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28605

Sigma-Aldrich

3-Cyanoumbelliferone

BioReagent, suitable for fluorescence, ≥98.0% (TLC)

Synonym(s):

3-Cyano-7-hydroxycoumarin

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About This Item

Empirical Formula (Hill Notation):
C10H5NO3
CAS Number:
19088-73-4
Molecular Weight:
187.15
Beilstein:
153271
MDL number:
MFCD00037480
UNSPSC Code:
12352108
PubChem Substance ID:
57648313
NACRES:
NA.32

product line

BioReagent

Assay

≥98.0% (TLC)

form

powder

mp

≥250 °C (lit.)

solubility

DMF: soluble
alcohols: soluble

fluorescence

λex 408 nm; λem 450 nm in methanol

suitability

suitable for fluorescence

SMILES string

Oc1ccc2C=C(C#N)C(=O)Oc2c1

InChI

1S/C10H5NO3/c11-5-7-3-6-1-2-8(12)4-9(6)14-10(7)13/h1-4,12H

InChI key

IJQYTHQDUDCJEQ-UHFFFAOYSA-N

Gene Information

human ... MIF(4282)

Application

3-Cyano-7-hydroxycoumarin is closely related to 3-cyano-7-ethoxycoumarin which is used as a fluorometric substrate and inhibitor for cytochrome P-450 enzymes and cytochrome P-450-dependent mixed function oxidases. 3-Cyano-7-hydroxycoumarin may be useful to study the kinetics and substrate specificity of cytochrome P-450s.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - 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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Pui-Ying Lam et al.
Chembiochem : a European journal of chemical biology, 21(13), 1905-1910 (2020-02-01)
Doxorubicin is a highly effective chemotherapy agent used to treat many common malignancies. However, its use is limited by cardiotoxicity, and cumulative doses exponentially increase the risk of heart failure. To identify novel heart failure treatment targets, a zebrafish model
Samuel Koenig et al.
Aquatic toxicology (Amsterdam, Netherlands), 108, 11-17 (2011-11-19)
Variations in cytochrome P450 enzyme (CYPs) distribution and function between animal groups could result in differential metabolism and elimination kinetics for certain contaminants. Although a number of studies have suggested that differences in polychlorobiphenyl (PCB) accumulation profiles between crustacea and
Ilana Berger et al.
PloS one, 6(11), e26794-e26794 (2011-11-10)
Cytosolic sulfotransferases (SULTs) are mammalian enzymes that detoxify a wide variety of chemicals through the addition of a sulfate group. Despite extensive research, the molecular basis for the broad specificity of SULTs is still not understood. Here, structural, protein engineering
Corinna Krempl et al.
Insect biochemistry and molecular biology, 78, 69-77 (2016-10-18)
Gossypol is a polyphenolic secondary metabolite produced by cotton plants, which is toxic to many organisms. Gossypol's aldehyde groups are especially reactive, forming Schiff bases with amino acids of proteins and cross-linking them, inhibiting enzyme activities and contributing to toxicity.
I N White
Analytical biochemistry, 172(2), 304-310 (1988-08-01)
A direct fluorometric procedure for the continuous determination of cytochrome P-450-dependent mixed function oxidases, using 3-cyano-7-ethoxycoumarin substrate, is described. The reaction product, 3-cyano-7-hydroxycoumarin, is fluorescent at neutral pH values (excitation and emission wavelength maxima: 408 and 450 nm, respectively). Using
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