22160-26-5

Basic information

• Product Name: glucosylglycerol
• Synonyms: glucosylglycerol;2-O-α-D-Glucosylglycerol;Extremys GG;GLYCERYL GLUCOSIDE;Glycoin;GG;2-O-α-D-Glucosylglycerol:Glucosylglycerol:Extremys GG:Glycoin:GLYCERYL GLUCOSIDE
• CAS NO: 22160-26-5
• Molecular Formula: C₉H₁₈O₈
• Molecular Weight: 254.23442
• Mol File: 22160-26-5.mol
• Article Data: 10

Chemical Properties

• Melting Point: 121 °C
• Boiling Point: 606.1±55.0 °C(Predicted)
• Appearance: /
• Density: 1.58±0.1 g/cm3(Predicted)
• Vapor Pressure: 0.022Pa
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility: Methanol (Slightly), Water (Slightly, Sonicated)
• PKA: 12.85±0.70(Predicted)
• Stability: Very Hygroscopic
• CAS DataBase Reference: glucosylglycerol(CAS DataBase Reference)
• NIST Chemistry Reference: glucosylglycerol(22160-26-5)
• EPA Substance Registry System: glucosylglycerol(22160-26-5)

Safety Data

• Hazardous Substances Data: 22160-26-5(Hazardous Substances Data)

Usage

Uses

2-O-α-D-Glucosylglycerol is used to prepare glycoglycerolipid analogs active as antitumor-promoters the influence of the anomeric configuration.

Upstream product

• 76222-77-0 2-O-(β-D-glucopyranosyl)-1,3-O-benzylideneglycerol 
• 56-81-5 glycerol 
• 59-56-3 α-D-glucopyranosyl-1-phosphate 
• 57-50-1 Sucrose 
• 131831-29-3 2-O-β-D-glucopyranosyl-L-glyceraldehyde 
• 131831-31-7 2-O-β-D-glucopyranosyl-D-glyceraldehyde 
• 67-56-1 methanol 
• 120601-64-1 regaloside G 
• 132201-75-3 2,3,4,6-tetra-O-benzyl-D-glucopyranose trichloroacetimidate 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 80300-30-7 1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 585-88-6 MALTITOL 
• 213265-19-1 (2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-(2-benzyloxy-1-benzyloxymethyl-ethoxy)-6-benzyloxymethyl-tetrahydro-pyran 
• 7158-70-5 leucrose 

Downstream Products

• 158110-30-6 (2R)-1-O-acetyl-2-O-(β-D-glucopyranosyl)glycerol 
• 131831-28-2 (2S)-1-O-acetyl-2-O-β-D-glucopyranosyl-sn-glycerol 
• 176966-04-4 1-O-decanoyl-2-O-β-D-glucopyranosyl-sn-glycerol 

Relevant articles and documents

Regio- and stereoselective glucosylation of diols by sucrose phosphorylase using sucrose or glucose 1-phosphate as glucosyl donor

Previously it has been shown that glycerol can be regioselectively glucosylated by sucrose phosphorylase from Leuconostoc mesenteroides to form 2-O-α-d-glucopyranosyl-glycerol (Goedl et al., Angew. Chem. Int. Ed. 47 (2008) 10086-10089). A series of compounds related to glycerol were investigated by us to determine the scope of the α-glucosylation reaction of sucrose phosphorylase. Both sucrose and glucose 1-phosphate (G1P) were applied as glucosyl donor. Mono-alcohols were not accepted as substrates but several 1,2-diols were readily glucosylated, proving that the vicinal diol unit is crucial for activity. The smallest substrate that was accepted for glucosylation appeared to be ethylene glycol, which was converted to the monoglucoside for 69%. Using high acceptor and donor concentrations (up to 2.5 M), sucrose or G1P hydrolysis (with H2O being the 'acceptor') can be minimised. In the study cited above, a preference for glucosylation of glycerol on the 2-position has been observed. For 1,2-propanediol however, the regiochemistry appeared to be dependent on the configuration of the substrate. The (R)-enantiomer was preferentialy glucosylated on its 1-position (ratio 2.5:1), whereas the 2-glucoside is the major product for (S)-1,2-propanediol (1:4.1). d.e. ps of 71-83% were observed with a preference for the (S)-enantiomer of the glucosides of 1,2-propanediol and 1,2-butanediol and the (R)-enantiomer of the glucoside of 3-methoxy-1,2-propanediol. This is the first example of stereoselective glucosylation of a non-natural substrate by sucrose phosphorylase. 3-Amino-1,2-propanediol, 3-chloro-1,2-propanediol, 1-thioglycerol and glyceraldehyde were not accepted as substrates. Generally, the glucoside yield is higher when sucrose is used as a donor rather than G1P, due to the fact that the released phosphate is a stronger inhibitor of the enzyme (in case of G1P) than the released fructose (in case of sucrose). Essentially the same results are obtained with sucrose phosphorylase from Bifidobacterium adolescentis.

A high-yielding biocatalytic process for the production of 2-O-(α-D-glucopyranosyl)-sn-glycerol, a natural osmolyte and useful moisturizing ingredient

(Figure Presented) Fit for industry: Stereochemically pure 2-O-(α-D-glucopyranosyl)-sn-glycerol (αGG) was obtained in high yield from an efficient and selective biocatalytic process (see schematic outline). The sucrose phosphorylase catalyzed transfer of a glucosyl group from sucrose to glycerol unites the main advantages of transglycosidases, glycosyltransferases, and glycosynthases for glycoside synthesis and provides access to αGG as an industrial chemical.

Identification of alpha-D-glucosylglycerol in sake.

alpha-D-Glucosylglycerol (GG) was found for the first time in sake (Japanese rice wine) in an amount of about 0.5%. GG was also found in miso and mirin which had been brewed by using koji. GG was hydrolyzed into glucose and glycerol in an equimolar ratio with maltase (EC 3.2.1.20, alpha-glucosidase from yeast), but not with emulsin (EC 3.2.1.21, beta-glucosidase from almond). The retention times and mass spectra of trimethylsilyl derivatives by a GC-MS analysis of GG in sake were comparable to those of various GG samples synthesized by glycol cleavage. It was proven that GG in sake consisted of three components, viz., 2-O-alpha-D-glucosyl-glycerol (GG-II), (2R)-1-O-alpha-D-glucosylglycerol (R-GG-I) and (2S)-1-O-alpha-D-glucosylglycerol (S-GG-I). The ratio of the three components in GG was 6:66:28 for sake. It is considered that GG was formed by transglucosylation of the glucosyl groups to glycerol by alpha-glucosidase from koji in the sake mash.