3-Buten-2-one, 4-[2,5,6,6-tetramethyl-1(or 2)-cyclohexen-1-yl]- (CAS 54992-91-5) — Woody Middle Note Fragrance Ingredient
3-Buten-2-one, 4-[2,5,6,6-tetramethyl-1(or 2)-cyclohexen-1-yl]-
CAS 54992-91-5
What Is 3-Buten-2-one, 4-[2,5,6,6-tetramethyl-1(or 2)-cyclohexen-1-yl]-?
This synthetic compound is a specialty fragrance ingredient used by perfumers to create unique olfactory effects. It’s not commonly encountered in everyday products but may appear in niche or avant-garde fragrances. As a synthetic molecule, it offers perfumers precise control over scent profiles, allowing for innovative accords that can’t be achieved with natural materials alone.
Safety Profile
PROFESSIONAL USEWhat Does 3-Buten-2-one, 4-[2,5,6,6-tetramethyl-1(or 2)-cyclohexen-1-yl]- Smell Like?
This synthetic molecule presents a complex olfactory profile that evolves intriguingly on the skin. The initial impression is a sharp, almost metallic greenness with woody undertones, reminiscent of freshly cut branches with sap still flowing. As it develops, the scent reveals a dry, ambery warmth with subtle leathery facets. The dry-down leaves a lingering impression of sun-warmed pine needles and faintly smoky vetiver. Its character is simultaneously fresh and resinous, making it particularly useful for adding depth to modern woody compositions.
2D Molecular Structure
SMILES: CC1CCC(=C(C1(C)C)C=CC(=O)C)C
Chemistry, Properties & Perfumer Guide
The Chemistry
This synthetic compound belongs to the family of cyclohexenyl butenones, characterized by their unsaturated ketone structure. The molecule features a tetramethyl-substituted cyclohexene ring conjugated with a butenone moiety, creating a complex electron system that contributes to its distinctive olfactory properties. While not found in nature, its structure draws inspiration from terpenoid compounds, particularly those found in woody and resinous materials. Synthesis typically involves multi-step organic reactions including alkylation and condensation processes to build the complex cyclic structure.
Physical & Chemical Properties
| Boiling Point | Not available |
|---|---|
| Density | Not available |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.1-0.5% | Up to 1% | Used as an accent note |
| Functional Fragrance | 0.01-0.1% | Up to 0.2% | Limited use in functional products |
Classic Accords
Tip: Use sparingly in woody bases to add lift and dimension without overwhelming the composition.
Alternatives & Comparisons
A more widely used woody-amber material with better stability and safety profile for similar applications.
Provides intense woody-dry effects with greater diffusion power when a stronger impact is desired.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
No specific IFRA restriction found. General usage guidelines for unsaturated ketones apply.
RIFM Assessment
No RIFM assessment publicly available. Assume restricted until proven otherwise.
Sustainability
As a synthetic material, this compound’s environmental impact depends primarily on the manufacturing process. While it doesn’t deplete natural resources, the multi-step synthesis may involve energy-intensive processes and potentially hazardous intermediates. Perfumers should balance its unique olfactory properties against greener alternatives when sustainability is a priority.
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Ingredient Data Sheet
CAS 54992-91-5Physical Properties
| Molecular Weight | 206.32 g/mol🔬 PubChem |
| LogP (Octanol-Water) | 3.2🔬 PubChem |
| log Kp (skin permeability) | -1.687💻 Calculated |
| SMILES | CC1CCC(=C(C1(C)C)C=CC(=O)C)C🔬 PubChem |
Odor & Flavor
| Functional Groups | ketonealkene💻 RDKit |
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: DTXSID00904392
Physical Properties
| Molecular Weight | 206.32 g/mol🔬 PubChem |
Partition & Solubility
| LogP (Octanol-Water) | 3.2 Log10 unitless🔬 PubChem |
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 |
| Molar Refractivity | 64.7 cm^3/mol💻 Computed |
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.
