6160-78-7

Basic information

• Product Name: 4-Methylumbelliferyl beta-D-galactoside
• Synonyms: MUG;MU-GAL;MUGALACTOSIDE;MUGGAL;4-methylumbelliferyl-galactopyranoside;7-(beta-d-galactopyranosyloxy)-4-methyl-2h-1-benzopyran-2-on;METHYLUMBELLIFERYL-B-D-GALACTOPYRANOSIDE, 4-;7-HYDROXY-4-METHYLCUMARIN-BETA-D-GALACTOPYRANOSID
• CAS NO: 6160-78-7
• Molecular Formula: C₁₆H₁₈O₈
• Molecular Weight: 338.31
• EINECS: 228-185-5
• Product Categories: Substrates;Enzyme Substrates;Fluorescent Labels & Indicators;Labeling and Diagnostics Reagents;substrate
• Mol File: 6160-78-7.mol
• Article Data: 6

Chemical Properties

• Melting Point: 258-263 °C (dec.)
• Boiling Point: 626.9 °C at 760 mmHg
• Flash Point: 233.9 °C
• Appearance: White to slightly off-white/Powder
• Density: 1.522 g/cm³
• Vapor Pressure: 1.39E-16mmHg at 25°C
• Refractive Index: 1.641
• Storage Temp.: 2-8°C
• Solubility: Soluble in DMSO (40 mg/ml)
• PKA: 12.73±0.70(Predicted)
• Water Solubility: soluble
• Sensitive: Moisture Sensitive & Hygroscopic
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month.
• BRN: 94673
• CAS DataBase Reference: 4-Methylumbelliferyl beta-D-galactoside(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Methylumbelliferyl beta-D-galactoside(6160-78-7)
• EPA Substance Registry System: 4-Methylumbelliferyl beta-D-galactoside(6160-78-7)

Safety Data

• Hazard Codes: T+
• Statements: 26/27/28
• Safety Statements: 24/25
• WGK Germany: 3
• F: 3-10-21
• Hazardous Substances Data: 6160-78-7(Hazardous Substances Data)

Usage

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

Chemical Properties

White Powder

Uses

Different sources of media describe the Uses of 6160-78-7 differently. You can refer to the following data:
1. Substrate for fluorometric assay of ?-D-galactosidase
2. It is a substrate used for fluorometric assay for β-galactosidase. It is used to detect E-coli n the fluorogenic medium.

Definition

ChEBI: A beta-D-galactoside having a 4-methylumbelliferyl substituent at the anomeric position.

References

Chiu et al. (2017), Measuring ?-Galactosidase Activity in Gram-Positive Bacteria Using a Whole-Cell Assay with MUG as a Fluorescent Reporter; Curr. Protoc. Toxicol., Supp 74 4.44.1 Kytidou et al. (2018), Nicotiana benthamiana α-galactosidase A1,1 can functionally complement human α-galactosidase A deficiency associated with Fabry disease; J. Biol. Chem., 293 10042 Hernandez-Guzman et al. (2016), Purification and characterization of an extracellular ?-glucosidase from Sporothrix schenckii; FEBS Open Bio., 6 1067

InChI:InChI=1/C16H18O8/c1-7-4-12(18)23-10-5-8(2-3-9(7)10)22-16-15(21)14(20)13(19)11(6-17)24-16/h2-5,11,13-17,19-21H,6H2,1H3/t11-,13-,14+,15-,16-/m0/s1

Synthetic route

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

Conditions	Yield
With sodium methylate In methanol at 20℃; for 0.5h;	95%
With sodium carbonate In methanol; water at 20℃; for 0.5h;	91%
With sodium methylate In methanol at 20℃; for 0.5h; Deacetylation;	83%
With methanol; sodium methylate at 20℃; for 0.5h;	64%
With methanol; sodium methylate

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

Conditions	Yield
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 View Scheme
Multi-step reaction with 2 steps 1: acetone; aq. NaOH solution 2: sodium methylate; methanol View Scheme

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)

