3-Deoxyglucosone

Base Information

• Chemical Name: 3-Deoxyglucosone
• CAS No.: 4084-27-9
• Molecular Formula: C₆H₁₀O₅
• Molecular Weight: 162.142
• Hs Code.: 29329990
• European Community (EC) Number: 811-252-3
• UNII: EXV5374VEY
• DSSTox Substance ID: DTXSID00193820
• Nikkaji Number: J408.678C
• Wikipedia: 3-Deoxyglucosone
• Wikidata: Q4634133
• Metabolomics Workbench ID: 61260
• Mol file: 4084-27-9.mol

Synonyms:2-keto-3-deoxyglucose;3-deoxy-D-erythro-hexosulose;3-deoxy-D-glucosone;3-deoxyglucosone;3-deoxyhexosulose

Chemical Property of 3-Deoxyglucosone

Chemical Property:

• Vapor Pressure: 4.59E-08mmHg at 25°C
• Melting Point: 73-75oC
• Refractive Index: 1.4230 (estimate)
• Boiling Point: 400.1°Cat760mmHg
• PKA: 13.17±0.20(Predicted)
• Flash Point: 209.9°C
• PSA: 94.83000
• Density: 1.406g/cm³
• LogP: -2.14140
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: Methanol (Slightly), Water (Slightly, Sonicated)
• Water Solubility.: Soluble in water, methanol or hot ethanol.
• XLogP3: -2.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 162.05282342
• Heavy Atom Count: 11
• Complexity: 144

Purity/Quality:

98%, ^*data from raw suppliers

3-Deoxyglucosone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical 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
• 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.
• 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 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.

Technology Process of 3-Deoxyglucosone

There total 14 articles about 3-Deoxyglucosone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

D-glucose (50-99-7) → furfural (98-01-1) + 5-hydroxymethyl-2-furfuraldehyde (67-47-0) + D-Fructose (57-48-7,18875-34-8) + 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one (28564-83-2) + D-glucosone (643-71-0,25990-59-4,26187-86-0,26345-59-5,49865-02-3,54142-77-7,81844-97-5,81844-98-6,81845-00-3,89576-70-5,90457-64-0,1854-25-7) + 3-deoxygalactosone (4084-27-9,30382-30-0,50455-94-2,82399-12-0,4134-97-8) + 3-deoxyglucosone (4134-97-8,30382-30-0,50455-94-2,82399-12-0,4084-27-9) + 1-deoxy-2,3-D-erythro-hexo-2,3-diulose + 3-deoxypentos-2-ulose + 1,4-dideoxyhexosulose

Guidance literature:

With L-alanin; In water; at 130 ℃; for 5h; pH=5.0; Time; Sealed tube;

DOI:10.1021/acs.jafc.7b04105

Reference yield:

D-glucose (50-99-7) → furfural (98-01-1) + 5-hydroxymethyl-2-furfuraldehyde (67-47-0) + D-Fructose (57-48-7,18875-34-8) + 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one (28564-83-2) + D-glucosone (643-71-0,25990-59-4,26187-86-0,26345-59-5,49865-02-3,54142-77-7,81844-97-5,81844-98-6,81845-00-3,89576-70-5,90457-64-0,1854-25-7) + 3-deoxygalactosone (4084-27-9,30382-30-0,50455-94-2,82399-12-0,4134-97-8) + 3-deoxyglucosone (4134-97-8,30382-30-0,50455-94-2,82399-12-0,4084-27-9) + 1-deoxy-2,3-D-erythro-hexo-2,3-diulose + 3-deoxypentos-2-ulose + 1,4-dideoxyhexosulose

Guidance literature:

With L-alanin; In water; at 130 ℃; for 5h; pH=5.0; Time; Sealed tube;

DOI:10.1021/acs.jafc.7b04105

Reference yield:

D-maltose (69-79-4) → furfural (98-01-1) + 1-(2-furyl)-1-ethanone (1192-62-7,80145-44-4) + 5-hydroxymethyl-2-furfuraldehyde (67-47-0) + Maltol (118-71-8) + D-Fructose (57-48-7,18875-34-8) + 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one (28564-83-2) + D-glucose (50-99-7) + D-glucosone (643-71-0,25990-59-4,26187-86-0,26345-59-5,49865-02-3,54142-77-7,81844-97-5,81844-98-6,81845-00-3,89576-70-5,90457-64-0,1854-25-7) + 3-deoxygalactosone (4084-27-9,30382-30-0,50455-94-2,82399-12-0,4134-97-8) + 3-deoxyglucosone (4134-97-8,30382-30-0,50455-94-2,82399-12-0,4084-27-9) + 1-deoxymaltosone + 3-deoxymaltosone + 3-deoxypentos-2-ulose + 1,4-dideoxyhexosulose

Guidance literature:

With L-alanin; In water; at 130 ℃; for 5h; pH=5.0; Time; Sealed tube;

DOI:10.1021/acs.jafc.7b04105

upstream raw materials:

D-maltose

D-glucose

N-(1-deoxy-D-fructos-1-yl)-L-glycine

L-Lysine hydrochloride

Downstream raw materials:

5-chloromethylfurfural

5-hydroxymethyl-2-furfuraldehyde

5-bromomethyl-furan-2-carbaldehyde

dimethylglyoxal

Refernces

• 1、 Jenny, Gobert,Glomb, Marcus A.. "Degradation of glucose: reinvestigation of reactive α-dicarbonyl compounds". experimental part. p. 8591 - 8597. Retrieved 2010/07/15.
• 2、 Martins, Sara I.F.S.,Marcelis, Antonius T.M.,Van Boekel, Martinus A.J.S.. "Kinetic modelling of Amadori N-(1-deoxy-D-fructos-1-yl)-glycine degradation pathways. Part I - Reaction mechanism". . p. 1651 - 1663. Retrieved 2007/10/03.