1,5-Anhydro-D-glucitol

Base Information

• Chemical Name: 1,5-Anhydro-D-glucitol
• CAS No.: 154-58-5
• Molecular Formula: C6H12O5
• Molecular Weight: 164.158
• Hs Code.: 29329990
• European Community (EC) Number: 205-829-3
• UNII: 54BB3B7XMZ,Y79RBL5ZLQ
• DSSTox Substance ID: DTXSID10893389,DTXSID60893379
• Nikkaji Number: J11.394H
• Wikipedia: 1,5-Anhydroglucitol
• Wikidata: Q4545703
• Metabolomics Workbench ID: 38193
• ChEMBL ID: CHEMBL344637
• Mol file: 154-58-5.mol

Synonyms:1,5-anhydro-D-glucitol;1,5-anhydro-D-sorbitol;1,5-anhydroglucitol;1,5-anhydrosorbitol;1,5-sorbitan;1-deoxy-D-glucopyranose;1-deoxy-D-glucose;1-deoxyglucose;aceritol;D-glucitol, 1,5-anhydro-;D-glucose, 1-deoxy-;polygalitol

Chemical Property of 1,5-Anhydro-D-glucitol

Chemical Property:

• Appearance/Colour: White crystals
• Melting Point: 142-143 °C
• Refractive Index: 1.581
• Boiling Point: 376.8 °C at 760 mmHg
• PKA: 13.44±0.70(Predicted)
• Flash Point: 181.7 °C
• PSA: 90.15000
• Density: 1.533 g/cm³
• LogP: -2.53980
• Storage Temp.: -20°C Freezer
• Solubility.: Ethyl Acetate (Slightly), Methanol (Slightly), Water (Slightly)
• XLogP3: -2.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 164.06847348
• Heavy Atom Count: 11
• Complexity: 128

Purity/Quality:

98%, ^*data from raw suppliers

1,5-Anhydroglucitol ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C(C(C(C(O1)CO)O)O)O
• Isomeric SMILES: C1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O
• Uses: This compound has been isolated from several plant and animal sources, discovered in human cerebrospinal fluid and blood plasma and found to be an inhibitor of several enzymes. Anhydroalditols are a class of reduced sugars which are present in many natural systems and which have been employed as synthesis intermediates. 1,5-Anhydro-D-glucitol is used as a reference in analytical procedures that assess the metabolism of 1,5 anhydro-D-fructose, a food supplement with potential benefits as an antioxidant, antimicrobial, and antidiabetic agent. 1,5-Anhydro-D-sorbitol, a cyclic polyol, is a metabolic product of 1,5 anhydro-D-fructose. 1,5-Anhydro-D-sorbitol is used as a reference in analytical procedures that assess the metabolism of 1,5 anhydro-D-fructose, a food supplement with potential benefits as an antioxidant, antimicrobial, and antidiabetic agent.

Technology Process of 1,5-Anhydro-D-glucitol

There total 87 articles about 1,5-Anhydro-D-glucitol 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: 100.0%

1,5-anhydro-2,3,4,6-tetra-O-allyl-D-glucitol (1338660-78-8) → 1,5-anhydro-D-glucitol (154-58-5,53319-04-3)

Guidance literature:

With methanol; palladium dichloride; at 60 ℃; for 8h;

DOI:10.1016/j.tetlet.2011.07.082

Reference yield: 98.0%

1-deoxy-D-glucose tetraacetate (13137-69-4) → 1,5-anhydro-D-glucitol (154-58-5,53319-04-3)

Guidance literature:

With sodium methylate; In methanol; at 45 ℃; for 0.333333h;

DOI:10.1016/j.bmc.2006.05.068

Reference yield: 90.0%

sucrose octakis(trimethylsilyl) ether (19159-25-2) → mannitol (69-65-8) + D-sorbitol (50-70-4) + 1,5-anhydro-D-glucitol (154-58-5,53319-04-3)

Guidance literature:

sucrose octakis(trimethylsilyl) ether; With bis(pentafluorophenyl)borinic acid; 1,1,3,3-tetramethyldisilazane; In chloroform-d1; at 25 ℃; for 3h; Inert atmosphere; Glovebox;

In methanol; Inert atmosphere; Glovebox;

DOI:10.1002/anie.201708109

upstream raw materials:

1-deoxy-D-glucose tetraacetate

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

1-O-methyl-2,3,4,6-tetra-O-trimethylsilyl-β-D-glucopyranoside

methyl 2,3,4,6-tetrakis-O-trimethylsilyl-α-D-glucopyranoside

Downstream raw materials:

(2R,3R,4R,5S)-3,4,5-Tris-benzyloxy-2-trityloxymethyl-tetrahydro-pyran

1,5-anhydro-2,3-dipivaloyl-4,6-O-benzylidene-D-glucitol

1,5-anhydro-6-diphenolphosphate-D-glucitol

1,5-anhydroglucitol-6-phosphate

Refernces

• 1、 Kamimura, Akio,Murata, Kengo,Kawamoto, Takuji. "An efficient and selective conversion of sorbitol in ionic liquids: Use of ion exchange resin as a solid acid catalyst". . p. 3616 - 3618. Retrieved 2017.
• 2、 Fletcher. "-". . p. 706. Retrieved 1947.
• 3、 Kamimura, Akio,Murata, Kengo,Tanaka, Yoshiki,Okagawa, Tomoki,Matsumoto, Hiroshi,Kaiso, Kouji,Yoshimoto, Makoto. "Rapid conversion of sorbitol to isosorbide in hydrophobic ionic liquids under microwave irradiation". . p. 3257 - 3259. Retrieved 2014.
• 4、 Richtmyer et al.. "-". . p. 1477. Retrieved 1943.
• 5、 Baty, John William,Sinnott, Michael L.. "The kinetics of the spontaneous, proton- and AlIII-catalysed hydrolysis of 1,5-anhydrocellobiitol - Models for cellulose depolymerization in paper aging and alkaline pulping, and a benchmark for cellulase efficiency". . p. 1516 - 1524. Retrieved 2005.
• 6、 Ballantine et al.. "-". . p. C9. Retrieved 1976.
• 7、 Li, Gefei,Noguchi, Masato,Nakamura, Kensuke,Hayasaka, Ryohei,Tanaka, Yuuki,Shoda, Shin-ichiro. "First protection-free protocol for synthesis of 1-deoxy sugars through glycosyl dithiocarbamate intermediates". . p. 3428 - 3431. Retrieved 2018.
• 8、 Wan, Chunpeng,Yuan, Tao,Li, Liya,Kandhi, Vamsikrishna,Cech, Nadja B.,Xie, Mingyong,Seeram, Navindra P.. "Maplexins, new α-glucosidase inhibitors from red maple (Acer rubrum) stems". . p. 597 - 600. Retrieved 2012.
• 9、 De Fenza, Maria,Eremeeva, Elena,Troisi, Romualdo,Yang, Hui,Esposito, Anna,Sica, Filomena,Herdewijn, Piet,D'Alonzo, Daniele,Guaragna, Annalisa. "Structure–Activity Relationship Study of a Potent α-Thrombin Binding Aptamer Incorporating Hexitol Nucleotides". . p. 9589 - 9597. Retrieved 2020/07/13.
• 10、 Seo, Youngran,Lowe, Jared M.,Gagné, Michel R.. "Controlling Sugar Deoxygenation Products from Biomass by Choice of Fluoroarylborane Catalyst". . p. 6648 - 6652. Retrieved 2019/08/26.