(2.alpha.,4a.alpha.,8.alpha.)-Hexahydro-1,1,5,5-tetramethyl-2H-2,4a-methanonaphthalen-8(5H)-one (CAS 29461-14-1) — Woody Base Note Fragrance Ingredient
(2.alpha.,4a.alpha.,8.alpha.)-Hexahydro-1,1,5,5-tetramethyl-2H-2,4a-methanonaphthalen-8(5H)-one
CAS 29461-14-1
What Is (2.alpha.,4a.alpha.,8.alpha.)-Hexahydro-1,1,5,5-tetramethyl-2H-2,4a-methanonaphthalen-8(5H)-one?
This synthetic fragrance ingredient is a complex ketone used in modern perfumery. It’s typically found in niche and artisanal fragrances seeking unique woody-ambery effects. While not widely recognized by name, it contributes to sophisticated scent profiles that consumers encounter in premium products.
Safety Profile
USE WITH AWARENESSWhat Does (2.alpha.,4a.alpha.,8.alpha.)-Hexahydro-1,1,5,5-tetramethyl-2H-2,4a-methanonaphthalen-8(5H)-one Smell Like?
A sophisticated woody-amber molecule with a complex olfactory profile. Opens with crisp camphoraceous facets that quickly evolve into a rich, dry cedarwood character with subtle leathery undertones. The dry-down reveals a smooth ambery warmth with hints of tobacco-like richness. Exceptionally tenacious, it provides excellent diffusion and longevity while maintaining clarity throughout the fragrance evolution.
2D Molecular Structure
SMILES: [H][C@@]12C(=O)CCC(C)(C)[C@]11CC[C@@H](C1)C2(C)C
Chemistry, Properties & Perfumer Guide
The Chemistry
This bicyclic ketone belongs to the family of decalin derivatives with a complex bridged ring structure. The molecule features multiple quaternary carbons contributing to its stability and tenacity. Synthesized through Diels-Alder reactions of appropriate terpene precursors followed by oxidation, it represents a modern approach to creating durable woody-amber notes. The rigid molecular framework prevents rapid volatilization while allowing excellent diffusion.
Physical & Chemical Properties
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.5-2% | Up to 5% | Foundation for woody accords |
| Home Fragrance | 1-3% | Up to 8% | Provides longevity |
Classic Accords
Tip: Use with ionones to soften sharp edges while maintaining projection.
Alternatives & Comparisons
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
No current IFRA restrictions. Not evaluated under latest amendments.
RIFM Assessment
Not currently evaluated by RIFM. Limited toxicological data available.
Sustainability
As a purely synthetic material, this ingredient avoids natural resource depletion concerns. However, its complex synthesis may involve multi-step processes with moderate environmental impact. Modern green chemistry approaches are being explored to optimize production efficiency.
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Physicochemical Properties
DTXSID: DTXSID5047168
Physical Properties
| Molecular Weight | 220.356 g/mol🔬 EPA CompTox |
| Density | 1.002 g/cm^3🔬 EPA CTX |
| Boiling Point | 295.9 °C🔬 EPA CTX |
| Melting Point | -22 °C🔬 EPA CTX |
| Flash Point | 134.28 °C🔬 EPA CTX |
| Refractive Index | 1.509 Dimensionless📊 OPERA |
| Molar Volume | 219.2 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 4.905 Log10 unitless🔬 EPA CTX |
| LogD (pH 5.5) | 4.111 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 4.111 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 7.26 Log10 unitless📊 OPERA |
| Water Solubility | 0 mol/L🔬 EPA CTX |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0.011 mmHg🔬 EPA CTX |
| Surface Tension | 34.347 dyn/cm📊 OPERA |
| Thermal Conductivity | 110.947 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 | 0 count💻 Computed |
| Aromatic Rings | 0 count💻 Computed |
| Molar Refractivity | 65.464 cm^3/mol📊 OPERA |
| Polarizability | 25.952 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.
