Ethyl 2-methyl-4-oxo-6-pentylcyclohex-2-ene-1-carboxylate (CAS 59151-19-8) — Woody Middle Note Fragrance Ingredient
Ethyl 2-methyl-4-oxo-6-pentylcyclohex-2-ene-1-carboxylate
CAS 59151-19-8
What Is Ethyl 2-methyl-4-oxo-6-pentylcyclohex-2-ene-1-carboxylate?
Ethyl 2-methyl-4-oxo-6-pentylcyclohex-2-ene-1-carboxylate is a synthetic fragrance ingredient used in perfumes and scented products. It contributes to complex, modern scent profiles. This molecule is valued for its ability to add depth and longevity to fragrances, often working behind the scenes to enhance other notes without being easily identifiable on its own.
Safety Profile
GENERALLY SAFEWhat Does Ethyl 2-methyl-4-oxo-6-pentylcyclohex-2-ene-1-carboxylate Smell Like?
This synthetic molecule offers a complex olfactory profile with subtle fruity and woody undertones. It evolves from a slightly sharp, almost citrus-like top note to a warmer, more rounded heart with hints of dried fruits and a faintly resinous quality. The dry-down reveals a soft, powdery woodiness that lingers close to the skin, making it useful for adding subtle persistence to fragrance compositions without overpowering other elements.
2D Molecular Structure
SMILES: CCCCCC1CC(=O)C=C(C1C(=O)OCC)C
Chemistry, Properties & Perfumer Guide
The Chemistry
Ethyl 2-methyl-4-oxo-6-pentylcyclohex-2-ene-1-carboxylate belongs to the class of cyclohexene carboxylate esters. It is exclusively synthetic, typically produced through esterification and alkylation reactions. The pentyl side chain contributes to its lipophilic character, while the conjugated carbonyl system provides stability and influences its olfactory properties. The molecule’s structure allows for good volatility while maintaining sufficient persistence in fragrance applications.
Physical & Chemical Properties
| Boiling Point | Not available |
|---|---|
| Density | Not available |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 1-3% | Up to 5% | Used as a modifier |
| Functional Fragrance | 0.5-2% | Up to 3% | Adds persistence |
| Personal Care | 0.1-1% | Up to 2% | Used in trace amounts |
Classic Accords
Tip: Use in small amounts to add depth without dominating the composition.
Alternatives & Comparisons
Similar structure without pentyl group, offers lighter fruity character with less persistence.
Provides similar subtle fruity-woody effects with better documented safety profile.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
Not currently restricted by IFRA.
RIFM Assessment
No RIFM assessment currently available for this specific compound.
Sustainability
As a synthetic material, this compound’s environmental impact depends on production methods and sourcing of precursors. Being petroleum-derived, it avoids agricultural land use but requires energy-intensive synthesis. The absence of natural sources means no biodiversity concerns, but responsible manufacturing practices should be verified.
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Ingredient Data Sheet
CAS 59151-19-8Physical Properties
| Molecular Weight | 252.35 g/mol🔬 PubChem |
| LogP (Octanol-Water) | 3.3🔬 PubChem |
| Boiling Point | 315 °C🔬 EPA CompTox |
| Vapor Pressure | 0 mmHg @ 25°C📊 OPERA |
| Flash Point | 158.5 °C🔬 EPA CompTox |
| log Kp (skin permeability) | -1.896💻 Calculated |
| SMILES | CCCCCC1CC(=O)C=C(C1C(=O)OCC)C🔬 PubChem |
Volatility & Performance
| Fragrance Note | Base💻 Calculated |
| Volatility Class | Very slow💻 Calculated |
| Persistence Score | 9.3 / 5💻 Calculated |
Odor & Flavor
| Functional Groups | ketoneesteretheralkene💻 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: DTXSID40866743
Physical Properties
| Molecular Weight | 252.35 g/mol🔬 PubChem |
| Density | 0.996 g/cm^3🔬 PubChem |
| Boiling Point | 315 °C🔬 PubChem |
| Flash Point | 158.5 °C🔬 PubChem |
Partition & Solubility
| LogP (Octanol-Water) | 3.3 Log10 unitless🔬 PubChem |
| Water Solubility | 0.001 mol/L🔬 PubChem |
Transport Properties
| Vapor Pressure | 0 mmHg🔬 PubChem |
Molecular Descriptors
| Topological Polar Surface Area | 43.37 Ų💻 Computed |
| H-Bond Donors | 0 count💻 Computed |
| H-Bond Acceptors | 3 count💻 Computed |
| Rotatable Bonds | 6 count💻 Computed |
| Molar Refractivity | 71.14 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.
