|
Category:information only not used for fragrances or flavors
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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 | | | water, 1000000 mg/L @ 20 °C (exp) |
Organoleptic Properties:
| Odor Strength:low |
| Odor Description:at 100.00 %. mild sour |
| Odor and/or flavor descriptions from others (if found). |
Cosmetic Information:
Suppliers:
| BASF |
| Glyoxal 40%
Odor: characteristic Use: Glyoxal shows a wide range of activities, e.g. as a versatile crosslinker, as an intermediate for organic syntheses, as a biocide, and as a scavenger for a diverse range of nucleophiles. |
| BOC Sciences |
| For experimental / research use only. |
| Glyfosfin >98%
|
| Covalent Chemical |
| Glyoxal
|
| EMD Millipore |
| For experimental / research use only. |
| Glyoxal
|
| Penta International |
| GLYOXAL 40% SOL. IN WATER
|
| Santa Cruz Biotechnology |
| For experimental / research use only. |
| Glyoxal, 40 % Solution
|
| Sigma-Aldrich |
| For experimental / research use only. |
| Glyoxal solution 40 wt. % in H2O
|
| Silver Fern Chemical |
| Glyoxal 40
Odor: characteristic Use: Glyoxal links a wide range of polymers, e.g. starch, cellulose, proteinaceous material, polyacrylamide, polyvinyl alcohols. |
| Universal Preserv-A-Chem Inc. |
| Ethanedial, Oxalaldehyde
Odor: characteristic Use: Is used as a solubilizer and cross-linking agent in polymer chemistry for: proteins (leather tanning process), collagen, cellulose derivatives (textiles), hydrocolloids, and starch (paper coatings). |
Safety Information:
| European information : |
| Most important hazard(s): | | Xn - Harmful. |
R 20 - Harmful by inhalation.
R 36/38 - Irritating to skin and eyes.
R 43 - May cause sensitisation by skin contact.
R 68 - Possible risk of irreversible effects.
S 02 - Keep out of the reach of children.
S 20/21 - When using do not eat, drink or smoke.
S 23 - Do not breath fumes.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36/37 - Wear suitable protective clothing and gloves.
|
| |
| 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: |
oral-guinea pig LD50 760 mg/kg
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
GASTROINTESTINAL: OTHER CHANGES
Journal of Industrial Hygiene and Toxicology. Vol. 23, Pg. 259, 1941.
oral-guinea pig LD50 > 10000 mg/kg
National Technical Information Service. Vol. OTS0538086
intraperitoneal-mouse LD50 200 mg/kg
National Technical Information Service. Vol. AD438-895
oral-mouse LD50 400 mg/kg
National Technical Information Service. Vol. AD438-895
oral-mouse LD50 1280 mg/kg
National Technical Information Service. Vol. OTS0538086
intravenous-rabbit LD50 60 mg/kg
National Technical Information Service. Vol. OTS0535072
oral-rabbit LD50 > 3175 mg/kg
National Technical Information Service. Vol. OTS0538086
oral-rat LD50 4290 mg/kg
Union Carbide Data Sheet. Vol. 11/4/1971
oral-rat LD50 2960 mg/kg
LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
National Technical Information Service. Vol. OTS0535124
oral-rat LD50 200 mg/kg
BEHAVIORAL: MUSCLE WEAKNESS
National Technical Information Service. Vol. OTS0533618
intravenous-dog LDLo 300 uL/kg
National Technical Information Service. Vol. OTS0535072
oral-guinea pig LD50 10000 mg/kg
National Technical Information Service. Vol. OTS0538086
oral-mouse LD50 400 mg/kg
BEHAVIORAL: MUSCLE WEAKNESS
National Technical Information Service. Vol. OTS0533618
intraperitoneal-rabbit LD50 60 mg/kg
National Technical Information Service. Vol. OTS0535072
intraperitoneal-rat LDLo 100 mg/kg
National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. Vol. 5, Pg. 9, 1953.
|
| Dermal Toxicity: |
skin-guinea pig LD50 6600 mg/kg
"Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 291, 1969.
skin-rabbit LD50 10 ml/kg
LIVER: OTHER CHANGES
LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA
KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"
National Technical Information Service. Vol. OTS0535072
skin-rabbit LD50 10 ml/kg
Union Carbide Data Sheet. Vol. 11/4/1971
skin-rat LD50 > 2000 mg/kg
SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
National Technical Information Service. Vol. OTS0535506
skin-rabbit LD50 10 ml/kg
LIVER: OTHER CHANGES
LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA
KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"
National Technical Information Service. Vol. OTS0535072
skin-rabbit LD50 10 mL/kg
Union Carbide Data Sheet. Vol. 11/12/1965
|
| Inhalation Toxicity: |
inhalation-rat LC50 2410 mg/m3/4H
SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION
LUNGS, THORAX, OR RESPIRATION: DYSPNEA
National Technical Information Service. Vol. OTS0535127
|
Safety in Use Information:
| 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.
|
Safety References:
References:
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 |
| FDA Indirect Additives used in Food Contact Substances: | View |
| CHEBI: | View |
| CHEMBL: | View |
| KEGG (GenomeNet): | C14448 |
| HMDB (The Human Metabolome Database): | Search |
| FooDB: | FDB007802 |
| Export Tariff Code: | 2912.19.3000 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
| Wikipedia: | View |
Formulations/Preparations:
•commercially available in anhydrous form as crystalline dihydrate, or as a 40% aqueous solution which may contain polymerization inhibitors. dihydrate
•grades: 40% solution; pure, solid; vp.
•glyoxal is a dialdehyde supplied commercially as 30% aqueous solution, consisting of mixture of monomeric & polymeric hydrates along with small amounts of impurities which render the solution acid.
•glyoxal can undertake rotational isomerization between the planar cis and trans conformations, with trans-glyoxal being the more stable isomer.
•...it is generally employed as an aqueous solutionin which hydrated oligomers are present due to nucleophilic addition. ...some of the most important hydrated derivatives of glyoxal formed by nucleophilic addition in aqueous solutioninclude the monomer ethane-1,1,2,2-tetraol (i), the dimer 2-dihydroxymethyl-(1,3)dioxolane-4,5-transdiol (ii), and the trimer bis(dioxolane) (i.e., 2,2'-bi-1,3-dioxolanyl-4,4',5,5'-tetraol) (iii) - both cis and trans configurations. however, the proportion of the different structures varies with concentration and ph.
|
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
Synonyms:
| | diformal | | | ethandial | | | ethane dial | | | ethane-1,2-dial | | | ethanedial | | | ethanedione | | 1,2- | ethanedione | | | gelifundol | | | glyoxal aldehyde | | | glyoxylaldehyde | | | oxalaldehyde | | | oxaldehyde |
Articles:
| 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. |
|
3D/inchi