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Merck
CN

28605

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
UNSPSC Code:
12352108
NACRES:
NA.32
PubChem Substance ID:
57648313
MDL number:
MFCD00037480
Beilstein/REAXYS Number:
153271

Key Documents

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Product Name

3-Cyanoumbelliferone, BioReagent, suitable for fluorescence, ≥98.0% (TLC)

InChI

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

SMILES string

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

InChI key

IJQYTHQDUDCJEQ-UHFFFAOYSA-N

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

Quality Level

100

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
BCCD8354
BCCC4530
1416841V
BCBM5012V
1369184V

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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.
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.
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
Gowtham Sathyanarayanan et al.
Analytical chemistry, 92(21), 14693-14701 (2020-10-27)
The superfamily of hepatic cytochrome P450 (CYP) enzymes is responsible for the intrinsic clearance of the majority of therapeutic drugs in humans. However, the kinetics of drug clearance via CYPs varies significantly among individuals due to both genetic and external
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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