Benzoic acid, 2-[[3-(4-methoxyphenyl)-2-methylpropylidene]amino]-, methyl ester (CAS 111753-62-9) — Floral Middle Note Fragrance Ingredient
Benzoic acid, 2-[[3-(4-methoxyphenyl)-2-methylpropylidene]amino]-, methyl ester
CAS 111753-62-9
What Is Benzoic acid, 2-[[3-(4-methoxyphenyl)-2-methylpropylidene]amino]-, methyl ester?
This synthetic fragrance ingredient is a specialized aromatic compound used in modern perfumery. It’s found in select niche fragrances where its unique molecular structure contributes to complex scent profiles. As a synthetic molecule, it allows perfumers to create consistent, reproducible effects that might be difficult to achieve with natural materials alone.
Safety Profile
USE WITH AWARENESSWhat Does Benzoic acid, 2-[[3-(4-methoxyphenyl)-2-methylpropylidene]amino]-, methyl ester Smell Like?
This synthetic molecule presents a sophisticated aromatic character with subtle nuances. The initial impression suggests a delicate balance between powdery musk and soft floral undertones, evolving into a clean, slightly woody dry-down. Its odor profile carries faint reminiscences of antique paper and dried petals, with a refined persistence that makes it valuable for modern fragrance architectures.
2D Molecular Structure
SMILES: COC(=O)C1=C(C=CC=C1)N=CC(C)CC1=CC=C(OC)C=C1
Chemistry, Properties & Perfumer Guide
The Chemistry
This benzoic acid derivative belongs to the class of Schiff base esters, characterized by its imine functional group (-C=N-) bridging the aromatic and aliphatic portions of the molecule. The methoxyphenyl moiety contributes electron density to the system, influencing both its chemical reactivity and olfactory properties. Synthesis typically involves condensation reactions between appropriately substituted benzaldehyde derivatives and amino esters.
Physical & Chemical Properties
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.5-2% | Up to 5% | Used as a subtle modifier |
| Functional Fragrance | 0.1-0.5% | Up to 1% | For sophisticated effects |
Classic Accords
Tip: Use in trace amounts to add depth to floral-woody compositions without overpowering.
Alternatives & Comparisons
Offers similar powdery floral character with more established safety profile and natural occurrence in some essential oils.
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 published RIFM assessment currently available for this specific compound.
Sustainability
As a synthetic material, this compound offers consistent quality without natural sourcing pressures. However, its specialized synthesis route may involve multiple steps with associated energy requirements. The environmental impact depends heavily on the specific manufacturing processes employed.
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Ingredient Data Sheet
CAS 111753-62-9Physical Properties
| Molecular Weight | 311.4 g/mol🔬 PubChem |
| LogP (Octanol-Water) | 3.8🔬 PubChem |
| Boiling Point | 356 °C🔬 EPA CompTox |
| Vapor Pressure | 0 mmHg @ 25°C📊 OPERA |
| Flash Point | 190.1 °C🔬 EPA CompTox |
| log Kp (skin permeability) | -1.902💻 Calculated |
| SMILES | CC(CC1=CC=C(C=C1)OC)C=NC2=CC=CC=C2C(=O)OC🔬 PubChem |
Volatility & Performance
| Fragrance Note | Base💻 Calculated |
| Volatility Class | Very slow💻 Calculated |
| Persistence Score | 14.2 / 5💻 Calculated |
Odor & Flavor
| Functional Groups | esteretheraromatic💻 RDKit |
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: DTXSID20888847
Physical Properties
| Molecular Weight | 311.381 g/mol🔬 EPA CompTox |
| Density | 1.11 g/cm^3📊 OPERA |
| Boiling Point | 404.241 °C📊 OPERA |
| Melting Point | 72.539 °C📊 OPERA |
| Flash Point | 190.172 °C📊 OPERA |
| Refractive Index | 1.533 Dimensionless📊 OPERA |
| Molar Volume | 293.791 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 4.106 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 3.895 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 4.101 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 9.72 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 |
| Surface Tension | 35.984 dyn/cm📊 OPERA |
Molecular Descriptors
| Topological Polar Surface Area | 47.89 Ų💻 Computed |
| H-Bond Donors | 0 count💻 Computed |
| H-Bond Acceptors | 4 count💻 Computed |
| Rotatable Bonds | 6 count💻 Computed |
| Aromatic Rings | 2 count💻 Computed |
| Molar Refractivity | 91.142 cm^3/mol📊 OPERA |
| Polarizability | 36.131 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.
