1,2,3,4,5,6,7,8,9,10-Decahydro-5,9-methanobenzocycloocten-11-one (CAS 22690-27-3) — Woody Base Note Fragrance Ingredient
1,2,3,4,5,6,7,8,9,10-Decahydro-5,9-methanobenzocycloocten-11-one
CAS 22690-27-3
What Is 1,2,3,4,5,6,7,8,9,10-Decahydro-5,9-methanobenzocycloocten-11-one?
This synthetic compound is a specialized fragrance ingredient used in high-end perfumery for its unique woody-amber character. It’s found in niche fragrances where perfumers seek novel olfactory effects. Its complex structure allows it to bridge woody and animalic accords, making it valuable for creating modern interpretations of classic amber bases.
Safety Profile
USE WITH AWARENESSWhat Does 1,2,3,4,5,6,7,8,9,10-Decahydro-5,9-methanobenzocycloocten-11-one Smell Like?
A powerful woody-amber molecule with a multidimensional character. Opens with dry cedar-like facets that recall pencil shavings and vintage cigar boxes. As it evolves, reveals a subtle animalic warmth reminiscent of sun-worn leather, balanced by a clean musk undertone. The drydown presents an intriguing mineralic quality, like smooth river stones warmed by sunlight. Exceptionally tenacious, it adds depth and diffusion to woody compositions.
In Famous Fragrances
Fragrance associations may not reflect actual formulations.
Used here to amplify the resinous amber core with its woody-mineralic facets, creating an impression of ancient incense treasures.
Provides the flinty mineral undertone that makes this fragrance’s vetiver accord smell like sun-baked pebbles.
2D Molecular Structure
SMILES: CC1C2CCCC(C2=O)C2=C1CCCC2
Chemistry, Properties & Perfumer Guide
The Chemistry
A bridged bicyclic ketone with a complex decahydrobenzocyclooctene structure. Synthesized through Diels-Alder reactions followed by hydrogenation and oxidation steps. The strained ring system contributes to its unusual odor properties, with the ketone functionality providing hydrogen bonding sites that influence volatility and tenacity. No known natural occurrence.
Physical & Chemical Properties
| Appearance | Colorless to pale yellow liquid |
|---|---|
| Boiling Point | Estimated >250°C |
| Flash Point | >100°C |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.1-0.5% | Up to 1% | Used sparingly for woody-amber effects |
| Functional Fragrance | 0.01-0.1% | Up to 0.2% | Adds sophistication to masculine bases |
Classic Accords
Tip: Use with ionones to soften its sharp edges while maintaining diffusion.
Alternatives & Comparisons
When a cleaner, more marine amber effect is desired without the woody-mineralic character.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
Not currently restricted under IFRA standards. Recommended maximum 1% in finished products.
EU Allergen Declaration
Not listed in EU allergen regulation (EC) No 1223/2009.
GHS Classification
RIFM Assessment
Under review by RIFM. Preliminary data suggests moderate skin sensitization potential.
Sustainability
Synthesized from petrochemical precursors. Energy-intensive production process offset by high odor potency allowing minimal usage. No known ecological toxicity at typical fragrance use levels.
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References
- Bauer et al. (2001). Novel Woody-Amber Materials. Perfumer & Flavorist.
- IFRA Standards Library Amendment 49
Data: PubChem (NIH), PubMed, RIFM, IFRA. Last reviewed: Apr 2026.
Report a data errorPhysicochemical Properties
DTXSID: DTXSID4051877
Physical Properties
| Molecular Weight | 204.313 g/mol🔬 EPA CompTox |
| Density | 1.058 g/cm^3📊 OPERA |
| Boiling Point | 307.124 °C📊 OPERA |
| Melting Point | 94.275 °C📊 OPERA |
| Flash Point | 137.27 °C📊 OPERA |
| Refractive Index | 1.529 Dimensionless📊 OPERA |
| Molar Volume | 195.268 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 3.688 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 3.688 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 3.688 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 7.46 Log10 unitless📊 OPERA |
| Water Solubility | 0.002 mol/L📊 OPERA |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0 mmHg📊 OPERA |
| Viscosity | 13.342 cP📊 OPERA |
| Surface Tension | 36.772 dyn/cm📊 OPERA |
| Thermal Conductivity | 124.355 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 | 60.243 cm^3/mol📊 OPERA |
| Polarizability | 23.882 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.
