2,3,4,4a,5,6-hexahydro-2,2-dimethyl-1,3-methanonaphthalen-7(1H)-one (CAS 68433-81-8) — Woody Base Note Fragrance Ingredient
2,3,4,4a,5,6-hexahydro-2,2-dimethyl-1,3-methanonaphthalen-7(1H)-one
CAS 68433-81-8
What Is 2,3,4,4a,5,6-hexahydro-2,2-dimethyl-1,3-methanonaphthalen-7(1H)-one?
This synthetic ingredient is a complex bicyclic ketone used in modern perfumery. It’s found in niche fragrances seeking avant-garde woody-amber effects. Perfumers value it for its ability to add diffusion and tenacity without traditional amber materials, making it useful in sustainable formulations.
Safety Profile
GENERALLY SAFEWhat Does 2,3,4,4a,5,6-hexahydro-2,2-dimethyl-1,3-methanonaphthalen-7(1H)-one Smell Like?
A powerful woody-amber molecule with camphoraceous facets. Opens with a dry cedar-like sharpness reminiscent of pencil shavings, evolving into a warm ambery heart with subtle animalic undertones. The dry-down reveals a clean muskiness, behaving like a synthetic analog of natural ambergris but with better stability.
2D Molecular Structure
SMILES: CC1(C2CC3CCC(=O)C=C3C1C2)C
Chemistry, Properties & Perfumer Guide
The Chemistry
A synthetic bicyclic ketone belonging to the methanonaphthalenone class. Typically produced via Diels-Alder reactions followed by selective hydrogenation. The rigid molecular structure contributes to its excellent stability and longevity in fragrance applications. Lacks chirality due to its symmetrical structure.
Physical & Chemical Properties
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.5-2% | Up to 5% | For woody-amber effects |
| Functional Fragrance | 0.1-0.5% | Up to 1% | For diffusion enhancement |
Classic Accords
Tip: Use with citrus top notes to prevent heaviness.
Alternatives & Comparisons
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
No current restrictions under IFRA standards.
RIFM Assessment
Not currently assessed by RIFM.
Sustainability
Synthetic production avoids harvesting of natural resources. Typical petrochemical origin but used at low levels reduces environmental impact compared to traditional amber materials.
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Ingredient Data Sheet
CAS 68433-81-8Physical Properties
| Molecular Weight | 190.28 g/mol🔬 PubChem |
| LogP (Octanol-Water) | 2.4🔬 PubChem |
| Boiling Point | 272 °C🔬 EPA CompTox |
| Vapor Pressure | 0.0096 mmHg @ 25°C📊 OPERA |
| Flash Point | 124.5 °C🔬 EPA CompTox |
| Involatility Index | 0.0007💻 Calculated |
| log Kp (skin permeability) | -2.157💻 Calculated |
| SMILES | CC1(C2CC3CCC(=O)C=C3C1C2)C🔬 PubChem |
Volatility & Performance
| Fragrance Note | Heart💻 Calculated |
| Volatility Class | Very slow💻 Calculated |
| Persistence Score | 3.4 / 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: DTXSID6052409
Physical Properties
| Molecular Weight | 190.28 g/mol🔬 PubChem |
| Density | 1.022 g/cm^3📊 PubChem |
| Boiling Point | 272 °C📊 PubChem |
| Melting Point | 78 °C📊 PubChem |
| Flash Point | 124.5 °C📊 PubChem |
Partition & Solubility
| LogP (Octanol-Water) | 2.4 Log10 unitless🔬 PubChem |
| Water Solubility | 0.004 mol/L📊 PubChem |
Transport Properties
| Vapor Pressure | 0.01 mmHg📊 PubChem |
Molecular Descriptors
| Topological Polar Surface Area | 17.07 Ų💻 Computed |
| H-Bond Donors | 0 count💻 Computed |
| H-Bond Acceptors | 1 count💻 Computed |
| Molar Refractivity | 55.81 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.