Conditions	Yield
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 View Scheme
Multi-step reaction with 3 steps 1.1: dichloromethane / 1 h / 0 °C / Inert atmosphere 1.2: 0.5 h / 0 °C / Inert atmosphere 2.1: boron trifluoride dimethyl etherate / dichloromethane / 20 °C / Inert atmosphere 3.1: methanol; sodium methylate / 0.5 h / 20 °C View Scheme

2-(2',3',4',6'-tetra-O-acetyl-α-D-galactopyranosyloxy)-1,3,2-dioxaphosphinane 2-oxide (281207-18-9) → 4-methylumbelliferyl-β-D-galactopyranoside (6160-78-7)

Conditions	Yield
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 View Scheme

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside (3068-32-4) → 4-methylumbelliferyl-β-D-galactopyranoside (6160-78-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetone; aq. NaOH solution 2: sodium methylate; methanol View Scheme

uridine 5'-diphospho-D-galactose (2956-16-3) + 7-hydroxy-4-methyl-chromen-2-one (90-33-5, 79566-13-5) → 4-methylumbelliferyl-β-D-galactopyranoside (6160-78-7)

Conditions	Yield
With magnesium chloride at 37℃; for 0.25h; pH=7.5; Kinetics; Concentration; aq. phosphate buffer; Enzymatic reaction;

D-galactose pentaacetate (25878-60-8) → 4-methylumbelliferyl-β-D-galactopyranoside (6160-78-7)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: morpholine / dichloromethane / 20 °C / Inert atmosphere 2.1: dichloromethane / 1 h / 0 °C / Inert atmosphere 2.2: 0.5 h / 0 °C / Inert atmosphere 3.1: boron trifluoride dimethyl etherate / dichloromethane / 20 °C / Inert atmosphere 4.1: methanol; sodium methylate / 0.5 h / 20 °C View Scheme

2,3,4,6-tetra-O-acetyl-D-galactopyranosyl trichloroacetimidate (74808-10-9, 86520-63-0, 87119-53-7, 92052-29-4, 121238-27-5, 142831-80-9, 127061-80-7) → 4-methylumbelliferyl-β-D-galactopyranoside (6160-78-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: boron trifluoride dimethyl etherate / dichloromethane / 20 °C / Inert atmosphere 2: methanol; sodium methylate / 0.5 h / 20 °C View Scheme

recorcinol (108-46-3) → 4-methylumbelliferyl-β-D-galactopyranoside (6160-78-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: sulfuric acid / 12 h / 20 °C 2: sodium hydroxide; tetrabutylammomium bromide / chloroform; water / 16 h / 20 °C 3: sodium carbonate / water; methanol / 0.5 h / 20 °C View Scheme

β-D-galactose peracetate (4163-60-4) → 4-methylumbelliferyl-β-D-galactopyranoside (6160-78-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogen bromide; acetic acid / 4 h / 20 °C 2: sodium hydroxide; tetrabutylammomium bromide / chloroform; water / 16 h / 20 °C 3: sodium carbonate / water; methanol / 0.5 h / 20 °C View Scheme

tert-butylchlorodiphenylsilane (58479-61-1) + 4-methylumbelliferyl-β-D-galactopyranoside (6160-78-7) → 4-methylumbelliferyl 6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside (296776-03-9)

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃;	87%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 8h; Substitution;	79%

benzoyl chloride (98-88-4) + 4-methylumbelliferyl-β-D-galactopyranoside (6160-78-7) → C37H30O11 (849207-61-0)

Conditions	Yield
With pyridine In N,N-dimethyl-formamide at -15 - 20℃; for 16h;	43%

4-methylumbelliferyl-β-D-galactopyranoside (6160-78-7) → 7-hydroxy-4-methyl-chromen-2-one (90-33-5, 79566-13-5) + β-D-galactopyranoside (7296-64-2)

Conditions	Yield
With β-galactosidase

N-((2S,3R,4R,5R,6R)-2-Allyloxy-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-acetamide (64650-83-5) + 4-methylumbelliferyl-β-D-galactopyranoside (6160-78-7) → allyl O-(β-D-galactopyranosyl)-(1<*>3)-2-acetamido-2-deoxy-α-D-galactopyranoside (110879-61-3)

Conditions	Yield
With McIlvain buffer at 37℃; for 50h; pH=4.3; Enzymatic reaction;	40 % Chromat.

