glyoxal
1,2-ethanedione
Identification
| Name | glyoxal |
| IUPAC | oxaldehyde |
| CAS Number | 107-22-2 |
| EINECS | 203-474-9 |
| FDA UNII | 50NP6JJ975 |
| Molecular Formula | C2 H2 O2 |
| Molecular Weight | 58.03634000 |
| MDL Number | MFCD00006957 |
| Nikkaji Number | J5.155A |
| Beilstein | 1732463 |
Regulatory
| FDA Mainterm (IAUFC) | 107-22-2 ; GLYOXAL |
Physical Properties
| Appearance | colorless to pale yellow clear liquid to solid (est) |
| Assay | 96.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Specific Gravity | 1.26500 @ 25.00 °C. |
| Melting Point | 14.00 to 16.00 °C. @ 760.00 mm Hg |
| Boiling Point | 49.00 to 51.00 °C. @ 760.00 mm Hg |
| Vapor Pressure | 255.000000 mmHg @ 25.00 °C. (est) |
| Flash Point | 24.00 °F. TCC ( -4.30 °C. ) (est) |
| logP (o/w) | -0.549 (est) |
| Shelf Life | 12.00 month(s) or longer if stored properly. |
| Storage | refrigerate in tightly sealed containers. |
| Soluble in | alcohol |
Cosmetic Information
| CosIng | cosmetic data |
| Cosmetic Uses | antimicrobial agents |
Organoleptic Properties
| Odor Strength | low |
| Odor Description | at 100.00 %. |
Safety Information
| European information | Most important hazard(s): |
| Oral/Parenteral Toxicity | oral-guinea pig LD50 760 mg/kg |
| Dermal Toxicity | skin-guinea pig LD50 6600 mg/kg |
| Inhalation Toxicity | inhalation-rat LC50 2410 mg/m3/4H |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | information only not used for fragrances or flavors |
| Recommendation for glyoxal usage levels up to | not for fragrance use. |
| Recommendation for glyoxal flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
diformal
ethandial
ethane dial
ethane-1,2-dial
ethanedial
ethanedione
1,2-
ethanedione
gelifundol
glyoxal aldehyde
glyoxylaldehyde
oxalaldehyde
oxaldehyde
PubMed:
Impact of the N-terminal amino acid on the formation of pyrazines from peptides in Maillard model systems.
J-Stage:
Cleavage of a-Dicarbonyl Compounds by Terpene Hydroperoxide
PubMed:
Automated and quantitative headspace in-tube extraction for the accurate determination of highly volatile compounds from wines and beers.
PubMed:
Thermal generation of 3-amino-4,5-dimethylfuran-2(5H)-one, the postulated precursor of sotolone, from amino acid model systems containing glyoxylic and pyruvic acids.
PubMed:
Formation of pyrazines in Maillard model systems of lysine-containing dipeptides.
PubMed:
Degradation of glucose: reinvestigation of reactive alpha-Dicarbonyl compounds.
PubMed:
alpha-Dicarbonyl compounds--key intermediates for the formation of carbohydrate-based melanoidins.
PubMed:
Formation of flavor components by the reaction of amino acid and carbonyl compounds in mild conditions.
PubMed:
Determination of Antioxidant Capacities, α-Dicarbonyls, and Phenolic Phytochemicals in Florida Varietal Honeys using HPLC-DAD-ESI-MS(n.)
PubMed:
Investigation of α-Dicarbonyl Compounds in Baby Foods by High-Performance Liquid Chromatography Coupled with Electrospray Ionization Mass Spectrometry.
PubMed:
Methylglyoxal is associated with bacteriostatic activity of high fructose agave syrups.
PubMed:
Structure- and Concentration-Specific Assessment of the Physiological Reactivity of α-Dicarbonyl Glucose Degradation Products in Peritoneal Dialysis Fluids.
PubMed:
Free α-dicarbonyl compounds in coffee, barley coffee and soy sauce and effects of in vitro digestion.
PubMed:
Model Studies on the Oxidation of Benzoyl Methionine in a Carbohydrate Degradation System.
PubMed:
Arginine-derived advanced glycation end products generated in peptide-glucose mixtures during boiling.
PubMed:
High-performance liquid chromatography determination of glyoxal, methylglyoxal, and diacetyl in urine using 4-methoxy-o-phenylenediamine as derivatizing reagent.
