13224-94-7

Basic information

• Product Name: 3-O-METHYL-ALPHA-D-GLUCOPYRANOSE
• Synonyms: 3-O-METHYL-D-GLUCOPYRANOSE;3-O-METHYL-D-GLUCOSE;3-O-METHYLGLUCOSE;3-O-METHYL-ALPHA-D-GLUCOPYRANOSE;A-METHYL-D-GLUCOSIDE;METHYL-A-D-GLUCOPYRANOSE, 3-O-;3-O-Methoxyglucose;3-O-Methyl-a-D-glucopyranose
• CAS NO: 13224-94-7
• Molecular Formula: C₇H₁₄O₆
• Molecular Weight: 194.18
• EINECS: 236-197-7
• Product Categories: Sugars, Carbohydrates & Glucosides
• Mol File: 13224-94-7.mol
• Article Data: 6

Chemical Properties

• Melting Point: 167-169 °C(lit.)
• Boiling Point: 250.62°C (rough estimate)
• Flash Point: 199.5 °C
• Appearance: white fine crystalline powder
• Density: 1.2501 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.5600 (estimate)
• Storage Temp.: 0-6°C
• PKA: 12.05±0.70(Predicted)
• CAS DataBase Reference: 3-O-METHYL-ALPHA-D-GLUCOPYRANOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-O-METHYL-ALPHA-D-GLUCOPYRANOSE(13224-94-7)
• EPA Substance Registry System: 3-O-METHYL-ALPHA-D-GLUCOPYRANOSE(13224-94-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26
• WGK Germany: 3
• Hazardous Substances Data: 13224-94-7(Hazardous Substances Data)

Usage

Chemical Properties

white fine crystalline powder

InChI:InChI=1/C7H14O6/c1-12-6-4(9)3(2-8)13-7(11)5(6)10/h3-11H,2H2,1H3/t3-,4-,5-,6+,7-/m1/s1

Upstream product

• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 97834-06-5 (3aR,5R,6S,6aR)-5-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-methoxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]-dioxol 
• 54649-66-0 1,2:5,6-di-O-isopropylidene-α-D-gulose 
• 29587-01-7 5-[2,2-dimethyl-(4R)-1,3-dioxolan-4-yl]-2,2-dimethyl-(3aR,5R,6R,6aR)-perhydrofuro[2,3-d][1,3]dioxol-6-yl methyl ether 
• 14686-89-6 (1,2:5,6)-di-O-isopropylidene-D-gulose 
• 2847-00-9 1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose 

Downstream Products

• 126874-18-8 (S,S)-1,2:4,6-di-O-benzylidene-3-O-methyl-α-D-gulose 
• 126797-42-0 (S)-4,6-O-benzylidene-3-O-methyl-D-gulose 
• 195703-48-1 Benzoic acid (S)-[(4R,4aS,6R,7R,8R,8aR)-7-acetoxy-6-(2,2-dimethyl-propionyloxymethyl)-8-methoxy-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl]-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-methyl ester 
• 195703-47-0 Benzoic acid (S)-[(4S,4aS,6R,7R,8R,8aR)-7-acetoxy-6-(2,2-dimethyl-propionyloxymethyl)-8-methoxy-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl]-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-methyl ester 
• 195703-50-5 Benzoic acid (S)-((4R,4aS,8aR,9R,9aR,10aR)-9-methoxy-7,7-dimethyl-hexahydro-1,3,6,8,10-pentaoxa-anthracen-4-ylcarbamoyl)-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-methyl ester 
• 195703-49-2 Benzoic acid (S)-((4S,4aS,8aR,9R,9aR,10aR)-9-methoxy-7,7-dimethyl-hexahydro-1,3,6,8,10-pentaoxa-anthracen-4-ylcarbamoyl)-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-methyl ester 

Relevant articles and documents

Systematic Hydrogen-Bond Manipulations To Establish Polysaccharide Structure–Property Correlations

A dense hydrogen-bond network is responsible for the mechanical and structural properties of polysaccharides. Random derivatization alters the properties of the bulk material by disrupting the hydrogen bonds, but obstructs detailed structure–function correlations. We have prepared well-defined unnatural oligosaccharides including methylated, deoxygenated, deoxyfluorinated, as well as carboxymethylated cellulose and chitin analogues with full control over the degree and pattern of substitution. Molecular dynamics simulations and crystallographic analysis show how distinct hydrogen-bond modifications drastically affect the solubility, aggregation behavior, and crystallinity of carbohydrate materials. This systematic approach to establishing detailed structure–property correlations will guide the synthesis of novel, tailor-made carbohydrate materials.

A sulfated galactan with antioxidant capacity from the green variant of tetrasporic Gigartina skottsbergii (Gigartinales, Rhodophyta)

The water soluble polysaccharide produced by the green variant of tetrasporic Gigartina skottsbergii was found to be composed of d-galactose and sulfate groups in a molar ratio of 1.0:0.65. 1H and 13C NMR spectroscopy studies of the desulfated polysaccharide showed a major backbone structure of alternating 3-linked β-d-galactopyranosyl and 4-linked α-d-galactopyranosyl units, and minor signals ascribed to 3-O-methyl-substitution on the latter unit. Ethylation analysis of the polysaccharide indicated that the sulfate groups are mainly located at position O-2 of 4-linked α-d-galactopyranosyl residue and partially located at positions O-6 of the same unit and at position O-2 of 3-linked β-d-galactopyranosyl residue, and confirmed the presence of 3-O-methyl-galactose in minor amounts (4.4%). The sulfated d-galactan presents a similar structure to λ carrageenan but with much lower sulfation at position O-6 of the α-residue and at position O-2 of β-residue. The antioxidant capacity of the sulfated d-galactan was evaluated by the peroxyl radicals (ORAC method), hydroxyl radicals, chelating activity, and ABTS + assays. Kinetic results obtained in these assays were compared with those obtained for the commercial λ carrageenan. The antioxidant activity toward peroxyl radicals was higher for commercial λ carrageenan, this agrees with its higher content of sulfate group. The kinetics of the reaction of both polysaccharides with hydroxyl and ABTS+ radicals showed a complex mechanism, but the antioxidant activity was higher for the polysaccharide from the green variant of tetrasporic Gigartina skottsbergii.

Studies on synthesis of 3-O-alkyl-D-glucose and 3-O-alkyl-D-allose derivatives and their biological activities

-