2,4,6-Trimethylphenol (CAS 527-60-6) — Balsamic Base Note Fragrance Ingredient
2,4,6-Trimethylphenol
CAS 527-60-6
What Is 2,4,6-Trimethylphenol?
2,4,6-Trimethylphenol is a synthetic aromatic compound used in industrial applications and some niche fragrances. It’s not commonly found in consumer products but may appear in specialty scents. This ingredient is valued for its unique phenolic character, which adds depth and complexity to fragrance compositions when used judiciously by perfumers.
Safety Profile
PROFESSIONAL USEWhat Does 2,4,6-Trimethylphenol Smell Like?
2,4,6-Trimethylphenol presents a sharp, medicinal phenolic odor with intense smoky and tar-like facets. The initial impression is aggressively chemical, reminiscent of disinfectants or creosote, with a burning rubber undertone. As it evolves, the harshness softens slightly to reveal a dry, woody character, though the phenolic nature remains dominant throughout. In dilution, it can contribute leathery or birch tar-like nuances to fragrance bases.
In Famous Fragrances
Fragrance associations may not reflect actual formulations.
2D Molecular Structure
SMILES: CC1=CC(C)=C(O)C(C)=C1
Chemistry, Properties & Perfumer Guide
The Chemistry
2,4,6-Trimethylphenol is a trisubstituted phenol with three methyl groups symmetrically arranged around the aromatic ring. This structure creates significant steric hindrance and influences its chemical reactivity. Industrially produced through methylation of phenol or cresols, its symmetrical substitution pattern makes it more thermally stable than other phenolic isomers. The electron-donating methyl groups increase the electron density on the aromatic ring, affecting both its odor characteristics and chemical behavior.
Physical & Chemical Properties
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Industrial Fragrances | 0.1-0.5% | Up to 1% | Extreme caution required |
Classic Accords
Tip: Use in trace amounts only for leather or smoke accords, always with extensive testing for skin compatibility.
Alternatives & Comparisons
Less aggressive phenolic character, safer at low levels for leather accords.
Smoky phenolic note with better safety profile for fragrance use.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
Not specifically restricted by IFRA but falls under general phenolic compound guidelines.
GHS Classification
RIFM Assessment
No specific RIFM assessment found – use with extreme caution.
Sustainability
As a synthetic petrochemical derivative, 2,4,6-Trimethylphenol has significant environmental considerations in production. The manufacturing process involves hazardous chemicals and generates waste streams requiring specialized treatment. Its limited fragrance applications and safety concerns make it unsuitable for sustainable fragrance development.
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Physicochemical Properties
DTXSID: DTXSID7022049
Physical Properties
| Molecular Weight | 136.194 g/mol🔬 EPA CompTox |
| Density | 1.001 g/cm^3📊 OPERA |
| Boiling Point | 220.22 °C🔬 EPA CTX |
| Melting Point | 72.25 °C🔬 EPA CTX |
| Flash Point | 96.775 °C🔬 EPA CTX |
| Refractive Index | 1.536 Dimensionless📊 OPERA |
| Molar Volume | 136.689 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 2.73 Log10 unitless🔬 EPA CTX |
| LogD (pH 5.5) | 2.738 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 2.738 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 6.99 Log10 unitless📊 OPERA |
| Water Solubility | 0.009 mol/L🔬 EPA CTX |
| Henry's Law Constant | 0 atm-m3/mole🔬 EPA CTX |
Transport Properties
| Vapor Pressure | 0.066 mmHg🔬 EPA CTX |
| Viscosity | 5.711 cP📊 OPERA |
| Surface Tension | 35.693 dyn/cm📊 OPERA |
| Thermal Conductivity | 139.123 mW/(m*K)📊 OPERA |
Molecular Descriptors
| Topological Polar Surface Area | 20.23 Ų💻 Computed |
| H-Bond Donors | 1 count💻 Computed |
| H-Bond Acceptors | 1 count💻 Computed |
| Rotatable Bonds | 0 count💻 Computed |
| Aromatic Rings | 1 count💻 Computed |
| Molar Refractivity | 42.609 cm^3/mol📊 OPERA |
| Polarizability | 16.892 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.
