4-METHYLUMBELLIFERYL-ALPHA-D-GLUCOPYRANOSIDE HYDRATE

Base Information

• Chemical Name: 4-METHYLUMBELLIFERYL-ALPHA-D-GLUCOPYRANOSIDE HYDRATE
• CAS No.: 17833-43-1
• Molecular Formula: C16H18O8
• Molecular Weight: 338.314
• Hs Code.: 2934999090
• European Community (EC) Number: 241-794-0
• DSSTox Substance ID: DTXSID20863699
• Nikkaji Number: J287.165C
• Metabolomics Workbench ID: 147210
• Mol file: 17833-43-1.mol

Synonyms:Coumarin,7-(a-D-glucopyranosyloxy)-4-methyl-(8CI);4-Methylumbelliferyl a-D-glucopyranoside;4-Methylumbelliferyl a-D-glucose;4-Methylumbelliferyl a-D-glucoside;4'-Methylumbelliferyl a-D-glucopyranoside;

Chemical Property of 4-METHYLUMBELLIFERYL-ALPHA-D-GLUCOPYRANOSIDE HYDRATE

Chemical Property:

• Vapor Pressure: 1.39E-16mmHg at 25°C
• Melting Point: 171-173 °C
• Refractive Index: 1.641
• Boiling Point: 626.9 °C at 760 mmHg
• PKA: 12.73±0.70(Predicted)
• Flash Point: 233.9 °C
• PSA: 129.59000
• Density: 1.522 g/cm³
• LogP: -0.71990
• Storage Temp.: 2-8°C
• Solubility.: DMSO: 50 mg/mL, clear, colorless to faintly yellow
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 338.10016753
• Heavy Atom Count: 24
• Complexity: 506

Purity/Quality:

98%, ^*data from raw suppliers

4-Methylumbelliferyl a-D-Glucopyranoside ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=O)OC2=C1C=CC(=C2)OC3C(C(C(C(O3)CO)O)O)O
• Isomeric SMILES: CC1=CC(=O)OC2=C1C=CC(=C2)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
• Description: 4-Methylumbelliferyl-α-D-glucopyranoside is a fluorogenic substrate for α-glucosidase. 4-Methylumbelliferyl-α-D-glucopyranoside is cleaved by α-glucosidase to release the fluorescent moiety 4-methylumbelliferyl (4-MU). 4-MU fluorescence is pH-dependent with excitation maxima of 320 and 360 nm at low (1.97-6.72) and high pH (7.12-10.3), respectively, and an emission maximum ranging from 445 to 455 nm, increasing as pH decreases. 4-Methylumbelliferyl-α-D-glucopyranoside has been used to quantify α-glucosidase activity in infant blood spot samples as a biomarker of Fabry and Pompe diseases, lysosomal storage disorders characterized by a deficiency in the enzyme.
• Uses: 4-Methylumbelliferyl-α-D-glucopyranoside is a fluorogenic substrate in the assay of a-glucosidase,it has been used in the study of Pompe disease. 4-Methylumbelliferyl α-D-glucopyranoside is used as a flurogenic substrate for the identification, characterization and kinetic analysis of α-D-glucosidase(s).

Technology Process of 4-METHYLUMBELLIFERYL-ALPHA-D-GLUCOPYRANOSIDE HYDRATE

There total 4 articles about 4-METHYLUMBELLIFERYL-ALPHA-D-GLUCOPYRANOSIDE HYDRATE 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: 98.0%

4′-methylumbelliferyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside (67945-53-3) → 4-methyl-umbelliferyl α-D-glucopyranoside (17833-43-1,39940-54-0)

Guidance literature:

With methanol; sodium methylate; at 20 ℃; for 3h; pH=10; Inert atmosphere;

DOI:10.1039/c9ob02540e

Reference yield:

→ 4-methyl-umbelliferyl α-D-glucopyranoside (17833-43-1,39940-54-0)

Guidance literature:

aus entspr. Tetraacetat 2, MeOH/Triaethylamin/H2O;

DOI:10.1016/S0008-6215(00)84209-3

Reference yield:

7-hydroxy-4-methyl-chromen-2-one (90-33-5,79566-13-5) → 4-methyl-umbelliferyl α-D-glucopyranoside (17833-43-1,39940-54-0)

Guidance literature:

Multi-step reaction with 3 steps

1: methanol; water / 1 h / 20 °C / Inert atmosphere

2: acetonitrile / 72 h / 20 °C / Inert atmosphere

3: sodium methylate; methanol / 3 h / 20 °C / pH 10 / Inert atmosphere

With methanol; sodium methylate; In methanol; water; acetonitrile;

DOI:10.1039/c9ob02540e

upstream raw materials:

7-hydroxy-4-methyl-chromen-2-one

7-hydroxy-4-methyl-2-oxo-2H-1-benzopyran tetrabutylammonium salt

4′-methylumbelliferyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside

Downstream raw materials:

7-hydroxy-4-methyl-chromen-2-one

alpha-D-glucopyranose

D-glucose