M1381

Sigma-Aldrich

4-Methylumbelliferone

≥98%

Synonym(s):
β-Methylumbelliferone, 4-MU, 7-Hydroxy-4-methylcoumarin
Empirical Formula (Hill Notation):
C10H8O3
CAS Number:
Molecular Weight:
176.17
Beilstein/REAXYS Number:
142217
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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.

Packaging

25, 100 g in poly bottle

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

Pyranocoumarins: A new class of anti-hyperglycemic and anti-dyslipidemic agents.
Kumar A, et al.
Bioorganic & Medicinal Chemistry Letters, 19(22), 6447-6451 (2009)
Joseph E Agbaji et al.
AAS open research, 3, 7-7 (2020-10-24)
Background: Environmental sustainability is the driver for finding the optimal bioremediation cocktail with the combination of highly potent hydrocarbonoclastic strains and the nutrient additives that significantly enhance mineralization of crude oil in polluted soil in order to mitigate its deleterious...
Yiyi Liu et al.
ACS nano, 13(6), 6760-6769 (2019-05-31)
Thiol-polystyrene (SH-PS)-capped plasmonic nanoparticles can be fabricated into free-standing, one-nanoparticle-thick superlattice sheets (termed plasmene) based on physical entanglement between ligands, which, however, suffer from irreversible dissociation in organic solvents. To address this issue, we introduce coumarin-based photo-cross-linkable moieties to the...
Na+ triggered fluorescence sensors for Mg2+ detection based on a coumarin salen moiety.
Dong Y, et al.
Organic Letters, 13(9), 2252-2255 (2011)
Tz-Ching Yeh et al.
Freshwater biology, 65(11), 1973-1988 (2020-12-09)
Bamboo, as a pioneer vegetation, often forms forests on bare lands after catastrophic landslides. Compared to evergreen forest soil, bamboo forest soil is much more labile, with a higher percentage of microbially derived organic carbon (OC), lower molecular weight, and...

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