Ethyl Olivetolate (CAS No.38862-65-6) is a synthetic organic chemical belonging to the important class of alkylresorcinol derivatives. Its structure, featuring a resorcinol core modified with a pentyl chain and an ethyl ester, makes it a valuable intermediate in specialized chemical research and development.
Name :
Ethyl OlivetolateCAS No. :
38862-65-6MF :
C₁₄H₂₀O₄MW :
252.31Purity :
98%Appearance :
White to light brown solid or viscous oil (depending on purity)Storage Condition :
Store in a cool, dry place away from oxidizers and direct sunlight.Chemical Properties
Molecular Formula: C₁₄H₂₀O₄
Molecular Weight: 252.31 g/mol
Systematic Name: Ethyl 2,4-dihydroxy-6-pentylbenzoate
CAS Number: 38862-65-6
Solubility: It is typically soluble in common organic solvents (e.g., ethanol, methanol, ethyl acetate, acetone, DMSO, chloroform) but is practically insoluble in water due to the long alkyl chain.
Appearance: White to light brown solid or viscous oil (depending on purity)
Structural and Physical Properties:
Core Structure: The molecule is based on a 1,3-dihydroxybenzene (resorcinol) core. This makes it a phenolic compound.
Functional Groups:
Two Phenolic Hydroxyl Groups (-OH): Located at the metaposition to each other. These groups are weakly acidic, can form hydrogen bonds, and are susceptible to electrophilic substitution reactions and derivatization (e.g., alkylation, acylation).
Ethyl Ester Group (-COOCH₂CH₃): This group is hydrolyzable under acidic or basic conditions and contributes to the molecule's lipophilicity.
n-Pentyl Chain (-C₅H₁₁): A hydrophobic alkyl chain attached to the aromatic ring, which significantly increases the molecule's lipid solubility.
Amphiphilic Nature: The combination of a polar, hydrophilic dihydroxy aromatic ring and a hydrophobic pentyl tail gives the molecule surfactant-like properties.
Biological Activities
While specific studies on this exact ester may be limited, its biological activity can be inferred from its structural class—alkylresorcinols.
•Antimicrobial Activity: Alkylresorcinols are well-known for their antibacterial and antifungal properties. The alkyl chain length is a critical factor in this activity, with C5-C17 chains generally showing efficacy by disrupting microbial cell membranes.
•Antioxidant Activity: The resorcinol (1,3-dihydroxybenzene) structure is a potent free radical scavenger. The phenolic hydroxyl groups can donate hydrogen atoms to neutralize reactive oxygen species (ROS), making this compound and its derivatives of interest for combating oxidative stress.
•Potential in Cannabinoid Research: The structure, featuring a pentyl-substituted resorcinol, is a classic pharmacophore found in natural and synthetic cannabinoids. This compound can serve as a key synthetic precursor or a model compound in the study of cannabinoid receptor interactions.
•Enzyme Inhibition: Some alkylresorcinols exhibit activity as enzyme inhibitors (e.g., against lipoxygenase, tyrosinase), which could be relevant for pharmaceutical or cosmetic applications.
Synthesis
The synthesis of this compound is not a standard undergraduate procedure but is achieved through classic organic synthesis methods, often involving a Friedel-Crafts Acylation as a key step. A common route might involve:
1.Protection of a Resorcinol Derivative: One hydroxyl group of resorcinol may be protected (e.g., with a benzyl or MOM group) to control regioselectivity.
2.Introduction of the Pentyl Chain: A common method is via Friedel-Crafts acylation with a pentanoyl chloride derivative, followed by Clemmensen reduction or Wolff-Kishner reduction to convert the resulting ketone (-COC₄H₉) to the alkyl chain (-C₅H₁₁).
3.Esterification: The carboxylic acid functionality can be introduced via a reaction like the Kolbe-Schmitt reaction (with CO₂ under pressure) on the alkylresorcinol, which would directly provide the hydroxybenzoic acid. This acid is then esterified with ethanol under standard conditions (e.g., acid-catalyzed Fischer esterification or via acyl chloride).
4.Deprotection: If protecting groups were used, a final deprotection step yields the target dihydroxy compound.
