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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:
5980-33-6
Molecular Weight:
198.15
EC Number:
227-790-1
MDL number:
MFCD00069856
UNSPSC Code:
12352204
PubChem Substance ID:
24896658
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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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
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.
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
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.
Peter Pushko et al.
Virology, 501, 176-182 (2016-12-10)
Avian influenza (AI) viruses circulating in wild birds pose a serious threat to public health. Human and veterinary vaccines against AI subtypes are needed. Here we prepared triple-subtype VLPs that co-localized H5, H7 and H9 antigens derived from H5N1, H7N3
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