4-methylumbelliferyl-β-D-galactopyranoside (6160-78-7) → 4-methylumbelliferyl 4-azido-4-deoxy-β-D-glucopyranoside

Conditions	Yield
Multi-step reaction with 4 steps 1: 43 percent / pyridine / dimethylformamide / 16 h / -15 - 20 °C 2: pyridine / CH2Cl2 / 1.5 h / -15 °C 3: NaN3; Bu4NHSO4 / dimethylformamide / 16 h / 20 °C 4: 100 percent / MeONa / methanol / 16 h / 20 °C View Scheme

4-methylumbelliferyl-β-D-galactopyranoside (6160-78-7) → C37H29N3O10 (849207-62-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 43 percent / pyridine / dimethylformamide / 16 h / -15 - 20 °C 2: pyridine / CH2Cl2 / 1.5 h / -15 °C 3: NaN3; Bu4NHSO4 / dimethylformamide / 16 h / 20 °C View Scheme

4-methylumbelliferyl-β-D-galactopyranoside (6160-78-7) → C38H29F3O13S

Conditions	Yield
Multi-step reaction with 2 steps 1: 43 percent / pyridine / dimethylformamide / 16 h / -15 - 20 °C 2: pyridine / CH2Cl2 / 1.5 h / -15 °C View Scheme

4-methylumbelliferyl-β-D-galactopyranoside (6160-78-7) → 4-methylumbelliferyl 6'-O-(tert-butyldiphenylsilyl)-3'-O-(2'',3'',4''-tri-O-acetyl-α-L-fucopyranosyl)-β-D-galactopyranoside (296776-04-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 79 percent / imidazole / dimethylformamide / 8 h / 20 °C 2: 27 percent / Et4NBr; molecular sieves 4 Angstroem / CH2Cl2 / 48 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: 79 percent / imidazole / dimethylformamide / 8 h / 20 °C 2: 52 percent / TMSOTf / CH2Cl2 / 1 h / -78 °C View Scheme

4-methylumbelliferyl-β-D-galactopyranoside (6160-78-7) → 4-methylumbelliferyl 6'-O-(tert-butyldiphenylsilyl)-2'-O-(2'',3'',4''-tri-O-acetyl-α-L-fucopyranosyl)-β-D-galactopyranoside

Conditions	Yield
Multi-step reaction with 2 steps 1: 79 percent / imidazole / dimethylformamide / 8 h / 20 °C 2: 51 percent / Et4NBr; molecular sieves 4 Angstroem / CH2Cl2 / 48 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: 79 percent / imidazole / dimethylformamide / 8 h / 20 °C 2: TMSOTf / CH2Cl2 / 1 h / -78 °C View Scheme

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

Conditions	Yield
With β-galactosidase In aq. phosphate buffer; dimethyl sulfoxide for 1h; pH=7.4; Reagent/catalyst; Irradiation;

Upstream product

• 4163-60-4 β-D-galactose peracetate 
• 108-46-3 recorcinol 
• 74808-10-9 2,3,4,6-tetra-O-acetyl-D-galactopyranosyl trichloroacetimidate 
• 25878-60-8 D-galactose pentaacetate 
• 2956-16-3 uridine 5'-diphospho-D-galactose 
• 90-33-5 7-hydroxy-4-methyl-chromen-2-one 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 281207-18-9 2-(2',3',4',6'-tetra-O-acetyl-α-D-galactopyranosyloxy)-1,3,2-dioxaphosphinane 2-oxide 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-α/β-D-galactopyranose 
• 6160-79-8 4-methylumbelliferyl-2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 

