Record Information
Version1.0
Creation date2015-05-07 20:46:25 UTC
Update date2018-05-29 01:54:56 UTC
Primary IDFDB031000
Secondary Accession Numbers
  • FDB008295
Chemical Information
FooDB Namemethylglyoxal
DescriptionMethylglyoxal, also known as 2-ketopropionaldehyde or 2-oxopropanal, is a member of the class of compounds known as alpha ketoaldehydes. Alpha ketoaldehydes are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon. Methylglyoxal is soluble (in water) and an extremely weak acidic compound (based on its pKa). Methylglyoxal can be found in a number of food items such as shiitake, yellow zucchini, roman camomile, and carob, which makes methylglyoxal a potential biomarker for the consumption of these food products. Methylglyoxal can be found primarily in blood and urine, as well as throughout most human tissues. Methylglyoxal exists in all living species, ranging from bacteria to humans. In humans, methylglyoxal is involved in few metabolic pathways, which include glycine and serine metabolism, pyruvaldehyde degradation, pyruvate metabolism, and spermidine and spermine biosynthesis. Methylglyoxal is also involved in several metabolic disorders, some of which include hyperglycinemia, non-ketotic, pyruvate kinase deficiency, non ketotic hyperglycinemia, and pyruvate decarboxylase E1 component deficiency (PDHE1 deficiency). Moreover, methylglyoxal is found to be associated with diabetes mellitus type 2. Methylglyoxal, also called pyruvaldehyde or 2-oxopropanal, is the organic compound with the formula CH3C(O)CHO. Gaseous methylglyoxal has two carbonyl groups, an aldehyde and a ketone but in the presence of water, it exists as hydrates and oligomers. It is a reduced derivative of pyruvic acid .
CAS Number78-98-8
Structure
Thumb
Synonyms
SynonymSource
1,2-PropanedioneChEBI
2-KetopropionaldehydeChEBI
2-OxopropanalChEBI
2-OxopropionaldehydeChEBI
AcetylformaldehydeChEBI
AcetylformylChEBI
alpha-KetopropionaldehydeChEBI
CH3COCHOChEBI
Pyruvic aldehydeChEBI
a-KetopropionaldehydeGenerator
Α-ketopropionaldehydeGenerator
1-KetopropionaldehydeHMDB
2-Keto propionaldehydeHMDB
2-oxo-PropionaldehydeHMDB
KetopropionaldehydeHMDB
MethylglyoxalHMDB
PropanedioneHMDB
PropanoloneHMDB
Pyroracemic aldehydeHMDB
Aldehyde, pyruvicHMDB
OxopropanalHMDB
Predicted Properties
PropertyValueSource
Water Solubility180 g/LALOGPS
logP-0.38ALOGPS
logP0.2ChemAxon
logS0.4ALOGPS
pKa (Strongest Acidic)16.38ChemAxon
pKa (Strongest Basic)-8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity17.05 m³·mol⁻¹ChemAxon
Polarizability6.42 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC3H4O2
IUPAC name2-oxopropanal
InChI IdentifierInChI=1S/C3H4O2/c1-3(5)2-4/h2H,1H3
InChI KeyAIJULSRZWUXGPQ-UHFFFAOYSA-N
Isomeric SMILESCC(=O)C=O
Average Molecular Weight72.0627
Monoisotopic Molecular Weight72.021129372
Classification
Description belongs to the class of organic compounds known as alpha ketoaldehydes. These are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlpha ketoaldehydes
Alternative Parents
Substituents
  • Alpha-ketoaldehyde
  • Ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Short-chain aldehyde
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference