N-Furfurylpyrrole (CAS 1438-94-4) — Balsamic Heart Note Fragrance Ingredient
N-Furfurylpyrrole
CAS 1438-94-4
What Is N-Furfurylpyrrole?
N-Furfurylpyrrole is a synthetic aroma chemical rarely encountered in everyday products. It’s primarily used by professional perfumers to add unique roasted nuances to fragrances. This obscure ingredient matters for creating complex gourmand or coffee-like accords, though most consumers would never recognize it by name.
Safety Profile
USE WITH AWARENESSWhat Does N-Furfurylpyrrole Smell Like?
N-Furfurylpyrrole delivers a peculiar, multifaceted aroma profile. Initially presenting with sharp, almost burnt coffee grounds character, it evolves into a deep roasted nuttiness reminiscent of hazelnut skins. The dry-down reveals subtle earthy-phenolic undertones with a faintly sweet, bread-crust quality. Its persistence is moderate but impactful, serving as a bridge between top and heart notes in compositions requiring toasted or roasted nuances without overwhelming sweetness.
2D Molecular Structure
SMILES: C(N1C=CC=C1)C1=CC=CO1
Chemistry, Properties & Perfumer Guide
The Chemistry
N-Furfurylpyrrole belongs to the heterocyclic pyrrole class, specifically an N-substituted pyrrole derivative. While pyrroles occur naturally in some foods and tobacco, this particular variant is exclusively synthetic. It’s typically synthesized through furfurylamine reactions with appropriate carbonyl compounds. The molecule’s planar structure and electron-rich nitrogen contribute to its intense aromatic properties. Unlike some pyrroles, it lacks significant volatility due to the furfuryl substituent.
Physical & Chemical Properties
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.1-0.5% | Up to 1% | For roasted accent notes |
| Functional Fragrance | 0.05-0.2% | Up to 0.5% | Coffee/roasted food flavors |
Classic Accords
Tip: Use trace amounts to enhance roasted notes without dominating the composition.
Alternatives & Comparisons
More intense roasted coffee character but higher volatility and stronger sulfurous notes.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
Not currently restricted by IFRA. Listed as safe at current usage levels.
RIFM Assessment
Limited safety assessment available. Considered safe at reported usage levels.
Sustainability
As a synthetic material, N-Furfurylpyrrole’s environmental impact depends on manufacturing processes. No known natural sources exist, eliminating concerns about overharvesting. Being used in minute quantities, its overall ecological footprint is small compared to more widely used aroma chemicals.
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Layer 3 · Practical
- Odor Profile: alliaceous, earthy, pungent, smoky, vegetable
- FEMA GRAS: 3284
- Molecular Weight: 147.17 g/mol
- LogP (XLogP): 1.40
Ingredient Data Sheet
CAS 1438-94-4Physical Properties
| Molecular Weight | 147.17 g/mol🔬 PubChem |
| LogP (Octanol-Water) | 1.4🔬 PubChem |
| Boiling Point | 77 °C🔬 EPA CompTox |
| log Kp (skin permeability) | -2.604💻 Calculated |
| SMILES | C1=CN(C=C1)CC2=CC=CO2🔬 PubChem |
Volatility & Performance
| Fragrance Note | Top💻 Calculated |
Odor & Flavor
| Primary Descriptors | earthypungentsmoky• leffingwell |
| Functional Groups | aromatic💻 RDKit |
| n-Furfuryl pyrrole has a vegetable, green, earthy, pungent (horseradish) odor. It is used to garnish flavors for soup. -📖 Fenaroli | |
Sensory Thresholds
| Odor Detection Threshold | 0.1 ppm (n=2)📖 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: DTXSID5047663
Physical Properties
| Molecular Weight | 147.177 g/mol🔬 EPA CompTox |
| Density | 1.081 g/cm^3🔬 EPA CTX |
| Boiling Point | 252.544 °C📊 OPERA |
| Melting Point | -16.729 °C📊 OPERA |
| Flash Point | 91.726 °C📊 OPERA |
| Refractive Index | 1.557 Dimensionless📊 OPERA |
| Molar Volume | 137.557 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 2.064 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 2.064 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 2.064 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 5.08 Log10 unitless📊 OPERA |
| Water Solubility | 0.107 mol/L📊 OPERA |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0.058 mmHg📊 OPERA |
| Viscosity | 5.744 cP📊 OPERA |
| Surface Tension | 38.101 dyn/cm📊 OPERA |
Molecular Descriptors
| Topological Polar Surface Area | 18.07 Ų💻 Computed |
| H-Bond Donors | 0 count💻 Computed |
| H-Bond Acceptors | 2 count💻 Computed |
| Rotatable Bonds | 2 count💻 Computed |
| Aromatic Rings | 2 count💻 Computed |
| Molar Refractivity | 44.267 cm^3/mol📊 OPERA |
| Polarizability | 17.549 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.
