Methyl 2,6,10-trimethylcyclododeca-2,5,9-trien-1-yl ketone (CAS 28371-99-5) — Woody Base Note Fragrance Ingredient
Methyl 2,6,10-trimethylcyclododeca-2,5,9-trien-1-yl ketone
CAS 28371-99-5
What Is Methyl 2,6,10-trimethylcyclododeca-2,5,9-trien-1-yl ketone?
Methyl 2,6,10-trimethylcyclododeca-2,5,9-trien-1-yl ketone is a synthetic fragrance ingredient used in modern perfumery. It’s found in niche and designer fragrances where complex woody-ambery notes are desired. This molecule contributes depth and longevity to fragrance compositions, often acting as a base note enhancer that adds a subtle animalic warmth without being overpowering.
Safety Profile
USE WITH AWARENESSWhat Does Methyl 2,6,10-trimethylcyclododeca-2,5,9-trien-1-yl ketone Smell Like?
This ketone unfolds with an intriguing duality – opening with a dry, woody character reminiscent of aged cedar chests, then revealing a complex heart of ambery warmth with hints of sun-warmed animal fur. The dry-down carries a sophisticated musk-like persistence, behaving like an invisible velvet cloak that subtly amplifies surrounding notes. Its odor profile bridges the gap between woody and animalic families, with a faint metallic edge that prevents it from becoming cloying.
2D Molecular Structure
SMILES: CC(=O)C1CCC(C)=CCCC(C)=CCC=C1C
Chemistry, Properties & Perfumer Guide
The Chemistry
Methyl 2,6,10-trimethylcyclododeca-2,5,9-trien-1-yl ketone belongs to the macrocyclic ketone family, structurally related to muscone but with a more rigid framework. The molecule’s three conjugated double bonds contribute to its distinctive woody-amber character. Synthesized through Diels-Alder reactions followed by ketone functionalization, this material represents a modern approach to creating complex woody-amber notes without relying on natural animal-derived materials.
Physical & Chemical Properties
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.5-2% | Up to 5% | Base note amplifier |
| Home Care | 0.1-0.5% | Up to 1% | Longevity enhancer |
| Personal Care | 0.2-1% | Up to 2% | Stabilizes floral bases |
Classic Accords
Tip: Use below 3% to avoid overpowering floral heart notes.
Alternatives & Comparisons
More diffusive amber note with less animalic character, suitable when a cleaner profile is desired.
For true musk reconstitution, though significantly more expensive and restricted in some markets.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
Not currently restricted under IFRA standards. Listed on IFRA Transparency List.
RIFM Assessment
Under review by RIFM as of 2023. Preliminary data suggests safe use at current industry levels.
Sustainability
As a synthetic material, this ketone provides an ethical alternative to animal-derived musks while avoiding the agricultural impacts of plant-derived alternatives. Its efficient synthesis from petrochemical precursors results in consistent quality and reduced batch variability compared to natural materials. Future development may explore bio-based synthetic routes.
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Ingredient Data Sheet
CAS 28371-99-5Physical Properties
| Molecular Weight | 246.4 g/mol🔬 PubChem |
| LogP (Octanol-Water) | 3.3🔬 PubChem |
| Boiling Point | 331 °C🔬 EPA CompTox |
| Vapor Pressure | 0 mmHg @ 25°C📊 OPERA |
| Flash Point | 146.5 °C🔬 EPA CompTox |
| log Kp (skin permeability) | -1.86💻 Calculated |
| SMILES | CC1=CCCC(=CCC=C(C(CC1)C(=O)C)C)C🔬 PubChem |
Volatility & Performance
| Fragrance Note | Base💻 Calculated |
| Volatility Class | Very slow💻 Calculated |
| Persistence Score | 9.7 / 5💻 Calculated |
Odor & Flavor
| Functional Groups | ketonealkene💻 RDKit |
Regulatory Status
| IFRA Listed | Yes — see IFRA Standards for category limits⚖️ IFRA 51 |
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: DTXSID3051963
Physical Properties
| Molecular Weight | 246.394 g/mol🔬 EPA CompTox |
| Density | 0.893 g/cm^3📊 OPERA |
| Boiling Point | 332.833 °C📊 OPERA |
| Melting Point | 36.501 °C📊 OPERA |
| Flash Point | 136.925 °C📊 OPERA |
| Refractive Index | 1.469 Dimensionless📊 OPERA |
| Molar Volume | 277.966 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 4.904 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 4.904 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 4.904 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 7.93 Log10 unitless📊 OPERA |
| Water Solubility | 0 mol/L📊 OPERA |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0 mmHg📊 OPERA |
| Viscosity | 5.461 cP📊 OPERA |
| Surface Tension | 29.038 dyn/cm📊 OPERA |
| Thermal Conductivity | 130.989 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 | 77.469 cm^3/mol📊 OPERA |
| Polarizability | 30.711 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.
