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28605

3-Cyanoumbelliferone

Name: 3-Cyanoumbelliferone
Brand: SIGMA

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

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product line

BioReagent

Quality Level

100

assay

≥98.0% (TLC)

form

powder

solubility

DMF: soluble, alcohols: soluble

fluorescence

λ_ex 408 nm; λ_em 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

GHS07

signalword

Warning

hcodes

H302 + H312 + H332,H315,H319,H335

pcodes

P261 - P280 - P301 + P312 - P302 + P352 + P312 - P304 + P340 + P312 - P305 + P351 + P338

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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Gossypol toxicity and detoxification in Helicoverpa armigera and Heliothis virescens.

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.

Differences in cytochrome P450 enzyme activities between fish and crustacea: relationship with the bioaccumulation patterns of polychlorobiphenyls (PCBs).

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

Cyp1 Inhibition Prevents Doxorubicin-Induced Cardiomyopathy in a Zebrafish Heart-Failure Model.

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

Ionic effects on the proton transfer mechanism in aqueous solutions.

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.

Assessment of cytochrome P450 fluorometric substrates with rainbow trout and killifish exposed to dexamethasone, pregnenolone-16alpha-carbonitrile, rifampicin, and beta-naphthoflavone.

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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Global Trade Item Number

SKU	GTIN
28605-500MG	04061833488850
28605-100MG	04061826259696

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