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Details

Stereochemistry ACHIRAL
Molecular Formula C5H4O2
Molecular Weight 96.0843
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FURFURAL

SMILES

c1cc(C=O)oc1

InChI

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

HIDE SMILES / InChI

Molecular Formula C5H4O2
Molecular Weight 96.0843
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

Curator's Comment:: Furfural was first isolated in 1832 by J.W. Döbereiner

Approval Year

PubMed

PubMed

TitleDatePubMed
Aerosol particle and organic vapor concentrations at industrial work sites in Malaysia.
2001
Evaluation of certain food additives and contaminants.
2001
[5-hydroxymethylfurfural as indicator of quality of juices for child nutrition].
2001
Volatile flavor constituents of acerola (Malpighia emarginata DC.) fruit.
2001 Dec
Diastereoselective addition reactions of furyl aldehydes using chiral boronates as auxiliary: application to the enantioselective synthesis of 2,3-disubstituted furyl alcohols.
2001 Dec 13
Effects of furfural on anaerobic continuous cultivation of Saccharomyces cerevisiae.
2001 Dec 5
Supercritical fluid extraction of 5-hydroxymethyl-2-furaldehyde from raisins.
2001 Feb
Derivative spectrophotometric determination of 5-(hydroxymethyl)-2-furaldehyde (HMF) and furfural in Locust bean extract.
2001 Feb
Degradation in peritoneal dialysis fluids may be avoided by using low pH and high glucose concentration.
2001 Jul-Aug
Determination of carboxylic acids, carbohydrates, glycerol, ethanol, and 5-HMF in beer by high-performance liquid chromatography and UV-refractive index double detection.
2001 Jun
Structure determination of a novel 3(6H)-pyranone chromophore and clarification of its formation from carbohydrates and primary amino acids.
2001 Mar
Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens.
2001 Mar
Formation kinetics of hydroxymethylfurfural, lactulose and furosine in milk heated under isothermal and non-isothermal conditions.
2001 May
Enantioselective synthesis of N-Cbz-protected 6-amino-6-deoxymannose, -talose, and -gulose.
2001 Nov 29
Quantitative gas chromatography-olfactometry carried out at different dilutions of an extract. Key differences in the odor profiles of four high-quality Spanish aged red wines.
2001 Oct
Some furfural derivatives as nitrification inhibitors.
2001 Oct
Lack of effect of furfural on unscheduled DNA synthesis in the in vivo rat and mouse hepatocyte DNA repair assays and in precision-cut human liver slices.
2001 Oct
Synthesis, structure and biological activity of nickel(II) complexes of 5-methyl 2-furfural thiosemicarbazone.
2001 Sep
Detoxification of lignocellulose hydrolysates with ion-exchange resins.
2001 Spring
Furfural, 5-hydroxymethyl furfural, and acetoin act as external electron acceptors during anaerobic fermentation of xylose in recombinant Saccharomyces cerevisiae.
2002 Apr 20
Influence of oak wood on the aromatic composition and quality of wines with different tannin contents.
2002 Apr 24
The influence of bark on the fermentation of Douglas-fir whitewood pre-hydrolysates.
2002 Aug
Thresholds of carcinogenicity of flavors.
2002 Aug
The metabolites of the mangrove fungus Verruculina enalia No. 2606 from a salt lake in the Bahamas.
2002 Feb
A comparison of liquid hot water and steam pretreatments of sugar cane bagasse for bioconversion to ethanol.
2002 Jan
Efficient lipase-catalyzed enantioselective desymmetrization of prochiral 2,2-disubstituted 1,3-propanediols and meso 1,2-diols using 1-ethoxyvinyl 2-furoate.
2002 Jan 25
Methanogenesis from furfural by defined mixed cultures.
2002 Jun
Reaction of 1,4-phthalazinedione with furfural: formation of the [5,6]benza-3a,7a-diazaindane system via an unusual skeletal rearrangement.
2002 Mar 7
Inhibition effects of furfural on alcohol dehydrogenase, aldehyde dehydrogenase and pyruvate dehydrogenase.
2002 May 1
Application of (1)h NMR and multivariate statistics for screening complex mixtures: quality control and authenticity of instant coffee.
2002 May 22
Furfural-cysteine model reaction in food grade nonionic oil/water microemulsions for selective flavor formation.
2002 May 8
Evaluation of lipophilicity and antitumour activity of parallel carboxamide libraries.
2002 Nov 25
Antioxidant effects of isorhamnetin 3,7-di-O-beta-D-glucopyranoside isolated from mustard leaf (Brassica juncea) in rats with streptozotocin-induced diabetes.
2002 Sep 11
