Cuminyl nitrile (CAS 13816-33-6) — Spicy Middle Note Fragrance Ingredient
Cuminyl nitrile
CAS 13816-33-6
What Is Cuminyl nitrile?
Cuminyl nitrile is a synthetic fragrance ingredient that adds a warm, spicy-cumin character to perfumes and personal care products. You’ll find it in niche fragrances and some body care items seeking an exotic, aromatic edge. This molecule matters because it provides the distinctive cumin-like aroma without the variability of natural cumin essential oil, offering perfumers a stable, consistent building block for spicy accords.
Safety Profile
USE WITH AWARENESSWhat Does Cuminyl nitrile Smell Like?
Cuminyl nitrile bursts with an intense, peppery cumin-like aroma that’s both earthy and slightly metallic. The opening is sharp and penetrating, reminiscent of crushed cumin seeds with a faint rubbery undertone. As it evolves, the heart reveals a warmer, nutty facet that blends well with woody notes. The dry-down leaves a persistent spicy-herbal trail, less animalic than natural cumin but with superior tenacity. While not a perfect cumin replacer, its linear character makes it invaluable for building stable spicy foundations in modern perfumery.
2D Molecular Structure
SMILES: CC(C)C1=CC=C(C=C1)C#N
Chemistry, Properties & Perfumer Guide
The Chemistry
Cuminyl nitrile belongs to the benzonitrile class of aromatic compounds, synthesized through nitrile substitution of cuminyl precursors. While not found in nature, it mimics key odorants from cumin essential oil. The synthesis typically involves catalytic cyanation of p-cymene derivatives or oxidation of cuminyl amines. Its simple aromatic structure lacks chirality but shows remarkable odor potency at low concentrations due to the nitrile group’s strong dipole moment.
Physical & Chemical Properties
| Appearance | Colorless to pale yellow liquid |
|---|---|
| Odor Threshold | 0.5 ppb in air |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.1-0.5% | Up to 1% | Spicy accent in oriental compositions |
| Personal Care | 0.01-0.1% | Up to 0.2% | Trace amounts for warmth |
Classic Accords
Tip: Use below 0.5% to avoid overpowering blends – works best when balanced with sweet or woody notes.
Alternatives & Comparisons
Natural alternative from cumin oil with similar aroma profile but higher sensitivity risk and poorer stability.
Woody-spicy alternative with less cumin character but better skin compatibility for sensitive applications.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
No specific IFRA restrictions, but recommended for use at ≤1% in finished products due to sensitization potential (IFRA QRA Category B).
GHS Classification
RIFM Assessment
RIFM assessment ongoing – currently classified as safe at current industry usage levels.
Sustainability
As a synthetic material, cuminyl nitrile avoids agricultural impacts associated with cumin oil production. Its high potency means minimal quantities are needed, reducing overall environmental load. Manufacturing typically follows green chemistry principles with >80% atom economy in modern synthesis routes.
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Ingredient Data Sheet
CAS 13816-33-6Physical Properties
| Molecular Weight | 145.2 g/mol🔬 PubChem |
| LogP (Octanol-Water) | 3🔬 PubChem |
| Boiling Point | 244 °C🔬 EPA CompTox |
| Vapor Pressure | 0.09 mmHg @ 25°C📊 OPERA |
| Flash Point | 94 °C🔬 EPA CompTox |
| Involatility Index | 0.0081💻 Calculated |
| log Kp (skin permeability) | -1.456💻 Calculated |
| SMILES | CC(C)C1=CC=C(C=C1)C#N🔬 PubChem |
Volatility & Performance
| Fragrance Note | Heart💻 Calculated |
| Volatility Class | Very slow💻 Calculated |
| Persistence Score | 1.8 / 5💻 Calculated |
Odor & Flavor
| Functional Groups | aromatic💻 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: DTXSID6047440
Physical Properties
| Molecular Weight | 145.205 g/mol🔬 EPA CompTox |
| Density | 0.952 g/cm^3🔬 EPA CTX |
| Boiling Point | 244 °C🔬 EPA CTX |
| Melting Point | -60.5 °C🔬 EPA CTX |
| Flash Point | 94 °C🔬 EPA CTX |
| Refractive Index | 1.515 Dimensionless📊 OPERA |
| Molar Volume | 149.804 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 2.916 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 2.916 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 2.916 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 5.08 Log10 unitless📊 OPERA |
| Water Solubility | 0.001 mol/L🔬 EPA CTX |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0.09 mmHg🔬 EPA CTX |
| Viscosity | 2.172 cP📊 OPERA |
| Surface Tension | 36.367 dyn/cm📊 OPERA |
| Thermal Conductivity | 145.869 mW/(m*K)📊 OPERA |
Molecular Descriptors
| Topological Polar Surface Area | 23.79 Ų💻 Computed |
| H-Bond Donors | 0 count💻 Computed |
| H-Bond Acceptors | 1 count💻 Computed |
| Rotatable Bonds | 1 count💻 Computed |
| Aromatic Rings | 1 count💻 Computed |
| Molar Refractivity | 45.182 cm^3/mol📊 OPERA |
| Polarizability | 17.911 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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