7-[(3,7-Dimethyl-2,6-octadienyl)oxy]-4-methyl-2H-1-benzopyran-2-one (CAS 50542-90-0) — Balsamic Middle to base Note Fragrance Ingredient
7-[(3,7-Dimethyl-2,6-octadienyl)oxy]-4-methyl-2H-1-benzopyran-2-one
CAS 50542-90-0
What Is 7-[(3,7-Dimethyl-2,6-octadienyl)oxy]-4-methyl-2H-1-benzopyran-2-one?
This synthetic fragrance ingredient is a specialized coumarin derivative used in niche perfumery. It’s found in select high-end fragrances where its unique molecular structure creates novel effects. The compound matters because it represents modern perfumery’s ability to engineer precisely tuned aroma molecules that don’t exist in nature.
Safety Profile
USE WITH AWARENESSWhat Does 7-[(3,7-Dimethyl-2,6-octadienyl)oxy]-4-methyl-2H-1-benzopyran-2-one Smell Like?
This synthetic coumarin derivative presents a complex olfactory profile that evolves dramatically. The initial impression suggests a fusion of bitter almond and dried hay, with an underlying phenolic sharpness. As it develops, the coumarinic character emerges more clearly – imagine tonka bean that’s been oxidized and given a citrusy twist. The dry-down reveals a persistent woody-ambergris quality with surprising tenacity for a synthetic material.
2D Molecular Structure
SMILES: CC(C)=CCCC(C)=CCOC1=CC2=C(C=C1)C(C)=CC(=O)O2
Chemistry, Properties & Perfumer Guide
The Chemistry
This compound belongs to the coumarin class, specifically a prenylated coumarin derivative. The molecule features a benzopyrone core with a dimethyloctadienyl ether substituent at the 7-position. While coumarins are naturally occurring, this particular substitution pattern is synthetic. The extended conjugated system contributes to its unique photophysical properties and likely influences its olfactory characteristics. Synthesis typically involves Williamson ether synthesis between a phenolic coumarin precursor and the appropriate prenyl halide.
Physical & Chemical Properties
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.1-0.5% | Up to 1% | Used as special effect modifier |
| Functional Fragrance | Not used | N/A | Too specialized for mass market |
Classic Accords
Tip: Use sparingly in woody-oriental bases to add coumarinic depth without the sweetness of natural derivatives.
Alternatives & Comparisons
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
No RIFM assessment found for this specific compound.
Sustainability
As a synthetic material, this compound avoids natural resource depletion but requires petrochemical feedstocks. The multi-step synthesis suggests moderate energy requirements. Being used in trace amounts minimizes environmental impact through the product lifecycle.
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Physicochemical Properties
DTXSID: DTXSID8052140
Physical Properties
| Molecular Weight | 312.409 g/mol🔬 EPA CompTox |
| Density | 1.068 g/cm^3📊 OPERA |
| Boiling Point | 410.621 °C📊 OPERA |
| Melting Point | 96.752 °C📊 OPERA |
| Flash Point | 196.966 °C📊 OPERA |
| Refractive Index | 1.542 Dimensionless📊 OPERA |
| Molar Volume | 294.476 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 5.357 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 5.357 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 5.357 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 10.33 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 | 22.066 cP📊 OPERA |
| Surface Tension | 37.556 dyn/cm📊 OPERA |
Molecular Descriptors
| Topological Polar Surface Area | 39.44 Ų💻 Computed |
| H-Bond Donors | 0 count💻 Computed |
| H-Bond Acceptors | 3 count💻 Computed |
| Rotatable Bonds | 6 count💻 Computed |
| Aromatic Rings | 2 count💻 Computed |
| Molar Refractivity | 92.646 cm^3/mol📊 OPERA |
| Polarizability | 36.728 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.
