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Basic Description
| Synonyms | CCRIS 4272 | erythro-Hexosulose, 3-deoxy- | UNII-EXV5374VEY | EXV5374VEY | (4S,5R)-4,5,6-trihydroxy-2-oxohexanal | 3-deoxy-2-ketoglucose | ZGCHLOWZNKRZSN-NTSWFWBYSA-N | 3-Deoxy-erythro-hexosulose | 0797E864-9E7E-48FF-A385-2CCDC0C15AB6 | HY-N7426 | 2-Keto- |
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| Biochemical and Physiological Mechanisms | 3-Deoxyglucosone (3-Deoxy-D-glucosone) is a reactive intermediate of the Maillard reaction and the polyol pathway. 3-Deoxyglucosone rapidly reacts with protein amino groups to form advanced glycation end products ( AGEs ), such as imidazolone, it is the m |
| Storage Temp | Store at -20°C |
| Shipped In |
Ice chest + Ice pads This product requires cold chain shipping. Ground and other economy services are not available. |
| Product Description |
3-Deoxyglucosone (3-Deoxy-D-glucosone) is a reactive intermediate of the Maillard reaction and the polyol pathway. 3-Deoxyglucosone rapidly reacts with protein amino groups to form advanced glycation end products ( AGEs ), such as imidazolone, it is the most specific AGE for 3-DG. 3-Deoxyglucosone synergizes with low glucose to potentiate GLP-1 secretion and is considered as a biomarker for diabetes . In Vitro 3-Deoxyglucosone (80 ng/ml-1000 ng/ml; 1 hour) markedly increases GLP-1 secretion by 1.23-folds in 300 ng/ml or 1000 ng/ml 3DG-treated group. But at alower concentration (80 ng/ml) has no effects. 3-Deoxyglucosone (300 ng/ml; 1 hour) dramatically increases intracellular Ca 2+ levels by Fluo-3/AM determination (2.5 μM for 30 mins). But 3DG does not affect intracellular cAMP levels in a cAMP Elisa assay. 3-Deoxyglucosone (300 ng/ml; 1 hour) significantly increases the protein expression levels of TAS1R2, TAS1R3, and TRPM5 under both glucose-free and highconditions. MCE has not independently confirmed the accuracy of these methods. They are for reference only. Western Blot AnalysisCell Line: STC-1 cells Concentration: 300 ng/ml Incubation Time: 1 hour Result: Upregulated TAS1R2, TAS1R3, and TRPM5 expression. In Vivo 3-Deoxyglucosone (intragastric administration; 20 mg/kg; single dose) impairs glucose tolerance with increased AUC, but the plasma Glukagon levels are not significantly different. It developes impaired glucose regulation (IGR) with obviously pancreatic islet cell dysfunction in kunming mice and SD-rats. 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. MCE has not independently confirmed the accuracy of these methods. They are for reference only. Animal Model: SD ratsDosage: 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. |
Taxonomic Classification
Taxonomy Tree
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Kingdom
Organic compounds
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Superclass
Lipids and lipid-like molecules
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Class
Fatty Acyls
- Subclass Fatty alcohols
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Class
Fatty Acyls
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Superclass
Lipids and lipid-like molecules
| Kingdom | Organic compounds |
|---|---|
| Superclass | Lipids and lipid-like molecules |
| Class | Fatty Acyls |
| Subclass | Fatty alcohols |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Fatty alcohols |
| Alternative Parents | Medium-chain aldehydes Beta-hydroxy ketones Alpha ketoaldehydes Secondary alcohols Polyols Primary alcohols Organic oxides Hydrocarbon derivatives |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Fatty alcohol - Medium-chain aldehyde - Beta-hydroxy ketone - Alpha-ketoaldehyde - Secondary alcohol - Ketone - Polyol - Primary alcohol - Organooxygen compound - Organic oxide - Organic oxygen compound - Carbonyl group - Alcohol - Aldehyde - Hydrocarbon derivative - Aliphatic acyclic compound |
| Description | This compound belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms. |
| External Descriptors | deoxyketohexose - deoxyglucose |
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Names and Identifiers
| IUPAC Name | (4S,5R)-4,5,6-trihydroxy-2-oxohexanal |
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| INCHI | InChI=1S/C6H10O5/c7-2-4(9)1-5(10)6(11)3-8/h2,5-6,8,10-11H,1,3H2/t5-,6+/m0/s1 |
| InChIKey | ZGCHLOWZNKRZSN-NTSWFWBYSA-N |
| Smiles | C(C(C(CO)O)O)C(=O)C=O |
| Isomeric SMILES | C([C@@H]([C@@H](CO)O)O)C(=O)C=O |
| WGK Germany | 3 |
| RTECS | MQ3390000 |
| PubChem CID | 114839 |
| Molecular Weight | 162.14 |
Certificates（CoA,COO,BSE/TSE and Analysis Chart)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Chemical and Physical Properties
| Refractive Index | n20D1.51 (Predicted) |
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| Boil Point(°C) | 400.09° C at 760 mmHg (Predicted) |
| Melt Point(°C) | 73-75° C |
| Molecular Weight | 162.140 g/mol |
| XLogP3 | -2.400 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 5 |
| Exact Mass | 162.053 Da |
| Monoisotopic Mass | 162.053 Da |
| Topological Polar Surface Area | 94.800 Ų |
| Heavy Atom Count | 11 |
| Formal Charge | 0 |
| Complexity | 144.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 2 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 1 |
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