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CAS 22976-40-5 Olivetol Dimethyl Ether,98%

Olivetol Dimethyl Ether C₁₃H₂₀O₂ CAS 22976-40-5

Olivetol Dimethyl Ether Off-White Solid CAS 22976-40-5

CAS 22976-40-5 Olivetol Dimethyl Ether,98%

Olivetol Dimethyl Ether (CAS No.22976-40-5) is a key intermediate in organic synthesis, particularly in cannabinoid chemistry. Below is a detailed overview of its properties, applications, and related information.Olivetol Dimethyl Ether is a synthetic aromatic organic compound. It is the fully methylated (protected) form of olivetol (5-pentylresorcinol), where the two phenolic hydroxyl groups (-OH) of olivetol are converted into methoxy groups (-OCH₃). This structural modification dramatically alters its chemical reactivity: it is less polar, more stable, and non-acidic compared to olivetol. It serves as a crucial protected intermediate in organic synthesis, particularly in the controlled, stepwise construction of cannabinoids and other complex natural products, preventing unwanted side reactions involving the phenolic groups.

Name :
Olivetol dimethyl ether
CAS No. :
22976-40-5
MF :
C₁₃H₂₀O₂
MW :
208.3
Purity :
98%
Appearance :
Off-white to yellow solid
Storage Condition :
Sealed in dry, Room Temperature

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Chemical Properties

CAS Number.: 22976-40-5

IUPAC Name: 1,3-Dimethoxy-5-pentylbenzene

Synonyms: 5-Pentyl-1,3-dimethoxybenzene; Olivetol dimethyl ether; 1,3-Dimethoxy-5-amylbenzene

Molecular Formula: C₁₃H₂₀O₂

Molecular Weight: 208.30 g/mol

Appearance: Off-white to yellow solid

Boiling Point: ~295-298°C

Solubility:

•Soluble in organic solvents (ethanol, methanol, DMSO, chloroform)

•Insoluble in water

Key Structural Features:

•Dimethyl-protected resorcinol core (methoxy groups at positions 1 and 3)

•n-Pentyl chain (-C₅H₁₁) at position 5

Functional Advantages & Applications

Olivetol Dimethyl Ether itself has no significant direct biological activity as a cannabinoid or pharmacologically active agent. Its biological profile is inert because the methoxy groups block its ability to interact with biological targets (like cannabinoid receptors) that typically require free phenolic hydroxyls. Its significance is purely chemical and synthetic. Any observed biological activity would be attributed to its metabolic de-methylation back to olivetol or other downstream products, which is not a primary or efficient pathway.

A. Primary Role: Protected Synthetic Intermediate

•Stability Enhancement: Methoxy groups prevent oxidation of phenolic hydroxyls, enabling long-term storage and simplified handling compared to olivetol.

•Synthetic Flexibility: Serves as a key precursor for:

•Cannabinoid synthesis (selective deprotection enables controlled functionalization)

•Pharmaceutical intermediates (alkylresorcinol-based bioactive molecules)

•Material science ligands (coordination chemistry frameworks)

B. Key Applications by Industry

Industry	Application	Advantage
Pharmaceutical R&D	Cannabinoid analog production	Enables multi-step synthesis without degradation
Organic Chemistry	Building block for complex molecules	Stable under acidic/basic conditions
Chemical Biology	Probe development for receptor studies	Improved cell permeability vs. phenolics

Synthetic Utility Comparison

Property	Olivetol Dimethyl Ether	Olivetol (Free Phenol)
Stability	High (stable at RT for months)	Low (oxidizes rapidly; requires -20°C)
Handling	Standard laboratory conditions	Cryogenic storage/argon protection
Functionalization	Selective deprotection (e.g., BBr₃)	Direct coupling (pH-sensitive)
Synthetic Yield	Higher in multi-step sequences	Limited by degradation

Natural Occurrence: This specific dimethyl ether is not a known natural product. Olivetol itself is a biosynthetic precursor in Cannabis sativa, but it is not stored or used in its methylated form in the plant's natural pathways.

Synthetic Production: It is produced synthetically in the laboratory via a simple and high-yielding alkylation reaction of olivetol. The standard method involves treating olivetol with an excess of methyl iodide (CH₃I) or dimethyl sulfate ((CH₃)₂SO₄) in the presence of a strong base (e.g., potassium carbonate, K₂CO₃) in a polar aprotic solvent like acetone or DMF. This reaction quantitatively converts the phenolic -OH groups into -OCH₃ groups.

Applications

Key Synthetic Intermediate in Cannabinoid Chemistry
This is its primary and most important application. It is used in classic total synthesis routes (e.g., the Mechoulam synthesis) to produce Δ⁹-THC, CBD, and their analogs. The dimethoxy group protects the reactive phenol sites during critical steps (like alkylation or cyclization) and is removed in a final deprotection step to reveal the active cannabinoid structure.
Organic Synthesis Building Block
Serves as a versatile precursor for synthesizing other substituted resorcinol derivatives, fragrances, and ligands for metal-organic complexes.
Chemical Standard & Research Tool
Used in analytical chemistry as a reference standard for chromatographic methods (GC-MS, HPLC) to study cannabinoid synthesis pathways or to identify related compounds.
Fragrance and Flavor Research
As a benzene derivative with an alkane chain, it may be used in the research and development of aromatic compounds, though not a major commercial product itself.