PubMed:
Modulation of GSH with exogenous agents leads to changes in glyoxalase 1 enzyme activity in VL-17A cells exposed to chronic alcohol plus high glucose.
PubMed:
Hydroxyl radical induced by lipid in Maillard reaction model system promotes diet-derived N(ε)-carboxymethyllysine formation.
PubMed:
Hazardous airborne carbonyls emissions in industrial workplaces in China.
PubMed:
Advanced glycation endproducts in food and their effects on health.
PubMed:
Formation of 4(5)-methylimidazole and its precursors, α-dicarbonyl compounds, in Maillard model systems.
PubMed:
Cytotoxicity of α-dicarbonyl compounds submitted to in vitro simulated digestion process.
PubMed:
Response surface methodology as optimization strategy for reduction of reactive carbonyl species in foods by means of phenolic chemistry.
PubMed:
Propolis induced antibacterial activity and other technical properties of cotton textiles.
PubMed:
DJR-1.2 of Caenorhabditis elegans is induced by DAF-16 in the dauer state.
PubMed:
Roasting-induced changes in arabinotriose, a model of coffee arabinogalactan side chains.
PubMed:
Effect of in vitro digestion on free α-dicarbonyl compounds in balsamic vinegars.
PubMed:
Analysis of sugar degradation products with α-dicarbonyl structure in carbonated soft drinks by UHPLC-DAD-MS/MS.
PubMed:
Determination of toxic α-dicarbonyl compounds, glyoxal, methylglyoxal, and diacetyl, released to the headspace of lipid commodities upon heat treatment.
PubMed:
Non-enzymatic glycation of melamine with sugars and sugar like compounds.
PubMed:
Double Schiff base adducts of 2,3-butanedione with glycine: formation of pyrazine rings with the participation of amino acid carbon atoms.
PubMed:
Small reactive carbonyl compounds as tissue lipid oxidation products; and the mechanisms of their formation thereby.
PubMed:
Influence of phenolic compounds on the mechanisms of pyrazinium radical generation in the Maillard reaction.
PubMed:
Flavour chemistry of methylglyoxal and glyoxal.
PubMed:
Impact of the N-terminal amino acid on the formation of pyrazines from peptides in Maillard model systems.
PubMed:
Survey of 1,2-dicarbonyl compounds in commercial honey of different floral origin.
PubMed:
Identification and quantification of six major α-dicarbonyl process contaminants in high-fructose corn syrup.
PubMed:
Effect of coffee filtrate, methylglyoxal, glyoxal, and caffeine on Salmonella typhimurium and S. enteritidis survival in ground chicken breasts.
PubMed:
Phlorotannins from brown algae (Fucus vesiculosus) inhibited the formation of advanced glycation endproducts by scavenging reactive carbonyls.
PubMed:
Antioxidant content and activity of the Indian fresh-water pearl mussel in the prevention of arthritis in an experimental animal model.
PubMed:
Chemical and physiological relevance of glucose degradation products in peritoneal dialysis.
PubMed:
Multistep ultrahigh performance liquid chromatography/tandem mass spectrometry analysis for untargeted quantification of glycating activity and identification of most relevant glycation products.
PubMed:
The potential of biodetoxification activity as a probiotic property of Lactobacillus reuteri.
PubMed:
Development of active polyvinyl alcohol/β-cyclodextrin composites to scavenge undesirable food components.
PubMed:
Chemical modifications of peptides and their impact on food properties.
PubMed:
Cranberry phytochemicals inhibit glycation of human hemoglobin and serum albumin by scavenging reactive carbonyls.
PubMed:
Microbial oxidases catalyzing conversion of glycolaldehyde into glyoxal.
PubMed:
Quantification of the six major α-dicarbonyl contaminants in peritoneal dialysis fluids by UHPLC/DAD/MSMS.
PubMed:
Taste modulating N-(1-methyl-4-oxoimidazolidin-2-ylidene) α-amino acids formed from creatinine and reducing carbohydrates.
PubMed:
Thermal generation of 3-amino-4,5-dimethylfuran-2(5H)-one, the postulated precursor of sotolone, from amino acid model systems containing glyoxylic and pyruvic acids.
PubMed:
Lipid glycation and protein glycation in diabetes and atherosclerosis.
PubMed:
3-deoxygalactosone, a "new" 1,2-dicarbonyl compound in milk products.
