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55155

Sigma-Aldrich

7-Hydroxycoumarin-3-carboxylic acid

suitable for fluorescence, ≥98.0% (capillary electrophoresis)

Sinónimos:

Umbelliferone-3-carboxylic acid

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About This Item

Fórmula empírica (notación de Hill):
C10H6O5
Número de CAS:
779-27-1
Peso molecular:
206.15
Beilstein/REAXYS Number:
384141
MDL number:
MFCD00017491
UNSPSC Code:
12352106
PubChem Substance ID:
57651515
NACRES:
NA.32

assay

≥98.0% (capillary electrophoresis)

form

solid

pKa 

7.04

mp

261 °C (lit.)

solubility

DMF: soluble
DMSO: soluble
alcohols: soluble

fluorescence

λex 342 nm; λem 447 nm (pH 4.0)
λex 386 nm; λem 448 nm in 0.1 M Tris pH 9.0

suitability

suitable for fluorescence

SMILES string

OC(=O)C1=Cc2ccc(O)cc2OC1=O

InChI

1S/C10H6O5/c11-6-2-1-5-3-7(9(12)13)10(14)15-8(5)4-6/h1-4,11H,(H,12,13)

InChI key

LKLWLDOUZJEHDY-UHFFFAOYSA-N

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Application

7-Hydroxycoumarin-3-carboxylic acid (7-OHCCA) is used as a fluorogenic substrate for glycosyltransferase assays. 7-OHCCA may be used as a non-cinnamate-class substrate analog to study 4-hydroxycinnamate decarboxylase (4-HCD)-inducing activity in Klebsiella oxytoca cells. It is suitable as a pH indicator.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

Immobilized on a support to give a pH sensor

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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H. Offenbacher et al.
Sens. Actuators, 9, 73-73 (1986)
Yuichiro Hori et al.
Journal of the American Chemical Society, 131(46), 16610-16611 (2009-11-03)
Protein labeling provides significant information about protein function. In this research, we developed a novel protein labeling technique by utilizing photoactive yellow protein (PYP). PYP is a small protein (14 kDa) derived from purple bacteria and binds to 7-hydroxycoumarin-3-carboxylic acid
K Higai et al.
Biological & pharmaceutical bulletin, 22(4), 333-338 (1999-05-18)
We developed a novel fluorometric assay method for the measurement of glycosyltransferase activities using mono- and di-saccharides aminated and tagged with 7-hydroxycoumarin-3-carboxylic acid (coumarin) as substrates, N-acetylglucosamine (GlcNAc)-coumarin for beta1,4-galactosyltransferase from bovine milk and Gal beta1-4GlcNAc-coumarin for alpha2,3- and alpha2,6-sialyltransferases
Y Hashidoko et al.
Bioscience, biotechnology, and biochemistry, 65(12), 2604-2612 (2002-02-06)
The 4-hydroxycinnamate decarboxylase (4-HCD)-inducing activity of several substrate analogs toward Klebsiella oxytoca was investigated. Four E-cinnamate-class compounds, E-4-hydroxycinnamic acid (1), caffeic acid (2), ferulic acid (3) and E-2,4-dihydroxycinnamic acid (4), all of which were accepted as substrates, all of which
Wei-Hai Chen et al.
ACS nano, 12(8), 7538-7545 (2018-07-04)
Zeolitic Zn2+-imidazolate cross-linked framework nanoparticles, ZIF-8 NMOFs, are used as "smart" glucose-responsive carriers for the controlled release of drugs. The ZIF-8 NMOFs are loaded with the respective drug and glucose oxidase (GOx), and the GOx-mediated aerobic oxidation of glucose yields
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