Product Name :
3-Deoxyglucosone (CAS 4084-27-9)
Synonym :
3-Deoxy-D-erythro-hexulose; 2-Keto-3-deoxyglucose; D-3-Deoxyglucosone
Application :
3-Deoxyglucosone is an intermediate in the Maillard reaction of proteins with glucose
CAS:
4084-27-9
Purity:
95%
Molecular Weight:
162.14
Formula :
C6H10O5
Physical state:
Solid
solubility :
Soluble in ethanol (hot), methanol, and water.
Shipping Condition :
Store at -20° C
Melting point:
73-75° C
SMILES:
C([C@@H]([C@@H](CO)O)O)C(=O)C=O
References:
:Protein glycation: a firm link to endothelial cell dysfunction.71989-14-5 web | Wautier, JL. and Schmidt, AM. 2004.278788-66-2 manufacturer Circ Res.PMID:33665778 95: 233-8. PMID: 15297385Pyridoxamine protects proteins from functional damage by 3-deoxyglucosone: mechanism of action of pyridoxamine. | Chetyrkin, SV., et al. 2008. Biochemistry. 47: 997-1006. PMID: 18161948Metabolism of 3-deoxyglucosone, an intermediate compound in the Maillard reaction, administered orally or intravenously to rats. | Kato, H., et al. 1990. Biochim Biophys Acta. 1035: 71-6. PMID: 23835813-Deoxyglucosone: a potential glycating agent accountable for structural alteration in H3 histone protein through generation of different AGEs. | Ashraf, JM., et al. 2015. PLoS One. 10: e0116804. PMID: 25689368Accumulation of intestinal tissue 3-deoxyglucosone attenuated GLP-1 secretion and its insulinotropic effect in rats. | Zhang, L., et al. 2016. Diabetol Metab Syndr. 8: 78. PMID: 27956941Formation of 3-deoxyglucosone in the malting process. | Nobis, A., et al. 2019. Food Chem. 290: 187-195. PMID: 31000036Dicarbonyl Stress at the Crossroads of Healthy and Unhealthy Aging. | Nigro, C., et al. 2019. Cells. 8: PMID: 31331077Alteration of Intestinal Microbiota in 3-Deoxyglucosone-Induced Prediabetic Rats. | Cai, J., et al. 2020. Biomed Res Int. 2020: 8406846. PMID: 32908918Pleiotropic Actions of Aldehyde Reductase (AKR1A). | Fujii, J., et al. 2021. Metabolites. 11: PMID: 34073440Increase in 3-deoxyglucosone levels in diabetic rat plasma. Specific in vivo determination of intermediate in advanced Maillard reaction. | Yamada, H., et al. 1994. J Biol Chem. 269: 20275-80. PMID: 8051120Monkey 3-deoxyglucosone reductase: tissue distribution and purification of three multiple forms of the kidney enzyme that are identical with dihydrodiol dehydrogenase, aldehyde reductase, and aldose reductase. | Sato, K., et al. 1993. Arch Biochem Biophys. 307: 286-94. PMID: 8274014Selective induction of heparin-binding epidermal growth factor-like growth factor by methylglyoxal and 3-deoxyglucosone in rat aortic smooth muscle cells. The involvement of reactive oxygen species formation and a possible implication for atherogenesis in diabetes. | Che, W., et al. 1997. J Biol Chem. 272: 18453-9. PMID: 9218489Beta2-Microglobulin dialysis amyloid and its formation: role of 3-deoxyglucosone and advanced glycation end products. | Niwa, T. 1997. Nephron. 76: 373-91. PMID: 9274834Overexpression of aldehyde reductase protects PC12 cells from the cytotoxicity of methylglyoxal or 3-deoxyglucosone. | Suzuki, K., et al. 1998. J Biochem. 123: 353-7. PMID: 9538214