PubMed:
Carbonyl compounds methylglyoxal and glyoxal affect interleukin-8 secretion in intestinal cells by superoxide anion generation and activation of MAPK p38.
PubMed:
Model studies on chemical and textural modifications in gelatin films by reaction with glyoxal and glycolaldehyde.
PubMed:
Formation of pyrazines in Maillard model systems of lysine-containing dipeptides.
PubMed:
Quantification of N2-carboxymethyl-2'-deoxyguanosine in calf thymus DNA and cultured human kidney epithelial cells by capillary high-performance liquid chromatography-tandem mass spectrometry coupled with stable isotope dilution method.
PubMed:
Glutathione reacts with glyoxal at the N-terminal.
PubMed:
Profiling of alpha-dicarbonyl content of commercial honeys from different botanical origins: identification of 3,4-dideoxyglucoson-3-ene (3,4-DGE) and related compounds.
PubMed:
Isotope labeling studies on the origin of 3,4-hexanedione and 1,2-butanedione in an alanine/glucose model system.
PubMed:
Degradation of glucose: reinvestigation of reactive alpha-Dicarbonyl compounds.
PubMed:
Food derived carbonyl compounds affect basal and stimulated secretion of interleukin-6 and -8 in Caco-2 cells.
PubMed:
Development and validation of an HPLC method to quantify 3,4-dideoxyglucosone-3-ene in peritoneal dialysis fluids.
PubMed:
Characterization of porcine plasma protein-based films as affected by pretreatment and cross-linking agents.
PubMed:
Chromium(III) ion selective electrode based on glyoxal bis(2-hydroxyanil).
PubMed:
Identification and monitoring of intermediates and products in the acrylamide pathway using online analysis.
PubMed:
Acrylamide and pyrazine formation in model systems containing asparagine.
PubMed:
Oral glycotoxins determine the effects of calorie restriction on oxidant stress, age-related diseases, and lifespan.
PubMed:
Methylglyoxal: its presence and potential scavengers.
PubMed:
Induction of heat shock proteins and the proteasome system by casein-N epsilon-(carboxymethyl)lysine and N epsilon-(carboxymethyl)lysine in Caco-2 cells.
PubMed:
alpha-Dicarbonyl compounds--key intermediates for the formation of carbohydrate-based melanoidins.
PubMed:
Methylglyoxal: its presence in beverages and potential scavengers.
PubMed:
Determination of N epsilon-(carboxymethyl)lysine in foods and related systems.
PubMed:
Rapid analysis of alpha-dicarbonyl compounds by laser desorption/ionization mass spectrometry using 9-(3,4-diaminophenyl)acridine (DAA) as a reactive matrix.
PubMed:
Identification and quantification of methylglyoxal as the dominant antibacterial constituent of Manuka (Leptospermum scoparium) honeys from New Zealand.
PubMed:
Isolation, identification, and quantification of roasted coffee antibacterial compounds.
PubMed:
Simultaneous determination of ketoacids and dicarbonyl compounds, key Maillard intermediates on the generation of aged wine aroma.
PubMed:
Isolation and determination of alpha-dicarbonyl compounds by RP-HPLC-DAD in green and roasted coffee.
PubMed:
Preventing cell death induced by carbonyl stress, oxidative stress or mitochondrial toxins with vitamin B anti-AGE agents.
PubMed:
Molecular action mechanism against apoptosis by aqueous extract from guava budding leaves elucidated with human umbilical vein endothelial cell (HUVEC) model.
PubMed:
Determination of glyoxal and methylglyoxal in environmental and biological matrices by stir bar sorptive extraction with in-situ derivatization.
PubMed:
Structure-reactivity relationships of flavan-3-ols on product generation in aqueous glucose/glycine model systems.
PubMed:
Reducing the formation of glucose degradation products in peritoneal dialysis solutions by ultrahigh temperature ohmic heating.
PubMed:
Copper-catalyzed ascorbate oxidation results in glyoxal/AGE formation and cytotoxicity.
PubMed:
Investigations on the promoting effect of ammonium hydrogencarbonate on the formation of acrylamide in model systems.
PubMed:
Chemical modification of wheat protein-based natural polymers: cross-linking effect on mechanical properties and phase structures.
PubMed:
Trapping reactions of reactive carbonyl species with tea polyphenols in simulated physiological conditions.