Applications
•Organic Synthesis Intermediate: This is its primary application. It serves as a versatile building block (synthon) for the synthesis of more complex molecules, particularly:
•Cannabinoid Analogs: It is a crucial precursor in the research and development of novel synthetic cannabinoids for pharmacological study.
•Ligands for Material Science: Used to create ligands for metal-organic frameworks (MOFs) or other coordination polymers.
•Specialty Surfactants & Ligands: Its amphiphilic nature makes it useful for designing new surfactants or extractants.
•Pharmaceutical Research: Used in early-stage drug discovery for screening compounds with antimicrobial, antioxidant, or anti-inflammatory potential.
•Agrochemical Research: Potential use as an intermediate in the synthesis of new fungicides or herbicides, leveraging its innate bioactive properties.
•Fragrance and Flavor Industry: Some alkylresorcinol derivatives find use as intermediates in the synthesis of aroma chemicals.
Summary: Benzoic acid, 2,4-Dihydroxy-6-pentyl-, ethyl ester (CAS 38862-65-6) is a specialty fine chemical whose value lies in its unique molecular structure. It acts as a key intermediate in organic synthesis, most notably in cannabinoid research, and exhibits intrinsic biological activities common to alkylresorcinols, including antimicrobial and antioxidant effects. Its synthesis involves multi-step organic transformations, and its applications are primarily within research and development laboratories.
Safety and Handling
No standard Safety Data Sheet (SDS) is widely publicized for this specific compound.
General precautions for laboratory chemicals should be strictly followed:
•Assume it may cause skin and eye irritation.
•Avoid creating or breathing dust.
•Use in a well-ventilated area or fume hood.
•Wear appropriate personal protective equipment (PPE): safety glasses, gloves, and a lab coat.
For safe handling, always consult a product-specific Safety Data Sheet (SDS) from a reliable supplier before use.
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Reducing energy consumption by 20% compared to industry averages.
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.
FAQ
Q1: What is the primary application of this specific ester derivative?
A: This compound serves as a key protected intermediate in organic synthesis, particularly valuable for constructing cannabinoid analogs and other alkylresorcinol-based bioactive molecules. The ethyl ester group provides enhanced stability and modified reactivity compared to carboxylic acid derivatives.
Q2: What advantages does the ethyl ester offer over methyl ester analogs?
A: The ethyl ester provides:
•Improved lipophilicity for better membrane permeability in biological systems
•Different metabolic stability profiles in pharmacological studies
•Alternative crystallization properties for purification
•Expanded versatility in synthetic route design
Q3: What purity specifications are available?
A: We supply:
•Research Grade: ≥97% purity
•High Purity Grade: ≥99% purity
All batches include HPLC purity analysis and NMR structural confirmation with full documentation.
Q4: How does the pentyl chain length affect the compound's properties?
A: The C5 alkyl chain:
•Provides optimal lipid solubility for biological activity
•Matches the natural cannabinoid pharmacophore length
•Influences crystal packing and physical properties
•Affects receptor binding affinity in downstream molecules
Q5: What is the recommended storage and handling?
A: Store in sealed containers under inert atmosphere at 2-8°C. Protect from moisture and light. The compound is stable for at least 24 months when properly stored.
Q6: Can you customize the alkyl chain length or ester group?
A: Yes, we offer:
•Chain length variations (C3-C8 alkyl groups)
•Ester modifications (methyl, propyl, butyl esters)
•Bulk custom synthesis services
Contact our synthesis team with specific requirements.
Q7: Is this compound subject to regulatory restrictions?
A: This synthetic intermediate is not regulated under international drug conventions. However, customers should verify compliance with their local regulations regarding cannabinoid synthesis precursors.
Q8: What documentation accompanies orders?
A: All shipments include:
•Certificate of Analysis with chromatographic data
•Structural characterization reports (NMR, MS)
•Material Safety Data Sheet
•Stability and handling guidelines
Q9: What's the lead time for custom synthesis projects?
A: •Standard compounds: 2-3 weeks
•Custom analogs: 4-6 weeks
•Kilogram quantities: 5-8 weeks
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Ethyl Olivetolate (CAS No.38862-65-6) is a synthetic organic chemical belonging to the important class of alkylresorcinol derivatives. Its structure, featuring a resorcinol core modified with a pentyl chain and an ethyl ester, makes it a valuable intermediate in specialized chemical research and development.
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