Downstream Products

• 90-33-5 7-hydroxy-4-methyl-chromen-2-one 
• 296776-04-0 4-methylumbelliferyl 6'-O-(tert-butyldiphenylsilyl)-3'-O-(2'',3'',4''-tri-O-acetyl-α-L-fucopyranosyl)-β-D-galactopyranoside 
• 296776-06-2 4-methylumbelliferyl 3-O-(α-L-fucopyranosyl)-β-D-galactopyranoside 
• 849207-62-1 C₃₇H₂₉N₃O₁₀ 
• 7296-64-2 β-D-galactopyranoside 
• 849207-61-0 C₃₇H₃₀O₁₁ 
• 296776-03-9 4-methylumbelliferyl-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside 

Relevant articles and documents

A 4-methyl umbrella-type keto -β-D method for preparing-galactopyranoside

The invention discloses a preparation method of 4-methyl umbrella-shaped keto-beta-D-pyran galactoside. The method comprises the following steps: step 1, preparing 4-methyl umbrella-shaped ketone; step 2, preparing tetra acetyl-Alpha-D-pyran galactoside; step 3, preparing 4-methyl umbrella-shaped keto-2,3,4,6-tetra acetyl-beta-D-pyran galactoside; and step 4, preparing the 4-methyl umbrella-shaped keto-beta-D-pyran galactoside. The method is moderate in reaction condition, namely, the reactions are carried out at a room temperature; heavy metallic salts are not required, so that the environmental friendliness is realized; the yield is high, namely, the one-step yield of glycosylations can reach 73.1% and the total yield of the glycosylations can rach 32.9%. The microbiology experiment proves that the effects of the 4-methyl umbrella-shaped keto-beta-D-pyran galactoside are equal to the effects of an imported substrate, so that the 4-methyl umbrella-shaped keto-beta-D-pyran galactoside can be used for replacing an imported product.

Glycosyl coumarin carbonic anhydrase IX and XII inhibitors strongly attenuate the growth of primary breast tumors

A series of 7-substituted coumarins incorporating various glycosyl moieties were synthesized and investigated for the inhibition of the zinc enzyme carbonic anhydrase (CA, EC 4.2.1.1). These coumarins were very weak or ineffective as inhibitors of the housekeeping, offtarget isoforms CA I and II, but some of them inhibited tumor-associated CA IX and XII in the low nanomolar range. They also significantly inhibited the growth of primary tumors by the highly aggressive 4T1 syngeneic mouse mammary tumor cells at 30 mg/kg, constituting interesting candidates for the development of conceptually novel anticancer drugs. Because CA IX is overexpressed in hypoxic tumors and exhibits very limited expression in normal tissues, such compounds may be useful for treating cancers not responsive to classic chemo- and radiotherapy.

Natural sialoside analogues for the determination of enzymatic rate constants

Two isomeric 4-methylumbelliferyl-α-d-N- acetylneuraminylgalactopyranosides (1 and 2) were synthesised. These compounds contain either the natural α-2,3 or α-2,6 sialyl-galactosyl linkages, as well as an attached 4-methylumbelliferone for convenient detection of their hydrolyses. These compounds were designed as natural sialoside analogues to be used in a continuous assay of sialidase activity, where the sialidase-catalysed reaction is coupled with an exo-β-galactosidase- catalysed hydrolysis of the released galactoside to give free 4-methylumbelliferone. The kinetic parameters for 1 and 2 were measured using the wild-type and nucleophilic mutant Y370G recombinant sialidase from Micromonospora viridifaciens. Kinetic parameters for these analogues measured using the new continuous assay were in good agreement with the parameters for the natural substrate, 3′-sialyl lactose. Given the selection of commercially available exo-β-galactosidases that possess a variety of pH optima, this new method was used to characterise the full pH profile of the wild-type sialidase with the natural sialoside analogue 1. Thus, use of these new substrates 1 and 2 in a continuous assay mode, which can be detected by UV/Vis or fluorescence spectroscopy, makes characterisation of sialidase activity with natural sialoside linkages much more facile. The Royal Society of Chemistry.