Methylglyoxal

Methylglyoxal Basic information
Chemical Properties Description Sources References
Product Name:Methylglyoxal
Synonyms:2-oxo-propana;2-oxo-propionaldehyd;METHYLGLYOXAL;FEMA 2969;2-Ketopropionaldehyde;ACETYLFORMALDEHYDE;PYRUVIC ALDEHYDE, 40 WT. % SOLUTION IN WATER;METHYLGLYOXAL SOLUTION, ~40% IN WATER
CAS:78-98-8
MF:C3H4O2
MW:72.06
EINECS:201-164-8
Product Categories:Pyridines;Building Blocks;C1 to C6;Carbonyl Compounds;Chemical Synthesis;Nutrition Research;Organic Building Blocks;Other Biochemical;Phytochemicals by Chemical Classification;Aliphatics;Aldehydes;blocks;BuildingBlocks;bc0001;Elisa Kit-Mouse Elisa Kit
Mol File:78-98-8.mol
Methylglyoxal Structure
Methylglyoxal Chemical Properties
Melting point 25 °C
Boiling point 72 °C
density 1.19 g/mL at 20 °C
vapor pressure 25.09hPa at 20℃
FEMA 2969 | PYRUVALDEHYDE
refractive index n20/D 1.4209
RTECS UZ0700000
storage temp. 2-8°C
solubility DMSO (Slightly), Methanol (Slightly), Water (Soluble)
form Solution
color Clear yellow to yellow-brown
Odorat 1.00 % in propylene glycol. sweet acidic ethereal brown rum
Odor Typecaramellic
Water Solubility >=10 g/100 mL at 17 ºC
Sensitive Air Sensitive
JECFA Number937
Merck 14,6081
BRN 906750
InChIKeyAIJULSRZWUXGPQ-UHFFFAOYSA-N
LogP-1.06 at 25℃
CAS DataBase Reference78-98-8(CAS DataBase Reference)
IARC3 (Vol. 51) 1991
NIST Chemistry ReferencePropanal, 2-oxo-(78-98-8)
EPA Substance Registry SystemMethylglyoxal (78-98-8)
Safety Information
Hazard Codes Xn,Xi,C
Risk Statements 22-36-35
Safety Statements 26-36-45-36/37/39
RIDADR UN 3265 8 / PGIII
WGK Germany -
Hazard Note Irritant
TSCA Yes
HS Code 29121900
Hazardous Substances Data78-98-8(Hazardous Substances Data)
MSDS Information
ProviderLanguage
Pyruvaldehyde English
SigmaAldrich English
ACROS English
ALFA English
Methylglyoxal Usage And Synthesis
Chemical PropertiesMethylglyoxal (MG, C3H4O2) is also known as 2-oxopropanal, pyruvaldehyde, pyruvic aldehyde, 2-ketopropionaldehyde, acetylformaldehyde, propanedione, or propionaldehyde, which is a clear yellow slightly viscous liquid with a pungent odor which polymerizes readily and forms a variety of cyclic and acyclic structures. It is faintly acidic to litmus. The solubility of methylglyoxal is more than 10 g/100 mL water at 17°C. In water, MG is present mostly in the mono and dihydrate forms, while non hydrated MG is only present in traces.
DescriptionMethylglyoxal is an organic compound formed as a side-product of several metabolic pathways. It has been proved to be an intermediate in the metabolism of acetone and its derivatives. It is produced to insure every cell's health, which is used commonly as a reagent in organic synthesis, as a flavoring agent, and in tanning. However, the most important application is in pharmaceuticals. Methylglyoxal is found in all honeys, especially in manuka honey, in which it has strong antibacterial and antiviral property. Methylglyoxal is transferred into the honey where it remains stable. Dietary Methylglyoxal found in Manuka Honey is resistant to heat, light, body fluids and enzymatic activity. This property makes MGO Manuka Honey superior to any other honey. Its anti-cancer potential has been already demonstrated in human body and it has proved to be effective to eradicate most cancer types.
