N-(2-(Pyridin-2-yl)ethyl)-3-p-menthanecarboxamide (CAS 847565-09-7) — Green Middle to base Note Fragrance Ingredient
N-(2-(Pyridin-2-yl)ethyl)-3-p-menthanecarboxamide
CAS 847565-09-7
What Is N-(2-(Pyridin-2-yl)ethyl)-3-p-menthanecarboxamide?
N-(2-(Pyridin-2-yl)ethyl)-3-p-menthanecarboxamide is a synthetic cooling agent used in modern fragrances and personal care products. It provides a fresh, tingling sensation often found in body sprays, aftershaves, and cooling gels. This ingredient matters because it mimics natural cooling effects without using menthol, making it useful for sensitive skin formulations and long-lasting freshness in perfumery.
Safety Profile
USE WITH AWARENESSWhat Does N-(2-(Pyridin-2-yl)ethyl)-3-p-menthanecarboxamide Smell Like?
This synthetic molecule delivers a crisp, clean cooling sensation with subtle herbal undertones. Unlike menthol, it lacks the sharp medicinal punch, offering instead a refined, almost metallic freshness that evolves into a smooth, slightly woody base. The effect is like chilled mint leaves brushed against skin, with a whisper of camphoraceous depth that lingers subtly in the dry-down.
2D Molecular Structure
SMILES: [H][C@]1(CC[C@@H](C)C[C@@]1([H])C(=O)NCCC1=CC=CC=N1)C(C)C
Chemistry, Properties & Perfumer Guide
The Chemistry
N-(2-(Pyridin-2-yl)ethyl)-3-p-menthanecarboxamide belongs to the carboxamide class of cooling agents, structurally combining a p-menthane skeleton with a pyridine moiety. The synthesis typically involves condensation reactions between p-menthane carboxylic acid derivatives and aminoethylpyridine. Unlike traditional cooling agents, this molecule activates TRPM8 receptors without the volatility and odor characteristics of menthol.
Physical & Chemical Properties
| Appearance | White crystalline powder |
|---|---|
| Solubility | Soluble in ethanol, propylene glycol |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Body Sprays | 0.5-2% | Up to 3% | Provides sustained cooling effect |
| Aftershaves | 1-3% | Up to 5% | Combines well with citrus and herbal notes |
| Fine Fragrance | 0.1-0.5% | Up to 1% | Used as cooling accent |
Classic Accords
Tip: Use in ethanol-based sprays for optimal cooling sensation and stability.
Alternatives & Comparisons
More potent cooling agent with similar receptor activation but higher volatility.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
Not currently restricted by IFRA. Listed as safe for use in cosmetic applications.
RIFM Assessment
Under evaluation by RIFM. Preliminary data suggests low skin sensitization potential.
Sustainability
As a synthetic compound, this cooling agent avoids the agricultural impacts of natural menthol production. Its manufacturing process uses standard petrochemical feedstocks, though energy efficiency varies by production facility. The molecule’s potency allows for lower usage rates compared to natural cooling agents.
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References
- Patent WO2004071409 Cooling agent synthesis
- Cosmetic Ingredient Review (2018). Safety assessment of carboxamide cooling agents.
Data: PubChem (NIH), PubMed, RIFM, IFRA. Last reviewed: Apr 2026.
Report a data errorIngredient Data Sheet
CAS 847565-09-7Physical Properties
| Molecular Weight | 288.4 g/mol🔬 PubChem |
| LogP (Octanol-Water) | 4🔬 PubChem |
| Boiling Point | 346 °C🔬 EPA CompTox |
| Vapor Pressure | 0 mmHg @ 25°C📊 OPERA |
| Flash Point | 208 °C🔬 EPA CompTox |
| log Kp (skin permeability) | -1.619💻 Calculated |
| SMILES | CC1CCC(C(C1)C(=O)NCCC2=CC=CC=N2)C(C)C🔬 PubChem |
Volatility & Performance
| Fragrance Note | Base💻 Calculated |
| Volatility Class | Very slow💻 Calculated |
| Persistence Score | 13.5 / 5💻 Calculated |
Odor & Flavor
| Functional Groups | aromatic💻 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: DTXSID701345909
Physical Properties
| Molecular Weight | 288.435 g/mol🔬 EPA CompTox |
| Density | 1.09 g/cm^3🔬 EPA CTX |
| Boiling Point | 346 °C🔬 EPA CTX |
| Melting Point | 114.904 °C📊 OPERA |
| Flash Point | 208 °C🔬 EPA CTX |
| Refractive Index | 1.509 Dimensionless📊 OPERA |
| Molar Volume | 289.053 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 3.862 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 3.297 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 3.836 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 11.26 Log10 unitless📊 OPERA |
| Water Solubility | 0.001 mol/L🔬 EPA CTX |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0 mmHg🔬 EPA CTX |
| Viscosity | 127.934 cP📊 OPERA |
| Surface Tension | 37.617 dyn/cm📊 OPERA |
| Thermal Conductivity | 139.317 mW/(m*K)📊 OPERA |
Molecular Descriptors
| Topological Polar Surface Area | 41.99 Ų💻 Computed |
| H-Bond Donors | 1 count💻 Computed |
| H-Bond Acceptors | 2 count💻 Computed |
| Rotatable Bonds | 5 count💻 Computed |
| Aromatic Rings | 1 count💻 Computed |
| Molar Refractivity | 86.255 cm^3/mol📊 OPERA |
| Polarizability | 34.194 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.
