1-(1,2,3,4-Tetrahydro-4,4-dimethyl-1-naphthyl)propan-1-one (CAS 74499-60-8) — Woody Middle Note Fragrance Ingredient
1-(1,2,3,4-Tetrahydro-4,4-dimethyl-1-naphthyl)propan-1-one
CAS 74499-60-8
What Is 1-(1,2,3,4-Tetrahydro-4,4-dimethyl-1-naphthyl)propan-1-one?
This synthetic fragrance ingredient is a complex molecule rarely encountered by name in consumer products. Perfumers use it as a specialty modifier in niche fragrances, where it contributes subtle woody-amber nuances. Though obscure, it represents the cutting edge of modern perfumery, allowing creators to achieve effects impossible with traditional materials while maintaining safety standards.
Safety Profile
USE WITH AWARENESSWhat Does 1-(1,2,3,4-Tetrahydro-4,4-dimethyl-1-naphthyl)propan-1-one Smell Like?
A sophisticated chameleon with initial crisp, almost metallic woodiness that evolves into a warm ambery glow. Imagine polished mahogany lacquered with beeswax, then set near smoldering incense. The dry-down reveals unexpected facets – a whisper of dried fruits like dates or prunes macerated in aged rum, grounded by a clean muskiness reminiscent of sun-warmed stones. Despite its complexity, it remains transparent in blends, never overwhelming but always present.
2D Molecular Structure
SMILES: CCC(=O)C1CCC(C)(C)C2=C1C=CC=C2
Chemistry, Properties & Perfumer Guide
The Chemistry
This ketone belongs to the family of cyclic terpenoid derivatives, structurally resembling norpatchoulenol but with distinctive branching. The propanone side chain introduces conformational flexibility, allowing the molecule to interact with multiple olfactory receptors. Industrial synthesis typically involves Friedel-Crafts acylation of tetrahydrodimethylnaphthalene precursors, followed by careful purification to remove positional isomers. The 4,4-dimethyl substitution pattern creates significant steric hindrance, influencing both volatility and odor persistence.
Physical & Chemical Properties
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.1-0.5% | Up to 1% | Background modifier |
| Functional Fragrance | 0.05-0.2% | Up to 0.3% | Cost-prohibitive for mass use |
Classic Accords
Tip: Use micro-doses to add dimensionality to woody-amber bases without altering their fundamental character.
Alternatives & Comparisons
More affordable woody-amber with similar diffusion properties but less nuance.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
No current IFRA restrictions. Classified as safe at anticipated usage levels.
RIFM Assessment
Pending full evaluation. Preliminary data shows no significant dermal concerns at perfumery concentrations.
Sustainability
As a synthetic material, production involves petrochemical feedstocks but requires relatively small quantities due to high potency. No known ecological accumulation concerns. The complex synthesis pathway makes renewable sourcing currently impractical, though bioengineering approaches are being explored.
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Physicochemical Properties
DTXSID: DTXSID30868312
Physical Properties
| Molecular Weight | 216.324 g/mol🔬 EPA CompTox |
| Density | 0.98 g/cm^3📊 OPERA |
| Boiling Point | 304.783 °C📊 OPERA |
| Melting Point | 39.595 °C📊 OPERA |
| Flash Point | 132.47 °C📊 OPERA |
| Refractive Index | 1.507 Dimensionless📊 OPERA |
| Molar Volume | 222.433 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 4.021 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 4.021 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 4.021 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 7.51 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 | 6.792 cP📊 OPERA |
| Surface Tension | 34.561 dyn/cm📊 OPERA |
| Thermal Conductivity | 127.387 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 | 1 count💻 Computed |
| Molar Refractivity | 66.198 cm^3/mol📊 OPERA |
| Polarizability | 26.243 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.
