2,6-Dimethylpyrazine (CAS 108-50-9) — Sweet Middle Note Fragrance Ingredient
2,6-Dimethylpyrazine
CAS 108-50-9
What Is 2,6-Dimethylpyrazine?
2,6-Dimethylpyrazine is a synthetic aroma chemical that creates roasted, nutty scents. You’ll encounter it in coffee, chocolate, and savory flavorings. This pyrazine compound matters because it adds depth to gourmand fragrances and food aromas, mimicking natural roasting processes with precision.
Safety Profile
USE WITH AWARENESSWhat Does 2,6-Dimethylpyrazine Smell Like?
A potent roasted nut character with coffee-like depth, evolving into earthy cocoa tones. The initial burst suggests freshly ground coffee beans, settling into a dry, woody hazelnut persistence. At higher concentrations, it develops a savory umami edge reminiscent of roasted meats or toasted bread crusts.
In Famous Fragrances
Fragrance associations may not reflect actual formulations.
Provides the coffee-tinged gourmand foundation that blends with patchouli and vanilla, creating a distinctive roasted sweetness.
Contributes to the dark, resinous coffee accord that defines this provocative fragrance’s addictive quality.
2D Molecular Structure
SMILES: CC1=CN=CC(C)=N1
Chemistry, Properties & Perfumer Guide
The Chemistry
A heterocyclic aromatic compound belonging to the pyrazine family. Synthesized through condensation reactions of diketones with diamines. The methyl groups at positions 2 and 6 create steric hindrance that affects volatility and odor strength compared to other pyrazine derivatives.
Physical & Chemical Properties
| Boiling Point | 155-157 °C |
|---|---|
| Density | 1.03 g/cm³ |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.01-0.1% | Up to 0.5% | Powerful modifier for gourmand accords |
| Food Flavors | 1-10 ppm | Up to 50 ppm | Coffee/chocolate applications |
Classic Accords
Tip: Use in trace amounts with sweet materials to avoid overpowering savory effects.
Alternatives & Comparisons
Less roasted character, more earthy potato-like notes. Used when subtler pyrazine effects are desired.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
Not restricted under current IFRA standards.
RIFM Assessment
Evaluated by RIFM with no significant safety concerns at typical usage levels.
Sustainability
Synthesized from petrochemical feedstocks. Production requires careful waste management due to nitrogen-containing byproducts. More sustainable than natural pyrazine extraction from roasted materials.
Explore 2,6-Dimethylpyrazine
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References
- Burdock, G.A. (2010). Fenaroli’s Handbook of Flavor Ingredients. CRC Press. PMID 30000920
Data: PubChem (NIH), PubMed, RIFM, IFRA. Last reviewed: Apr 2026.
Report a data errorIngredient Data Sheet
CAS 108-50-9Physical Properties
| Molecular Weight | 108.14 g/mol🔬 PubChem |
| LogP (Octanol-Water) | 0.5🔬 PubChem |
| Boiling Point | 154 °C🔬 EPA CompTox |
| Flash Point | 52.8 °C🔬 EPA CompTox |
| log Kp (skin permeability) | -3.005💻 Calculated |
| SMILES | CC1=CN=CC(=N1)C🔬 PubChem |
Volatility & Performance
| Fragrance Note | Top💻 Calculated |
Odor & Flavor
| Primary Descriptors | chocolateroasted• leffingwell |
| Functional Groups | aromatic💻 RDKit |
| “Sweet, "fried" odor, resembling that of fried Potatoes, but not as typical as that of the 2,5-isomer (see previous monograph).”📖 Arctander | |
| 2,6-Dimethylpyrazine has a chocolate, roasted nuts, fried potato odor.📖 Fenaroli | |
Flavor Notes (Arctander)
| “in alcohol and most flavor oils. Reacts with aldehydes and some ketones. Has been suggested for use in flavors for reconditioning of the aroma of potato chips, "instant" coffee, etc.”📖 Arctander |
Sensory Thresholds
| Odor Detection Threshold | 3.2405 ppm (n=4)📖 van Gemert |
Regulatory Status
| IOFI Classification | Nature Identical📖 Fenaroli |
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: DTXSID5047619
Physical Properties
| Molecular Weight | 108.144 g/mol🔬 EPA CompTox |
| Density | 1.005 g/cm^3📊 OPERA |
| Boiling Point | 154.7 °C🔬 EPA CTX |
| Melting Point | 43.688 °C🔬 EPA CTX |
| Flash Point | 52.875 °C🔬 EPA CTX |
| Refractive Index | 1.504 Dimensionless📊 OPERA |
| Molar Volume | 108.431 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 0.54 Log10 unitless🔬 EPA CTX |
| LogD (pH 5.5) | 0.638 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 0.639 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 3.73 Log10 unitless📊 OPERA |
| Water Solubility | 2.925 mol/L📊 OPERA |
| Henry's Law Constant | 0 atm-m3/mole🔬 EPA CTX |
Transport Properties
| Vapor Pressure | 3.197 mmHg📊 OPERA |
| Viscosity | 1.951 cP📊 OPERA |
| Surface Tension | 36.479 dyn/cm📊 OPERA |
| Thermal Conductivity | 131.323 mW/(m*K)📊 OPERA |
Molecular Descriptors
| Topological Polar Surface Area | 25.78 Ų💻 Computed |
| H-Bond Donors | 0 count💻 Computed |
| H-Bond Acceptors | 2 count💻 Computed |
| Rotatable Bonds | 0 count💻 Computed |
| Aromatic Rings | 1 count💻 Computed |
| Molar Refractivity | 32.085 cm^3/mol📊 OPERA |
| Polarizability | 12.72 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.
