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M1508

Sigma-Aldrich

4-Methylumbelliferone sodium salt

fluorogenic, ≥98% (HPLC), crystalline

Synonym(s):

β-Methylumbelliferone, 7-Hydroxy-4-methylcoumarin

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About This Item

Linear Formula:
C10H7O3Na
CAS Number:
Molecular Weight:
198.15
EC Number:
MDL number:
UNSPSC Code:
12352204
PubChem Substance ID:
NACRES:
NA.32

product name

4-Methylumbelliferone sodium salt, ≥98% (HPLC), crystalline

Assay

≥98% (HPLC)

form

crystalline

color

yellow

solubility

water: 50 mg/mL

SMILES string

[Na+].CC1=CC(=O)Oc2cc([O-])ccc12

InChI

1S/C10H8O3.Na/c1-6-4-10(12)13-9-5-7(11)2-3-8(6)9;/h2-5,11H,1H3;/q;+1/p-1

InChI key

JGMQHDNPUCPRQE-UHFFFAOYSA-M

General description

4-methylumbelliferone (4-MU) is a coumarin derivative.

Application

4-Methylumbelliferone sodium salt has been used:
  • as a substrate to analyze the enzyme kinetics of its glucuronidation in the human liver
  • as a standard to quantify the free 4-methylumbelliferone released as a result of enzyme-substrate action
  • in cell survival assay to inhibit hyaluronan (HA) production and to study its effect on chemoresistance in ovarian cancer

Biochem/physiol Actions

4-methylumbelliferone (4-MU) serves as a hyaluronan (HA) synthesis blocker. It exhibits anti-inflammatory, anti-fibrogenic, and antitumor properties. 4-MU is used to treat biliary spasms and might also be beneficial in nonalcoholic steatohepatitis (NASH), inflammation, hepatocyte injury, and fibrotic response. 4-MU is known to be glucuronidated by most of the uridine 5ฺ-diphospho-glucuronosyltransferase (UGT) isoforms of the human liver. This makes it a potent probe substrate to examine the overall hepatic UGTs activity.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Valérie Jaulneau et al.
Journal of biomedicine & biotechnology, 2010, 525291-525291 (2010-05-07)
The industrial use of elicitors as alternative tools for disease control needs the identification of abundant sources of them. We report on an elicitor obtained from the green algae Ulva spp. A fraction containing most exclusively the sulfated polysaccharide known
Ai-Sheng Xiong et al.
PloS one, 6(11), e26773-e26773 (2011-11-19)
A β-glucuronidase variant, GUS-TR3337, that was obtained by directed evolution exhibited higher thermostability than the wild-type enzyme, GUS-WT. In this study, the utility of GUS-TR337 as an improved reporter was evaluated. The corresponding gus-tr3337 and gus-wt genes were independently cloned
Gale E Smith et al.
Virology, 509, 90-97 (2017-06-19)
Avian influenza A (H5N1) viruses represent a growing threat for an influenza pandemic. The presence of widespread avian influenza virus infections further emphasizes the need for vaccine strategies for control of pre-pandemic H5N1 and other avian influenza subtypes. Influenza neuraminidase
Matías A Pibuel et al.
Glycobiology, 31(1), 29-43 (2020-05-31)
Glioblastoma (GBM), the most frequent primary tumor of the central nervous system, has a median survival of 14.6 months. 4-Methylumbelliferone (4MU) is a coumarin derivative widely used as a hyaluronan synthesis inhibitor with proven antitumor activity and without toxic effects reported.
Rebecca M DuBois et al.
PLoS pathogens, 7(12), e1002398-e1002398 (2011-12-07)
Highly pathogenic avian influenza viruses of the H5N1 subtype continue to threaten agriculture and human health. Here, we use biochemistry and x-ray crystallography to reveal how amino-acid variations in the hemagglutinin (HA) protein contribute to the pathogenicity of H5N1 influenza

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