2-Ethoxy-2,6,6-trimethyl-9-methylenebicyclo[3.3.1]nonane (CAS 68845-00-1) — Woody Middle to base Note Fragrance Ingredient
2-Ethoxy-2,6,6-trimethyl-9-methylenebicyclo[3.3.1]nonane
CAS 68845-00-1
What Is 2-Ethoxy-2,6,6-trimethyl-9-methylenebicyclo[3.3.1]nonane?
2-Ethoxy-2,6,6-trimethyl-9-methylenebicyclo[3.3.1]nonane is a synthetic fragrance compound used in modern perfumery. It’s found in some contemporary fragrances where a unique woody-ambergris character is desired. This ingredient matters because it represents the cutting edge of synthetic aroma chemistry, allowing perfumers to create novel scent profiles that don’t exist in nature.
Safety Profile
USE WITH AWARENESSWhat Does 2-Ethoxy-2,6,6-trimethyl-9-methylenebicyclo[3.3.1]nonane Smell Like?
This synthetic molecule offers a complex olfactory profile that evolves from initial sharp, almost metallic top notes to a warm, woody-ambergris heart. The dry-down reveals subtle marine facets with a clean, slightly ozonic character reminiscent of sea air. Its odor has been described as a bridge between traditional woody notes and modern synthetic ambergris alternatives, with a faintly sweet, mineral-like persistence.
2D Molecular Structure
SMILES: CCOC1(C)CCC2C(=C)C1CCC2(C)C
Chemistry, Properties & Perfumer Guide
The Chemistry
2-Ethoxy-2,6,6-trimethyl-9-methylenebicyclo[3.3.1]nonane is a synthetic bicyclic ether derivative. Its complex structure features multiple stereocenters, making chirality an important factor in its olfactory properties. The molecule is synthesized through multi-step organic reactions, typically starting from camphor or similar bicyclic precursors. The ethoxy group at position 2 contributes significantly to its unique scent profile, differentiating it from simpler woody odorants.
Physical & Chemical Properties
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.5-2% | Up to 5% | Used as a modern woody-amber modifier |
| Functional Fragrance | 0.1-0.5% | Up to 1% | For subtle woody-marine effects |
Classic Accords
Tip: Use in small quantities to add depth to woody compositions without overwhelming other notes.
Alternatives & Comparisons
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
No current IFRA restrictions. Not specifically regulated under any amendment.
RIFM Assessment
Limited RIFM assessment available. Considered safe at current usage levels based on structural analogs.
Sustainability
As a purely synthetic material, this compound doesn’t rely on natural resource extraction. However, its complex synthesis requires multiple chemical steps with associated energy inputs. Future green chemistry approaches may improve its sustainability profile.
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Ingredient Data Sheet
CAS 68845-00-1Physical Properties
| Molecular Weight | 222.37 g/mol🔬 PubChem |
| LogP (Octanol-Water) | 3.6🔬 PubChem |
| Boiling Point | 263 °C🔬 EPA CompTox |
| Vapor Pressure | 0.015 mmHg @ 25°C📊 OPERA |
| Flash Point | 104 °C🔬 EPA CompTox |
| Involatility Index | 0.0011💻 Calculated |
| log Kp (skin permeability) | -1.5💻 Calculated |
| SMILES | CCOC1(CCC2C(=C)C1CCC2(C)C)C🔬 PubChem |
Volatility & Performance
| Fragrance Note | Heart💻 Calculated |
| Volatility Class | Very slow💻 Calculated |
| Persistence Score | 3.8 / 5💻 Calculated |
Odor & Flavor
| Functional Groups | etheralkene💻 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: DTXSID4052421
Physical Properties
| Molecular Weight | 222.37 g/mol🔬 PubChem |
| Density | 0.925 g/cm^3🔬 EPA CTX |
| Boiling Point | 263 °C🔬 EPA CTX |
| Melting Point | 34.312 °C📊 OPERA |
| Flash Point | 104 °C🔬 EPA CTX |
| Refractive Index | 1.48 Dimensionless📊 OPERA |
| Molar Volume | 241.905 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 5.164 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 5.164 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 5.164 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 6.9 Log10 unitless📊 OPERA |
| Water Solubility | 0 mol/L🔬 EPA CTX |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0.015 mmHg🔬 EPA CTX |
| Viscosity | 9.681 cP📊 OPERA |
| Surface Tension | 30.103 dyn/cm📊 OPERA |
| Thermal Conductivity | 124.617 mW/(m*K)📊 OPERA |
Molecular Descriptors
| Topological Polar Surface Area | 9.23 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 | 68.663 cm^3/mol📊 OPERA |
| Polarizability | 27.22 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.
