4,7,7-Trimethyl-2-(3-methyl-2-butenyl)bicyclo[4.1.0]heptan-3-one (CAS 74499-58-4) — Woody Base Note Fragrance Ingredient
4,7,7-Trimethyl-2-(3-methyl-2-butenyl)bicyclo[4.1.0]heptan-3-one
CAS 74499-58-4
What Is 4,7,7-Trimethyl-2-(3-methyl-2-butenyl)bicyclo[4.1.0]heptan-3-one?
4,7,7-Trimethyl-2-(3-methyl-2-butenyl)bicyclo[4.1.0]heptan-3-one is a synthetic fragrance compound used in perfumery to create unique woody-spicy accords. It’s typically found in niche and artisanal fragrances. This ingredient matters because it adds depth and complexity to fragrance compositions, often serving as a building block for modern woody or amber bases.
Safety Profile
USE WITH AWARENESSWhat Does 4,7,7-Trimethyl-2-(3-methyl-2-butenyl)bicyclo[4.1.0]heptan-3-one Smell Like?
This bicyclic ketone presents a complex olfactory profile, opening with sharp woody facets reminiscent of freshly split cedar. As it evolves, a subtle spiciness emerges, akin to black pepper with a camphoraceous edge. The dry-down reveals a refined, slightly smoky character that blends beautifully with amber bases. Its tenacious nature makes it particularly valuable for creating long-lasting woody foundations in modern perfumery.
2D Molecular Structure
SMILES: CC1CC2C(C(CC=C(C)C)C1=O)C2(C)C
Chemistry, Properties & Perfumer Guide
The Chemistry
4,7,7-Trimethyl-2-(3-methyl-2-butenyl)bicyclo[4.1.0]heptan-3-one belongs to the bicyclic terpenoid ketone class, structurally related to camphor derivatives. The molecule features a strained cyclopropane ring fused to a cyclohexanone core, with isoprenoid substitution at the 2-position. Synthesis typically involves cyclopropanation of appropriate terpene precursors followed by oxidation. The stereochemistry at multiple centers contributes to its distinctive olfactory properties, with different diastereomers potentially exhibiting varying odor characteristics.
Physical & Chemical Properties
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.5-2% | Up to 5% | Woody accord enhancer |
| Home Care | 0.1-0.5% | Up to 1% | Long-lasting woody note |
Classic Accords
Tip: Use in trace amounts to enhance woody accords without overpowering the composition.
Alternatives & Comparisons
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
Not currently restricted by IFRA standards.
RIFM Assessment
RIFM evaluation pending for this material.
Sustainability
As a synthetic material, this compound’s environmental impact depends primarily on manufacturing processes. Being produced in controlled laboratory settings eliminates concerns about overharvesting of natural resources. However, like all synthetic fragrance ingredients, its carbon footprint includes petrochemical sourcing and energy-intensive production steps.
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Ingredient Data Sheet
CAS 74499-58-4Physical Properties
| Molecular Weight | 220.35 g/mol🔬 PubChem |
| LogP (Octanol-Water) | 4.1🔬 PubChem |
| Boiling Point | 282 °C🔬 EPA CompTox |
| Vapor Pressure | 0.1259 mmHg @ 25°C📊 OPERA |
| Flash Point | 114.8 °C🔬 EPA CompTox |
| Involatility Index | 0.0091💻 Calculated |
| log Kp (skin permeability) | -1.133💻 Calculated |
| SMILES | CC1CC2C(C2(C)C)C(C1=O)CC=C(C)C🔬 PubChem |
Volatility & Performance
| Fragrance Note | Heart💻 Calculated |
| Volatility Class | Very slow💻 Calculated |
| Persistence Score | 2 / 5💻 Calculated |
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: DTXSID70868311
Physical Properties
| Molecular Weight | 220.356 g/mol🔬 EPA CompTox |
| Density | 0.922 g/cm^3📊 OPERA |
| Boiling Point | 282.106 °C📊 OPERA |
| Melting Point | 48.844 °C📊 OPERA |
| Flash Point | 110.642 °C📊 OPERA |
| Refractive Index | 1.474 Dimensionless📊 OPERA |
| Molar Volume | 240.624 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 4.599 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 4.599 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 4.599 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 7.25 Log10 unitless📊 OPERA |
| Water Solubility | 0.001 mol/L📊 OPERA |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0.043 mmHg📊 OPERA |
| Viscosity | 1.435 cP📊 OPERA |
| Surface Tension | 28.411 dyn/cm📊 OPERA |
| Thermal Conductivity | 113.539 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 | 2 count💻 Computed |
| Aromatic Rings | 0 count💻 Computed |
| Molar Refractivity | 67.62 cm^3/mol📊 OPERA |
| Polarizability | 26.807 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.
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