologically significant molecule. Its role in the biosynthesis of cannabinoids, combined with its antioxidant and antimicrobial properties, has positioned it as a compound of interest in natural product chemistry and drug discovery.

References

2024. Optimizing hexanoic acid biosynthesis in Saccharomyces cerevisiae for the de novo production of olivetolic acid. Biotechnology for Biofuels and Bioproducts, 17(1).
DOI: 10.1186/s13068-024-02586-2

2023. Anti-obesity effects of olivetol in adult zebrafish model induced by short-term high-fat diet. Scientific Reports, 13(1).
DOI: 10.1038/s41598-023-44462-3

2025. A series of cannabinoids including, cannabidiol, cannabigerol, cannabichromene, and δ8- and δ9-tetrahydrocannabinol are estimated using synthetic and retrosynthetic analysis, group additivity, and experiment. Structural Chemistry, 36(6).
DOI: 10.1007/s11224-025-02545-z