5H-5-Methyl-6,7-dihydrocyclopenta(b)pyrazine (CAS 23747-48-0) — Sweet Middle Note Fragrance Ingredient
5H-5-Methyl-6,7-dihydrocyclopenta(b)pyrazine
CAS 23747-48-0
What Is 5H-5-Methyl-6,7-dihydrocyclopenta(b)pyrazine?
5H-5-Methyl-6,7-dihydrocyclopenta(b)pyrazine is a synthetic aroma chemical primarily used in professional fragrance creation. Consumers may encounter it in gourmand or nutty fragrance compositions. This ingredient matters because it contributes unique roasted, nutty nuances that are difficult to replicate with natural materials, allowing perfumers to create more complex and modern scent profiles.
Safety Profile
USE WITH AWARENESSWhat Does 5H-5-Methyl-6,7-dihydrocyclopenta(b)pyrazine Smell Like?
This pyrazine derivative delivers an intense roasted character reminiscent of freshly brewed coffee beans and toasted hazelnuts. The opening is powerfully nutty with a slightly burnt sugar undertone, evolving into a heart that suggests dark chocolate and roasted barley. In drydown, it leaves a persistent gourmand trail with subtle earthy-malty facets. The overall effect is warm, edible, and deeply comforting – like the scent of a high-end coffee roastery blended with artisan chocolate shop aromas.
2D Molecular Structure
SMILES: CC1CCC2=C1N=CC=N2
Chemistry, Properties & Perfumer Guide
The Chemistry
As a substituted pyrazine, this molecule belongs to the heterocyclic nitrogen-containing compounds that are potent aroma contributors. Pyrazines are formed during Maillard reactions in food cooking, explaining the roasted notes. Synthetic production typically involves controlled cyclization reactions of appropriate diketones with diamines. The methyl group at the 5-position and the partially saturated ring structure modify the volatility and odor intensity compared to simpler pyrazines.
Physical & Chemical Properties
| Appearance | Colorless to pale yellow liquid |
|---|---|
| Odor Threshold | Extremely low (ppb range) |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.1-0.5% | Up to 1% | Powerful modifier for gourmand accords |
| Functional Fragrance | 0.01-0.1% | Up to 0.3% | Used sparingly in food-like scents |
Classic Accords
Tip: Use in trace amounts to avoid overwhelming compositions – works best when balanced with sweet and creamy notes.
Alternatives & Comparisons
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
Evaluated as part of pyrazine group safety assessment.
Sustainability
As a synthetic material, production avoids agricultural land use. Manufacturing requires controlled chemical processes with proper waste management. Being highly potent, small quantities deliver significant olfactory impact, reducing overall material consumption in fragrance formulas.
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References
- Burdock, G.A. (2010). Fenaroli’s Handbook of Flavor Ingredients. CRC Press.
- Pyrazine derivatives in flavor chemistry
Data: PubChem (NIH), PubMed, RIFM, IFRA. Last reviewed: Apr 2026.
Report a data errorIngredient Data Sheet
CAS 23747-48-0Physical Properties
| Molecular Weight | 134.18 g/mol🔬 PubChem |
| LogP (Octanol-Water) | 0.8🔬 PubChem |
| Boiling Point | 190 °C🔬 EPA CompTox |
| Vapor Pressure | 0.0051 mmHg @ 25°C📊 OPERA |
| Flash Point | 78.9 °C🔬 EPA CompTox |
| Involatility Index | 0.0005💻 Calculated |
| log Kp (skin permeability) | -2.95💻 Calculated |
| SMILES | CC1CCC2=NC=CN=C12🔬 PubChem |
Volatility & Performance
| Fragrance Note | Heart💻 Calculated |
| Volatility Class | Very slow💻 Calculated |
| Persistence Score | 2.7 / 5💻 Calculated |
Odor & Flavor
| Primary Descriptors | nutty• leffingwell |
| Functional Groups | aromatic💻 RDKit |
| 5H-5-Methyl-6,7-dihydrocyclopenta(b)pyrazine has an earthy, baked potato, peanut, roasted odor.📖 Fenaroli | |
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: DTXSID7047196
Physical Properties
| Molecular Weight | 134.182 g/mol🔬 EPA CompTox |
| Density | 1.054 g/cm^3🔬 EPA CTX |
| Boiling Point | 200.941 °C📊 OPERA |
| Melting Point | 29.487 °C📊 OPERA |
| Flash Point | 79.18 °C📊 OPERA |
| Refractive Index | 1.542 Dimensionless📊 OPERA |
| Molar Volume | 124.964 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 1.429 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 1.429 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 1.429 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 4.97 Log10 unitless📊 OPERA |
| Water Solubility | 0.349 mol/L📊 OPERA |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0.127 mmHg📊 OPERA |
| Viscosity | 5.23 cP📊 OPERA |
| Surface Tension | 40.3 dyn/cm📊 OPERA |
| Thermal Conductivity | 135.95 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 | 39.318 cm^3/mol📊 OPERA |
| Polarizability | 15.587 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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