1,5-Dimethylbicyclo[3.2.1]octan-8-one-oxime (CAS 75147-23-8) — Woody Middle to base Note Fragrance Ingredient
1,5-Dimethylbicyclo[3.2.1]octan-8-one-oxime
CAS 75147-23-8
What Is 1,5-Dimethylbicyclo[3.2.1]octan-8-one-oxime?
1,5-Dimethylbicyclo[3.2.1]octan-8-one-oxime is a synthetic fragrance ingredient primarily used in perfumery to add unique woody and camphoraceous nuances. It’s found in niche fragrances seeking avant-garde olfactory profiles. This molecule matters because it offers perfumers a novel structural framework, creating unconventional scent signatures that stand out in modern compositions while maintaining good stability in formulations.
Safety Profile
USE WITH AWARENESSWhat Does 1,5-Dimethylbicyclo[3.2.1]octan-8-one-oxime Smell Like?
This intriguing oxime delivers a complex interplay of dry woody facets with camphoraceous coolness, reminiscent of antique wooden chests and alpine air. The initial impression is a crisp, almost mentholated top note that evolves into a heart of smoothed cedar and vetiver-like earthiness. In drydown, it reveals subtle animalic undertones that add depth without overt muskiness. The bicyclic structure contributes exceptional tenacity, allowing this material to serve as both a modifier and a fixative in woody-amber accords.
In Famous Fragrances
Fragrance associations may not reflect actual formulations.
Featured as the sole active ingredient, showcasing its full spectrum from fresh camphoraceous opening to persistent woody drydown that interacts uniquely with skin chemistry.
Used as a structural backbone to amplify cedar and sandalwood notes while adding mineralic freshness to this modern woody composition.
2D Molecular Structure
SMILES: CC12CCC(C)(CCC1)C2=NO
Chemistry, Properties & Perfumer Guide
The Chemistry
1,5-Dimethylbicyclo[3.2.1]octan-8-one-oxime belongs to the bicyclic ketoxime class, featuring a rigid molecular framework that contributes to its odor persistence. The oxime functional group (-NOH) attached to the strained bicyclic system creates unique vibrational modes that our olfactory receptors interpret as simultaneously woody and cooling. Industrial synthesis typically involves the oximation of the corresponding ketone precursor under acidic conditions. The molecule’s stereochemistry is crucial – different diastereomers exhibit varying odor profiles and intensity.
Physical & Chemical Properties
| Appearance | Colorless to pale yellow liquid |
|---|---|
| Boiling Point | Estimated 240-260 °C |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.5-2% | Up to 3% | Used as an accent note |
| Functional Fragrance | 0.1-0.5% | Up to 1% | For subtle woody enhancement |
Classic Accords
Tip: Use with citrus top notes to create an unexpected contrast between freshness and woody depth.
Alternatives & Comparisons
Offers stronger woody-diffusive properties when more projection is desired, though lacks the camphoraceous nuance.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
Not currently restricted under IFRA standards. Monitor for future amendments due to structural similarity to restricted materials.
RIFM Assessment
Under evaluation by RIFM as of 2023. Preliminary data suggests acceptable safety profile at current usage levels.
Sustainability
As a synthetic material, production avoids natural resource depletion but requires petrochemical feedstocks. Manufacturing processes should employ green chemistry principles to minimize environmental impact. The material’s potency allows for low dosage, reducing ecological footprint per fragrance application.
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Physicochemical Properties
DTXSID: DTXSID2052495
Physical Properties
| Molecular Weight | 167.252 g/mol🔬 EPA CompTox |
| Density | 1.1 g/cm^3📊 OPERA |
| Boiling Point | 241.682 °C📊 OPERA |
| Melting Point | 105.488 °C📊 OPERA |
| Flash Point | 139.64 °C📊 OPERA |
| Refractive Index | 1.567 Dimensionless📊 OPERA |
| Molar Volume | 147.412 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 2.295 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 2.295 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 2.205 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 7.04 Log10 unitless📊 OPERA |
| Water Solubility | 0.001 mol/L🔬 EPA CTX |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0.004 mmHg📊 OPERA |
| Surface Tension | 37.925 dyn/cm📊 OPERA |
Molecular Descriptors
| Topological Polar Surface Area | 32.59 Ų💻 Computed |
| H-Bond Donors | 1 count💻 Computed |
| H-Bond Acceptors | 2 count💻 Computed |
| Rotatable Bonds | 0 count💻 Computed |
| Aromatic Rings | 0 count💻 Computed |
| Molar Refractivity | 48.131 cm^3/mol📊 OPERA |
| Polarizability | 19.081 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.
