Methyl olivetolate (CAS No.58016-28-7) is a specialty chemical synthon belonging to the class of alkyl-substituted dihydroxybenzoate esters. This compound features a unique molecular architecture that combines a resorcinol-derived aromatic core with a lipophilic pentyl chain and a versatile methyl ester group, making it a valuable intermediate for advanced organic synthesis and pharmaceutical research.
Name :
Methyl olivetolateCAS No. :
58016-28-7MF :
C₁₃H₁₈O₄MW :
238.28Purity :
98%Appearance :
Yellow solid or oil (depending on purity)Storage Condition :
Store in a cool, dry place under inert atmosphereChemical Identity and Structural Features
CAS Number: 58016-28-7
Systematic IUPAC Name: Methyl 2,4-dihydroxy-6-pentylbenzoate
Molecular Formula: C₁₃H₁₈O₄
Molecular Weight: 238.28 g/mol
Appearance: Yellow solid or oil (depending on purity)
Melting Point: 105–106°C (benzene solvent)
Boiling Point: Predicted 409.3 ± 30.0°C
Density: 1.153 ± 0.06 g/cm³ (predicted)
Solubility: Sparingly soluble in water; soluble in dichloromethane, ethyl acetate, ethanol, and chloroform
pKa: 8.30 ± 0.23 (predicted)
Structural Features:
The molecule consists of three key functional elements:
Resorcinol core (1,3-dihydroxybenzene ring) providing hydrogen-bonding capacity and weak acidity
n-Pentyl chain (-C₅H₁₁) at the 6-position conferring lipophilicity
Methyl ester group (-COOCH₃) offering a site for hydrolysis or further functionalization
Synthesis and Production
Synthesis Pathway:
Alkylation: Introduce pentyl chain via Friedel-Crafts alkylation.
Hydroxylation: Introduce hydroxyl groups at positions 2 and 4 using oxidative agents.
Esterification: React with methanol to form the methyl ester
Functional Properties and Characteristicsproduct introduction
Amphiphilic Nature: The compound exhibits dual solubility characteristics due to its polar phenolic groups and non-polar alkyl chain
Chemical Reactivity: The phenolic -OH groups can participate in hydrogen bonding and can be selectively functionalized (e.g., alkylation, acylation)
Stability: The methyl ester provides improved stability compared to free acid forms while remaining synthetically accessible
Spectroscopic Properties: Provides characteristic NMR signatures (¹H NMR: δ 6.0-7.0 ppm for aromatic protons; δ 3.8 ppm for -OCH₃)
Primary Applications and Synthetic Utility
Pharmaceutical Intermediate:
•Cannabinoid Research: Serves as a key precursor in the synthesis of cannabinoid analogs and related compounds due to its alkylresorcinol structure
•Bioactive Molecule Development: Used in constructing molecules with potential antioxidant, antimicrobial, and anti-inflammatory properties
Organic Synthesis Building Block:
•Multifunctional Synthon: The three distinct functional groups allow for sequential and selective modifications
•Complex Molecule Construction: Used in the synthesis of natural product analogs and specialized polymers
•Ligand Design: applicable in designing chelating agents for metal-organic frameworks
Material Science Applications:
•Specialty Polymers: Can be incorporated into polymer backbones to impart specific solubility or bioactive properties
•Surface Modification: Used in creating functionalized surfaces with specific interaction capabilities
Safety and Handling Considerations
Storage Conditions: Store in a cool, dry place in a tightly sealed container protected from light
Handling Precautions: Use appropriate PPE including gloves and safety glasses; avoid inhalation of dust
Stability: Stable under recommended storage conditions but may be sensitive to prolonged exposure to light and air
Commercial Availability and Specifications
Purity Grades: Typically available in research grade (≥95%) and high purity grade (≥98%)
Packaging Options: Available in research quantities (100mg, 500mg, 1g, 5g) with custom synthesis available for larger quantities
Documentation: Comprehensive Certificate of Analysis (CoA) with HPLC purity report and NMR characterization data available
Lead Time: Generally 2-4 weeks for custom synthesis projects
FAQ
Q1: What is the primary application of this compound?
A: This compound is a specialty chemical synthon, primarily serving as a key intermediate in the synthesis of cannabinoid analogs and other bioactive alkylresorcinol derivatives. It is essential for R&D in medicinal chemistry and material science.
Q2: What purity grades do you offer, and how is it analyzed?
A: We routinely offer ≥95% (Research Grade) and ≥98% (High Purity Grade) specifications. Every batch is rigorously characterized by HPLC and NMR to confirm identity and purity. A comprehensive Certificate of Analysis (CoA) is provided with each shipment.
Q3: What packaging options are available?
A: We provide a range of packaging to support projects from early R&D to pilot-scale synthesis:
•R&D Quantities: 100 mg, 500 mg, 1 g, 5 g
•Larger Scale: 10 g, 25 g, 50 g, 100 g
•Custom Synthesis: Kilogram-scale production is available upon request (lead time applies).
Q4: What is the typical lead time for orders?
A: Small-scale R&D orders (≤25 g) are typically in stock or shipped within 1-2 weeks. For larger, custom-synthesized batches, please allow 3-5 weeks for production and quality control. Contact us for an exact timeline.
Q5: Are there any special storage or handling requirements?
A: For long-term stability, we recommend storing the product sealed under an inert atmosphere, protected from light, and at -20°C. It is air and moisture sensitive and should be handled in a well-ventilated area using standard personal protective equipment (PPE).
Q6: Do you offer custom synthesis services for analogous structures?
A: Yes, we specialize in custom synthesis. We can modify the alkyl chain length (e.g., butyl, heptyl) or other functional groups to produce a suite of tailored alkylresorcinol derivatives for your research. Please inquire with your specific molecular requirements.
Q7: Can I get a Safety Data Sheet (SDS) for this product?
A: Absolutely. An up-to-date, GHS-compliant Safety Data Sheet (SDS) is available for download on the product page and is automatically included with all orders. You can also request one directly from our sales team.
Q8: What is the known biological activity of this compound?
A: Its alkylresorcinol core is associated with potential antioxidant and antimicrobial properties. However, its primary value is as a versatile building block. Its derivatives are of significant interest in research areas such neuroscience (e.g., cannabinoid receptor modulation) and inflammation.
Q9: Is this compound suitable for my research in [my field]?
A: This synthon is highly relevant for:
•Medicinal Chemistry: cannabinoid research, drug discovery.
•Organic Synthesis: complex natural product synthesis.
•Material Science: functionalized polymer design.
For specific applications, please contact our technical support team for expert guidance.
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