U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

Molecular Formula C5H4O2
Molecular Weight 96.0841
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
Occupational exposure to harmful chemical substances while processing phenol-formaldehyde resins.
2001
Changes of volatile compounds during heating of bacuri pulp.
2001 Dec
Volatile flavor constituents of acerola (Malpighia emarginata DC.) fruit.
2001 Dec
Effects of furfural on anaerobic continuous cultivation of Saccharomyces cerevisiae.
2001 Dec 5
Degradation in peritoneal dialysis fluids may be avoided by using low pH and high glucose concentration.
2001 Jul-Aug
Enantioselective synthesis of N-Cbz-protected 6-amino-6-deoxymannose, -talose, and -gulose.
2001 Nov 29
Formation of furfurylthiol exhibiting a strong coffee aroma during oak barrel fermentation from furfural released by toasted staves.
2001 Oct
Some furfural derivatives as nitrification inhibitors.
2001 Oct
Manufacture of xylose-based fermentation media from corncobs by posthydrolysis of autohydrolysis liquors.
2001 Sep
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
Synthesis and biological activity of new 1,4-benzodioxan-arylpiperazine derivatives. Further validation of a pharmacophore model for alpha(1)-adrenoceptor antagonists.
2002 Feb
High-performance liquid chromatographic determination of furfural compounds in infant formulas. Changes during heat treatment and storage.
2002 Feb 15
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
Enantioselective synthesis of 2-deoxy- and 2,3-dideoxyhexoses.
2002 May 16
Furfural-cysteine model reaction in food grade nonionic oil/water microemulsions for selective flavor formation.
2002 May 8
Comparison of the fermentability of enzymatic hydrolyzates of sugarcane bagasse pretreated by steam explosion using different impregnating agents.
2002 Spring
Xylose reductase and xylitol dehydrogenase activities of Candida guilliermondii as a function of different treatments of sugarcane bagasse hemicellulosic hydrolysate employing experimental design.
2002 Spring
Syntheses of 2, 5-dialkylfuran and tetrahydrofuran carbinols and their cytotoxic activity.
2003 Aug
Removal of mercury (II) from aqueous solution by activated carbon obtained from furfural.
2003 Aug
Extraction and formation dynamic of oak-related volatile compounds from different volume barrels to wine and their behavior during bottle storage.
2003 Aug 27
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
Kinetics of hydroxymethylfurfural, lactulose and furosine formation in milk with different fat content.
2003 Feb
"Action-at-a distance" of a new DNA oxidative damage product 6-furfuryl-adenine (kinetin) on template properties of modified DNA.
2003 Feb 20
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
Chemical constituents from the Hydrangea chinensis.
2003 Jan
Modeling of the hydrolysis of sugar cane bagasse with hydrochloric acid.
2003 Jan
Furoyl and benzofuroyl pyrroloquinolones as potent and selective PDE5 inhibitors for treatment of erectile dysfunction.
2003 Jan 30
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
Quantification of 5-HMF and dextrose in commercial aqueous dextrose solutions.
2003 Jul 14
3-Hydroxy-4,5-dimethyl-2(5H)-furanone: a key odorant of the typical aroma of oxidative aged Port wine.
2003 Jul 16
2-Furoylmethyl amino acids and hydroxymethylfurfural as indicators of honey quality.
2003 Jul 16
Generation of thiols by biotransformation of cysteine-aldehyde conjugates with baker's yeast.
2003 Jun 4
Impurities in a morphine sulfate drug product identified as 5-(hydroxymethyl)-2-furfural, 10-hydroxymorphine and 10-oxomorphine.
2003 Mar
Influence of seasonal variation on kinetics of time temperature integrators for thermally processed milk.
2003 May
Availability of corn stover as a sustainable feedstock for bioethanol production.
2003 May
Thermal decomposition of specifically phosphorylated D-glucoses and their role in the control of the Maillard reaction.
2003 May 21
One-pot, two-step, practical catalytic synthesis of 2,5-diformylfuran from fructose.
2003 May 29
Analysis of aldehydes in beer using solid-phase microextraction with on-fiber derivatization and gas chromatography/mass spectrometry.
2003 Nov 19
Prazosin-related compounds. Effect of transforming the piperazinylquinazoline moiety into an aminomethyltetrahydroacridine system on the affinity for alpha1-adrenoreceptors.
2003 Nov 6
Insecticidal compounds against Drosophila melanogaster from Cornus officinalis Sieb. et Zucc.
