Cyclohexanol, 5-methyl-2-(1-methylethenyl)-, (1.alpha.,2.beta.,5.alpha.)-(.+-.)- (CAS 50373-36-9) — Woody Middle Note Fragrance Ingredient
Cyclohexanol, 5-methyl-2-(1-methylethenyl)-, (1.alpha.,2.beta.,5.alpha.)-(.+-.)-
CAS 50373-36-9
What Is Cyclohexanol, 5-methyl-2-(1-methylethenyl)-, (1.alpha.,2.beta.,5.alpha.)-(.+-.)-?
This synthetic fragrance ingredient is a modified cyclohexanol compound used in modern perfumery to create fresh, woody aromas. While not found in nature, it appears in various household and personal care products. Its importance lies in providing stable, long-lasting woody notes that complement both floral and citrus compositions without the variability of natural materials.
Safety Profile
USE WITH AWARENESSWhat Does Cyclohexanol, 5-methyl-2-(1-methylethenyl)-, (1.alpha.,2.beta.,5.alpha.)-(.+-.)- Smell Like?
This cyclohexanol derivative presents a crisp, woody character with subtle pine-like freshness. Initially sharp and slightly camphoraceous, it evolves into a clean, dry wood note reminiscent of freshly sanded cedar. The dry-down reveals faint earthy undertones with exceptional tenacity. Its synthetic nature lends a consistent, almost ‘polished’ woody quality compared to natural terpenes.
2D Molecular Structure
SMILES: C[C@@H]1CC[C@H]([C@H](O)C1)C(C)=C
Chemistry, Properties & Perfumer Guide
The Chemistry
A synthetic terpenoid alcohol with a modified cyclohexane backbone featuring methyl and isopropenyl substituents. The stereochemistry at positions 1, 2, and 5 creates its distinctive odor profile. Typically synthesized via acid-catalyzed cyclization of terpene precursors followed by selective oxidation. The racemic mixture is commonly used in fragrance applications.
Physical & Chemical Properties
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 1-3% | Up to 5% | Woody note enhancer |
| Functional Fragrance | 0.5-2% | Up to 3% | Clean woody base |
Classic Accords
Tip: Use as a bridge between citrus top notes and woody bases to enhance freshness without volatility.
Alternatives & Comparisons
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
No IFRA restrictions currently apply.
RIFM Assessment
Not currently evaluated by RIFM.
Sustainability
As a fully synthetic material, production avoids natural resource depletion. Manufacturing typically uses petrochemical feedstocks, though newer green chemistry routes may utilize bio-based precursors. Offers consistent quality without seasonal variation.
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Physicochemical Properties
DTXSID: DTXSID90110001
Physical Properties
| Molecular Weight | 154.253 g/mol🔬 EPA CompTox |
| Density | 0.912 g/cm^3📊 OPERA |
| Boiling Point | 210.819 °C📊 OPERA |
| Melting Point | 48.609 °C📊 OPERA |
| Flash Point | 82.384 °C📊 OPERA |
| Refractive Index | 1.472 Dimensionless📊 OPERA |
| Molar Volume | 168.964 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 3.005 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 3.005 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 3.005 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 6.86 Log10 unitless📊 OPERA |
| Water Solubility | 0.008 mol/L📊 OPERA |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0.075 mmHg📊 OPERA |
| Viscosity | 10.534 cP📊 OPERA |
| Surface Tension | 30.123 dyn/cm📊 OPERA |
| Thermal Conductivity | 133.784 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 | 47.346 cm^3/mol📊 OPERA |
| Polarizability | 18.769 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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