SourcesMany food products, beverages, water, rain, clouds, fog water, and urban atmosphere as well as cigarette smoke represent exogenous sources of methylglyoxal. The origins of MG in food and beverages are sugars, the products of the Maillard reaction, lipids and microorganisms formed during industrial processing, cooking, and prolonged storage. In vivo Methylglyoxal can be formed in many enzymatic and nonenzymatic pathways. Enzymatic pathways include reactions catalyzed by triosephosphate isomerase, cytochrome P450 2E1, myeloperoxidase, and aminooxidase, whereas nonenzymatic pathways include decomposition of dihydroxyacetone phosphate (DAP), the Maillard reaction, oxidation of acetol, and lipid peroxidation.
Referenceshttps://en.wikipedia.org/wiki/Methylglyoxal
https://pubchem.ncbi.nlm.nih.gov/compound/880#section=Top
http://www.cancertreatmentsresearch.com/methilglyoxal/

DescriptionMethylglyoxal (MG) is a highly reactive a-dicarbonyl compound that is primarily generated endogenously during glycolytic pathways (glucose and fructose metabolism) in cells and exogenously due to autoxidation of sugar, degradation of lipids, and fermentation during food and drink processing. Methylglyoxal polymerizes readily; it is hygroscopic and incompatible with strong oxidizing agents and bases. Methylglyoxal may be present as a free molecule in the diet or bound to biological materials, such as proteins, and as advanced glycation end products (AGEs), which are poorly absorbed. Methylglyoxal has been indicated in pathological events associated with hyperglycemia in both type 1 and type 2 diabetes and in other diabetic complications as either a direct toxin or as a precursor for AGEs. In animal studies, MG has been shown to induce tumorigenesis, but has also been reported as a tumoristatic agent. Methylglyoxal has been identified as the dominant antibacterial constituent of manuka honey.
Chemical PropertiesPyruvaldehyde has a characteristic, pungent, stinging odor with a pungent, caramellic, sweet flavor.
Chemical Propertiesclear yellow to yellow-brown solution
OccurrenceReported found in the dry distillate of Manilla copal. Also reported found in apple juice, orange juice, celery root, rutabaga, tomato, wheaten bread, white bread, roasted and raw turkey, cognac, roasted barley, beer, cocoa, coffee and roasted pecans.
UsesUsed in organic synthesis, as a flavoring agent, and in tanning leather. Commercial formulation is available as a 30% aqueous solution. No safety concern at current levels of intake when used as a flavoring agent.
UsesOrganic synthesis, as of complex chemical com- pounds such as pyrethrins, tanning leather, flavor- ing.
UsesMethylglyoxal solution has been used:
  • to assess glyoxalase 1 (GLO1) enzymatic activity
  • as an advanced glycation end (AGE) forming agent for the preparation of albumin in vitro
  • to regulate anxiety like behavior in mice
  • to induce peritoneal fibrosis in rats
  • to study the chromatographic retention characteristics of organic chemicals and metal DNA adducts
  • for intraplantar injection in mice to investigate peripheral and central components of methylglyoxal (MG)-transient receptor potential ankyrin 1 (TRPA1)-adenylyl cyclase 1 isoform (AC1) pathway
DefinitionChEBI: A 2-oxo aldehyde derived from propanal.
PreparationBy distilling a dilute solution of dihydroxyacetone from calcium carbonate; by oxidation of acetone with selenium dioxide; by heating dihydroxy acetone with phosphorus pentoxide; by warming isonitroso acetone with diluted H2SO4.
Taste threshold valuesTaste characteristics at 0.1%: sweet, caramellic with a dairy creamy nuance
General DescriptionClear yellow slightly viscous liquid with a pungent odor. Yellowish-green vapors. Faintly acidic to litmus.
Air & Water ReactionsWater soluble.
Reactivity ProfileMethylglyoxal polymerizes readily. Methylglyoxal is hygroscopic. Methylglyoxal is incompatible with strong oxidizing agents and bases. Methylglyoxal is an aldehyde. Aldehydes are frequently involved in self-condensation or polymerization reactions. These reactions are exothermic; they are often catalyzed by acid. Aldehydes are readily oxidized to give carboxylic acids. Flammable and/or toxic gases are generated by the combination of aldehydes with azo, diazo compounds, dithiocarbamates, nitrides, and strong reducing agents. Aldehydes can react with air to give first peroxo acids, and ultimately carboxylic acids. These autoxidation reactions are activated by light, catalyzed by salts of transition metals, and are autocatalytic (catalyzed by the products of the reaction). The addition of stabilizers (antioxidants) to shipments of aldehydes retards autoxidation.
