4-Methylumbelliferyl-galactopyranoside

Base Information

• Chemical Name: 4-Methylumbelliferyl-galactopyranoside
• CAS No.: 6160-78-7
• Molecular Formula: C16H18O8
• Molecular Weight: 338.314
• Hs Code.: 29329900
• European Community (EC) Number: 228-185-5
• DSSTox Substance ID: DTXSID30210615
• Nikkaji Number: J211.425I
• Wikidata: Q27163061
• Pharos Ligand ID: QKMZG5RFD39R
• ChEMBL ID: CHEMBL1393422
• Mol file: 6160-78-7.mol

Synonyms:4-methylumbelliferone-alpha-D-galactoside;4-methylumbelliferyl galactose;4-methylumbelliferyl-alpha-D-galactopyranoside;4-methylumbelliferyl-beta-D-galactopyranoside;4-methylumbelliferyl-beta-D-galactoside;4-methylumbelliferyl-galactopyranoside;4-methylumbelliferyl-galactopyranoside, ((alpha-D)-galactopyranosyloxy)-isomer;4-methylumbelliferyl-galactopyranoside, ((beta-D)-galactosyloxy)-isomer;4-MUBF-GP

Chemical Property of 4-Methylumbelliferyl-galactopyranoside

Chemical Property:

• Appearance/Colour: White Powder
• Vapor Pressure: 1.39E-16mmHg at 25°C
• Melting Point: 258-263oC (dec.)
• 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
• Sensitive.: Moisture Sensitive & Hygroscopic
• Solubility.: Soluble in DMSO (40 mg/ml)
• Water Solubility.: soluble
• 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 b-D-galactopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+
• Hazard Codes: T+
• Statements: 26/27/28
• Safety Statements: 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-MUG (6160-78-7) is a versatile fluorogenic substrate for ?-galactosidase1 for use in cell extracts or purified enzyme preparations.1-3? This substrate produces a water soluble blue fluorescent coumarin fluorophore. Ex: 342 nm; Em: 441 nm
• Uses: Substrate for fluorometric assay of ?-D-galactosidase It is a substrate used for fluorometric assay for β-galactosidase. It is used to detect E-coli n the fluorogenic medium.

Technology Process of 4-Methylumbelliferyl-galactopyranoside

There total 11 articles about 4-Methylumbelliferyl-galactopyranoside 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: 95.0%

4-methylumbelliferyl-2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside (6160-79-8) → 4-methylumbelliferyl-β-D-galactopyranoside (6160-78-7,39940-54-0)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 0.5h;

DOI:10.1039/b613909d

Reference yield:

7-hydroxy-4-methyl-chromen-2-one (90-33-5,79566-13-5) → 4-methylumbelliferyl-β-D-galactopyranoside (6160-78-7,39940-54-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / TMSOTf / CH₂Cl₂ / 0.5 h / -78 °C

2: 83 percent / NaOMe / methanol / 0.5 h / 20 °C

With trimethylsilyl trifluoromethanesulfonate; sodium methylate; In methanol; dichloromethane; 1: Substitution / 2: Deacetylation;

DOI:10.1039/b002754p

Reference yield:

2,3,4,6-tetra-O-acetyl-α/β-D-galactopyranose (3947-62-4,6207-76-7,10343-06-3,19235-21-3,22554-70-7,22860-22-6,57884-82-9,62057-79-8,70191-05-8,109525-54-4,140147-37-1,47339-09-3) → 4-methylumbelliferyl-β-D-galactopyranoside (6160-78-7,39940-54-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 1-methylimidazole / CH₂Cl₂ / 16 h / 20 °C

2: 68 percent / TMSOTf / CH₂Cl₂ / 0.5 h / -78 °C

3: 83 percent / NaOMe / methanol / 0.5 h / 20 °C

With 1-methyl-1H-imidazole; trimethylsilyl trifluoromethanesulfonate; sodium methylate; In methanol; dichloromethane; 1: Substitution / 2: Substitution / 3: Deacetylation;

DOI:10.1039/b002754p

upstream raw materials:

4-methylumbelliferyl-2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside

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

2,3,4,6-tetra-O-acetyl-α/β-D-galactopyranose

2-(2',3',4',6'-tetra-O-acetyl-α-D-galactopyranosyloxy)-1,3,2-dioxaphosphinane 2-oxide

Downstream raw materials:

4-methylumbelliferyl-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside

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

β-D-galactopyranoside

4-methylumbelliferyl 6'-O-(tert-butyldiphenylsilyl)-3'-O-(2'',3'',4''-tri-O-acetyl-α-L-fucopyranosyl)-β-D-galactopyranoside

Refernces

• 1、 -. "CARBONIC ANHYDRASE INHIBITORS WITH ANTIMETASTATIC ACTIVITY". Page/Page column 22-29. . Retrieved 2012/06/15.
• 2、 MacKenzie, Peter I.,Rogers, Anne,Elliot, David J.,Chau, Nuy,Hulin, Julie-Ann,Miners, John O.,Meech, Robyn. "The Novel UDP Glycosyltransferase 3A2: Cloning, catalytic properties, and tissue distribution". experimental part. p. 472 - 478. Retrieved 2012/02/02.