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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/REAXYS Number:
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

signalword

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

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

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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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.
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
Joonyoung F Joung et al.
Physical chemistry chemical physics : PCCP, 19(37), 25509-25517 (2017-09-14)
Proton dissociation (PD) reactions of weak acids and proton transfer (PT) processes in aqueous solutions are strongly influenced by ions. However, a detailed molecular picture that describes how ions affect the rates of PD and PT processes is still missing.
Jay J Agarwal et al.
PloS one, 8(5), e63028-e63028 (2013-05-15)
TRAM-34, a clotrimazole analog characterized as a potent and selective inhibitor of intermediate-conductance, calcium-activated K(+) (IKCa) channels, has been used extensively in vitro and in vivo to study the biological roles of these channels. The major advantage of TRAM-34 over
Emily M Smith et al.
Aquatic toxicology (Amsterdam, Netherlands), 97(4), 324-333 (2010-02-20)
Cytochrome P450s (CYPs) are important xenobiotic metabolizing proteins. While their functions are well understood in mammals, CYP function in non-mammalian vertebrate systems is much less defined, with function often inferred from mammalian data, assuming similar function across vertebrate species. In
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