3-DEOXYGLUCOSONE
3-DEOXYGLUCOSONE Basic information
- Product Name:
- 3-DEOXYGLUCOSONE
- Synonyms:
-
- 3-deoxy-d-erythro-hexos-2-ulose
- 3-deoxy-d-erythro-hexosulos
- d-3-deoxyglucosone
- 3DG
- 3-DEOXY-D-ERYTHRO-HEXULOSE2-KETO-3-DEOXYGLUCOSE
- 3-DEOXYGLUCOSONE
- 3-Deoxy-D-arabino-2-hexosulose
- 3-Deoxy-D-erythro-2-hexosulose
- CAS:
- 4084-27-9
- MF:
- C6H10O5
- MW:
- 162.14
- Product Categories:
-
- 13C & 2H Sugars
- aldehydes
- Carbohydrates & Derivatives
- Intermediates
- Mol File:
- 4084-27-9.mol
3-DEOXYGLUCOSONE Chemical Properties
- Melting point:
- 73-75°C
- Boiling point:
- 208.81°C (rough estimate)
- Density
- 1.2132 (rough estimate)
- refractive index
- 1.4230 (estimate)
- RTECS
- MQ3390000
- storage temp.
- Hygroscopic, -20°C Freezer, Under Inert Atmosphere
- solubility
- Methanol (Slightly), Water (Slightly, Sonicated)
- form
- Solid
- pka
- 13.17±0.20(Predicted)
- color
- Yellow
- Water Solubility
- Soluble in water, methanol or hot ethanol.
- Stability:
- Hygroscopic
3-DEOXYGLUCOSONE Usage And Synthesis
Description
3-deoxy Glucosone is a highly reactive 2-oxoaldehyde intermediate of the Maillard reaction produced during oxidative stress in response to excess sugar consumption and in association with diabetes. It is a precursor for the formation of advanced glycation endproducts and because it readily reacts with protein amino groups is also used for crosslinking studies. 3-deoxy Glucosone can be used as a reference for the analysis and detection of glucose degradation products and glycating agents.
Chemical Properties
Amorphous Yellow Solid
Uses
An intermediate in the Maillard reaction of proteins with glucose, which is metabolised to 3-Deoxyfructose. An intermediate in the formation of pyrraline, which might contribute to a pathological effect, such as carcinogenesis
Uses
Frequently used as a reference for the analysis and detection of glucose degradation products and glycating agents. Also used for cross-linking studies as it readily reacts with protein amino groups.
Definition
ChEBI: A deoxyketohexose comprising the open-chain form of D-glucose lacking the -OH group at the 3-position and having the keto group at the 2-position.
in vivo
3-Deoxyglucosone (intragastric administration; 20 mg/kg; single dose)?impairs glucose tolerance with increased AUC, but the plasma glucagon levels are not significantly different. It developes impaired glucose regulation (IGR) with obviously pancreatic islet cell dysfunction in kunming mice and SD-rats[2].3-deoxyglucosone?(gastric gavage; 5-50 mg/kg; once daily; 2 weeks) is significantly increased in the upper small intestine (1.4-fold), lower small intestine (1.4-fold), ileum (1.4-fold) and colon (two fold) compared with the basal levels in the corresponding control group. In addition, the protein expressions of TAS1R2, TAS1R3 and TRPM5 in both duodenum and colon are significantly decreased[3].
| Animal Model: | SD rats[3] |
| Dosage: | 5, 20 and 50 mg/kg |
| Administration: | oral administration; once daily; 2 weeks |
| Result: | Was capable of accumulating in?intestinal?tissue?and thereby decreased?secretion?of?GLP-1?and insulin. ? |
References
[1] H YAMADA. Increase in 3-deoxyglucosone levels in diabetic rat plasma. Specific in vivo determination of intermediate in advanced Maillard reaction.[J]. The Journal of Biological Chemistry, 1994, 269 32: 20275-20280.
[2] HITOMI KUSUNOKI. Relation between serum 3-deoxyglucosone and development of diabetic microangiopathy.[J]. Diabetes Care, 2003, 26 6: 1889-1894. DOI: 10.2337/diacare.26.6.1889
[3] TOSHIMITSU NIWA Saori T. 3-Deoxyglucosone and AGEs in uremic complications: Inactivation of glutathione peroxidase by 3-deoxyglucosone[J]. Kidney international, 2001, 59: Pages S37-S41. DOI: 10.1046/j.1523-1755.2001.59780037.x
[4] PAUL J THORNALLEY H M A Langborg. Formation of glyoxal, methylglyoxal and 3-deoxyglucosone in the glycation of proteins by glucose.[J]. The Ukrainian Biochemical Journal, 1999, 16 1: 109-116. DOI: 10.1042/bj3440109
3-DEOXYGLUCOSONESupplier
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