Product Name

  • Name

    4-Methylumbelliferyl beta-D-galactoside

  • EINECS 228-185-5
  • CAS No. 6160-78-7
  • Article Data8
  • CAS DataBase
  • Density 1.522 g/cm3
  • Solubility soluble in water
  • Melting Point 258-263oC (dec.)
  • Formula C16H18O8
  • Boiling Point 626.9 °C at 760 mmHg
  • Molecular Weight 338.314
  • Flash Point 233.9 °C
  • Transport Information
  • Appearance White Powder
  • Safety 24/25
  • Risk Codes 26/27/28
  • Molecular Structure Molecular Structure of 6160-78-7 (4-Methylumbelliferyl beta-D-galactoside)
  • Hazard Symbols VeryT+
  • Synonyms Coumarin,7-(b-D-galactopyranosyloxy)-4-methyl-(7CI,8CI);4-Methylumbelliferone b-D-galactopyranoside;4-Methylumbelliferone b-D-galactoside;4-Methylumbelliferyl b-D-galactopyranoside;4-Methylumbelliferyl b-D-galactoside;MUGal;b-Methylumbelliferyl-b-D-galactopyranoside;
  • PSA 129.59000
  • LogP -0.71990

Synthetic route

4-methylumbelliferyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside
6160-79-8

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

4-methylumbelliferyl-β-D-galactopyranoside
6160-78-7

4-methylumbelliferyl-β-D-galactopyranoside

Conditions
ConditionsYield
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

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

4-methylumbelliferyl-β-D-galactopyranoside
6160-78-7

4-methylumbelliferyl-β-D-galactopyranoside

Conditions
ConditionsYield
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

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

4-methylumbelliferyl-β-D-galactopyranoside
6160-78-7

4-methylumbelliferyl-β-D-galactopyranoside

Conditions
ConditionsYield
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

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

4-methylumbelliferyl-β-D-galactopyranoside
6160-78-7

4-methylumbelliferyl-β-D-galactopyranoside

Conditions
ConditionsYield
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

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside

4-methylumbelliferyl-β-D-galactopyranoside
6160-78-7

4-methylumbelliferyl-β-D-galactopyranoside

Conditions
ConditionsYield
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

uridine 5'-diphospho-D-galactose

7-hydroxy-4-methyl-chromen-2-one
90-33-5, 79566-13-5

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

4-methylumbelliferyl-β-D-galactopyranoside
6160-78-7

4-methylumbelliferyl-β-D-galactopyranoside

Conditions
ConditionsYield
With magnesium chloride at 37℃; for 0.25h; pH=7.5; Kinetics; Concentration; aq. phosphate buffer; Enzymatic reaction;
D-galactose pentaacetate
25878-60-8

D-galactose pentaacetate

4-methylumbelliferyl-β-D-galactopyranoside
6160-78-7

4-methylumbelliferyl-β-D-galactopyranoside

Conditions
ConditionsYield
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

2,3,4,6-tetra-O-acetyl-D-galactopyranosyl trichloroacetimidate

4-methylumbelliferyl-β-D-galactopyranoside
6160-78-7

4-methylumbelliferyl-β-D-galactopyranoside

Conditions
ConditionsYield
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

recorcinol

4-methylumbelliferyl-β-D-galactopyranoside
6160-78-7

4-methylumbelliferyl-β-D-galactopyranoside

Conditions
ConditionsYield
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

β-D-galactose peracetate

4-methylumbelliferyl-β-D-galactopyranoside
6160-78-7

4-methylumbelliferyl-β-D-galactopyranoside

Conditions
ConditionsYield
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

tert-butylchlorodiphenylsilane

4-methylumbelliferyl-β-D-galactopyranoside
6160-78-7

4-methylumbelliferyl-β-D-galactopyranoside

4-methylumbelliferyl 6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside
296776-03-9

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

Conditions
ConditionsYield
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

benzoyl chloride

4-methylumbelliferyl-β-D-galactopyranoside
6160-78-7

4-methylumbelliferyl-β-D-galactopyranoside

C37H30O11
849207-61-0

C37H30O11

Conditions
ConditionsYield
With pyridine In N,N-dimethyl-formamide at -15 - 20℃; for 16h;43%
4-methylumbelliferyl-β-D-galactopyranoside
6160-78-7

