2-Methyl-4-(2,6,6-trimethylcyclohex-1-en-1-yl)-2-butenal (CAS 3155-71-3) — Woody Heart to Base Note Fragrance Ingredient
2-Methyl-4-(2,6,6-trimethylcyclohex-1-en-1-yl)-2-butenal
CAS 3155-71-3
What Is 2-Methyl-4-(2,6,6-trimethylcyclohex-1-en-1-yl)-2-butenal?
2-Methyl-4-(2,6,6-trimethylcyclohex-1-en-1-yl)-2-butenal is a synthetic fragrance compound used to add woody, floral nuances to perfumes. It’s found in fine fragrances and personal care products. This ingredient helps create sophisticated scent profiles, often contributing to the heart or base notes of a composition.
Safety Profile
USE WITH AWARENESSWhat Does 2-Methyl-4-(2,6,6-trimethylcyclohex-1-en-1-yl)-2-butenal Smell Like?
This aldehyde delivers a complex bouquet blending woody, floral, and slightly fruity facets. The initial impression is a warm, slightly powdery woodiness reminiscent of sandalwood, which gradually reveals subtle floral undertones. As it dries down, it develops a smooth, slightly sweet character with hints of dried fruits and a delicate musky trail. The overall effect is elegant and long-lasting, making it valuable for creating depth in modern fragrance compositions.
2D Molecular Structure
SMILES: CC(C=O)=CCC1=C(C)CCCC1(C)C
Chemistry, Properties & Perfumer Guide
The Chemistry
2-Methyl-4-(2,6,6-trimethylcyclohex-1-en-1-yl)-2-butenal is a synthetic aldehyde with a complex cyclic structure. It belongs to the family of unsaturated aldehydes, characterized by their reactivity and distinctive odor profiles. The molecule features a trimethylcyclohexene ring conjugated with an unsaturated aldehyde chain, which contributes to its unique olfactory properties. Synthesis typically involves aldol condensation reactions using appropriate cyclohexene derivatives.
Physical & Chemical Properties
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.5-2% | Up to 5% | Adds woody-floral complexity |
| Personal Care | 0.1-0.5% | Up to 1% | Use cautiously due to potential sensitization |
Classic Accords
Tip: Use with antioxidants to prevent oxidation of the aldehyde group.
Alternatives & Comparisons
A more stable sandalwood alternative with similar woody character but lower sensitization potential.
Provides comparable woody richness with better stability in alkaline formulations.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
No specific IFRA restrictions. General aldehyde guidelines apply.
RIFM Assessment
Under evaluation by RIFM for comprehensive safety assessment.
Sustainability
As a synthetic material, this compound is produced through controlled chemical processes, reducing environmental impact compared to natural alternatives that might require extensive plant cultivation. However, its synthesis does involve petrochemical feedstocks. Manufacturers are exploring greener synthesis routes to improve sustainability.
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Ingredient Data Sheet
CAS 3155-71-3Physical Properties
| Molecular Weight | 206.32 g/mol🔬 PubChem |
| LogP (Octanol-Water) | 3.4🔬 PubChem |
| Boiling Point | 272 °C🔬 EPA CompTox |
| Vapor Pressure | 0.1023 mmHg @ 25°C📊 OPERA |
| Flash Point | 129 °C🔬 EPA CompTox |
| Involatility Index | 0.0077💻 Calculated |
| log Kp (skin permeability) | -1.545💻 Calculated |
| SMILES | CC1=C(C(CCC1)(C)C)CC=C(C)C=O🔬 PubChem |
Volatility & Performance
| Fragrance Note | Heart💻 Calculated |
| Volatility Class | Very slow💻 Calculated |
| Persistence Score | 2 / 5💻 Calculated |
Odor & Flavor
| Functional Groups | aldehydealkene💻 RDKit |
Trade Names
| Boronal (Symrise).📖 Surburg |
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: DTXSID9052000
Physical Properties
| Molecular Weight | 206.329 g/mol🔬 EPA CompTox |
| Density | 0.885 g/cm^3📊 OPERA |
| Boiling Point | 275.085 °C📊 OPERA |
| Melting Point | 38.581 °C📊 OPERA |
| Flash Point | 117.494 °C📊 OPERA |
| Refractive Index | 1.469 Dimensionless📊 OPERA |
| Molar Volume | 231.965 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 4.288 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 4.288 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 4.288 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 7.24 Log10 unitless📊 OPERA |
| Water Solubility | 0 mol/L📊 OPERA |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0.036 mmHg📊 OPERA |
| Viscosity | 2.405 cP📊 OPERA |
| Surface Tension | 27.715 dyn/cm📊 OPERA |
| Thermal Conductivity | 129.463 mW/(m*K)📊 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 | 3 count💻 Computed |
| Aromatic Rings | 0 count💻 Computed |
| Molar Refractivity | 64.608 cm^3/mol📊 OPERA |
| Polarizability | 25.613 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.
