4-(1,2-Epoxy-2,6,6-trimethylcyclohexyl)-3-buten-2-one (CAS 23267-57-4) — Woody Middle Note Fragrance Ingredient
4-(1,2-Epoxy-2,6,6-trimethylcyclohexyl)-3-buten-2-one
CAS 23267-57-4
What Is 4-(1,2-Epoxy-2,6,6-trimethylcyclohexyl)-3-buten-2-one?
4-(1,2-Epoxy-2,6,6-trimethylcyclohexyl)-3-buten-2-one is a synthetic fragrance compound used in perfumery. It is not commonly encountered in everyday products but may appear in niche or artistic fragrances. This ingredient matters because it contributes unique olfactory characteristics that are difficult to achieve with natural materials alone.
Safety Profile
USE WITH AWARENESSWhat Does 4-(1,2-Epoxy-2,6,6-trimethylcyclohexyl)-3-buten-2-one Smell Like?
This synthetic molecule offers a complex olfactory profile with woody, spicy, and slightly fruity nuances. The epoxy group contributes a sharp, almost metallic edge that evolves into a warmer, ambery dry-down. Its behavior resembles a cross between ionones and damascones, with a distinctive chemical brightness that persists through the heart phase.
2D Molecular Structure
SMILES: CC(=O)C=CC12OC1(C)CCCC2(C)C
Chemistry, Properties & Perfumer Guide
The Chemistry
4-(1,2-Epoxy-2,6,6-trimethylcyclohexyl)-3-buten-2-one belongs to the class of epoxy ketones with a cyclohexyl backbone. The molecule features both an epoxy group and an α,β-unsaturated ketone moiety, which contribute to its reactivity and olfactory properties. Synthesis typically involves epoxidation of a precursor unsaturated ketone derived from isophorone or related compounds.
Physical & Chemical Properties
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.1-0.5% | Up to 1% | Used as an accent note |
| Functional Fragrance | 0.05-0.2% | Up to 0.5% | Limited use due to potential sensitization |
Classic Accords
Tip: Use sparingly in blends to avoid overpowering other materials.
Alternatives & Comparisons
Similar fruity-woody character without epoxy sharpness, more widely used in perfumery.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
No specific IFRA restrictions found. Use caution due to structural alerts.
GHS Classification
RIFM Assessment
No RIFM assessment publicly available for this specific compound.
Sustainability
As a synthetic material, this compound is produced through chemical synthesis rather than extracted from natural sources. Environmental impact depends on manufacturing processes and waste management. Being a specialty chemical, it has limited production volume compared to major fragrance ingredients.
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Physicochemical Properties
DTXSID: DTXSID8051885
Physical Properties
| Molecular Weight | 208.301 g/mol🔬 EPA CompTox |
| Density | 1.057 g/cm^3📊 OPERA |
| Boiling Point | 262.771 °C📊 OPERA |
| Melting Point | 77.19 °C📊 OPERA |
| Flash Point | 109.947 °C📊 OPERA |
| Refractive Index | 1.549 Dimensionless📊 OPERA |
| Molar Volume | 193.691 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 3.369 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 3.369 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 3.369 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 6.56 Log10 unitless📊 OPERA |
| Water Solubility | 0.01 mol/L📊 OPERA |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0.008 mmHg📊 OPERA |
| Surface Tension | 44.321 dyn/cm📊 OPERA |
Molecular Descriptors
| Topological Polar Surface Area | 29.6 Ų💻 Computed |
| H-Bond Donors | 0 count💻 Computed |
| H-Bond Acceptors | 2 count💻 Computed |
| Rotatable Bonds | 2 count💻 Computed |
| Aromatic Rings | 0 count💻 Computed |
| Molar Refractivity | 61.568 cm^3/mol📊 OPERA |
| Polarizability | 24.407 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.
