1-[5(Or 6)-Methyl-7(or 8)-(1-methylethyl)bicyclo[2.2.2]oct-5-en-2-yl]ethan-1-one (CAS 68259-33-6) — Woody Middle Note Fragrance Ingredient
1-[5(Or 6)-Methyl-7(or 8)-(1-methylethyl)bicyclo[2.2.2]oct-5-en-2-yl]ethan-1-one
CAS 68259-33-6
What Is 1-[5(Or 6)-Methyl-7(or 8)-(1-methylethyl)bicyclo[2.2.2]oct-5-en-2-yl]ethan-1-one?
This synthetic fragrance ingredient is a complex bicyclic compound primarily used by professional perfumers. Consumers might encounter it in niche fragrances where it contributes woody, camphoraceous nuances. While not a household name, it plays a subtle role in creating modern aromatic accords.
Safety Profile
USE WITH AWARENESSWhat Does 1-[5(Or 6)-Methyl-7(or 8)-(1-methylethyl)bicyclo[2.2.2]oct-5-en-2-yl]ethan-1-one Smell Like?
The aroma is characterized by a bold, woody-camphoraceous profile with subtle pine-like freshness. Upon application, it reveals a crisp, slightly medicinal top note that evolves into a dry woody heart with faintly sweet undertones. The dry-down leaves a persistent, clean woody-musk impression that blends well with other structural materials.
2D Molecular Structure
SMILES: CC(C)C1CC2=C(C)CC1C(C2)C(C)=O
Chemistry, Properties & Perfumer Guide
The Chemistry
This bicyclic ketone belongs to the class of substituted norbornane derivatives. The complex structure with multiple methyl and isopropyl groups creates steric hindrance that influences its odor profile. Synthesized through Diels-Alder reactions followed by selective oxidation, the material exists as multiple isomers due to the positional variability of substituents. The rigid bicyclic framework contributes to its persistence and diffusion properties in fragrance applications.
Physical & Chemical Properties
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.5-2% | Up to 5% | Woody modifier |
| Functional Fragrance | 0.1-1% | Up to 3% | Freshness enhancer |
Classic Accords
Tip: Use as a bridge between fresh top notes and deep woody bases.
Alternatives & Comparisons
Simpler bicyclic structure with similar woody-camphoraceous character but less complexity.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
No specific IFRA restrictions currently apply to this material.
RIFM Assessment
Comprehensive safety assessment not yet available from RIFM.
Sustainability
As a synthetic material, production involves petrochemical feedstocks but offers consistent quality and reduces pressure on natural resources. The multi-step synthesis requires careful solvent management and energy input. Future green chemistry approaches may improve the environmental profile of this specialty ingredient.
Explore 1-[5(Or 6)-Methyl-7(or 8)-(1-methylethyl)bicyclo[2.2.2]oct-5-en-2-yl]ethan-1-one
Browse essential oils and aroma compounds.
Browse on iHerb →Affiliate disclosure: we may earn a small commission at no extra cost to you.
Ingredient Data Sheet
CAS 68259-33-6Physical Properties
| Molecular Weight | 206.32 g/mol🔬 PubChem |
| LogP (Octanol-Water) | 2.4🔬 PubChem |
| Boiling Point | 268 °C🔬 EPA CompTox |
| Vapor Pressure | 0.0288 mmHg @ 25°C📊 OPERA |
| Flash Point | 116.9 °C🔬 EPA CompTox |
| Involatility Index | 0.0022💻 Calculated |
| log Kp (skin permeability) | -2.255💻 Calculated |
| SMILES | CC1=C2CC(C(C1)C(C2)C(=O)C)C(C)C🔬 PubChem |
Volatility & Performance
| Fragrance Note | Heart💻 Calculated |
| Volatility Class | Very slow💻 Calculated |
| Persistence Score | 2.7 / 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: DTXSID60867555
Physical Properties
| Molecular Weight | 206.329 g/mol🔬 EPA CompTox |
| Density | 0.956 g/cm^3📊 OPERA |
| Boiling Point | 275.468 °C📊 OPERA |
| Melting Point | 19.378 °C📊 OPERA |
| Flash Point | 108.823 °C📊 OPERA |
| Refractive Index | 1.492 Dimensionless📊 OPERA |
| Molar Volume | 214.676 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 3.626 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 3.626 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 3.626 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 6.75 Log10 unitless📊 OPERA |
| Water Solubility | 0.001 mol/L📊 OPERA |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0.013 mmHg📊 OPERA |
| Viscosity | 10.509 cP📊 OPERA |
| Surface Tension | 32.144 dyn/cm📊 OPERA |
| Thermal Conductivity | 124.283 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 | 2 count💻 Computed |
| Aromatic Rings | 0 count💻 Computed |
| Molar Refractivity | 62.259 cm^3/mol📊 OPERA |
| Polarizability | 24.681 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.
