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H24003

Sigma-Aldrich

Umbelliferone

99%

Synonym(s):

7-Hydroxy-2H-1-benzopyran-2-one, 7-Hydroxycoumarin

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About This Item

Empirical Formula (Hill Notation):
C9H6O3
CAS Number:
93-35-6
Molecular Weight:
162.14
Beilstein:
127683
EC Number:
202-240-3
MDL number:
MFCD00006878
UNSPSC Code:
12352100
PubChem Substance ID:
24895162
NACRES:
NA.22

Assay

99%

mp

230 °C (dec.) (lit.)

solubility

dioxane: soluble
ethanol: soluble

SMILES string

Oc1ccc2C=CC(=O)Oc2c1

InChI

1S/C9H6O3/c10-7-3-1-6-2-4-9(11)12-8(6)5-7/h1-5,10H

InChI key

ORHBXUUXSCNDEV-UHFFFAOYSA-N

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Application

Umbelliferone can be used:
  • To synthesize fluorescent probes to detect cyanide anions in water at biological pH and for in vitro and in vivo detection of hydrogen peroxide.
  • In the preparation of coumarin-based polymer as optical data storage material.
  • As a precursor to synthesize novobiocin derivatives that exhibit antibacterial agents as well as inhibitors of DNA gyrase.
  • As the starting material to synthesize (+)-decursinol and (+)-angelmarin.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCG7078
BCCF0538
BCCC1923
MKCK6766
MKCK5425

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Fluorescent chemodosimeter for selective detection of cyanide in water.
Lee K S, et al.
Organic Letters, 10(1), 49-51 (2008)
Reversible two-photon optical data storage in coumarin-based copolymers.
Iliopoulos K, et al.
Journal of the American Chemical Society, 132(41), 14343-14345 (2010)
An efficient synthesis of (+)-decursinol from umbelliferone.
Lee J H, et al.
Tetrahedron Letters, 48(16), 2889-2892 (2007)
Total synthesis of (+)-angelmarin.
Magolan J and Coster M J
The Journal of Organic Chemistry, 74(14), 5083-5086 (2009)
Novobiocin: redesigning a DNA gyrase inhibitor for selective inhibition of hsp90.
Burlison J A, et al.
Journal of the American Chemical Society, 128(48), 15529-15536 (2006)
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