Molecular structure of 3-Deoxyglucosone, CAS Number: 4084-27-9
3-Deoxyglucosone (CAS 4084-27-9)
See product citations (14)
Alternate Names:
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 Number:
4084-27-9
Purity:
95%
Molecular Weight:
162.14
Molecular Formula:
C6H10O5
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.
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SDS & Certificate of Analysis
3-Deoxyglucosone (3-DG) is an intermediate in the Maillard reaction of proteins with glucose, which is metabolised to 3-Deoxyfructose. It is involved in the synthesis of glycoproteins, glycosaminoglycans, and glycolipids, as well as in the regulation of gene expression and cell signaling. 3-Deoxyglucosone is also an intermediate in the formation of pyrraline, which might contribute to pathological effects, such as carcinogenesis.
3-Deoxyglucosone (CAS 4084-27-9) References
- Protein glycation: a firm link to endothelial cell dysfunction. | Wautier, JL. and Schmidt, AM. 2004. Circ Res. 95: 233-8. PMID: 15297385
- Pyridoxamine protects proteins from functional damage by 3-deoxyglucosone: mechanism of action of pyridoxamine. | Chetyrkin, SV., et al. 2008. Biochemistry. 47: 997-1006. PMID: 18161948
- Metabolism 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: 2383581
- 3-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: 25689368
- Accumulation 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: 27956941
- Formation of 3-deoxyglucosone in the malting process. | Nobis, A., et al. 2019. Food Chem. 290: 187-195. PMID: 31000036
- Dicarbonyl Stress at the Crossroads of Healthy and Unhealthy Aging. | Nigro, C., et al. 2019. Cells. 8: PMID: 31331077
- Alteration of Intestinal Microbiota in 3-Deoxyglucosone-Induced Prediabetic Rats. | Cai, J., et al. 2020. Biomed Res Int. 2020: 8406846. PMID: 32908918
- Pleiotropic Actions of Aldehyde Reductase (AKR1A). | Fujii, J., et al. 2021. Metabolites. 11: PMID: 34073440
- Increase 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: 8051120
- Monkey 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: 8274014
- Selective 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: 9218489
- Beta2-Microglobulin dialysis amyloid and its formation: role of 3-deoxyglucosone and advanced glycation end products. | Niwa, T. 1997. Nephron. 76: 373-91. PMID: 9274834
- Overexpression 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
Activator of:
Aldose Reductase.Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
3-Deoxyglucosone, 5 mg | sc-220865A | 5 mg | $204.00 | |||
3-Deoxyglucosone, 10 mg | sc-220865 | 10 mg | $367.00 | |||
3-Deoxyglucosone, 25 mg | sc-220865B | 25 mg | $736.00 | |||
3-Deoxyglucosone, 50 mg | sc-220865C | 50 mg | $1336.00 |