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Details

Stereochemistry ACHIRAL
Molecular Formula C5H4O2
Molecular Weight 96.0841
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FURFURAL

SMILES

O=CC1=CC=CO1

InChI

InChIKey=HYBBIBNJHNGZAN-UHFFFAOYSA-N
InChI=1S/C5H4O2/c6-4-5-2-1-3-7-5/h1-4H

HIDE SMILES / InChI

Description

Furfural (also called 2-formylfuran, furan-2- aldehyde, 2-furancarboxaldehyde, 2-furyl-methanal, pyromucic aldehyde, 2-furanaldehyde, 2-furancarbonal, carboxylic aldehyde, furan-2-carbaldehyde, furancarbonal, 2-furaldehyde, or 2-furfural), contains a heteroaromatic furan ring and an aldehyde functional group. Furfural was first isolated in 1832 by J.W. Döbereiner, and has been industrially produced since 1922. Today, furfural is used for multiple purposes, for example as a selective extraction agent (in the recovery of butadiene from oil steam cracking or in the refining of petroleum, diesel fuels, lubricants and vegetable oils), as a solvent (for anthracene or resins), as an agent for vulcanization, as a nematicide and fungicide, as a flavoring agent in a variety of food products and alcoholic and non-alcoholic beverages, and as a component of commercial herbicides, insecticides, pesticides, antiseptics, disinfectors, and rust removers. Furfural is also involved in the manufacture of pharmaceuticals, cosmetics, fragrances, flavors and resins (in this latter case, by condensation with phenol, formaldehyde, acetone, or urea, to produce thermosetting resins with extreme physical strength); as well as in other products such as household cleaners and detergents. Furfural occurs naturally in some fruits and vegetables. It can be formed in other foods during cooking, and is present in wood smoke. Furfural is an ingredient contained in many fragrances and flavours. It may be found in fragrances used in decorative cosmetics, fine fragrances, shampoos, toilet soaps and other toiletries, in flavours of oral care products as well as in non-cosmetic products such as household cleaners and detergents. Furfural in the in the fragrance compound is reported to be 0.036% or less. The European Commission received a submission from the European Flavour & Fragrance Association with data supporting the safe use of Furfural as a fragrance ingredient. The predominant pathway of metabolism of Furfural in humans is oxidation of the aldehyde to yield furoic acid, which may either conjugate with amino acids or condense with acetyl coenzyme A to produce the furanacrylic acid. Furfural is a carcinogen classified in EU as a Category 3 carcinogen. Furfural was tested for carcinogenicity by oral administration in one study in mice and one study in rats. In mice, it increased the incidence of hepatocellular adenomas and carcinomas in males and of hepatocellular adenomas and forestomach papillomas in females. Male rats had a low incidence of cholangiocarcinomas, which occur rarely. In a two-stage assay on mouse skin, Furfural had weak initiating activity. On the basis of quantitative risk assessment it is concluded that Furfural at the maximum exposure stated by RIFM does not represent any significant cancer risk. However, the exposure should not be increased.

Originator

Approval Year

PubMed

Sample Use Guides

In Vivo Use Guide
The estimated daily intake of furfural from its use as a flavoring agent, calculated using 'poundage' data provided by the flavoring industry, was 9 ug/kg body weight in Europe and 8 ug/kg body weight in the U.S.
Route of Administration: Oral
In Vitro Use Guide
Precision-cut human liver slices from four donors were cultured for 24 h in medium containing [3H]thymidine and 0-10 mM furfural. Small increases in the net grain count (i.e. nuclear grain count less mean cytoplasmic grain count) observed with 2-10 mM furfural were not due to any increase in the nuclear grain count.