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E3763

Sigma-Aldrich

Resorufin ethyl ether

≥98% (TLC), powder

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
Beilstein:
225973
MDL number:
MFCD00037661
UNSPSC Code:
12161501
PubChem Substance ID:
24894527
NACRES:
NA.47

Quality Level

200

Assay

≥98% (TLC)

form

powder

storage condition

(Tightly closed. Dry)

technique(s)

activity assay: suitable

color

orange to red

mp

223-225 °C (lit.)

solubility

chloroform: 9.80-10.20 mg/mL, clear, orange

suitability

suitable for fluorescence

storage temp.

−20°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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General description

Resorufin ethers are used as markers or substrates for different cytochrome P (CYP) isoforms. Resorufin ethyl ether is the preferred resorufin ether to be metabolized by microsomes of 3-methylcholanthrene treated animals.
Resorufin is the reduced product of resazurin, also termed as Alamar Blu. It exhibits fluorescence at longer wavelengths and is flexible for modification in its hydroxyl group.

Research area: Cell Signaling

Application

Resorufin ethyl ether is suitable for the study of dealkylating activity of cytochrome P450 isozymes 1A1 and 1A2, where arylalkyl and alkyl isothiocyanates, and their glutathione, cysteine, and A′-acetylcysteine conjugates are used as inhibitors. It is suitable to study the ethoxyresorufin-O-deethylase (EROD) activity of cytochrome P450 activity (CYP1A1).

Substrates

Fluorimetric substrate for cytochrome P450 linked enzyme, CXPIA1/2

substrate

Product No.
Description
Pricing

M1544

Resorufin methyl ether

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

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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C C Conaway et al.
Carcinogenesis, 17(11), 2423-2427 (1996-11-01)
A series of arylalkyl and alkyl isothiocyanates, and their glutathione, cysteine, and N-acetylcysteine conjugates were used to study their inhibitory activity toward the dealkylation of ethoxyresorufin (EROD), pentoxyresorufin (PROD), and methoxyresorufin (MROD) in liver microsomes obtained from the 3-methylcholanthrene or
Reduction of resazurin to resorufin catalyzed by gold nanoparticles: dramatic reaction acceleration by laser or LED plasmon excitation
Alejo CJ, et al.
Catalysis Science & Technology, 1(8), 1506-1511 (2011)
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
V Villa-Cruz et al.
Chemosphere, 74(9), 1145-1151 (2009-01-16)
Tilapia fish (Oreochromis niloticus) were fed with enriched diets containing broccoli and its phytochemical sulforaphane over 30 d. The levels of cytochrome P450, superoxide dismutase, catalase, lipid peroxidation and glutathione-S-transferase activities were measured. Basal value of cytochrome P450 activity was
Shotaro Uehara et al.
The Journal of pharmacology and experimental therapeutics, 339(2), 654-661 (2011-08-19)
The cynomolgus monkey is widely used as a primate model in preclinical studies because of its evolutionary closeness to humans. Despite their importance in drug metabolism, the content of each cytochrome P450 (P450) enzyme has not been systematically determined in
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