2003 Oct
Extracting material parameters from x-ray attenuation: a CT feasibility study using kilovoltage synchrotron x-rays incident upon low atomic number absorbers.
2003 Oct 21
Stereochemistry of intramolecular Diels-Alder furan (IMDAF) reactions of furyl-substituted chiral ethanolamides.
2003 Oct 21
Quantitative analysis of 2-furfural and 5-methylfurfural in different Italian vinegars by headspace solid-phase microextraction coupled to gas chromatography-mass spectrometry using isotope dilution.
2003 Oct 31
The potential role of advanced glycation end product and iNOS in chronic renal failure-related testicular dysfunction. An experimental study.
2003 Sep-Oct
Limits for alkaline detoxification of dilute-acid lignocellulose hydrolysates.
2003 Spring
Response to different environmental stress conditions of industrial and laboratory Saccharomyces cerevisiae strains.
2004 Feb
Isolation of microorganisms for biological detoxification of lignocellulosic hydrolysates.
2004 Mar
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 Fri Dec 15 17:04:20 GMT 2023
Edited
by admin
on Fri Dec 15 17:04:20 GMT 2023
Record UNII
DJ1HGI319P
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FURFURAL
FCC   FHFI   HSDB   INCI   MI  
INCI  
Official Name English
ASCORBIC ACID IMPURITY A [EP IMPURITY]
Common 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 Fri Dec 15 17:04:20 GMT 2023 , Edited by admin on Fri Dec 15 17:04:20 GMT 2023
JECFA EVALUATION FURFURAL
Created by admin on Fri Dec 15 17:04:20 GMT 2023 , Edited by admin on Fri Dec 15 17:04:20 GMT 2023
Code System Code Type Description
MERCK INDEX
m5603
Created by admin on Fri Dec 15 17:04:20 GMT 2023 , Edited by admin on Fri Dec 15 17:04:20 GMT 2023
PRIMARY Merck Index
EVMPD
SUB115712
Created by admin on Fri Dec 15 17:04:20 GMT 2023 , Edited by admin on Fri Dec 15 17:04:20 GMT 2023
PRIMARY
FDA UNII
DJ1HGI319P
Created by admin on Fri Dec 15 17:04:20 GMT 2023 , Edited by admin on Fri Dec 15 17:04:20 GMT 2023
PRIMARY
ECHA (EC/EINECS)
202-627-7
Created by admin on Fri Dec 15 17:04:20 GMT 2023 , Edited by admin on Fri Dec 15 17:04:20 GMT 2023
PRIMARY
EPA CompTox
DTXSID1020647
Created by admin on Fri Dec 15 17:04:20 GMT 2023 , Edited by admin on Fri Dec 15 17:04:20 GMT 2023
PRIMARY
NSC
8841
Created by admin on Fri Dec 15 17:04:20 GMT 2023 , Edited by admin on Fri Dec 15 17:04:20 GMT 2023
PRIMARY
HSDB
542
Created by admin on Fri Dec 15 17:04:20 GMT 2023 , Edited by admin on Fri Dec 15 17:04:20 GMT 2023
PRIMARY
JECFA MONOGRAPH
169
Created by admin on Fri Dec 15 17:04:20 GMT 2023 , Edited by admin on Fri Dec 15 17:04:20 GMT 2023
PRIMARY
CHEBI
34768
Created by admin on Fri Dec 15 17:04:20 GMT 2023 , Edited by admin on Fri Dec 15 17:04:20 GMT 2023
PRIMARY
CAS
98-01-1
Created by admin on Fri Dec 15 17:04:20 GMT 2023 , Edited by admin on Fri Dec 15 17:04:20 GMT 2023
PRIMARY
ALANWOOD
furfural
Created by admin on Fri Dec 15 17:04:20 GMT 2023 , Edited by admin on Fri Dec 15 17:04:20 GMT 2023
PRIMARY
PUBCHEM
7362
Created by admin on Fri Dec 15 17:04:20 GMT 2023 , Edited by admin on Fri Dec 15 17:04:20 GMT 2023
PRIMARY
SMS_ID
100000142139
Created by admin on Fri Dec 15 17:04:20 GMT 2023 , Edited by admin on Fri Dec 15 17:04:20 GMT 2023
PRIMARY
WIKIPEDIA
FURFURAL
Created by admin on Fri Dec 15 17:04:20 GMT 2023 , Edited by admin on Fri Dec 15 17:04:20 GMT 2023
PRIMARY
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