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M1381

Sigma-Aldrich

4-Methylumbelliferone

≥98%

Synonym(s):

β-Methylumbelliferone, 4-MU, 7-Hydroxy-4-methylcoumarin

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About This Item

Empirical Formula (Hill Notation):
C10H8O3
CAS Number:
90-33-5
Molecular Weight:
176.17
Beilstein/REAXYS Number:
142217
EC Number:
201-986-7
MDL number:
MFCD00006866
UNSPSC Code:
12352100
PubChem Substance ID:
57654353
NACRES:
NA.22

assay

≥98%

color

off-white to yellow

fluorescence

λex 372 nm; λem 445 nm in ethanol

SMILES string

CC1=CC(=O)Oc2cc(O)ccc12

InChI

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

InChI key

HSHNITRMYYLLCV-UHFFFAOYSA-N

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Application

4-Methylumbelliferone is primarily used in synthesizing medicinal compounds and as a building block for fluorescent probes. Applications include synthesis of:
  • coumarin triazole derivatives as potential antimicrobial agents.
  • coumarin salen-based fluorescence sensors for Mg2+ detection.
  • pyranocoumarin derivatives as anti-hyperglycemic and anti-dyslipidemic agents.
  • coumarin piperazine derivatives as potential multireceptor atypical antipsychotics.
  • 4-methylumbelliferyl T-antigen as a substrate for endo-α-N-acetylgalactosaminidase.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

ppe

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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Na+ triggered fluorescence sensors for Mg2+ detection based on a coumarin salen moiety.
Dong Y, et al.
Organic Letters, 13(9), 2252-2255 (2011)
Synthesis and evaluation of a class of new coumarin triazole derivatives as potential antimicrobial agents.
Shi Y and Zhou C-H
Bioorganic & Medicinal Chemistry Letters, 21(3), 956-960 (2011)
Pyranocoumarins: A new class of anti-hyperglycemic and anti-dyslipidemic agents.
Kumar A, et al.
Bioorganic & Medicinal Chemistry Letters, 19(22), 6447-6451 (2009)
Yutaka Yoshioka et al.
Arthritis and rheumatism, 65(5), 1160-1170 (2013-01-22)
To clarify the roles of hyaluronan (HA) in joint inflammation and the process of joint destruction, using 4-methylumbelliferone (4-MU), an inhibitor of HA synthesis, in a mouse model of collagen-induced arthritis (CIA) and in a monolayer culture of fibroblast-like synoviocytes
Di-tert-butylsilylene-directed α-selective synthesis of 4-methylumbelliferyl T-antigen.
Imamura A, et al.
Organic Letters, 7(20), 4415-4418 (2005)
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