4-Methylumbelliferyl-beta-D-glucopyranoside Chemical Properties

Melting point:

258-263 °C (dec.)

Boiling point:

394.46°C (rough estimate)

Density 

1.522

refractive index 

1.4430 (estimate)

storage temp. 

Sealed in dry,Store in freezer, under -20°C

solubility 

DMF: 5 mg/ml; DMSO: 50 mg/ml

pka

12.73±0.70(Predicted)

form 

Powder

color 

White to off-white

Water Solubility 

Soluble in DMF or water

λmax

320nm(Buffer)(lit.)

BRN 

94672

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-/s3

InChIKey

YUDPTGPSBJVHCN-ZDHZLMEDNA-N

SMILES

C12OC(C=C(C)C=1C=CC(O[C@H]1[C@H](O)[C@H]([C@@H](O)[C@@H](CO)O1)O)=C2)=O |&1:11,12,14,15,17,r|

CAS DataBase Reference

18997-57-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

T+

Risk Statements 

26/27/28

Safety Statements 

22-24/25

WGK Germany 

3

F 

3-10-21

HS Code 

29389090

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

4-Methylumbelliferyl-beta-D-glucopyranoside Usage And Synthesis

Description

4-Methylumbelliferyl-β-D-Glucopyranoside (4-MUG) is a fluorogenic substrate of β-glucosidase and β-glucocerebrosidase (also known as glucosylceramidase). In addition to its use in characterizing novel β-glucosidases, 4-MUG is used in assays to evaluate deficiency in β- glucocerebrosidase activity related to Gaucher disease. Hydrolysis of 4-MUG releases the fluorescent product 4-MU, which has an emission maximum at 445-454 nm. The excitation maximum for 4-MU is pH-dependent: 330, 370, and 385 nm at pH 4.6, 7.4, and 10.4, respectively.

Chemical Properties

White Powder

Uses

A fluorogenic substrate in the assay of ?-glucosidase. Fluorescence: max. Abs. 316nm; max. Em. 372nm; e x 10-3: 15

Uses

4-Methylumbelliferyl β-D-glucopyranoside has been used as substrate:

• in glucosylceramidase β enzyme activity assay in lysosome-enriched fractions from primary hippocampal neurons
• in β-glucosidase assay during yeast fermentation
• to assay glucocerebrosidase 1 (GBA1)-related glucosidase activity in macrophage cell line (RAW)

Uses

A fluorogenic substrate in the assay of ?-glucosidase.Fluorescence: max. Abs. 316nm; max. Em. 372nm; e x 10-3: 15

Definition

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

Biochem/physiol Actions

4-Methylumbelliferyl β-D-glucopyranoside is a synthetic enzymatic substrate for glycosidase. It has been used as substrate for the β- glucosidase from enterococci.

Purification Methods

4-Methylumbellifer-7-yl--Dglucopyranoside crystallises as the half hydrate from hot H2O. [Constantzas & Kocourek Collect Czech Chem Commun 24 1099 1959, De Re et al. Ann Chim (Rome) 4 9 2089 1959, Courtin-Duchateau & Veyrière Carbohydr Research 65 23, 29 1978, Beilstein 18 III/IV 5152, 8 IV 433, 18/7 V 616.]

References

[1] ALICIA HERNáNDEZ-GUZMáN. Purification and characterization of an extracellular β-glucosidase from Sporothrix schenckii[J]. FEBS Open Bio, 2016, 6 11: 1067-1077. DOI: 10.1002/2211-5463.12108
[2] RADOS?AW KWAPISZEWSKI. A microfluidic device with fluorimetric detection for intracellular components analysis[J]. Biomedical Microdevices, 2011, 13 3: 431-440. DOI: 10.1007/s10544-011-9511-0
[3] MEERA SHANMUGANATHAN  Philip B M. Inhibitor screening of pharmacological chaperones for lysosomal β-glucocerebrosidase by capillary electrophoresis[J]. Analytical and Bioanalytical Chemistry, 2011, 399 8: 2843-2853. DOI: 10.1007/s00216-011-4671-6

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