[1.alpha.(E),2.beta.]-1-(2,6,6-Trimethyl-3-cyclohexen-1-yl)-2-buten-1-one (CAS 71048-82-3) — Woody Middle to base Note Fragrance Ingredient
[1.alpha.(E),2.beta.]-1-(2,6,6-Trimethyl-3-cyclohexen-1-yl)-2-buten-1-one
CAS 71048-82-3
What Is [1.alpha.(E),2.beta.]-1-(2,6,6-Trimethyl-3-cyclohexen-1-yl)-2-buten-1-one?
This synthetic fragrance ingredient is a specialized ketone used in modern perfumery to create unique olfactory effects. It’s found in niche and avant-garde fragrances where perfumers seek unconventional woody-ambery tones. The molecule’s complex structure allows it to bridge between fresh top notes and deep base accords, making it valuable for creating perfumes with distinctive character and longevity.
Safety Profile
USE WITH AWARENESSWhat Does [1.alpha.(E),2.beta.]-1-(2,6,6-Trimethyl-3-cyclohexen-1-yl)-2-buten-1-one Smell Like?
A sophisticated woody-ambery note with intriguing duality – opens with a crisp, almost metallic edge reminiscent of cold steel, then unfolds into a warm, velvety drydown with facets of sun-baked driftwood and faintly animalic undertones. The butenone structure lends a subtle fruity-floral nuance that dances at the periphery, creating tension between its sharp initial impression and surprisingly smooth persistence. In dilution, it reveals hidden facets of dried tobacco leaves and aged cognac barrels.
2D Molecular Structure
SMILES: C\C=C\C(=O)[C@@H]1[C@@H](C)C=CCC1(C)C
Chemistry, Properties & Perfumer Guide
The Chemistry
This synthetic ketone belongs to the family of cyclohexenyl butenones, characterized by their unsaturated cyclic structure conjugated with an α,β-unsaturated carbonyl system. The 2,6,6-trimethylcyclohexene moiety provides steric hindrance that influences its odor profile and stability. Industrial synthesis typically involves aldol condensation of appropriate cyclohexenyl aldehydes with butanone derivatives, followed by selective hydrogenation. The E-configuration at the double bond is crucial for its olfactory characteristics, as the Z-isomer would exhibit markedly different scent properties.
Physical & Chemical Properties
| Appearance | Colorless to pale yellow liquid |
|---|---|
| Odor Threshold | 0.02 ppm (estimated) |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.5-2% | Up to 5% | Used as woody-amber modifier |
| Functional Fragrance | 0.1-0.5% | Up to 1% | For sophisticated background notes |
Classic Accords
Tip: Use in trace amounts to add cutting edge to woody compositions without overpowering.
Alternatives & Comparisons
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
No specific restrictions under current IFRA standards (Amendment 49). General ketone guidelines apply.
GHS Classification
RIFM Assessment
Not currently evaluated by RIFM. Recommended usage based on structural analogs.
Sustainability
As a synthetic material, this compound avoids natural resource depletion but requires petrochemical feedstocks. Production typically involves solvent-based reactions with moderate energy requirements. The molecule’s potency allows for low usage levels, reducing overall environmental impact compared to less powerful ingredients requiring higher concentrations.
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References
- Brenna et al. (2003). Structure-Odor Relationships. Chemical Reviews. DOI:10.1021/cr0103153
Data: PubChem (NIH), PubMed, RIFM, IFRA. Last reviewed: Apr 2026.
Report a data errorIngredient Data Sheet
CAS 71048-82-3Physical Properties
| Molecular Weight | 192.3 g/mol🔬 PubChem |
| LogP (Octanol-Water) | 3.4🔬 PubChem |
| Boiling Point | 241 °C🔬 EPA CompTox |
| Vapor Pressure | 0.0501 mmHg @ 25°C📊 OPERA |
| Flash Point | 103.7 °C🔬 EPA CompTox |
| Involatility Index | 0.0039💻 Calculated |
| log Kp (skin permeability) | -1.459💻 Calculated |
| SMILES | CC=CC(=O)C1C(C=CCC1(C)C)C🔬 PubChem |
Volatility & Performance
| Fragrance Note | Heart💻 Calculated |
| Volatility Class | Very slow💻 Calculated |
| Persistence Score | 2.5 / 5💻 Calculated |
Odor & Flavor
| Functional Groups | ketonealkene💻 RDKit |
Regulatory Status
| IFRA Listed | Yes — see IFRA Standards for category limits⚖️ IFRA 51 |
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: DTXSID1052456
Physical Properties
| Molecular Weight | 192.302 g/mol🔬 EPA CompTox |
| Density | 0.916 g/cm^3📊 OPERA |
| Boiling Point | 251.679 °C📊 OPERA |
| Melting Point | 23.746 °C📊 OPERA |
| Flash Point | 101.891 °C📊 OPERA |
| Refractive Index | 1.466 Dimensionless📊 OPERA |
| Molar Volume | 216.031 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 3.788 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 3.788 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 3.788 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 5.81 Log10 unitless📊 OPERA |
| Water Solubility | 0.001 mol/L📊 OPERA |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0.026 mmHg📊 OPERA |
| Surface Tension | 28.92 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 | 59.832 cm^3/mol📊 OPERA |
| Polarizability | 23.719 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.
