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46121

Sigma-Aldrich

Resorufin ethyl ether

suitable for fluorescence, ≥95% (UV)

Synonyma:

7-Ethoxy-3H-phenoxazin-3-one, Ethoxyresorufin, O7-Ethylresorufin

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About This Item

Empirický vzorec (Hillův zápis):
C14H11NO3
Číslo CAS:
5725-91-7
Molekulová hmotnost:
241.24
Beilstein/REAXYS Number:
225973
MDL number:
MFCD00037661
UNSPSC Code:
12161501
PubChem Substance ID:
329757074
NACRES:
NA.32

assay

≥95% (UV)

form

solid

mp

223-225 °C (lit.)

solubility

DMF: soluble
DMSO: soluble
alcohols: soluble

fluorescence

λex 464 nm; λem 540 nm in methanol(lit.)
λex 571 nm; λem 585 nm in dealkylase(lit.)

suitability

suitable for fluorescence

storage temp.

2-8°C

SMILES string

CCOc1ccc2N=C3C=CC(=O)C=C3Oc2c1.Fc4c(F)c(F)c(OC(=O)CNC(=O)OCC5c6ccccc6-c7ccccc57)c(F)c4F

InChI

1S/C23H14F5NO4.C14H11NO3/c24-17-18(25)20(27)22(21(28)19(17)26)33-16(30)9-29-23(31)32-10-15-13-7-3-1-5-11(13)12-6-2-4-8-14(12)15;1-2-17-10-4-6-12-14(8-10)18-13-7-9(16)3-5-11(13)15-12/h1-8,15H,9-10H2,(H,29,31);3-8H,2H2,1H3

Inchi Key

ZOSYTBPPLWBBKM-UHFFFAOYSA-N

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Application

7-Ethoxyresorufin (7-ER) is a substrate used in environmental toxicology studies to monitor ethoxyresorufin-O-deethylase catalytic activity in the EROD assay. The EROD assay monitors the induction of the xenobiotic-metabolizing enzyme cytochrome P-450 (CYP) 1A1 and is a widely used biomarker for exposure of wildlife to substances that bind the aryl hydrocarbon (Ah) receptor. It provides evidence of receptor-mediated induction of cytochrome P450-dependant monooxygenases (the CYP1A subfamily specifically) by xenobiotic chemicals.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

Dealkylase substrate for the microfluorimetric analysis of microsomal cytochrome P-450

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Osvědčení o analýze (COA)

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Sigma-Aldrich

287897

Dicoumarol

3-Methylcholanthrene 98%

Sigma-Aldrich

213942

3-Methylcholanthrene

3-Methylcholanthrene solution 100 μg/mL in acetonitrile, PESTANAL®, analytical standard

Supelco

46434

3-Methylcholanthrene solution

Markus Brinkmann et al.
Aquatic toxicology (Amsterdam, Netherlands), 128-129, 13-24 (2012-12-25)
Increasing frequency and intensity of flood events are major concerns in the context of climate change. In addition to the direct hydrological implications of such events, potential ecotoxicological impacts are of increasing interest. It is vital to understand mechanisms of
Gillian E Manning et al.
Toxicology and applied pharmacology, 266(1), 38-47 (2012-11-13)
Avian-specific toxic equivalency factors (TEFs) were developed by the World Health Organization to simplify environmental risk assessments of dioxin-like compounds (DLCs), but TEFs do not account for differences in the toxic and biochemical potencies of DLCs among species of birds.
M D Burke et al.
The Biochemical journal, 212(1), 15-24 (1983-04-15)
A fluorescence-microscopic method has been developed for measurement of the intracellular kinetics of the cytochrome P-450 reaction, ethoxyresorufin O-de-ethylation, in individual hepatocytes in unfixed non-frozen liver sections obtained from control or 3-methylcholanthrene-pretreated mice. De-ethylation was enhanced in the presence of
J J Whyte et al.
Critical reviews in toxicology, 30(4), 347-570 (2000-08-24)
This review compiles and evaluates existing scientific information on the use, limitations, and procedural considerations for EROD activity (a catalytic measurement of cytochrome P4501A induction) as a biomarker in fish. A multitude of chemicals induce EROD activity in a variety
T E M Parente et al.
Comparative biochemistry and physiology. Toxicology & pharmacology : CBP, 150(2), 252-260 (2009-05-23)
We investigated the presence and inducibility of CYP1A in suckermouth catfish (Hypostomus affinis and Hypostomus auroguttatus, Loricariidae), tilapia (Oreochromis niloticus, Cichlidae) and mice (Mus musculus, Muridae). Alkoxyresorufin-O-dealkylases (EROD, MROD, PROD and BROD) were detected and proved to be inducible (beta-naphthoflavone
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