Methyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate (CAS 6386-38-5) — Woody N/A Note Fragrance Ingredient
Methyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate
CAS 6386-38-5
What Is Methyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate?
Methyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate is a synthetic antioxidant used in food packaging and industrial applications. It prevents oxidation in plastics and rubbers. Consumers encounter it indirectly through extended shelf life of packaged goods. While not a fragrance ingredient per se, its phenolic structure gives it potential odor-modifying properties that could interest experimental perfumers working with unconventional materials.
Safety Profile
PROFESSIONAL USEWhat Does Methyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate Smell Like?
This compound presents primarily as a functional antioxidant rather than a deliberate fragrance material. At room temperature, it may release faint phenolic, medicinal notes reminiscent of hospital disinfectants or rubber stabilizers. The tert-butyl groups mute typical phenol sharpness, creating a dull, waxy aroma profile without clear top/heart/base development. Dry-down reveals subtle plastic-like undertones that linger tenaciously on smelling strips.
2D Molecular Structure
SMILES: COC(=O)CCC1=CC(=C(O)C(=C1)C(C)(C)C)C(C)(C)C
Chemistry, Properties & Perfumer Guide
The Chemistry
This synthetic hindered phenol belongs to the antioxidant class of alkylated hydroxybenzoates. The molecule features a central phenolic ring with two bulky tert-butyl groups at the 3 and 5 positions, providing steric hindrance that enhances oxidative stability. The propionate ester group at position 4 improves compatibility with polymer matrices. Industrial synthesis typically involves Friedel-Crafts alkylation of p-cresol followed by esterification.
Physical & Chemical Properties
| Molecular Weight | 292.41 g/mol |
|---|---|
| Melting Point | 70-72 °C |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Industrial Antioxidant | 0.1-0.5% | Up to 1% | Polymer stabilization |
Classic Accords
Tip: Not recommended for perfumery – explore approved phenolic antioxidants like BHT instead.
Alternatives & Comparisons
Food-grade phenolic antioxidant with established safety profile for incidental contact applications.
High-performance polymer stabilizer with lower volatility and superior thermal stability.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
Not evaluated by IFRA – industrial chemical outside fragrance scope.
GHS Classification
RIFM Assessment
No RIFM assessment – primary use is industrial rather than fragrance.
Sustainability
This petrochemical-derived antioxidant raises environmental concerns regarding persistent organic pollutants. Production involves energy-intensive alkylation processes with significant carbon footprint. End-of-life considerations include potential microplastic contamination from stabilized polymer products. Green chemistry alternatives using tocopherol derivatives are gaining traction in sustainable packaging.
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References
- PubChem Compound Summary for CID 162173 PubChem
- Plastics Additives Handbook, 6th Ed. (2009)
Data: PubChem (NIH), PubMed, RIFM, IFRA. Last reviewed: Apr 2026.
Report a data errorIngredient Data Sheet
CAS 6386-38-5Physical Properties
| Molecular Weight | 292.4 g/mol🔬 PubChem |
| LogP (Octanol-Water) | 5🔬 PubChem |
| Boiling Point | 293 °C🔬 EPA CompTox |
| Vapor Pressure | 0 mmHg @ 25°C📊 OPERA |
| Flash Point | 165.2 °C🔬 EPA CompTox |
| log Kp (skin permeability) | -0.934💻 Calculated |
| SMILES | CC(C)(C)C1=CC(=CC(=C1O)C(C)(C)C)CCC(=O)OC🔬 PubChem |
Volatility & Performance
| Fragrance Note | Base💻 Calculated |
| Volatility Class | Very slow💻 Calculated |
| Persistence Score | 14.1 / 5💻 Calculated |
Odor & Flavor
| Functional Groups | esterphenoletheraromatic💻 RDKit |
Physical data: PubChem (NIH/NLM), U.S. EPA CompTox Dashboard, EPA OPERA models, RDKit. Odor & flavor: Arctander (Perfume & Flavor Chemicals), Fenaroli's Handbook of Flavor Ingredients, Leffingwell. Thresholds: van Gemert (Compilations of Odour Threshold Values). Regulatory: IFRA Standards 51st, FEMA GRAS. Trade names: Surburg (Common Fragrance & Flavor Materials). All data compiled and cross-referenced for perfumertools.com.
Physicochemical Properties
DTXSID: DTXSID7027623
Physical Properties
| Molecular Weight | 292.419 g/mol🔬 EPA CompTox |
| Density | 1.09 g/cm^3🔬 EPA CTX |
| Boiling Point | 314.257 °C📊 OPERA |
| Melting Point | 65.75 °C🔬 EPA CTX |
| Flash Point | 144.74 °C📊 OPERA |
| Refractive Index | 1.5 Dimensionless📊 OPERA |
| Molar Volume | 290.551 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 5.024 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 5.024 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 5.024 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 10.48 Log10 unitless📊 OPERA |
| Water Solubility | 0 mol/L🔬 EPA CTX |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0 mmHg🔬 EPA CTX |
| Surface Tension | 33.548 dyn/cm📊 OPERA |
| Thermal Conductivity | 123.174 mW/(m*K)📊 OPERA |
Molecular Descriptors
| Topological Polar Surface Area | 46.53 Ų💻 Computed |
| H-Bond Donors | 1 count💻 Computed |
| H-Bond Acceptors | 3 count💻 Computed |
| Rotatable Bonds | 3 count💻 Computed |
| Aromatic Rings | 1 count💻 Computed |
| Molar Refractivity | 85.499 cm^3/mol📊 OPERA |
| Polarizability | 33.894 Å^3📊 OPERA |
Data Sources:
🔬 EPA Experimental data from U.S. EPA CompTox Chemicals Dashboard & CTX APIs. 📊 OPERA Predicted using EPA's OPERA QSAR models. 💻 Computed Calculated from SMILES using RDKit.
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