Effect of different forms of alkali treatment on specific fermentation inhibitors and on the fermentability of lignocellulose hydrolysates for production of fuel ethanol.
2002 Sep 11
Reduction of furfural to furfuryl alcohol by ethanologenic strains of bacteria and its effect on ethanol production from xylose.
2002 Spring
Recovery of lignin and furfural from acetic acid-water-HCl pulping liquors.
2003 Dec
Antioxidative activities of volatile extracts from green tea, oolong tea, and black tea.
2003 Dec 3
Insertion of carbon fragments into P(III)-N bonds in aminophosphines and aminobis(phosphines): synthesis, reactivity, and coordination chemistry of resulting phosphine oxide derivatives. Crystal and molecular structures of (Ph(2)P(O)CH(2))(2)NR (R = Me, (n)Pr, (n)Bu), Ph(2)P(O)CH(OH)(n)()Pr, and cis-[MoO(2)Cl(2)((Ph(2)P(O)CH(2))(2)NEt-kappaO,kappaO)].
2003 Feb 24
Affinity adsorption of glucose degradation products improves the biocompatibility of conventional peritoneal dialysis fluid.
2003 Jan
An improved HPLC analysis of the metabolite furoic acid in the urine of workers occupationally exposed to furfural.
2003 Jan-Feb
Determination of furanic compounds in traditional balsamic vinegars by ion-exclusion liquid chromatography and diode-array detection.
2003 Jul
Influence of seasonal variation on kinetics of time temperature integrators for thermally processed milk.
2003 May
Thermal decomposition of specifically phosphorylated D-glucoses and their role in the control of the Maillard reaction.
2003 May 21
The potential role of advanced glycation end product and iNOS in chronic renal failure-related testicular dysfunction. An experimental study.
2003 Sep-Oct
Response to different environmental stress conditions of industrial and laboratory Saccharomyces cerevisiae strains.
2004 Feb
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment:: In oral subchronic studies in rodents, dose levels of Furfural greater than 50 mg/kg bw/d are primarily associated with hepatic effects. 11 mg/kg may be considered a LOAEL in rats. https://ec.europa.eu/health/archive/ph_risk/committees/sccp/documents/out279_en.pdf
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
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.
Substance Class Chemical
Created
by admin
on Sat Jun 26 11:28:08 UTC 2021
Edited
by admin
on Sat Jun 26 11:28:08 UTC 2021
Record UNII
DJ1HGI319P
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FURFURAL
FCC   FHFI   HSDB   INCI   MI  
INCI  
Official Name English
FURFURYLALDEHYDE
Common Name English
FURFUROLE
Common Name English
PYROMUCIC ALDEHYDE
Common Name English
FURFURAL [FHFI]
Common Name English
2-FURANCARBOXALDEHYDE
Systematic Name English
2-FURALDEHYDE
Systematic Name English
FURANCARBONAL
Common Name English
FURAL
Systematic Name English
FEMA NO. 2489
Code English
FURFURAL [MI]
Common Name English
FURFURAL [INCI]
Common Name English
FURFURAL [FCC]
Common Name English
FURFURAL [HSDB]
Common Name English
FURFURAL [IARC]
Common Name English
NSC-8841
Code English
FURALDEHYDES
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 43301
Created by admin on Sat Jun 26 11:28:08 UTC 2021 , Edited by admin on Sat Jun 26 11:28:08 UTC 2021
JECFA EVALUATION FURFURAL
Created by admin on Sat Jun 26 11:28:08 UTC 2021 , Edited by admin on Sat Jun 26 11:28:08 UTC 2021
Code System Code Type Description
MERCK INDEX
M5603
Created by admin on Sat Jun 26 11:28:08 UTC 2021 , Edited by admin on Sat Jun 26 11:28:08 UTC 2021
PRIMARY Merck Index
EVMPD
SUB115712
Created by admin on Sat Jun 26 11:28:08 UTC 2021 , Edited by admin on Sat Jun 26 11:28:08 UTC 2021
PRIMARY
FDA UNII
DJ1HGI319P
Created by admin on Sat Jun 26 11:28:08 UTC 2021 , Edited by admin on Sat Jun 26 11:28:08 UTC 2021
PRIMARY
ECHA (EC/EINECS)
202-627-7
Created by admin on Sat Jun 26 11:28:08 UTC 2021 , Edited by admin on Sat Jun 26 11:28:08 UTC 2021
PRIMARY
EPA CompTox
98-01-1
Created by admin on Sat Jun 26 11:28:08 UTC 2021 , Edited by admin on Sat Jun 26 11:28:08 UTC 2021
PRIMARY
HSDB
542
Created by admin on Sat Jun 26 11:28:08 UTC 2021 , Edited by admin on Sat Jun 26 11:28:08 UTC 2021
PRIMARY
CAS
98-01-1
Created by admin on Sat Jun 26 11:28:08 UTC 2021 , Edited by admin on Sat Jun 26 11:28:08 UTC 2021
PRIMARY
PUBCHEM
7362
Created by admin on Sat Jun 26 11:28:08 UTC 2021 , Edited by admin on Sat Jun 26 11:28:08 UTC 2021
PRIMARY
WIKIPEDIA
FURFURAL
Created by admin on Sat Jun 26 11:28:08 UTC 2021 , Edited by admin on Sat Jun 26 11:28:08 UTC 2021
PRIMARY
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