3370-81-8

Basic information

• Product Name: 3-O-METHYL-D-GLUCOPYRANOSE
• Synonyms: 3-O-METHYLGLUCOPYRANOSE;3-O-METHYLGLUCOSE;3-O-Methyl-D-glucopyranose, 99+%;D-Glucopyranose, 3-O-methyl-;NSC 61740;NSC 62383;(3R,4S,5R,6R)-6-(hydroxyMethyl)-4-Methoxytetrahydro-2H-pyran-2,3,5-triol;3-OME-D-GLC
• CAS NO: 3370-81-8
• Molecular Formula: C₇H₁₄O₆
• Molecular Weight: 194.18
• Product Categories: Carbohydrates & Derivatives
• Mol File: 3370-81-8.mol
• Article Data: 11

Chemical Properties

• Melting Point: 162-165 °C
• Boiling Point: 250.62°C (rough estimate)
• Flash Point: 199.5°C
• Appearance: /
• Density: 1.2501 (rough estimate)
• Vapor Pressure: 2.69E-08mmHg at 25°C
• Refractive Index: 1.5600 (estimate)
• Storage Temp.: 0-6°C
• Solubility: DMSO (Slightly), Water (Slightly)
• PKA: 12.05±0.70(Predicted)
• CAS DataBase Reference: 3-O-METHYL-D-GLUCOPYRANOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-O-METHYL-D-GLUCOPYRANOSE(3370-81-8)
• EPA Substance Registry System: 3-O-METHYL-D-GLUCOPYRANOSE(3370-81-8)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 3370-81-8(Hazardous Substances Data)

Usage

Description

3-O-METHYL-D-GLUCOPYRANOSE, also known as a methylated glucose, is a non-metabolizable hexose that plays a significant role in the interference of glucose metabolism. It is characterized by its white powder chemical properties and is utilized in various applications due to its unique properties.

Uses

Used in Research Applications:
3-O-METHYL-D-GLUCOPYRANOSE is used as a research compound for studying hexose translocation across the blood-brain interface. This is achieved by infusing it into one internal carotid artery, which helps researchers understand the transport mechanisms and metabolic processes involving glucose in the brain.
Used in Pharmaceutical Industry:
3-O-METHYL-D-GLUCOPYRANOSE is used as a pharmaceutical compound for its potential applications in drug development and therapeutic interventions. Its non-metabolizable nature allows for the investigation of glucose metabolism and its interference, which can be crucial in developing treatments for various metabolic disorders and conditions.
Used in Biochemical Studies:
In the field of biochemistry, 3-O-METHYL-D-GLUCOPYRANOSE serves as an essential tool for studying the interactions between glucose and other biomolecules, as well as the role of glucose in cellular processes. This knowledge can be applied to develop new strategies for managing glucose-related diseases and improving overall health.

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

Upstream product

• 89355-04-4 C₆₄H₁₀₆O₂₂ 
• 90138-32-2 C₆₆H₁₁₀O₂₃ 
• 77-78-1 dimethyl sulfate 
• 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 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 

Downstream Products

• 126797-39-5 4,6-O-benzylidene-3-O-methyl-D-glucopyranose 
• 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 
• 30694-99-6 Benzyl 3-O-methyl-D-glucopyranoside 
• 20770-95-0 methyl 4,6-O-benzylidene-3-O-methyl-α-D-glucopyranoside 
• 35775-68-9 methyl 4,6-O-benzylidene-3-O-methyl-β-D-glucopyranoside 
• 226064-62-6 Allyl 4,6-O-benzylidene-3-O-methyl-β-D-glucopyranoside 
• 332083-22-4 Allyl 4,6-O-benzylidene-3-O-methyl-α-D-glucopyranoside 
• 226064-76-2 Allyl 2-O-acetyl-4,6-O-benzylidene-3-O-methyl-β-D-glucopyranoside 
• 202647-43-6 Allyl 2-O-acetyl-6-O-benzyl-3-O-methyl-β-D-glucopyranoside 
• 202647-53-8 Allyl 2,6-di-O-benzyl-3-O-methyl-α-D-glucopyranosyl-(1->4)-2-O-acetyl-6-O-benzyl-3-O-methyl-β-D-glucopyranoside 
• 202647-45-8 Allyl (2,6-di-O-benzyl-4-O-levulinyl-3-O-methyl-α-D-glucopyranosyl)-(1->4)-2-O-acetyl-6-O-benzyl-3-O-methyl-β-D-glucopyranoside 
• 332083-23-5 Allyl 2-O-acetyl-6-O-benzyl-3-O-methyl-α-D-glucopyranoside 
• 202647-47-0 Prop-1'-enyl 2,6-di-O-benzyl-4-O-levulinyl-3-O-methyl-α-D-glucopyranosyl-(1->4)-2-O-acetyl-6-O-benzyl-3-O-methyl-β-D-glucopyranoside 

Relevant articles and documents

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.

The Synthesis and Reactivity of Cyclic Thiocarbonates Derived from Some Carbohydrate 1,2-Diols

The attempted synthesis of several carbohydrate 1,2-diols is reported, together with the transformation of two of these diols into cyclic thiocarbonates, namely 4,6-O-benzylidene-3-O-methyl-1,2-O-thiocarbonyl-α-D-glucose and 3,4-O-isopropylidene-1,2-O-thiocarbonyl-β-D-arabinose.The treatment of these thiocarbonates, and a furanose 1,2-thiocarbonate previously prepared by Mukaiyama, with methyl halides and with tributyltin hydride is discussed.A single-crystal X-ray diffraction study of 3,4-O-isopropylidene-1,2-O)-thiocarbonyl-β-D-arabinose is recorded.

CAUDINOSIDE A - A NEW TRITERPENE GLYCOSIDE FROM THE HOLOTHURIAN Paracaudina ransonetii

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