Safety & Handling

Storage Conditions:

•Stable at room temperature (no cryogenic requirement)

•Store in sealed containers under inert atmosphere (N₂/Ar)

Handling Precautions:

•Use standard PPE (gloves, goggles)

•Avoid prolonged skin contact (potential irritant)

Regulatory Status:

•Not controlled under international narcotics conventions

•Non-psychoactive and exempt from DEA scheduling

Our Advantage

Reducing energy consumption by 20% compared to industry averages.

Advanced Production Techniques
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Intellectual Property Dominance
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Digital Transformation
Integration of AI-driven systems optimizes production efficiency and enables predictive maintenance.

Shipment Guidelines

Packaging Requirements
Primary Packaging: Must be airtight, moisture-proof containers to prevent oxidation and humidity exposure.

Secondary Packaging: Use shockproof materials to avoid physical damage during transit.

Labeling: Include hazard symbols CAS number, and "Keep Away from Heat/Incompatible Substances" warnings.
Logistics Providers & Modes

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.
Temperature & Stability Control

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.

Q1: What is the main purpose of converting olivetol to its dimethyl ether?

A: The primary purpose is chemical protection. The free hydroxyl groups on olivetol are highly reactive, acidic, and can interfere with subsequent synthetic steps (e.g., by undergoing undesired O-alkylation or forming salts). Converting them to methoxy groups makes the molecule more stable and allows for selective reactions at other sites, which is essential for the precise, multi-step synthesis of cannabinoids.

Q2: Is Olivetol Dimethyl Ether legal?

A: It is generally legal to possess for research purposes as it is not a controlled substance (like THC) nor a direct precursor listed in many drug precursor monitoring regulations. However, because of its well-known and specific use in synthesizing controlled cannabinoids, its purchase by individuals may raise red flags with suppliers and authorities. Bulk commercial transactions are often monitored.

Q3: How is the dimethyl ether converted back to olivetol or a cannabinoid?

A: Through a deprotection reaction using a strong Lewis acid such as boron tribromide (BBr₃). This reagent cleaves the methyl ether bonds (demethylation), regenerating the free phenolic hydroxyl groups in the final step of a cannabinoid synthesis.

Q4: What are the key hazards and safety precautions?

A: It is an organic compound with likely irritation hazards. Always consult the Safety Data Sheet (SDS). Standard precautions include:

Use in a well-ventilated area or fume hood.

Wear appropriate PPE: safety glasses, gloves, and a lab coat.

Avoid contact with skin, eyes, and clothing.

It is likely flammable; keep away from heat and ignition sources.

Q5: How does it differ from Olivetol in terms of handling and storage?

A: Olivetol Dimethyl Ether is more stable and less sensitive to air oxidation than olivetol due to the protected phenols. While olivetol can darken upon exposure to air and light, the dimethyl ether is more robust. Both should still be stored in a cool, dry place, preferably under an inert atmosphere for long-term storage.

Q6: What is the key advantage of using this ether derivative over standard olivetol?

A: It provides significantly improved stability against oxidation compared to olivetol, while maintaining the essential pentylresorcinol structure. The protected phenolic groups prevent degradation during storage and handling, making it ideal for multi-step syntheses.

Q7: How is this compound typically used in cannabinoid research?

A: It serves as a protected intermediate in synthetic routes to various cannabinoids. The methyl ether groups can be selectively deprotected or utilized in direct coupling reactions, offering flexibility in synthetic strategy design.

Q8: What purity specifications do you offer?

A: We supply:

Research Grade: ≥97% purity

High Purity Grade: ≥99% purity

All batches are fully characterized by HPLC, GC-MS, and NMR with complete documentation.

Q9: Can the methyl ether groups be selectively removed?

A: Yes, the methyl ethers can be cleaved using standard demethylation conditions (e.g., BBr₃ in DCM) to regenerate the parent olivetol. This allows for strategic protection/deprotection in complex syntheses.

Q10: What is the recommended storage condition?

A: Store in sealed containers under inert atmosphere at room temperature. Unlike olivetol, it does not require cryogenic storage, demonstrating superior handling properties.

Q11: Do you provide custom synthesis of related ether derivatives?

A: Yes, we offer:

Analog synthesis with different alkyl chain lengths

Bulk quantities (up to kilogram scale)

Custom ether derivatives (e.g., ethyl, benzyl ethers)

Q12: Is this compound considered a controlled substance?

A: No. It is not listed in the UN Convention on Psychotropic Substances. However, regulations vary by country, and customers should verify compliance with their local regulations.

Q13: What documentation is provided with orders?

A: All shipments include:

Certificate of Analysis with full spectroscopic data

Material Safety Data Sheet (GHS compliant)

Stability and handling guidelines

Custom synthesis reports (for large orders)

Q14: What's the lead time for bulk orders?

A: Research quantities: 1-2 weeks

Bulk production: 3-5 weeks

Custom analogs: 4-6 weeks (consultation required)

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