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1-furfuryl-2-pyrrole carbaldehyde

1-furfuryl-2-pyrrole carbaldehyde is a volatile compound found in coffee and roasted chicory root oil noted for its slightly burnt, mildly acidic flavor characteristic.

General Material Description

1-furfuryl-2-pyrrole carbaldehyde is a heterocyclic aromatic aldehyde characterized by a molecular formula of C10H9NO2 and a molecular weight of approximately 175.19 g/mol. Structurally, it consists of a pyrrole ring substituted at the nitrogen atom with a furfuryl group and an aldehyde functional group attached at the 2-position of the pyrrole. This compound exhibits a slightly burnt and mildly acidic flavor profile, making it a significant contributor to the aroma and taste of roasted foods. It is recognized under various synonyms, including 1-(furan-2-ylmethyl)pyrrole-2-carbaldehyde, and is indexed in chemical databases such as PubChem. The compound naturally occurs in roasted chicory root oil and coffee and can be extracted or synthesized for analytical study. Its distinct sensory characteristics are valuable for flavor research, especially related to roasted and burnt notes in food chemistry.

Occurrence, Applicability & Potential Uses

This compound occurs naturally in roasted chicory root oil at trace levels and is also found in coffee, where it contributes to characteristic roasted and burnt flavor notes. In biological contexts, it likely arises from the thermal degradation of carbohydrates and amino acids during roasting processes. Applications focus primarily on its role as a natural substance and extractive in food flavor analysis. The compound is referenced within the FEMA (US) framework as a natural flavoring constituent, although it is not recommended for direct fragrance or flavor use due to safety considerations. Its sensory properties make it useful for understanding the chemical basis of roasted food aromas but limit its practical formulation uses in commercial flavor or fragrance products.

Physico-Chemical Properties Summary

1-furfuryl-2-pyrrole carbaldehyde exhibits moderate volatility with a boiling point ranging from 292 to 293°C at atmospheric pressure, indicating relative thermal stability at standard conditions. Its vapor pressure at 25°C is low (approximately 0.002 mmHg), reflecting limited volatility under room temperature. The compound shows moderate lipophilicity, with an estimated logP value near 1.0, suggesting balanced solubility between polar and nonpolar solvents. It dissolves in alcohols and has an estimated water solubility of 737.2 mg/L at 25°C, although some data indicate poor water solubility, possibly due to variable testing conditions or impurity effects. The flash point is approximately 130.5°C (267°F), implying moderate flammability risk under elevated temperatures. These properties influence its behavior during extraction, analytical procedures, and in sensory perception, affecting volatility and interaction with food matrices.

FAQ

What is 1-furfuryl-2-pyrrole carbaldehyde and where is it commonly found?
1-furfuryl-2-pyrrole carbaldehyde is an aromatic heterocyclic aldehyde featuring a substituted pyrrole and furan ring. It naturally occurs in roasted chicory root oil and coffee, contributing to their characteristic burnt and slightly acidic flavor notes. This compound is notable in food science for its role in the aroma profiles of roasted products.
How is 1-furfuryl-2-pyrrole carbaldehyde used and what are its typical properties?
This compound is primarily studied as a natural extractive and flavor component present in food matrices. Its physical properties include a boiling point near 292–293°C, a low vapor pressure at ambient temperature, and solubility in alcohol and moderately in water. It possesses a slightly burnt taste with mild acidity, influencing sensory perceptions in roasted foods. It is not used directly as a flavoring or fragrance ingredient due to regulatory constraints.
What regulatory standards apply to 1-furfuryl-2-pyrrole carbaldehyde, and how is it sourced?
1-furfuryl-2-pyrrole carbaldehyde is classified as a natural substance under FEMA (US) guidelines but is not recommended for intentional addition to flavors or fragrances. It is typically sourced via extraction from natural products such as roasted chicory root or coffee or synthesized for research purposes. Safety data indicate no classified hazards under OSHA regulations, but usage recommendations exclude direct flavor or fragrance use.

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Literature & References

1-(furan-2-ylmethyl)pyrrole-2-carbaldehyde
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):529880
Pubchem (sid):39356534
Publications by US Patents
3,952,024 - Furfurylthioacetone
Certain 2,5-dimethyl-3-thiopyrazines

Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
HMDB (The Human Metabolome Database):Search
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
EFSA Update of results on the monitoring of furan levels in food:Read Report
EFSA Previous report: Results on the monitoring of furan levels in food:Read Report
EFSA Report of the CONTAM Panel on provisional findings on furan in food:Read Report

General Material Information

Preferred name 1-furfuryl-2-pyrrole carbaldehyde
Trivial Name 1-(furan-2-ylmethyl)pyrrole-2-carbaldehyde
Short Description 1-(2-furylmethyl)-1H-pyrrole-2-carbaldehyde
Formula C10 H9 N O2
CAS Number 13788-32-4
FDA UNII Search
Nikkaji Number J642.730H
MDL MFCD09674985
xLogP3-AA 1.20 (est)
NMR Predictor External link
Synonyms
  • 1-( furan-2-ylmethyl)pyrrole-2-carbaldehyde
  • 1-(2-furanyl methyl)-2-formyl-1H-pyrrole
  • 1-(2-furanylmethyl)-2-formyl-1H-pyrrole
  • 1-furfuryl pyrrole-2-aldehyde
  • N- furfuryl-2-formyl pyrrole
  • N- furfuryl-2-formylpyrrole
  • 1-furfuryl-2-pyrrolecarbaldehyde
  • 1-furfuryl-pyrrole-2-aldehyde
  • 1-furfurylpyrrole-2-aldehyde
  • 1-(2-furyl methyl)-1H-pyrrole-2-carbaldehyde
  • 1-(2-furylmethyl)-1H-pyrrole-2-carbaldehyde

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 175.18713378906
Boiling Point 292 to 293°C @ 760 mm Hg
Vapor Pressure 0.002 mmHg @ 25 °C
Flash Point TCC Value 130.6 °C TCC
logP (o/w) 1.016 est
Solubility
alcohol Yes
water, 737.2 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Flavor Type: Burnt
burnt, acidic
General comment Slightly burnt taste, slightly acid

Occurrences

Safety Information

Safety information

Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

Category:
natural substances and extractives
Recommendation for 1-furfuryl-2-pyrrole carbaldehyde usage levels up to:
not for fragrance use.
Recommendation for 1-furfuryl-2-pyrrole carbaldehyde flavor usage levels up to:
not for flavor use.

Safety references

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :529880
National Institute of Allergy and Infectious Diseases:Data
1-(furan-2-ylmethyl)pyrrole-2-carbaldehyde