PubMed:
Epicatechin carbonyl-trapping reactions in aqueous maillard systems: Identification and structural elucidation.
PubMed:
Carbonyl emissions from commercial cooking sources in Hong Kong.
PubMed:
Development and characterization of films based on chemically cross-linked gliadins.
PubMed:
Inhibitory effect of some selected nutraceutic herbs on LDL glycation induced by glucose and glyoxal.
PubMed:
Binding residues and catalytic domain of soluble Saccharomyces cerevisiae processing alpha-glucosidase I.
PubMed:
Evaluation of advanced glycation end products and carbonyl compounds in patients with different conditions of oxidative stress.
PubMed:
Fate of the glucose degradation products 3-deoxyglucosone and glyoxal during peritoneal dialysis.
PubMed:
Formation of genotoxic dicarbonyl compounds in dietary oils upon oxidation.
PubMed:
Liver carcinogenesis and formation of 8-hydroxy-deoxyguanosine in C3H/HeN mice by oxidized dietary oils containing carcinogenic dicarbonyl compounds.
PubMed:
N-Terminal pyrazinones: a new class of peptide-bound advanced glycation end-products.
PubMed:
Maillard reaction and enzymatic browning affect the allergenicity of Pru av 1, the major allergen from cherry (Prunus avium).
PubMed:
Aqueous photolysis of niclosamide.
PubMed:
Aldehyde contamination of mineral water stored in PET bottles.
PubMed:
Glyoxal/glycolaldehyde: a redox system involved in malolactic fermentation of wine.
PubMed:
Chemical reactions in cottonseed protein cross-linking by formaldehyde, glutaraldehyde, and glyoxal for the formation of protein films with enhanced mechanical properties.
PubMed:
Amides are novel protein modifications formed by physiological sugars.
PubMed:
Identification and quantitative evaluation of the lysine-arginine crosslinks GODIC, MODIC, DODIC, and glucosepan in foods.
PubMed:
Isolation and characterization of glyoxal-arginine modifications.
PubMed:
Formation of flavor components by the reaction of amino acid and carbonyl compounds in mild conditions.
PubMed:
Role of carbonyl compounds in SO(2) binding phenomena in musts and wines from botrytized grapes.
PubMed:
Evidence for the involvement of N-methylthiourea, a ring cleavage metabolite, in the hepatotoxicity of methimazole in glutathione-depleted mice: structure-toxicity and metabolic studies.
PubMed:
Quantitative model studies on the formation of aroma-active aldehydes and acids by strecker-type reactions.
PubMed:
Current status of acrolein as a lipid peroxidation product.
PubMed:
Studies on radical intermediates in the early stage of the nonenzymatic browning reaction of carbohydrates and amino acids.
PubMed:
Molecular analysis of Salmonella hisG428 ochre revertants for rapid characterization of mutational specificity.
PubMed:
Analysis of the potential carcinogenicity of coffee and its related compounds in a medium-term liver bioassay of rats.
PubMed:
Inhibitory effect of 2"-O-glycosyl isovitexin and alpha-tocopherol on genotoxic glyoxal formation in a lipid peroxidation system.
PubMed:
Mechanism(s) involved in meat mutagen formation and inhibition.
PubMed:
Subchronic oral toxicity of glyoxal via drinking water in rats.
PubMed:
Spectrophotometric determination of copper in foods, feedingstuffs and plants: a comparison between the glyoxal bis(4-phenyl-3-thiosemicarbazone) and bathocuproine disulphonate methods.
PubMed:
Metabolism of 2-oxoaldehyde in mold. Purification and characterization of two methylglyoxal reductases from Aspergillus niger.
PubMed:
Comparative mutagenicity of nine brands of coffee to Salmonella typhimurium TA100, TA102, and TA104.
PubMed:
Desmutagenic effect of alpha-dicarbonyl and alpha-hydroxycarbonyl compounds against mutagenic heterocyclic amines.
PubMed:
Hydroxylation of guanine in nucleosides and DNA at the C-8 position by heated glucose and oxygen radical-forming agents.
PubMed:
Mutagens and carcinogens in foods.
PubMed:
Sulfite suppresses the mutagenic property of coffee.
PubMed:
Effect of malondialdehyde on nitrosamine formation.
PubMed:
Compounds new to essential orange oil from fruit treated with abscission chemicals.
PubMed:
Oxidative browning of Amadori compounds from amino acids and peptides.