2-O-(beta-D-glucosyl)glycerol

Base Information

• Chemical Name: 2-O-(beta-D-glucosyl)glycerol
• CAS No.: 10588-30-4
• Molecular Formula: C₉H₁₈O₈
• Molecular Weight: 254.237
• European Community (EC) Number: 924-528-4
• DSSTox Substance ID: DTXSID201219430
• Nikkaji Number: J15.667A
• Wikidata: Q27102591
• Metabolomics Workbench ID: 51030
• Mol file: 10588-30-4.mol

Synonyms:10588-30-4;2-O-(beta-D-glucosyl)glycerol;Lilioside B;2-(beta-Glucosyl)glycerol;glycerol 2-O-beta-D-glucoside;2-(beta-D-Glucopyranosyloxy)-1,3-propanediol;2-O-(beta-D-glucosyl)-sn-glycerol;1,3-dihydroxypropan-2-yl beta-D-glucopyranoside;(2R,3R,4S,5S,6R)-2-(1,3-dihydroxypropan-2-yloxy)-6-(hydroxymethyl)oxane-3,4,5-triol;beta,beta'-dihydroxyisopropyl beta-D-glucopyranoside;2-glyceryl beta-D-glucoside;2-O-beta-d-glucosyl-glycerol;SCHEMBL2300084;CHEBI:17765;DTXSID201219430;sn-glycerol 2-O-beta-D-glucoside;2-O-(beta-D-glucopyranosyl)-glycerol;W-200746;Q27102591;2-hydroxy-1-(hydroxymethyl)ethyl beta-D-glucopyranoside;WURCS=2.0/2,2,1/[h2h][a2122h-1b_1-5]/1-2/a2-b1;WURCS=2.0/2,2,1/[hxh][a2122h-1b_1-5]/1-2/a2-b1;(2R,3R,4S,5S,6R)-2-[(1,3-dihydroxypropan-2-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Chemical Property of 2-O-(beta-D-glucosyl)glycerol

Chemical Property:

• Melting Point: 130-135 °C
• Boiling Point: 606.1±55.0 °C(Predicted)
• PKA: 12.85±0.70(Predicted)
• PSA: 139.84000
• Density: 1.58±0.1 g/cm3(Predicted)
• LogP: -3.84390
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: Methanol (Slightly), Water (Slightly)
• XLogP3: -3.5
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 254.10016753
• Heavy Atom Count: 17
• Complexity: 221

Purity/Quality:

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

2-(β-Glucosyl)glycerol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C1C(C(C(C(O1)OC(CO)CO)O)O)O)O
• Isomeric SMILES: C([C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC(CO)CO)O)O)O)O
• Uses: A component contained in cosmetic formulation. Diesters of glycosylglycerols are active in cancer chemo-prevention.

Technology Process of 2-O-(beta-D-glucosyl)glycerol

There total 18 articles about 2-O-(beta-D-glucosyl)glycerol 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: 97.0%

(β,β'-dihydroxy-isopropyl)-(tetra-O-acetyl-β-D-glucopyranoside) (157024-67-4) → 2-O-β-D-glucosyl-glycerol (534-68-9,3879-81-0,5768-72-9,6245-27-8,10588-30-4,22160-26-5,40593-14-4,128163-38-2,5624-47-5)

Guidance literature:

With sodium methylate; In methanol;

DOI:10.1080/07328309808007465

Reference yield:

1,3-di-O-benzyl-2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-sn-glycerol (157024-66-3) → 2-O-β-D-glucosyl-glycerol (534-68-9,3879-81-0,5768-72-9,6245-27-8,10588-30-4,22160-26-5,40593-14-4,128163-38-2,5624-47-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / H₂ / Pd/C / methanol; acetic acid

2: 97 percent / NaOMe / methanol

With hydrogen; sodium methylate; palladium on activated charcoal; In methanol; acetic acid;

DOI:10.1080/07328309808007465

Reference yield:

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → 2-O-β-D-glucosyl-glycerol (534-68-9,3879-81-0,5768-72-9,6245-27-8,10588-30-4,22160-26-5,40593-14-4,128163-38-2,5624-47-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 30 percent / Ag₂CO₃, I₂ / CH₂Cl₂ / 120 h

2: 93 percent / H₂ / Pd/C / ethyl acetate; methanol

3: 97 percent / NaOMe / methanol

With hydrogen; iodine; sodium methylate; silver carbonate; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate;

DOI:10.1080/07328309808007465

upstream raw materials:

2-O-(β-D-glucopyranosyl)-1,3-O-benzylideneglycerol

methanol

regaloside G

2-O-β-D-glucopyranosyl-D-glyceraldehyde

Downstream raw materials:

(β,β'-bis-benzoyloxy-isopropyl)-(tetra-O-benzoyl-β-D-glucopyranoside)

(β,β'-dimethoxy-isopropyl)-(tetra-O-methyl-β-D-glucopyranoside)

(2R)-1-O-acetyl-2-O-(β-D-glucopyranosyl)glycerol

(2S)-1-O-acetyl-2-O-β-D-glucopyranosyl-sn-glycerol

Refernces

• 1、 Luley-Goedl, Christiane,Nidetzky, Bernd. "Small-molecule glucosylation by sucrose phosphorylase: Structure-activity relationships for acceptor substrates revisited". experimental part. p. 1492 - 1496. Retrieved 2010/10/02.
• 2、 Albini,Murelli,Patritti,Rovati. "A simple synthesis of glucosyl glycerols". . p. 1651 - 1661. Retrieved 2007/10/02.