2,5 or 6-Methoxy-3-methylpyrazine (mixture of isomers) (CAS 68378-13-2) — Woody Middle Note Fragrance Ingredient
2,5 or 6-Methoxy-3-methylpyrazine (mixture of isomers)
CAS 68378-13-2
What Is 2,5 or 6-Methoxy-3-methylpyrazine (mixture of isomers)?
2,5 or 6-Methoxy-3-methylpyrazine is a synthetic aroma chemical used to create earthy, nutty, and coffee-like notes in fragrances. You’ll encounter it in gourmand perfumes and some masculine scents. This ingredient matters because it adds depth and complexity to fragrance compositions, particularly in modern interpretations of woody and oriental accords.
Safety Profile
USE WITH AWARENESSWhat Does 2,5 or 6-Methoxy-3-methylpyrazine (mixture of isomers) Smell Like?
A complex pyrazine compound that delivers an intriguing olfactory profile – opening with sharp green bell pepper nuances that quickly evolve into rich, roasted coffee bean and cocoa powder tones. The dry-down reveals a persistent earthy character reminiscent of freshly turned soil, with subtle nutty almond facets that add warmth. At higher concentrations, it develops an almost meaty, savory quality that makes it particularly useful in modern masculine compositions.
2D Molecular Structure
SMILES: C*.COC1=NC=CN=C1 |c:5,7,t:3,lp:3:2,5:1,8:1,m:1:9.7|
Chemistry, Properties & Perfumer Guide
The Chemistry
This pyrazine derivative exists as a mixture of methoxy-substituted isomers at positions 2, 5, or 6 on the pyrazine ring. The methyl group at position 3 contributes to its volatility and odor strength. Synthesized through nucleophilic substitution reactions on chlorinated pyrazine precursors, these isomers collectively create its distinctive olfactory profile. The methoxy groups increase polarity compared to alkylpyrazines, affecting both solubility and vapor pressure.
Physical & Chemical Properties
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.1-0.5% | Up to 1% | Powerful modifier |
| Functional Fragrance | 0.01-0.1% | Up to 0.3% | Background note |
| Home Care | 0.001-0.01% | Up to 0.05% | Trace amounts |
Classic Accords
Tip: Use sparingly in gourmand accords to add roasted depth without overwhelming sweetness.
Alternatives & Comparisons
More intense bell pepper character, useful when a sharper green note is desired.
Provides similar earthy notes but with more nutty character and less coffee-like intensity.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
No specific IFRA restrictions. General pyrazine guidelines apply.
RIFM Assessment
Not currently evaluated by RIFM. Pyrazine class has established safety data.
Sustainability
Synthetic production avoids agricultural impacts. Manufacturing requires controlled conditions to minimize environmental release of intermediates. Energy-intensive synthesis offset by low usage levels in final products.
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Ingredient Data Sheet
CAS 68378-13-2Odor & Flavor
| 2 or 5 or 6-Methoxy-3-methylpyrazine has an aroma reminiscent of hazelnut, almond and peanut. The methyl methoxypyrazines are used as nut-like flavoring agents for foods and beverages. The 2-methoxy-3-methyl derivative is used as a coffee aroma enhancing agent.📖 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: DTXSID801015676
Partition & Solubility
| LogP (Octanol-Water) | 1.069 dimensionless💻 Computed |
Molecular Descriptors
| Topological Polar Surface Area | 35.01 Ų💻 Computed |
| H-Bond Donors | 0 count💻 Computed |
| H-Bond Acceptors | 3 count💻 Computed |
| Rotatable Bonds | 1 count💻 Computed |
| Aromatic Rings | 1 count💻 Computed |
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.
