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

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]

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. Great Britain. 68 (10): 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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