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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

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

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
384040/1
365730/1
070884/1

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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
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
H. Offenbacher et al.
Sens. Actuators, 9, 73-73 (1986)
Hang Wang et al.
European journal of mass spectrometry (Chichester, England), 22(1), 19-29 (2016-02-11)
Mass spectrometry has been applied to the targeted analysis of commonly used additives (such as Irganox 1010, Irganox 1076, Irgafos 168, etc.) in plastic materials, but a fast and straightforward method for the non-targeted identification and quantification of unusual or
Kateřina Tomanová et al.
Physical chemistry chemical physics : PCCP, 19(43), 29402-29408 (2017-10-28)
Formation yields of ˙OH radicals were precisely determined in aqueous solutions of coumarin-3-carboxylic acid and ferrous sulfate (i.e., Fricke dosimeter) exposed to 253.7 nm radiation delivered from a continuous source. Quantum yield of ˙OH radicals was determined as ∼0.08, i.e.
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