4-(2-Butenylidene)-3,5,5-trimethylcyclohex-2-en-1-one (CAS 13215-88-8) — Woody Base Note Fragrance Ingredient
4-(2-Butenylidene)-3,5,5-trimethylcyclohex-2-en-1-one
CAS 13215-88-8
What Is 4-(2-Butenylidene)-3,5,5-trimethylcyclohex-2-en-1-one?
4-(2-Butenylidene)-3,5,5-trimethylcyclohex-2-en-1-one is a synthetic fragrance ingredient used to add woody, amber-like nuances to perfumes. It’s found in fine fragrances and personal care products. This molecule helps create depth and longevity in modern perfumery, often used as a base note to anchor lighter components.
Safety Profile
USE WITH AWARENESSWhat Does 4-(2-Butenylidene)-3,5,5-trimethylcyclohex-2-en-1-one Smell Like?
This molecule opens with a sharp, woody-camphoraceous burst reminiscent of dry pine needles. As it settles, it reveals a warm, slightly sweet amber character with hints of tobacco leaf. The dry-down is persistent, leaving a smooth, musky-woody trail that blends exceptionally well with vanilla and patchouli bases.
2D Molecular Structure
SMILES: CC=CC=C1C(C)=CC(=O)CC1(C)C
Chemistry, Properties & Perfumer Guide
The Chemistry
A cyclic enone with a conjugated diene system, this synthetic molecule belongs to the ionone family. Industrially produced via aldol condensation followed by dehydration, its structure allows for excellent stability in formulations. The butenylidene side chain contributes to its amber-woody character while the trimethylcyclohexenone core provides tenacity.
Physical & Chemical Properties
| Boiling Point | Not publicly available |
|---|---|
| Density | Not publicly available |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.5-2% | Up to 5% | Provides amber-woody foundation |
| Personal Care | 0.1-0.5% | Up to 1% | Used for longevity |
Classic Accords
Tip: Use with ionones to enhance woody character without becoming too sharp.
Alternatives & Comparisons
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
Not currently restricted by IFRA. Monitor for future amendments due to structural similarity to known sensitizers.
RIFM Assessment
No specific RIFM assessment found. General enone safety guidelines apply.
Sustainability
As a synthetic molecule, production involves petrochemical feedstocks. No known natural sources. Manufacturers are increasingly adopting green chemistry principles to reduce environmental impact during synthesis.
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Physicochemical Properties
DTXSID: DTXSID20863497
Physical Properties
| Molecular Weight | 190.286 g/mol🔬 EPA CompTox |
| Density | 0.997 g/cm^3🔬 EPA CTX |
| Boiling Point | 252.5 °C🔬 EPA CTX |
| Melting Point | -59.2 °C🔬 EPA CTX |
| Flash Point | 137 °C🔬 EPA CTX |
| Refractive Index | 1.54 Dimensionless📊 OPERA |
| Molar Volume | 196.483 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 3.105 Log10 unitless🔬 EPA CTX |
| LogD (pH 5.5) | 3.613 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 3.613 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 6.36 Log10 unitless📊 OPERA |
| Water Solubility | 0.002 mol/L📊 OPERA |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0.071 mmHg🔬 EPA CTX |
| Surface Tension | 32.936 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 | 1 count💻 Computed |
| Aromatic Rings | 0 count💻 Computed |
| Molar Refractivity | 61.635 cm^3/mol📊 OPERA |
| Polarizability | 24.434 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.
