N-[(Ethoxycarbonyl)methyl)-p-menthane-3-carboxamide (CAS 68489-14-5) — Woody Middle Note Fragrance Ingredient
N-[(Ethoxycarbonyl)methyl)-p-menthane-3-carboxamide
CAS 68489-14-5
What Is N-[(Ethoxycarbonyl)methyl)-p-menthane-3-carboxamide?
This synthetic compound is a specialized fragrance ingredient primarily used in professional perfumery. Consumers may encounter it in modern woody or amber compositions where it contributes cooling and minty nuances. While not a household name, it plays an important role in creating sophisticated scent profiles by adding depth and diffusion to fragrance formulas.
Safety Profile
USE WITH AWARENESSWhat Does N-[(Ethoxycarbonyl)methyl)-p-menthane-3-carboxamide Smell Like?
This molecule presents a complex olfactory profile beginning with a crisp, cooling mint-like freshness reminiscent of crushed eucalyptus leaves. The initial sharpness gradually unfolds into a woody-ambery heart with subtle camphoraceous undertones. During dry-down, it reveals a clean, slightly sweet muskiness that enhances diffusion. The overall effect is reminiscent of alpine air with a sophisticated synthetic edge – like walking through a pine forest after rain with a faint whiff of mentholated balm.
2D Molecular Structure
SMILES: CCOC(=O)CNC(=O)[C@@H]1C[C@H](C)CC[C@H]1C(C)C
Chemistry, Properties & Perfumer Guide
The Chemistry
This synthetic carboxamide derivative belongs to the p-menthane family, structurally related to menthol but with an ethoxycarbonylmethyl substitution. The molecule features a rigid cyclohexane ring system that contributes to its cooling properties. While not found in nature, its synthesis typically involves the modification of p-menthane precursors through carboxamide formation. The stereochemistry of the menthane skeleton significantly impacts its odor profile, with different isomers exhibiting varying intensity of cooling effects.
Physical & Chemical Properties
| Appearance | Colorless to pale yellow liquid |
|---|---|
| Molecular Class | Carboxamide derivative |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.5-2% | Up to 5% | Cooling modifier |
| Functional Fragrance | 0.1-1% | Up to 3% | Freshness enhancer |
Classic Accords
Tip: Use sparingly in fougère compositions to add an unexpected cooling twist.
Alternatives & Comparisons
More intense cooling agent with similar chemical structure but stronger physiological cooling effect.
Natural-derived cooling agent with milder effect and different olfactory profile.
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
Limited safety assessment available. Considered safe at current usage levels.
Sustainability
As a synthetic material, this ingredient avoids natural resource depletion concerns. However, its production requires petrochemical feedstocks and energy-intensive processes. The carbon footprint depends on manufacturing efficiency and solvent recovery systems. Future green chemistry approaches may improve its sustainability profile.
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Ingredient Data Sheet
CAS 68489-14-5Physical Properties
| Molecular Weight | 269.38 g/mol🔬 PubChem |
| LogP (Octanol-Water) | 3.4🔬 PubChem |
| Boiling Point | 151 °C🔬 EPA CompTox |
| Vapor Pressure | 0 mmHg @ 25°C📊 OPERA |
| Flash Point | 100 °C🔬 EPA CompTox |
| log Kp (skin permeability) | -1.929💻 Calculated |
| SMILES | CCOC(=O)CNC(=O)C1CC(CCC1C(C)C)C🔬 PubChem |
Volatility & Performance
| Fragrance Note | Base💻 Calculated |
| Volatility Class | Very slow💻 Calculated |
| Persistence Score | 12.3 / 5💻 Calculated |
Odor & Flavor
| Functional Groups | esterether💻 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: DTXSID501134437
Physical Properties
| Molecular Weight | 269.385 g/mol🔬 EPA CompTox |
| Density | 0.006 g/cm^3🔬 EPA CTX |
| Boiling Point | 151 °C🔬 EPA CTX |
| Melting Point | 81 °C🔬 EPA CTX |
| Flash Point | 100 °C🔬 EPA CTX |
| Refractive Index | 1.462 Dimensionless📊 OPERA |
| Molar Volume | 271.624 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 2.73 Log10 unitless🔬 EPA CTX |
| LogD (pH 5.5) | 3.454 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 3.554 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 10.15 Log10 unitless📊 OPERA |
| Water Solubility | 0.001 mol/L📊 OPERA |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0 mmHg🔬 EPA CTX |
| Viscosity | 74.448 cP📊 OPERA |
| Surface Tension | 33.221 dyn/cm📊 OPERA |
| Thermal Conductivity | 145.6 mW/(m*K)📊 OPERA |
Molecular Descriptors
| Topological Polar Surface Area | 55.4 Ų💻 Computed |
| H-Bond Donors | 1 count💻 Computed |
| H-Bond Acceptors | 3 count💻 Computed |
| Rotatable Bonds | 5 count💻 Computed |
| Aromatic Rings | 0 count💻 Computed |
| Molar Refractivity | 74.717 cm^3/mol📊 OPERA |
| Polarizability | 29.62 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.
