4-Methylumbelliferyl-alpha-D-galactopyranoside

Base Information

• Chemical Name: 4-Methylumbelliferyl-alpha-D-galactopyranoside
• CAS No.: 38597-12-5
• Molecular Formula: C16H18O8
• Molecular Weight: 338.314
• Hs Code.: 29400090
• European Community (EC) Number: 254-031-1
• DSSTox Substance ID: DTXSID701020648
• Nikkaji Number: J319.810C
• Wikidata: Q27163060
• Mol file: 38597-12-5.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-alpha-D-galactopyranoside

Chemical Property:

• Appearance/Colour: white to almost white crystalline powder
• Melting Point: 171-173 °C
• Boiling Point: 626.9 °C at 760 mmHg
• Flash Point: 233.9 °C
• PSA: 129.59000
• Density: 1.522 g/cm³
• LogP: -0.71990
• Storage Temp.: 2-8°C
• Solubility.: H2O: 10 mg/mL hot, clear, colorless
• 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-Galactopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+
• Hazard Codes: T+
• Statements: 26/27/28
• Safety Statements: 24/25

MSDS Files:

Total 1 MSDS from other Authors

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
• Uses: A fluorogenic substrate in the assay of a-galactosidase A fluorogenic substrate in the assay of α-galactosidase. FFluorescent substrate for ?-galactosidase activity in cell extracts, lysosomes and human blood serum. The lower pKa of the hydrolysis product, allows its detection at phisiological pH5.

Technology Process of 4-Methylumbelliferyl-alpha-D-galactopyranoside

There total 5 articles about 4-Methylumbelliferyl-alpha-D-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: 80.0%

4′-methylumbelliferyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside (67909-26-6) → 4-methylumbellifenyl α-D-galactopyranoside (38597-12-5,39940-54-0)

Guidance literature:

With potassium hydroxide; In tetrahydrofuran; at 20 ℃; for 0.25h;

DOI:10.3390/molecules201219789

Reference yield:

7-hydroxy-4-methyl-chromen-2-one (90-33-5,79566-13-5) + β-D-galactose peracetate (4163-60-4) → 4-methylumbellifenyl α-D-galactopyranoside (38597-12-5,39940-54-0)

Guidance literature:

Multi-step reaction with 2 steps

1: boron trifluoride diethyl etherate; dmap / 1,2-dichloro-ethane / 5 h / 60 °C / Inert atmosphere

2: potassium hydroxide / tetrahydrofuran / 0.25 h / 20 °C

With dmap; boron trifluoride diethyl etherate; potassium hydroxide; In tetrahydrofuran; 1,2-dichloro-ethane; 1: |Helferich Method;

DOI:10.3390/molecules201219789

Reference yield:

7-hydroxy-4-methyl-chromen-2-one (90-33-5,79566-13-5) → 4-methylumbellifenyl α-D-galactopyranoside (38597-12-5,39940-54-0)

Guidance literature:

Multi-step reaction with 2 steps

1: zinc chloride; xylene

2: sodium methylate; methanol

With methanol; sodium methylate; zinc(II) chloride; xylene;

upstream raw materials:

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

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

β-D-galactose peracetate

Downstream raw materials:

D-Galactose

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

Refernces

• 1、 Wei, Xianhu,Ma, Yanxia,Wu, Qingping,Zhang, Jumei,Cai, Zhihe,Lu, Mianfei,Ferro, Vito. "An improved helferich method for the α/β-stereoselective synthesis of 4-methylumbelliferyl glycosides for the detection of microorganisms". . p. 21681 - 21699. Retrieved 2016/01/25.