d-Menthol (CAS 15356-60-2) — Green Top to middle Note Fragrance Ingredient
d-Menthol
CAS 15356-60-2
What Is d-Menthol?
d-Menthol is the dextrorotatory form of menthol, commonly encountered in mint-flavored products like chewing gum, toothpaste, and topical analgesics. It provides the characteristic cooling sensation associated with mint. This isomer matters because its spatial arrangement affects both its cooling potency and odor profile compared to the more common l-menthol, offering perfumers and flavorists precise control over sensory experiences.
Safety Profile
GENERALLY SAFEWhat Does d-Menthol Smell Like?
d-Menthol delivers an intense, crystalline mint aroma with sharper top notes than its l-isomer. The initial burst is like crushed peppermint leaves with a metallic edge, evolving into a cleaner, more linear cooling sensation without the woody undertones of natural menthol. Its dry-down lacks the camphoraceous warmth found in racemic mixtures, leaving a pure refrigerative effect that lingers like winter air on bare skin.
In Famous Fragrances
Fragrance associations may not reflect actual formulations.
Used alongside synthetic calone to amplify the aquatic freshness with a bracing mint accent that enhances the perfume’s signature ‘blue’ character.
Provides subtle cooling counterpoint to the violet leaf and iris, creating a dewy morning grass effect in this classic fougère.
2D Molecular Structure
SMILES: CC(C)[C@H]1CC[C@H](C)C[C@@H]1O
Chemistry, Properties & Perfumer Guide
The Chemistry
d-Menthol is a monocyclic terpene alcohol with the hydroxyl group in the (1R,2S,5R) configuration. Unlike the naturally predominant l-menthol, this isomer is typically produced through stereoselective synthesis or resolution of racemic mixtures. Industrial production often involves hydrogenation of pulegone followed by chiral separation techniques. The spatial arrangement of its three chiral centers significantly impacts its receptor binding affinity, resulting in distinct physiological cooling effects.
Physical & Chemical Properties
| Melting Point | 42-45°C |
|---|---|
| Boiling Point | 212°C |
| Optical Rotation | +48° (c=10, ethanol) |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Oral Care | 0.1-0.5% | Up to 1% | Provides fresh breath sensation |
| Topical Analgesics | 1-3% | Up to 5% | Cooling without overpowering odor |
Classic Accords
Tip: Use in trace amounts (0.01-0.05%) to add cooling lift to citrus colognes without dominating the blend.
Alternatives & Comparisons
The naturally predominant form with warmer, woodier character and stronger cooling effect at equivalent concentrations.
Synthetic coolant with 3x the potency of menthol and minimal odor interference for neutral cooling applications.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
No IFRA restrictions. Classified as a flavoring agent rather than fragrance material.
GHS Classification
RIFM Assessment
Considered safe at current use levels based on menthol group assessment (RIFM Monograph 2011).
Sustainability
While naturally derived menthol requires extensive peppermint cultivation, synthetic d-menthol production avoids agricultural land use but requires energy-intensive separation processes. New enzymatic resolution methods show promise for reducing environmental impact.
Explore d-Menthol
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References
- Eccles R. (1994). Menthol and related cooling compounds. Journal of Pharmacy and Pharmacology. PMID 7529306
Data: PubChem (NIH), PubMed, RIFM, IFRA. Last reviewed: Apr 2026.
Report a data errorIngredient Data Sheet
CAS 15356-60-2Physical Properties
| Molecular Weight | 156.26 g/mol🔬 PubChem |
| LogP (Octanol-Water) | 3🔬 PubChem |
| Boiling Point | 216.1 °C🔬 EPA CompTox |
| Vapor Pressure | 1 mmHg @ 25°C📊 OPERA |
| Flash Point | 91.1 °C🔬 EPA CompTox |
| Involatility Index | 0.0862💻 Calculated |
| log Kp (skin permeability) | -1.523💻 Calculated |
| SMILES | CC1CCC(C(C1)O)C(C)C🔬 PubChem |
Volatility & Performance
| Fragrance Note | Top💻 Calculated |
| Volatility Class | Slow💻 Calculated |
| Persistence Score | 0.5 / 5💻 Calculated |
Odor & Flavor
| Primary Descriptors | greenmentholspicy• leffingwell |
| Functional Groups | alcohol💻 RDKit |
Sensory Thresholds
| Odor Detection Threshold | 1.2025 ppm (n=3)📖 van Gemert |
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: DTXSID8029733
Physical Properties
| Molecular Weight | 156.269 g/mol🔬 EPA CompTox |
| Density | 0.888 g/cm^3📊 OPERA |
| Boiling Point | 214.254 °C📊 OPERA |
| Melting Point | 38.35 °C🔬 EPA CTX |
| Flash Point | 94 °C🔬 EPA CTX |
| Refractive Index | 1.457 Dimensionless📊 OPERA |
| Molar Volume | 175.542 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 3.15 Log10 unitless🔬 EPA CTX |
| LogD (pH 5.5) | 3.242 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 3.242 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 6.6 Log10 unitless📊 OPERA |
| Water Solubility | 0.005 mol/L📊 OPERA |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0.471 mmHg🔬 EPA CTX |
| Viscosity | 9.449 cP📊 OPERA |
| Surface Tension | 29.625 dyn/cm📊 OPERA |
| Thermal Conductivity | 129.72 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 | 1 count💻 Computed |
| Aromatic Rings | 0 count💻 Computed |
| Molar Refractivity | 47.833 cm^3/mol📊 OPERA |
| Polarizability | 18.963 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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