4-methylumbelliferyl-β-D-galactopyranoside

A

7-hydroxy-4-methyl-chromen-2-one
90-33-5, 79566-13-5

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

B

β-D-galactopyranoside
7296-64-2

β-D-galactopyranoside

Conditions
ConditionsYield
With β-galactosidase
N-((2S,3R,4R,5R,6R)-2-Allyloxy-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-acetamide
64650-83-5

N-((2S,3R,4R,5R,6R)-2-Allyloxy-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-acetamide

4-methylumbelliferyl-β-D-galactopyranoside
6160-78-7

4-methylumbelliferyl-β-D-galactopyranoside

allyl O-(β-D-galactopyranosyl)-(1<*>3)-2-acetamido-2-deoxy-α-D-galactopyranoside
110879-61-3

allyl O-(β-D-galactopyranosyl)-(1<*>3)-2-acetamido-2-deoxy-α-D-galactopyranoside

Conditions
ConditionsYield
With McIlvain buffer at 37℃; for 50h; pH=4.3; Enzymatic reaction;40 % Chromat.
4-methylumbelliferyl-β-D-galactopyranoside
6160-78-7

4-methylumbelliferyl-β-D-galactopyranoside

4-methylumbelliferyl 4-azido-4-deoxy-β-D-glucopyranoside

4-methylumbelliferyl 4-azido-4-deoxy-β-D-glucopyranoside

Conditions
ConditionsYield
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

4-methylumbelliferyl-β-D-galactopyranoside

C37H29N3O10
849207-62-1

C37H29N3O10

Conditions
ConditionsYield
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

4-methylumbelliferyl-β-D-galactopyranoside

C38H29F3O13S

C38H29F3O13S

Conditions
ConditionsYield
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-β-D-galactopyranoside

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

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

Conditions
ConditionsYield
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-β-D-galactopyranoside

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

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

Conditions
ConditionsYield
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

4-methylumbelliferyl-β-D-galactopyranoside

7-hydroxy-4-methyl-chromen-2-one
90-33-5, 79566-13-5

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

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

4-Methylumbelliferyl beta-D-galactoside Chemical Properties

Molecular Structure of 2H-1-Benzopyran-2-one,7-(b-D-galactopyranosyloxy)-4-methyl- (CAS NO.6160-78-7):

IUPAC Name: 4-Methyl-7-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-2-one 
CAS: 31005-02-4
EINECS: 250-429-4
Melting Point: 88-90 °C(lit.)
Empirical Formula: C16H18O8
Molecular Weight: 338.3093
H bond acceptors: 8
H bond donors: 4
Freely Rotating Bonds: 7
Polar Surface Area: 81.68 Å2
Index of Refraction: 1.641
Molar Refractivity: 80.17 cm3
Molar Volume: 222.1 cm3
Surface Tension: 73.1 dyne/cm
Density: 1.522 g/cm3
Flash Point: 233.9 °C
Enthalpy of Vaporization: 97.54 kJ/mol
Boiling Point: 626.9 °C at 760 mmHg
Vapour Pressure: 1.39E-16 mmHg at 25 °C
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-/m1/s1
Smiles: c12c(c(cc(o2)=O)C)ccc(c1)O[C@H]1[C@@H]([C@@H](O)[C@H]([C@H](O1)CO)O)O
Product Categories: Coumarin; romatics Compounds; romatics

4-Methylumbelliferyl beta-D-galactoside Safety Profile

Hazard Codes: IrritantXi
Safety Statements: 22-24/25 
S22:Do not breathe dust. 
S24/25:Avoid contact with skin and eyes.
WGK Germany: 3
F: 8
Hazard Note: Irritant

4-Methylumbelliferyl beta-D-galactoside Specification

 2H-1-Benzopyran-2-one,7-(b-D-galactopyranosyloxy)-4-methyl- , with CAS number of 6160-78-7, can be called 7-Ethoxy-1-benzopyran-2-one ; 7-ethoxy-1-benzopyrane-2-one ; 7-ethoxycoumarin ; ethoxycoumarin, 7-;2h-1-benzopyran-2-one, 7-ethoxy- ; coumarin, 7-ethoxy- ; ethylumbelliferone ; 7-ethoxycoumarin, 99.5% ; MUG .It is a beige crystalline powder, can be used as a substrate for CYP2B6.  2H-1-Benzopyran-2-one,7-(b-D-galactopyranosyloxy)-4-methyl- (CAS NO.6160-78-7) is a white powder,  be useful for fluorometric assay.

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