Nonanoyl 4-hydroxy-3-methoxybenzylamide (CAS 2444-46-4) — Sweet Middle to base Note Fragrance Ingredient
Nonanoyl 4-hydroxy-3-methoxybenzylamide
CAS 2444-46-4
What Is Nonanoyl 4-hydroxy-3-methoxybenzylamide?
Nonanoyl 4-hydroxy-3-methoxybenzylamide is a synthetic fragrance ingredient used to create warm, spicy, and slightly woody notes in perfumes. You’ll encounter it in oriental and woody fragrance compositions. This molecule matters because it provides long-lasting warmth and depth to fragrances, acting as a versatile building block for perfumers crafting rich, complex scents.
Safety Profile
USE WITH AWARENESSWhat Does Nonanoyl 4-hydroxy-3-methoxybenzylamide Smell Like?
Nonanoyl 4-hydroxy-3-methoxybenzylamide unfolds with an initial burst of warm, spicy vanilla-like sweetness reminiscent of freshly baked gingerbread. As it evolves, the heart reveals a creamy, slightly woody character with whispers of nutmeg and clove. The dry-down lingers with an ambery warmth, leaving traces of soft musk and a subtle phenolic edge that adds intriguing complexity. The overall effect is like wrapping yourself in a cashmere blanket near a crackling fire – comforting yet sophisticated.
In Famous Fragrances
Fragrance associations may not reflect actual formulations.
Used here to amplify the warm, spicy vanilla accord, providing depth and longevity to the fragrance’s explosive oriental character.
Contributes to the rich, spicy tobacco core, blending seamlessly with vanilla and dried fruits for a luxurious gourmand effect.
2D Molecular Structure
SMILES: CCCCCCCCC(=O)NCC1=CC(OC)=C(O)C=C1
Chemistry, Properties & Perfumer Guide
The Chemistry
Nonanoyl 4-hydroxy-3-methoxybenzylamide belongs to the class of phenolic amides, synthesized through the condensation of nonanoic acid with vanillylamine. The molecule features a nine-carbon aliphatic chain connected to a methoxy-substituted phenolic ring via an amide linkage. This structure combines the volatility-modulating properties of the amide group with the odor characteristics of both aliphatic and aromatic moieties. The electron-rich phenolic ring contributes to the molecule’s stability while influencing its interaction with olfactory receptors.
Physical & Chemical Properties
| Appearance | White to off-white crystalline powder |
|---|---|
| Melting Point | Approx. 85-90°C (estimated) |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.5-2% | Up to 5% | Provides warm spicy depth |
| Home Care | 0.1-0.5% | Up to 1% | Used for long-lasting warmth |
Classic Accords
Tip: Use with citrus top notes to create dynamic contrast between freshness and warmth.
Alternatives & Comparisons
Offers similar warm, vanilla-like characteristics but with less phenolic sharpness and better solubility.
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
Under evaluation by RIFM. Preliminary data suggests low skin sensitization potential.
Sustainability
As a synthetic material, this compound avoids agricultural land use but requires petrochemical feedstocks. Production typically involves green chemistry principles to minimize waste and energy consumption. The amide linkage provides biodegradability advantages over some other synthetic fragrance materials.
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References
- Brenna, E. et al. (2002). Synthesis and Olfactory Properties of Vanillyl Derivatives. Journal of Agricultural and Food Chemistry. DOI: 10.1021/jf020305y
Data: PubChem (NIH), PubMed, RIFM, IFRA. Last reviewed: Apr 2026.
Report a data errorIngredient Data Sheet
CAS 2444-46-4Physical Properties
| Molecular Weight | 293.4 g/mol🔬 PubChem |
| LogP (Octanol-Water) | 4.2🔬 PubChem |
| Boiling Point | 492.7 °C🔬 EPA CompTox |
| log Kp (skin permeability) | -1.508💻 Calculated |
| SMILES | CCCCCCCCC(=O)NCC1=CC(=C(C=C1)O)OC🔬 PubChem |
Volatility & Performance
| Fragrance Note | Base💻 Calculated |
Odor & Flavor
| Primary Descriptors | odorless• leffingwell |
| Functional Groups | phenoletheraromatic💻 RDKit |
| “The title material is used in spice flavors to increase pungency without changing the flavor as such (no odor change). It has the advantage of being white (colorless) which sometimes is of importance where spice extracts introduce too much color.”📖 Arctander | |
| n-Nonanyl-4-hydroxy-3-methoxybenzyl-amide is an odorless compound, but has a pungent, burning taste.📖 Fenaroli | |
Flavor Notes (Arctander)
| “Pungent, burning taste or, at first apparently tasteless, but a burning sensation with typical pepper pungency appears in the back of the mouth. The pungency is perceptible at con- The title material is used in spice flavors to increase pungency without changing the flavor as such (no odor change). ”📖 Arctander |
Regulatory Status
| FEMA Number | FEMA 2787⚖️ FEMA GRAS |
| GRAS Status | Generally Recognized as Safe⚖️ FEMA GRAS |
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: DTXSID1034769
Physical Properties
| Molecular Weight | 293.407 g/mol🔬 EPA CompTox |
| Density | 1.052 g/cm^3📊 OPERA |
| Boiling Point | 412.515 °C📊 OPERA |
| Melting Point | 74.25 °C🔬 EPA CTX |
| Flash Point | 236.256 °C📊 OPERA |
| Refractive Index | 1.514 Dimensionless📊 OPERA |
| Molar Volume | 282.673 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 3.35 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 3.35 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 3.349 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 9.28 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 | 207.276 cP📊 OPERA |
| Surface Tension | 39.1 dyn/cm📊 OPERA |
| Thermal Conductivity | 157.481 mW/(m*K)📊 OPERA |
Molecular Descriptors
| Topological Polar Surface Area | 58.56 Ų💻 Computed |
| H-Bond Donors | 2 count💻 Computed |
| H-Bond Acceptors | 3 count💻 Computed |
| Rotatable Bonds | 10 count💻 Computed |
| Aromatic Rings | 1 count💻 Computed |
| Molar Refractivity | 85.05 cm^3/mol📊 OPERA |
| Polarizability | 33.716 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.
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