Glucosone

Glucosone is a reactive carbonyl compound that can be produced by an Amadori rearrangement of a derivative of glucose. It is a dicarbonyl intermediate of the Maillard reaction whose production is higher under oxidative versus non-oxidative conditions.[2]

d-Glucosone

Skeletal formula of d-Glucosone
Names
IUPAC name
d-arabino-Hexos-2-ulose[1]
Systematic IUPAC name
(3S,4R,5R)-3,4,5,6-tetrahydroxy-2-oxohexanal
Other names
  • 2-Keto-D-glucose
  • 2-Ketoglucose
Identifiers
3D model (JSmol)
MeSH glucosone
  • InChI=1S/C6H10O6/c7-1-3(9)5(11)6(12)4(10)2-8/h1,4-6,8,10-12H,2H2/t4-,5-,6-/m1/s1
    Key: DCNMIDLYWOTSGK-HSUXUTPPSA-N
  • C(C(C(C(C(=O)C=O)O)O)O)O
  • C([C@H]([C@H]([C@@H](C(=O)C=O)O)O)O)O
Properties
C6H10O6
Molar mass 178.140 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References
  1. McNaught, Alan D. (1996). "Nomenclature of Carbohydrates" (PDF). International Union of Pure and Applied Chemistry and International Union of Biochemistry and Molecular Biology. 68 (10). Great Britain: 1929. Retrieved December 22, 2023.
  2. Nemet, I; Strauch, CM; Monnier, VM (2011). "Favored and disfavored pathways of protein crosslinking by glucose: glucose lysine dimer (GLUCOLD) and crossline versus glucosepane". Amino Acids. 40 (1): 167–81. doi:10.1007/s00726-010-0631-2. PMC 2972412. PMID 20607325.
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