4-(2,4,6-Trimethyl-3-cyclohexen-1-yl)-3-buten-2-one (CAS 67801-38-1) — Woody Base Note Fragrance Ingredient
4-(2,4,6-Trimethyl-3-cyclohexen-1-yl)-3-buten-2-one
CAS 67801-38-1
What Is 4-(2,4,6-Trimethyl-3-cyclohexen-1-yl)-3-buten-2-one?
4-(2,4,6-Trimethyl-3-cyclohexen-1-yl)-3-buten-2-one is a synthetic fragrance ingredient used in perfumery for its unique woody and ambery characteristics. It is found in niche and high-end fragrances, often contributing to complex accords. This molecule is valued for its ability to add depth and longevity to fragrance compositions, making it a favorite among perfumers seeking sophisticated woody-amber bases.
Safety Profile
USE WITH AWARENESSWhat Does 4-(2,4,6-Trimethyl-3-cyclohexen-1-yl)-3-buten-2-one Smell Like?
4-(2,4,6-Trimethyl-3-cyclohexen-1-yl)-3-buten-2-one opens with a warm, woody aroma reminiscent of aged cedar and vetiver, gradually revealing a subtle ambery sweetness. The heart note develops into a rich, slightly resinous character with hints of dried fruits and a touch of smokiness. The dry-down is long-lasting, leaving a sophisticated woody-amber trail that blends seamlessly with other base notes, enhancing their depth and complexity.
2D Molecular Structure
SMILES: CC1CC(C)=CC(C)C1C=CC(C)=O
Chemistry, Properties & Perfumer Guide
The Chemistry
4-(2,4,6-Trimethyl-3-cyclohexen-1-yl)-3-buten-2-one is a synthetic ketone belonging to the cyclohexene family. It is synthesized through the condensation of trimethylcyclohexenone with butenone, resulting in a molecule with a complex cyclic structure. The compound’s chirality and stereochemistry play a significant role in its olfactory profile, with specific enantiomers contributing to its woody-amber character. Its stability and low volatility make it an excellent base note in perfumery.
Physical & Chemical Properties
| Boiling Point | N/A |
|---|---|
| Density | N/A |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 1-3% | Up to 5% | Adds depth to woody-amber accords |
| Home Fragrance | 0.5-2% | Up to 3% | Enhances longevity |
| Personal Care | 0.1-1% | Up to 2% | Used sparingly due to potency |
Classic Accords
Tip: Use in trace amounts to avoid overwhelming the composition.
Alternatives & Comparisons
A more commonly used woody-amber molecule with similar longevity but less intensity.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
No IFRA restrictions currently apply.
RIFM Assessment
RIFM assessment pending; limited data available.
Sustainability
As a synthetic molecule, 4-(2,4,6-Trimethyl-3-cyclohexen-1-yl)-3-buten-2-one is produced through controlled chemical processes, reducing environmental impact compared to natural extraction methods. Its synthesis can be optimized for minimal waste and energy use, aligning with green chemistry principles.
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Ingredient Data Sheet
CAS 67801-38-1Physical Properties
| Molecular Weight | 192.3 g/mol🔬 PubChem |
| LogP (Octanol-Water) | 2.7🔬 PubChem |
| Boiling Point | 252 °C🔬 EPA CompTox |
| Vapor Pressure | 0.0871 mmHg @ 25°C📊 OPERA |
| Flash Point | 116.9 °C🔬 EPA CompTox |
| Involatility Index | 0.0068💻 Calculated |
| log Kp (skin permeability) | -1.956💻 Calculated |
| SMILES | CC1CC(=CC(C1C=CC(=O)C)C)C🔬 PubChem |
Volatility & Performance
| Fragrance Note | Heart💻 Calculated |
| Volatility Class | Very slow💻 Calculated |
| Persistence Score | 1.9 / 5💻 Calculated |
Odor & Flavor
| Functional Groups | ketonealkene💻 RDKit |
| “The main drawback is perhaps, that the material is not very versatile in its use, it resembles the Ionones too much, and is priced about the same as Ionones. The softness is sometimes translated as weakness in odor, but the material can only be justly”📖 Arctander | |
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: DTXSID1052371
Physical Properties
| Molecular Weight | 192.302 g/mol🔬 EPA CompTox |
| Density | 0.914 g/cm^3📊 OPERA |
| Boiling Point | 262.067 °C📊 OPERA |
| Melting Point | 33.628 °C📊 OPERA |
| Flash Point | 109.585 °C📊 OPERA |
| Refractive Index | 1.508 Dimensionless📊 OPERA |
| Molar Volume | 207.227 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 3.96 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 3.96 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 3.96 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 6.1 Log10 unitless📊 OPERA |
| Water Solubility | 0.001 mol/L📊 OPERA |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0.034 mmHg📊 OPERA |
| Surface Tension | 31.517 dyn/cm📊 OPERA |
Molecular Descriptors
| Topological Polar Surface Area | 17.07 Ų💻 Computed |
| H-Bond Donors | 0 count💻 Computed |
| H-Bond Acceptors | 1 count💻 Computed |
| Rotatable Bonds | 2 count💻 Computed |
| Aromatic Rings | 0 count💻 Computed |
| Molar Refractivity | 61.802 cm^3/mol📊 OPERA |
| Polarizability | 24.5 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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