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55155

Sigma-Aldrich

7-Hydroxycoumarin-3-carboxylic acid

suitable for fluorescence, ≥98.0% (capillary electrophoresis)

Synonym(s):

Umbelliferone-3-carboxylic acid

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About This Item

Empirical Formula (Hill Notation):
C10H6O5
CAS Number:
779-27-1
Molecular Weight:
206.15
Beilstein:
384141
MDL number:
MFCD00017491
UNSPSC Code:
12352106
PubChem Substance ID:
57651515
NACRES:
NA.32
Pricing and availability is not currently available.

Quality Level

100

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[1]

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL1120
BCCK2238
365730/1
070884/1
384040/1

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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
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
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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