Glucosone

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
CAS Number	1854-25-7 26345-59-5 54142-77-7
3D model (JSmol)	Interactive image Interactive image
ChemSpider	140353
KEGG	C22525
MeSH	glucosone
PubChem CID	159630
CompTox Dashboard (EPA)	DTXSID90171773
InChI 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
SMILES 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
Chemical formula	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. 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.