Fire HazardLiterature sources indicate that Methylglyoxal is nonflammable.
Flammability and ExplosibilityNonflammable
Environmental FateMethylglyoxal production and use as a chemical intermediate and flavoring agent may result in its release to the environment through various waste streams. If released into water, MG is not expected to adsorb to suspended solids and sediment based on the estimated Koc. Volatilization from water surfaces is not expected to be an important fate process based upon the estimated Henry’s Law constant. If released to soil, MG is expected to have very high mobility based upon an estimated Koc of 1 determined from the structure estimation method. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions.
Methylglyoxal serves as a substrate for the isozymes E1, E2, and E3 of human aldehyde dehydrogenase. Oxidation of MG by these isozymes generated pyruvate. Methylglyoxal is a partially oxidized compound obtained from the tropospheric oxidation of numerous hydrocarbons, of both biogenic and anthropogenic origin. If released to the air, an estimated vapor pressure of 27 mm Hg at 25 ℃ indicates MG will exist solely as a vapor in the atmosphere. Vapor-phase MG will be degraded in the atmosphere by reaction with photochemically produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 30 h. Methylglyoxal absorbs light at wavelengths >290 nm and, therefore, is susceptible to direct photolysis by sunlight; half-lives of 2–4 h have been reported.
Purification MethodsCommercial 30% (w/v) aqueous solution is diluted to about 10% and distilled twice, taking the fraction boiling below 50o/20mm Hg. (This treatment does not remove lactic acid). [Beilstein 1 IV 3631.]
Toxicity evaluationEndogenously formed MG modifies arginine and lysine residues in proteins that form AGEs, which have been associated with diabetic complications and some neurodegenerative diseases. In different cell lines, MG treatment has been shown to induce apoptosis as measured by nuclear fragmentation and apoptotic body formation, indicating an increase in apoptosis. At the mitochondrial level, exogenous MG is highly toxic as it promotes proliferation, swelling, and membrane derangement. In both in vitro and in vivo studies, MG treatment has been shown to significantly reduce antioxidant enzymes and elevate reactive oxygen species that lead to oxidative stress-mediated cell death. Genotoxicity has been observed in both in vivo and in vitro studies, as MG is capable of binding to cellular macromolecules and forming DNA adducts.
Methylglyoxal Preparation Products And Raw materials
Preparation ProductsPyruvic acid-->2-Allyl-4-hydroxy-3-methyl-2-cyclopenten-1-one-->Prallethrin-->2-QUINOXALINECARBALDEHYDE-->4-Methylimidazole-->2-Methylquinoxaline-->Pyraclofos-->2-Methylpyrazine-->Mitoguazone-->2,4-Dimethylimidazole-->Methylglyoxal 1,1-dimethyl acetal-->Methyl lactate-->3-Butyn-2-one-->3-hydroxypropionaldehyde-->(R)-Lactate-->AMYL LACTATE-->D-Glyceraldehyde-->ISOBUTYL LACTATE-->1,3-Dihydroxyacetone
Pyruvaldehyde bis(N4-methylthiosemicarbazone) Methylglyoxal bis-4-methylthiosemicarbazone METHYLGLYOXAL 1, 1-DIMETHYL ACETAL,METHYLGLYOXAL DIMETHYL ACETAL,Methylglyoxal dimethyl acetal~Pyruvaldehyde dimethyl acetal Diethyl squarate di-N',N''-methylglyoxal bis(guanylhydrazone) 1-Methylglyoxal bis(amidinocyclopentyl hydrazone) POTASSIUM 1,2-NAPHTHOQUINONE-4-SULFONIC ACID O-BROMANIL RHODIZONIC ACID DIHYDRATE sodium phenylglyoxylate Pyruvaldehyde40% water solution RHODIZONIC ACID DIPOTASSIUM SALT methylglyoxal-ascorbate Methylglyoxal bis(guanylhydrazone) hydrate dihydrochloride methylglyoxal synthase methylglyoxal hydrate methylglyoxal bis(cyclopentylamidinohydrazone) TRIQUINOLYL 2-Oxopropanal oxime

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