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Merck
CN

46121

Resorufin ethyl ether

suitable for fluorescence, ≥95% (UV)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C14H11NO3
CAS Number:
5725-91-7
Molecular Weight:
241.24
UNSPSC Code:
12161501
NACRES:
NA.32
PubChem Substance ID:
329757074
MDL number:
MFCD00037661
Beilstein/REAXYS Number:
225973

Key Documents

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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

SMILES string

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

InChI key

ZOSYTBPPLWBBKM-UHFFFAOYSA-N

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

Quality Level

100

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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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCCP0264
BCCH6416
BCCD1452
BCBW8237
BCBT3131

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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
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.
J J Reiners et al.
Analytical biochemistry, 188(2), 317-324 (1990-08-01)
An assay was characterized that facilitated per-cell estimation of cytochrome P-450-dependent monooxygenase activities in whole-cell suspensions and cultures of murine epidermal keratinocytes (MEKs). 7-Ethoxycoumarin O-deethylase (7-ECD), 7-ethoxyresorufin O-deethylase (7-ERD), and 7-pentoxyresorufin O-deethylase (7-PRD) activities were monitored by fluorescent detection 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
Ahmad F Abdull Razis et al.
Archives of toxicology, 86(10), 1505-1514 (2012-05-31)
As the Ah receptor target gene products play a critical role in chemical carcinogenesis, antagonists are considered as potential chemopreventive agents. It is demonstrated in this paper that the isothiocyanates R,S-sulforaphane and erucin are non-competitive antagonists of the aryl hydrocarbon
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