2-Formyl-6,6-dimethylbicyclo(3.1.1)hept-2-ene (CAS 564-94-3) — Woody Top to Middle Note Fragrance Ingredient
2-Formyl-6,6-dimethylbicyclo(3.1.1)hept-2-ene
CAS 564-94-3
What Is 2-Formyl-6,6-dimethylbicyclo(3.1.1)hept-2-ene?
2-Formyl-6,6-dimethylbicyclo(3.1.1)hept-2-ene is a synthetic fragrance compound used in perfumery to create fresh, woody, and slightly pine-like scents. It’s found in various modern fragrances, particularly those aiming for a crisp, outdoorsy character. This ingredient matters because it adds a unique structural complexity to fragrances, bridging the gap between traditional woody notes and more contemporary aromatic profiles.
Safety Profile
USE WITH AWARENESSWhat Does 2-Formyl-6,6-dimethylbicyclo(3.1.1)hept-2-ene Smell Like?
This molecule delivers a crisp, woody-pine aroma with a subtle aldehydic lift. The initial impression is reminiscent of a sun-warmed pine forest with a clean, almost citrusy brightness. As it evolves, the scent reveals a heart of dry woody notes with a faintly resinous undertone. The dry-down is surprisingly smooth for such a structured molecule, leaving a whisper of clean, slightly camphoraceous woodiness that blends well with other aromatics.
2D Molecular Structure
SMILES: CC1(C)C2CC1C(C=O)=CC2
Chemistry, Properties & Perfumer Guide
The Chemistry
2-Formyl-6,6-dimethylbicyclo(3.1.1)hept-2-ene belongs to the bicyclic terpene aldehyde class, characterized by its rigid bicyclo[3.1.1]heptene framework with an aldehyde functional group. While not found in nature, its structure mimics certain oxidized terpenes. Synthesis typically involves the oxidation of pinene derivatives or carefully controlled Diels-Alder reactions. The molecule’s constrained bicyclic structure creates unique olfactory properties distinct from simpler terpene aldehydes, with the formyl group positioned to maximize volatility and odor impact.
Physical & Chemical Properties
| Boiling Point | Not available |
|---|---|
| Density | Not available |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.5-2% | Up to 5% | Used as woody-aromatic modifier |
| Functional Fragrance | 0.1-1% | Up to 3% | Adds freshness to cleaning products |
Classic Accords
Tip: Use in small quantities to add structural complexity to woody bases without overwhelming the composition.
Alternatives & Comparisons
Similar bicyclic structure but with more pronounced herbal character, useful when needing greater aromatic impact.
Offers comparable pine-like notes with additional minty freshness for cooler fragrance directions.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
Not currently restricted by IFRA standards.
RIFM Assessment
Limited safety data available; recommended to follow general aldehyde handling precautions.
Sustainability
As a synthetic material, this compound avoids natural resource depletion concerns. Its production typically involves controlled chemical processes with efficient atom economy. However, like all synthetic aromatics, responsible manufacturing practices should ensure proper solvent recovery and waste management.
Explore 2-Formyl-6,6-dimethylbicyclo(3.1.1)hept-2-ene
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 564-94-3Physical Properties
| Molecular Weight | 150.22 g/mol🔬 PubChem |
| LogP (Octanol-Water) | 2.1🔬 PubChem |
| Boiling Point | 220.5 °C🔬 EPA CompTox |
| Vapor Pressure | 0.1654 mmHg @ 25°C📊 OPERA |
| Flash Point | 81 °C🔬 EPA CompTox |
| Involatility Index | 0.0145💻 Calculated |
| log Kp (skin permeability) | -2.125💻 Calculated |
| SMILES | CC1(C2CC=C(C1C2)C=O)C🔬 PubChem |
Volatility & Performance
| Fragrance Note | Heart💻 Calculated |
| Volatility Class | Slow💻 Calculated |
| Persistence Score | 1.2 / 5💻 Calculated |
Odor & Flavor
| Primary Descriptors | cinnamonherbalspicy• leffingwell |
| Functional Groups | aldehydealkene💻 RDKit |
| “Refreshing, spicy-herbaceous odor of Bay-leaf-Cinnamon character. The diffusive warmth is particularly typical (and appreciated).”📖 Arctander | |
| 2-Formyl-6,6-dimethylbicyclo(3.1.1)hept-2-ene has a refreshing, spicy-herbaceous odor of bay leaf, reminiscent of cinnamon.📖 Fenaroli | |
Regulatory Status
| IOFI Classification | Nature Identical📖 Fenaroli |
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: DTXSID8052227
Physical Properties
| Molecular Weight | 150.221 g/mol🔬 EPA CompTox |
| Density | 0.99 g/cm^3📊 OPERA |
| Boiling Point | 220.5 °C🔬 EPA CTX |
| Melting Point | 40.613 °C📊 OPERA |
| Flash Point | 80.996 °C📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 2.98 Log10 unitless🔬 EPA CTX |
| Water Solubility | 0.003 mol/L📊 OPERA |
Transport Properties
| Vapor Pressure | 0.165 mmHg📊 OPERA |
| Viscosity | 1.796 cP📊 OPERA |
| Surface Tension | 29.831 dyn/cm📊 OPERA |
| Thermal Conductivity | 121.599 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 | 1 count💻 Computed |
| Aromatic Rings | 0 count💻 Computed |
| Molar Refractivity | 44.14 cm^3/mol💻 Computed |
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.
