Methyl 2-[(3,5,5-trimethylhexylidene)amino]benzoate (CAS 67801-42-7) — Green Middle Note Fragrance Ingredient
Methyl 2-[(3,5,5-trimethylhexylidene)amino]benzoate
CAS 67801-42-7
What Is Methyl 2-[(3,5,5-trimethylhexylidene)amino]benzoate?
Methyl 2-[(3,5,5-trimethylhexylidene)amino]benzoate is a synthetic fragrance ingredient used in modern perfumery to create unique scent profiles. It is found in niche and designer fragrances where novel olfactory effects are desired. This compound matters because it represents perfumery’s ability to engineer entirely new scent molecules that don’t exist in nature, expanding creative possibilities beyond traditional botanical extracts.
Safety Profile
USE WITH AWARENESSWhat Does Methyl 2-[(3,5,5-trimethylhexylidene)amino]benzoate Smell Like?
This synthetic molecule offers a complex olfactory profile that evolves dramatically on skin. Initially presents with sharp, almost metallic green facets reminiscent of crushed stems, quickly transitioning to a warmer, ambery-musk character. The dry-down reveals subtle floral undertones wrapped in a velvety benzoate sweetness, creating an intriguing contrast between its crisp opening and plush finish. Performance is excellent, with the molecule demonstrating both projection and longevity.
2D Molecular Structure
SMILES: COC(=O)C1=CC=CC=C1N=CCC(C)CC(C)(C)C
Chemistry, Properties & Perfumer Guide
The Chemistry
Methyl 2-[(3,5,5-trimethylhexylidene)amino]benzoate belongs to the Schiff base class of compounds, formed through condensation reactions between amines and carbonyl compounds. The molecule features both ester and imine functional groups, contributing to its complex scent profile. Synthesis typically involves reacting methyl anthranilate with 3,5,5-trimethylhexanal under controlled conditions. The branched alkyl chain introduces steric effects that influence both volatility and odor characteristics.
Physical & Chemical Properties
| Appearance | Clear to pale yellow liquid |
|---|---|
| Molecular Weight | Not available |
| Solubility | Soluble in alcohol and oils |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.5-2% | Up to 5% | Used as a modifier |
| Functional Fragrance | 0.1-0.5% | Up to 1% | For novelty effects |
Classic Accords
Tip: Use in trace amounts to add dimensionality to modern woody-amber bases.
Alternatives & Comparisons
Provides similar benzoate character without the complex Schiff base structure, offering more predictable performance in formulations.
Delivers comparable ambery dry-down notes with better-established safety profiles and wider regulatory acceptance.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
Not currently restricted by IFRA standards.
RIFM Assessment
Under evaluation by RIFM as a novel fragrance material.
Sustainability
As a synthetic material, this compound avoids agricultural sourcing concerns but requires petrochemical feedstocks. Production energy requirements are moderate compared to some natural extracts. The Schiff base structure suggests potential biodegradability, though specific environmental fate studies are lacking. Perfumers should consider this when formulating for eco-conscious markets.
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References
- Brenna, E. et al. (2003). Schiff Bases in Fragrance Chemistry. Flavour and Fragrance Journal.
- Sell, C. (2006). The Chemistry of Fragrances. RSC Publishing.
Data: PubChem (NIH), PubMed, RIFM, IFRA. Last reviewed: Apr 2026.
Report a data errorPhysicochemical Properties
DTXSID: DTXSID30867345
Physical Properties
| Molecular Weight | 275.392 g/mol🔬 EPA CompTox |
| Density | 1.018 g/cm^3📊 OPERA |
| Boiling Point | 344.845 °C📊 OPERA |
| Melting Point | 35.666 °C📊 OPERA |
| Flash Point | 155.265 °C📊 OPERA |
| Refractive Index | 1.491 Dimensionless📊 OPERA |
| Molar Volume | 287.289 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 4.502 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 4.319 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 4.496 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 7.38 Log10 unitless📊 OPERA |
| Water Solubility | 0 mol/L📊 OPERA |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0 mmHg📊 OPERA |
| Surface Tension | 30.986 dyn/cm📊 OPERA |
Molecular Descriptors
| Topological Polar Surface Area | 38.66 Ų💻 Computed |
| H-Bond Donors | 0 count💻 Computed |
| H-Bond Acceptors | 3 count💻 Computed |
| Rotatable Bonds | 5 count💻 Computed |
| Aromatic Rings | 1 count💻 Computed |
| Molar Refractivity | 83.246 cm^3/mol📊 OPERA |
| Polarizability | 33.001 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.
