D-Arabino-hexos-2-ulose

Base Information

• Chemical Name: D-Arabino-hexos-2-ulose
• CAS No.: 1854-25-7
• Molecular Formula: C₆H₁₀O₆
• Molecular Weight: 178.142
• Hs Code.: 29144000
• DSSTox Substance ID: DTXSID90171773
• Nikkaji Number: J15.175K
• Wikipedia: Glucosone
• Wikidata: Q27123425
• Metabolomics Workbench ID: 58249
• Mol file: 1854-25-7.mol

Synonyms:2-ketoglucose;arabino-hexosulose;D-arabino-2-hexosulose;glucosone;glucosone, D isomer

Chemical Property of D-Arabino-hexos-2-ulose

Chemical Property:

• Appearance/Colour: off-white solid
• Vapor Pressure: 2.85E-11mmHg at 25°C
• Melting Point: 118-120°C
• Refractive Index: 1.55
• Boiling Point: 481 °C at 760 mmHg
• Flash Point: 258.8 °C
• PSA: 115.06000
• Density: 1.574 g/cm³
• LogP: -3.17060
• Storage Temp.: Hygroscopic, Store under Inert atmosphere -20°C Freezer
• Solubility.: Methanol (Slightly), Water (Slightly)
• XLogP3: -2.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 178.04773803
• Heavy Atom Count: 12
• Complexity: 167

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-Keto-D-glucose ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C(C(C(C(C(=O)C=O)O)O)O)O
• Isomeric SMILES: C([C@H]([C@H]([C@@H](C(=O)C=O)O)O)O)O
• Uses: 2-Keto-D-glucose is a useful synthetic intermediate.

Technology Process of D-Arabino-hexos-2-ulose

There total 38 articles about D-Arabino-hexos-2-ulose 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: 69.0%

glucosazone (534-97-4) → 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)

Guidance literature:

With benzaldehyde; In ethanol; water; acetic acid; for 4.25h; Heating;

DOI:10.1021/jo00207a048

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-Fructose

glucose

glucosazone

D-arabino-[2]hexosulose-bis-(methyl-phenyl-hydrazone)

Downstream raw materials:

lyxo-[2]Hexosulose-bis-phenylhydrazon

fructonic acid

D-glucoascorbic acid

D-arabino-[2]hexosulose-1-(ethyl-phenyl-hydrazone)-2-phenylhydrazone

Refernces

• 1、 Decamps, Karolien,Joye, Iris J.,Haltrich, Dietmar,Nicolas, Jacques,Courtin, Christophe M.,Delcour, Jan A.. "Biochemical characteristics of Trametes multicolor pyranose oxidase and Aspergillus niger glucose oxidase and implications for their functionality in wheat flour dough". . p. 1485 - 1492. Retrieved 2012.
• 2、 White,Carubelli. "". . p. 366,367-371. Retrieved 1974.
• 3、 Walton,D.J.. "-". . p. 3483 - 3487. Retrieved 1969.
• 4、 Olavi, P.,Virtanen, I.,Kurkisuo, Sinikka. "OXIDATION OF D-FRUCTOSE WITH VANADIUM(V): A KINETIC APPROACH". . p. 215 - 224. Retrieved 1985.
• 5、 Karmali, Amin,Coelho, José. "Bioconversion of d-glucose into d-glucosone by immobilized glucose 2-oxidase from Coriolus versicolor at moderate pressures". . p. 168 - 173. Retrieved 2011.
• 6、 Pitsawong, Warintra,Sucharitakul, Jeerus,Prongjit, Methinee,Tan, Tien-Chye,Spadiut, Oliver,Haltrich, Dietmar,Divne, Christina,Chaiyen, Pimchai. "A conserved active-site threonine is important for both sugar and flavin oxidations of pyranose 2-oxidase". . p. 9697 - 9705. Retrieved 2010.
• 7、 Usui, Teruyuki,Yoshino, Miku,Watanabe, Hirohito,Hayase, Fumitaka. "Determination of glyceraldehyde formed in glucose degradation and glycation". . p. 2162 - 2168. Retrieved 2007.
• 8、 Qi, Yajing,Zhang, Hui,Zhang, Hao,Wu, Gangcheng,Wang, Li,Qian, Haifeng,Qi, Xiguang. "Epicatechin Adducting with 5-Hydroxymethylfurfural as an Inhibitory Mechanism against Acrylamide Formation in Maillard Reactions". . p. 12536 - 12543. Retrieved 2018/11/25.
• 9、 Liu, Zhifen,Lv, Yue,An, Zesheng. "Enzymatic Cascade Catalysis for the Synthesis of Multiblock and Ultrahigh-Molecular-Weight Polymers with Oxygen Tolerance". supporting information. p. 13852 - 13856. Retrieved 2017/10/09.