2-Ethylpyrazine (CAS 13925-00-3) — Balsamic Top to mid Note Fragrance Ingredient
2-Ethylpyrazine
CAS 13925-00-3
What Is 2-Ethylpyrazine?
2-Ethylpyrazine is a synthetic compound used to add nutty, roasted, or coffee-like notes to fragrances and flavors. You might encounter it in gourmand perfumes or food flavorings like chocolate or roasted nuts. This ingredient matters because it adds realistic ‘browned food’ nuances at extremely low concentrations, creating warmth and depth in scents that mimic baking, coffee, or toasted ingredients.
Safety Profile
USE WITH AWARENESSWhat Does 2-Ethylpyrazine Smell Like?
2-Ethylpyrazine bursts with an intense, diffusive aroma of freshly roasted coffee beans and hazelnut skins, with an underlying burnt sugar character. The top note has a sharp, almost metallic edge that quickly mellows into warm cocoa and toasted bread crusts. As it dries down, it reveals a persistent, slightly smoky character reminiscent of a wood-fired oven, with subtle earthy undertones that recall roasted root vegetables or black sesame.
In Famous Fragrances
Fragrance associations may not reflect actual formulations.
Used in trace amounts to amplify the dark chocolate accord, adding roasted depth to the truffle and patchouli heart.
Provides the burnt caramel facet in this gourmand, blending with coffee and vanilla for a dessert-like warmth.
2D Molecular Structure
SMILES: CCC1=CN=CC=N1
Chemistry, Properties & Perfumer Guide
The Chemistry
2-Ethylpyrazine belongs to the alkylpyrazine class, heterocyclic compounds with nitrogen atoms in a six-membered ring. While pyrazines occur naturally in roasted foods (coffee, nuts, meats), this specific ethyl variant is primarily synthetic. Industrial synthesis typically involves condensation reactions of α-diketones with ethylenediamine derivatives. The molecule’s planar structure and nitrogen lone pairs make it highly odor-active, with detection thresholds in the parts-per-billion range.
Physical & Chemical Properties
| Appearance | Colorless to pale yellow liquid |
|---|---|
| Boiling Point | ~155-160 °C (estimated) |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.01-0.1% | Up to 0.5% | Powerful modifier – use sparingly |
| Functional Fragrance | 0.001-0.01% | Up to 0.05% | For coffee/chocolate air fresheners |
Classic Accords
Tip: Always pre-dilute to 1% in ethanol before blending – direct use can overpower a formula.
Alternatives & Comparisons
Less intense, more nutty character. Preferred when a softer roasted note is needed without coffee overtones.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
No IFRA restrictions (2019 Amendment 49).
RIFM Assessment
RIFM evaluation ongoing – currently approved for use at reported levels.
Sustainability
As a synthetic material, 2-ethylpyrazine production avoids agricultural land use. Modern synthesis routes aim for atom economy, though some processes still require solvents that require proper waste management. Being highly potent, its environmental load per unit of fragrance is low.
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Physicochemical Properties
DTXSID: DTXSID2065676
Physical Properties
| Molecular Weight | 108.144 g/mol🔬 EPA CompTox |
| Density | 0.985 g/cm^3🔬 EPA CTX |
| Boiling Point | 152.5 °C🔬 EPA CTX |
| Melting Point | 1.42 °C📊 OPERA |
| Flash Point | 42.875 °C🔬 EPA CTX |
| Refractive Index | 1.5 Dimensionless📊 OPERA |
| Molar Volume | 108.698 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 0.69 Log10 unitless🔬 EPA CTX |
| LogD (pH 5.5) | 0.689 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 0.689 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 3.74 Log10 unitless📊 OPERA |
| Water Solubility | 3.22 mol/L📊 OPERA |
| Henry's Law Constant | 0 atm-m3/mole🔬 EPA CTX |
Transport Properties
| Vapor Pressure | 1.67 mmHg🔬 EPA CTX |
| Viscosity | 1.846 cP📊 OPERA |
| Surface Tension | 36.478 dyn/cm📊 OPERA |
| Thermal Conductivity | 135.566 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 | 1 count💻 Computed |
| Aromatic Rings | 1 count💻 Computed |
| Molar Refractivity | 31.985 cm^3/mol📊 OPERA |
| Polarizability | 12.68 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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