2-Hydroxy-alpha,alpha,4-trimethylcyclohexanemethanol (CAS 42822-86-6) — Green Heart Note Fragrance Ingredient
2-Hydroxy-alpha,alpha,4-trimethylcyclohexanemethanol
CAS 42822-86-6
What Is 2-Hydroxy-alpha,alpha,4-trimethylcyclohexanemethanol?
2-Hydroxy-alpha,alpha,4-trimethylcyclohexanemethanol is a synthetic fragrance ingredient primarily used in fine perfumery. It’s not commonly encountered in everyday products but may appear in niche fragrances. This compound contributes unique woody-green facets to fragrance compositions, offering perfumers a versatile building block for modern accords.
Safety Profile
GENERALLY SAFEWhat Does 2-Hydroxy-alpha,alpha,4-trimethylcyclohexanemethanol Smell Like?
This synthetic molecule presents a complex olfactory profile, opening with crisp, slightly camphoraceous top notes that evolve into a heart of moist forest undergrowth and freshly cut green stems. The dry-down reveals a subtle woody character with faint floral undertones, reminiscent of damp moss on sun-warmed tree bark. The overall effect is fresh yet persistent, with a clean diffusion that makes it valuable for modern green fragrances.
2D Molecular Structure
SMILES: CC1CCC(C(O)C1)C(C)(C)O
Chemistry, Properties & Perfumer Guide
The Chemistry
2-Hydroxy-alpha,alpha,4-trimethylcyclohexanemethanol belongs to the cyclohexane methanol class of fragrance compounds. As a synthetic material, it’s typically produced through hydrogenation and hydroxylation of aromatic precursors. The molecule features three methyl groups at positions 1, 1, and 4 on the cyclohexane ring, with a hydroxymethyl substituent contributing to its polar character. This configuration creates a stereochemical center that may exist as different stereoisomers, though commercial samples are typically racemic mixtures.
Physical & Chemical Properties
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 1-3% | Up to 5% | Used as green-woody modifier |
| Functional Fragrance | 0.1-0.5% | Up to 1% | Provides natural freshness |
Classic Accords
Tip: Use with citrus top notes to enhance freshness without excessive sharpness.
Alternatives & Comparisons
Offers similar green-woody character with better solubility in alcohol bases.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
No IFRA restrictions currently apply to this material.
RIFM Assessment
Limited safety assessment available through RIFM.
Sustainability
As a synthetic material, this compound is produced through controlled chemical processes with consistent quality. While it doesn’t rely on natural resources, the environmental impact depends on the synthesis route and energy inputs. Future developments may focus on greener synthetic pathways to improve sustainability.
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Ingredient Data Sheet
CAS 42822-86-6Physical Properties
| Molecular Weight | 172.26 g/mol🔬 PubChem |
| LogP (Octanol-Water) | 2.2🔬 PubChem |
| Boiling Point | 242 °C🔬 EPA CompTox |
| Vapor Pressure | 0.0014 mmHg @ 25°C📊 OPERA |
| Flash Point | 120.7 °C🔬 EPA CompTox |
| Involatility Index | 0.0001💻 Calculated |
| log Kp (skin permeability) | -2.189💻 Calculated |
| SMILES | CC1CCC(C(C1)O)C(C)(C)O🔬 PubChem |
Volatility & Performance
| Fragrance Note | Base💻 Calculated |
| Volatility Class | Very slow💻 Calculated |
| Persistence Score | 4.6 / 5💻 Calculated |
Odor & Flavor
| Primary Descriptors | minty• leffingwell |
| Functional Groups | alcohol💻 RDKit |
| p-Menthane-3,8-diol has a faint mint odor. The cooling power is reported to be approximately 9.5 times that of (-)-menthol.📖 Fenaroli | |
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: DTXSID0035744
Physical Properties
| Molecular Weight | 172.268 g/mol🔬 EPA CompTox |
| Density | 0.99 g/cm^3📊 OPERA |
| Boiling Point | 255.707 °C📊 OPERA |
| Melting Point | 34.5 °C🔬 EPA CTX |
| Flash Point | 115.668 °C📊 OPERA |
| Refractive Index | 1.487 Dimensionless📊 OPERA |
| Molar Volume | 170.677 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 2.272 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 2.272 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 2.272 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 7.85 Log10 unitless📊 OPERA |
| Water Solubility | 0.002 mol/L🔬 EPA CTX |
| Henry's Law Constant | 0 atm-m3/mole🔬 EPA CTX |
Transport Properties
| Vapor Pressure | 0.001 mmHg🔬 EPA CTX |
| Viscosity | 21.926 cP📊 OPERA |
| Surface Tension | 35.445 dyn/cm📊 OPERA |
| Thermal Conductivity | 149.164 mW/(m*K)📊 OPERA |
Molecular Descriptors
| Topological Polar Surface Area | 40.46 Ų💻 Computed |
| H-Bond Donors | 2 count💻 Computed |
| H-Bond Acceptors | 2 count💻 Computed |
| Rotatable Bonds | 1 count💻 Computed |
| Aromatic Rings | 0 count💻 Computed |
| Molar Refractivity | 49.066 cm^3/mol📊 OPERA |
| Polarizability | 19.451 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.
