7506-68-5

Basic information

• Product Name: 2,3,4,6-TETRAMETHYL-D-GLUCOSE
• Synonyms: 2,3,4,6-TETRAMETHYL-D-GLUCOSE;2,3,4,6-TETRA-O-METHYL-D-GLUCOSE;Tetramethylglucose;D-Glucopyranose, 2,3,4,6-tetra-O-methyl-;2-O,3-O,4-O,6-O-Tetramethyl-D-glucopyranose
• CAS NO: 7506-68-5
• Molecular Formula: C₁₀H₂₀O₆
• Molecular Weight: 236.26
• Mol File: 7506-68-5.mol
• Article Data: 18

Chemical Properties

• Melting Point: 87-89 °C
• Boiling Point: 324.4 °C at 760 mmHg
• Flash Point: 150 °C
• Appearance: /
• Density: 1.14 g/cm³
• Vapor Pressure: 1.92E-05mmHg at 25°C
• Refractive Index: 1.456
• PKA: 11.85±0.70(Predicted)
• CAS DataBase Reference: 2,3,4,6-TETRAMETHYL-D-GLUCOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,6-TETRAMETHYL-D-GLUCOSE(7506-68-5)
• EPA Substance Registry System: 2,3,4,6-TETRAMETHYL-D-GLUCOSE(7506-68-5)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-40
• Safety Statements: 22-26-36
• Hazardous Substances Data: 7506-68-5(Hazardous Substances Data)

Usage

Description

2,3,4,6-Tetramethyl-D-glucose is a synthetic glucose derivative with four methyl groups attached at the 2nd, 3rd, 4th, and 6th carbon positions. This modification enhances the compound's stability and solubility, making it a versatile tool in scientific research and industrial applications. It is widely used in biochemical assays, metabolic studies, and as a reference standard in analytical chemistry, as well as for studying carbohydrate metabolism and transport in biological systems.

Uses

Used in Biochemical Assays:
2,3,4,6-Tetramethyl-D-glucose is used as a reference standard for the calibration of analytical instruments and the development of new assay methods. Its enhanced stability and solubility make it an ideal candidate for these applications.
Used in Metabolic Studies:
In metabolic research, 2,3,4,6-Tetramethyl-D-glucose serves as a valuable tool for studying carbohydrate metabolism. Its unique structure allows researchers to investigate the metabolic pathways and enzymes involved in glucose processing.
Used in Analytical Chemistry:
2,3,4,6-Tetramethyl-D-glucose is used as a reference standard in various analytical techniques, such as chromatography and mass spectrometry. Its stability and solubility contribute to the accuracy and reproducibility of these methods.
Used in Pharmaceutical Industry:
2,3,4,6-Tetramethyl-D-glucose is used as a building block for the synthesis of complex carbohydrates and glycoconjugates, which are important components of many pharmaceutical compounds. Its unique structure and properties make it a valuable asset in the development of new drugs and drug delivery systems.
Used in Chemical Biology:
In the field of chemical biology, 2,3,4,6-Tetramethyl-D-glucose is employed as a probe to study carbohydrate-protein interactions and the role of carbohydrates in cellular processes. Its modified structure allows for the investigation of specific binding events and the development of new therapeutic agents targeting carbohydrate-related pathways.

InChI:InChI=1/C10H20O6/c1-12-5-6-7(13-2)8(14-3)9(15-4)10(11)16-6/h6-11H,5H2,1-4H3

Upstream product

• 1633-35-8 1,2,3,4,2',3',4',6'-octa-O-methylgentiobiose 
• 74-88-4 methyl iodide 
• 23445-00-3 swertianolin 
• 482-35-9 quercetin-3-O-glucoside 
• 41670-15-9 C₆₆H₁₁₆O₂₄ 
• 90138-33-3 C₅₇H₉₄O₁₈ 
• 67-56-1 methanol 
• 186581-53-3 diazomethane 
• 474-58-8 Daucosterol 

Downstream Products

• 7434-09-5 tetra-O-methyl-N-phenyl-α-D-glucopyranosylamine 
• 194208-48-5 C₂₄H₄₃N₂O₇P 
• 172471-62-4 phenyl 2,3,4,6-tetra-O-methyl-1-thio-β-D-galactopyranoside 
• 172471-61-3 phenyl 2,3,4,6-tetra-O-methyl-1-thio-α-D-galactopyranoside 
• 1616345-57-3 1-O-{4-(trans-4-butylcyclohexyl)benzoyl}-2,3,4,6-tetra-O-methyl-β-D-glucopyranose 
• 132618-57-6 (D)-2,3,4,5,6-Penta-O-methyl-1-O-(triphenylmethyl)glucitol 
• 132540-39-7 (D)-2,3,4,6-Tetra-O-methyl-1-O-(triphenylmethyl)glucitol 
• 115514-28-8 β-1,5-anhydro-2,3,4,6-tetra-O-methyl-1-C-phenyl-D-glucitol 

Relevant articles and documents

Antibacterial activity of a triterpenoid saponin from the stems of Caesalpinia pulcherrima Linn.

A new compound 1 was isolated from the methanolic extract of the stems of the Caesalpinia pulcherrima Linn. along with a reported compound (2) 3-O-β-D-glucopyranosyl-(1→4)-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl hederagenin 28-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester. The new compound 1 has m.p. 272–274°C, m.f. C46H74O17, [M]+ m/z 898. It was characterised as 3-O-β-D-glucopyranosyl-(1→4)-α-L-arabinopyranosyl hederagenin 28-O-β-D- xylopyranosyl ester by various colour reactions, chemical degradations and spectral analyses. Antibacterial activity of compound 1 was screened against various Gram-positive and Gram-negative bacteria and showed significant results.

Microwave-accelerated methylation of starch

A novel microwave-accelerated method for methylating soluble starch is described. Soluble starch could be fully methylated in 72% yield within 4.66 min using iodomethane and 30% potassium hydroxide under microwave irradiation. The completely methylated starch thus obtained was hydrolyzed with 60% HCO2H for 1.5 min under 80% MW power, followed by 0.05 M H2SO4 for 2.0 min under 100% MW power. The partially methylated monosaccharides were separated by preparative paper chromatography and identified by their melting points and optical rotations.

New Phenolic Components from Dalbergia Volubilis

Phytochemical examination of non green branches of Dalbergia volubilis on extensive column and preparative thin layer chromatography yielded twelve compounds eight of which are already known compounds and were identified as sitosterol, 7-hydroxy-4-methyl-coumarin, dalbergin, biochanin-A, umbelliferone, p-hydroxy cinnamic acid, kaempferol and quercetin-3-O-glucoside.The other four compounds were new natural products, three of which were identified as novel 4-phenyl-2H-1-benzopyran-2-ones while the fourth one was a new 12a-hydroxy rotenoid.The structure of these new compounds has been established on the basis of chemical and spectral evidences and through derivatization, as 4',7-dihydroxy-3'-methoxy-4-phenyl-2H-1-benzopyran-2-one, 3',7-dihydroxy-4',5-dimethoxy-2H-1-benzopyran-2-one, 3',7-dihydroxy4',5-dimethoxy-6-formyl-2H-1-benzopyran-2-one and a complex rotenoid determined to be as (VII).The co-occurence of 4-methyl-2H-1-benzopyran-2-ones, 4-phenyl-2H-1-benzopyran-2-ones, isoflavones and rotenoids is of interest from biogenetic considerations.