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Methylglyoxal information


Methylglyoxal
Skeletal formula
Skeletal formula
Ball-and-stick model of methylglyoxal
Names
Preferred IUPAC name
2-Oxopropanal
Other names
Pyruvaldehyde
Identifiers
CAS Number
  • 78-98-8 checkY
  • 1186-47-6 (hydrate) ☒N
3D model (JSmol)
  • Interactive image
3DMet
  • B00127
Beilstein Reference
906750
ChEBI
  • CHEBI:17158 checkY
ChEMBL
  • ChEMBL170721 checkY
ChemSpider
  • 857 checkY
DrugBank
  • DB03587 checkY
ECHA InfoCard 100.001.059 Edit this at Wikidata
IUPHAR/BPS
  • 6303
KEGG
  • C00546 checkY
MeSH Methylglyoxal
PubChem CID
  • 880
UNII
  • 722KLD7415 checkY
CompTox Dashboard (EPA)
  • DTXSID0021628 Edit this at Wikidata
InChI
  • InChI=1S/C3H4O2/c1-3(5)2-4/h2H,1H3 checkY
    Key: AIJULSRZWUXGPQ-UHFFFAOYSA-N checkY
  • InChI=1/C3H4O2/c1-3(5)2-4/h2H,1H3
    Key: AIJULSRZWUXGPQ-UHFFFAOYAZ
SMILES
  • CC(=O)C=O
Properties
Chemical formula
C3H4O2
Molar mass 72.063 g·mol−1
Appearance Yellow liquid
Density 1.046 g/cm3
Melting point 25 °C (77 °F; 298 K)
Boiling point 72 °C (162 °F; 345 K)
Hazards
GHS labelling:
Pictograms
GHS05: CorrosiveGHS06: ToxicGHS08: Health hazard
Signal word
Danger
Hazard statements
H290, H302, H315, H317, H318, H319, H335, H341
Precautionary statements
P201, P202, P234, P261, P264, P270, P271, P272, P280, P281, P301+P312, P302+P352, P304+P340, P305+P351+P338, P308+P313, P310, P312, P321, P330, P332+P313, P333+P313, P337+P313, P362, P363, P390, P403+P233, P404, P405, P501
Related compounds
Related ketones, aldehydes
  • Glyoxal
  • Propionaldehyde
  • Propanedial
  • Acetone
  • Diacetyl
  • Acetylacetone
Related compounds
  • Glyoxylic acid
  • Pyruvic acid
  • Acetoacetic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Methylglyoxal (MGO) is the organic compound with the formula CH3C(O)CHO. It is a reduced derivative of pyruvic acid. It is a reactive compound that is implicated in the biology of diabetes. Methylglyoxal is produced industrially by degradation of carbohydrates using overexpressed methylglyoxal synthase.[1]

  1. ^ Lichtenthaler, Frieder W. (2010). "Carbohydrates as Organic Raw Materials". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.n05_n07. ISBN 978-3527306732.

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Methylglyoxal

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diabetes. Methylglyoxal is produced industrially by degradation of carbohydrates using overexpressed methylglyoxal synthase. Gaseous methylglyoxal has two...

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Methylglyoxal pathway

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The methylglyoxal pathway is an offshoot of glycolysis found in some prokaryotes, which converts glucose into methylglyoxal and then into pyruvate. However...

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Lactoylglutathione lyase

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spontaneous reaction between a glutathionyl group and aldehydes such as methylglyoxal. (R)-S-lactoylglutathione = glutathione + 2-oxopropanal Glyoxalase I...

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Methylglyoxal synthase

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The enzyme methylglyoxal synthase (EC 4.2.3.3) catalyzes the chemical reaction glycerone phosphate ⇌ {\displaystyle \rightleftharpoons } 2-oxopropanal...

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Glyoxalase system

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glyoxalase system is a set of enzymes that carry out the detoxification of methylglyoxal and the other reactive aldehydes that are produced as a normal part...

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Lethal synthesis

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the synthesis of fluorocitrate from fluoroacetate or the synthesis of methylglyoxal from glycerol. The term was first publicised by Rudolph Peters in his...

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Glycation

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glycation applies to DNA damage induced by reactive carbonyls (principally methylglyoxal and glyoxal) that are present in cells as by-products of sugar metabolism...

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Aminoacetone

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Aminoacetone is a metabolite that is implicated in the biosynthesis of methylglyoxal. Aminoacetone is also produced during catabolism of the amino acid threonine...

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Glutathione

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→ GSSR + H2O Glutathione is also employed for the detoxification of methylglyoxal and formaldehyde, toxic metabolites produced under oxidative stress...

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Lactaldehyde

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Lactaldehyde is an intermediate in the methylglyoxal metabolic pathway. Methylglyoxal is converted to D-lactaldehyde by glycerol dehydrogenase (gldA)....

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Adenosine triphosphate

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concentrations is taken up by the liver and undergoes detoxification through the methylglyoxal pathway which ends with lactate. Acetoacetate in high concentrations...

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Dicarbonyl

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large family of 1,2-diketones. A well-known compound of this class is methylglyoxal, CH3C(O)CHO, also known as pyruvaldehyde. These compounds are also known...

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Mitoguazone

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Mitoguazone (also known as methylglyoxal bis(guanylhydrazone) or MGBG) is a drug used in chemotherapy. Hoffmann H, Gutsche W, Amlacher R, Schulze W, Werner...

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Triosephosphate isomerase

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sequesters the reactive enediol intermediate to prevent decomposition to methylglyoxal and inorganic phosphate. The hydrogen bond between the enzyme and the...

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Argpyrimidine

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C11H18N4O3. It is an advanced glycation end-product formed from arginine and methylglyoxal through the Maillard reaction. Argpyrimidine has been studied for its...

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C3H4O2

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Compounds sharing the molecular formula: Acrylic acid Malondialdehyde Methylglyoxal 3-Oxetanone Propiolactone isomers: Alpha-Propiolactone (α-propiolactone)...

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Succinylacetone

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compound that is formed by the oxidation of glycine and is a precursor of methylglyoxal. It is a pathognomonic compound found in the urine of patients with...

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Procyanidin B2

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glycation end-products pentosidine, carboxymethyllysine (CML), and methylglyoxal (MGO). Phenolic content in wine Proanthocyanidin-B2 on liberherbarum...

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Paracetamol

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Lemon balm

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Isomuscimol Isonipecotic acid Kojic amine L-838,417 Lignans (e.g., honokiol) Methylglyoxal Monastrol Muscimol Nefiracetam Neuroactive steroids (e.g., allopregnanolone)...

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Cannabidiol

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