5(Or 6)-Methyl-7(or 8)-(1-methylethyl)bicyclo[2.2.2]oct-5-ene-2-carbaldehyde (CAS 68259-31-4) — Woody Middle Note Fragrance Ingredient
5(Or 6)-Methyl-7(or 8)-(1-methylethyl)bicyclo[2.2.2]oct-5-ene-2-carbaldehyde
CAS 68259-31-4
What Is 5(Or 6)-Methyl-7(or 8)-(1-methylethyl)bicyclo[2.2.2]oct-5-ene-2-carbaldehyde?
This synthetic fragrance compound is a complex bicyclic aldehyde primarily used by professional perfumers. Consumers might encounter it in niche or avant-garde fragrances where unusual woody-green notes are desired. Its intricate structure creates a unique olfactory signature that’s hard to replicate with natural materials, making it valuable for creating distinctive modern accords.
Safety Profile
PROFESSIONAL USEWhat Does 5(Or 6)-Methyl-7(or 8)-(1-methylethyl)bicyclo[2.2.2]oct-5-ene-2-carbaldehyde Smell Like?
This bicyclic aldehyde presents an intriguing duality – opening with a sharp, almost metallic greenness reminiscent of crushed stems, then unfolding into a damp woody character with hints of mushroom earthiness. The dry-down reveals subtle camphoraceous undertones and a lingering dry cedar-like persistence. Its complex structure creates an evolving scent profile that bridges the gap between herbal freshness and deep forest notes.
2D Molecular Structure
SMILES: CC(C)C1CC2CC(C=O)C1C=C2C
Chemistry, Properties & Perfumer Guide
The Chemistry
This bicyclic terpene aldehyde belongs to a class of structurally complex synthetic fragrance materials designed to mimic natural woody-green notes. The molecule features a strained bicyclo[2.2.2]octene core with aldehyde and isopropyl substituents that create significant steric hindrance. Synthesis typically involves Diels-Alder cycloaddition followed by oxidative transformations. The multiple possible substitution patterns (5/6 and 7/8 positions) often result in isomeric mixtures that contribute to its complex olfactory profile.
Physical & Chemical Properties
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.1-0.5% | Up to 1% | Used as woody-green modifier |
| Functional Fragrance | 0.01-0.1% | Up to 0.3% | Limited use due to potency |
Classic Accords
Tip: Use sparingly in woody bases to add structural complexity without overwhelming the composition.
Alternatives & Comparisons
A more stable and widely used synthetic green-woody note with better safety profile for mainstream applications.
For similar woody persistence but with ambered rather than green tonalities.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
Not currently restricted by IFRA, but usage should be monitored due to limited safety data.
GHS Classification
RIFM Assessment
No RIFM assessment currently available for this specific compound.
Sustainability
As a purely synthetic material, this compound avoids natural resource depletion but requires energy-intensive synthesis. Its complex structure may present challenges for biodegradation. Perfumers should consider its relatively high potency – small quantities can achieve significant effects, potentially reducing overall environmental load compared to less potent alternatives.
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Physicochemical Properties
DTXSID: DTXSID6052405
Physical Properties
| Molecular Weight | 192.302 g/mol🔬 EPA CompTox |
| Density | 0.965 g/cm^3📊 OPERA |
| Boiling Point | 258.564 °C📊 OPERA |
| Melting Point | 19.752 °C📊 OPERA |
| Flash Point | 95.846 °C📊 OPERA |
| Refractive Index | 1.531 Dimensionless📊 OPERA |
| Molar Volume | 192.915 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 3.747 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 3.747 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 3.747 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 6.09 Log10 unitless📊 OPERA |
| Water Solubility | 0 mol/L📊 OPERA |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0.017 mmHg📊 OPERA |
| Viscosity | 9.695 cP📊 OPERA |
| Surface Tension | 32.751 dyn/cm📊 OPERA |
| Thermal Conductivity | 125.664 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 | 59.728 cm^3/mol📊 OPERA |
| Polarizability | 23.678 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.
