Methylglyoxal

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Methylglyoxal
Skeletal formula
Skeletal formula
Ball-and-stick model of methylglyoxal
Names
Preferred IUPAC name
2-Oxopropanal
Other names
Pyruvaldehyde
Identifiers
3D model (
JSmol
)
3DMet
906750
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard
100.001.059 Edit this at Wikidata
IUPHAR/BPS
KEGG
MeSH Methylglyoxal
UNII
  • 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
  • CC(=O)C=O
Properties
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:
GHS05: CorrosiveGHS06: ToxicGHS08: Health hazard
Danger
H290, H302, H315, H317, H318, H319, H335, H341
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 compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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]

Chemical structure

Gaseous methylglyoxal has two

carbonyl groups, an aldehyde and a ketone. In the presence of water, it exists as hydrates and oligomers. The formation of these hydrates is indicative of the high reactivity of MGO, which is relevant to its biological behavior.[2]

Biochemistry

Biosynthesis and biodegradation

In organisms, methylglyoxal is formed as a side-product of several

Since methylglyoxal is highly

Biochemical function

Methylglyoxal is involved in the formation of

advanced glycation end products (AGEs).[4] In this process, methylglyoxal reacts with free amino groups of lysine and arginine and with thiol groups of cysteine forming AGEs. Histones are also heavily susceptible to modification by methylglyoxal and these modifications are elevated in breast cancer.[9][10]

AGEs derived from the action of methylglyoxal on arginine.[11]

PARK7
), has a key role in the repair of glycated DNA bases.

Biomedical aspects

Due to increased blood glucose levels, methylglyoxal has higher concentrations in

atherogenesis. Damage by methylglyoxal to low-density lipoprotein through glycation causes a fourfold increase of atherogenesis in diabetics.[13] Methylglyoxal binds directly to the nerve endings and by that increases the chronic extremity soreness in diabetic neuropathy.[14][15]

Occurrence, other

Methylglyoxal is a component of some kinds of honey, including

Research suggests that methylglyoxal contained in honey does not cause an increased formation of advanced glycation end products (AGEs) in healthy persons.[17][18]

See also

References

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  12. ^ a b Richarme G, Liu C, Mihoub M, Abdallah J, Leger T, Joly N, Liebart JC, Jurkunas UV, Nadal M, Bouloc P, Dairou J, Lamouri A. Guanine glycation repair by DJ-1/Park7 and its bacterial homologs. Science. 2017 Jul 14;357(6347):208-211. doi: 10.1126/science.aag1095. Epub 2017 Jun 8. PMID 28596309
  13. PMID 21617182
    .
  14. ^ Spektrum: Diabetische Neuropathie: Methylglyoxal verstärkt den Schmerz: DAZ.online. Deutsche-apotheker-zeitung.de (2012-05-21). Retrieved on 2012-06-11.
  15. S2CID 205389296
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