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T2803

Sigma-Aldrich

7-Ethoxy-4-(trifluoromethyl)coumarin

≥98% (TLC), powder

Synonym(s):

Ethyl 4-(trifluoromethyl)umbelliferyl ether

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About This Item

Empirical Formula (Hill Notation):
C12H9F3O3
CAS Number:
115453-82-2
Molecular Weight:
258.19
Beilstein/REAXYS Number:
8555209
MDL number:
MFCD00467588
UNSPSC Code:
12352204
PubChem Substance ID:
24900082
NACRES:
NA.32

product name

7-Ethoxy-4-(trifluoromethyl)coumarin, ≥98% (TLC)

assay

≥98% (TLC)

form

powder

solubility

chloroform: 100 mg/mL, clear, colorless (Soluble in chloroform, methanol, and DMSO.)

fluorescence

λex 333 nm; λem 415 nm in methanol

storage temp.

−20°C

SMILES string

CCOc1ccc2c(OC(=O)C=C2C(F)(F)F)c1

InChI

1S/C12H9F3O3/c1-2-17-7-3-4-8-9(12(13,14)15)6-11(16)18-10(8)5-7/h3-6H,2H2,1H3

InChI key

OLHOIERZAZMHGK-UHFFFAOYSA-N

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Features and Benefits

7-Ethoxy-4-(trifluoromethyl)coumarin is a fluorogenic substrate for cytochrome P-450 catalyzed O-de-ethylation.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

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)

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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J G DeLuca et al.
Biochemical pharmacology, 37(9), 1731-1739 (1988-05-01)
The microsomal O-deethylation of a novel coumarin analog, 7-ethoxy-4-trifluoromethylcoumarin (EFC), to a fluorescent product was characterized. Results indicate that this analog provides a rapid, convenient and highly sensitive means to assay cytochrome P-450-mediated metabolism. Like microsomal 7-ethoxycoumarin (7-EC) O-deethylation, EFC
S Löfgren et al.
Xenobiotica; the fate of foreign compounds in biological systems, 34(9), 811-834 (2005-03-04)
The aim was to characterize mouse gender and strain differences in the metabolism of commonly used human cytochrome (CYP) P450 probe substrates. Thirteen human CYP probe substrates (phenacetin, coumarin, 7-ethoxy-4-trifluoromethyl coumarin, amiodarone, paclitaxel, diclofenac, S-mephenytoin, bufuralol, dextromethorphan, chlorzoxazone, p-nitrophenol, testosterone
E S Roberts et al.
Chemical research in toxicology, 11(9), 1067-1074 (1998-10-07)
The addition of peroxynitrite to purified cytochrome P450 2B1 resulted in a concentration-dependent loss of the NADPH- and reductase-supported or tert-butylhydroperoxide-supported 7-ethoxy-4-(trifluoromethyl)coumarin O-deethylation activity of P450 2B1 with IC50 values of 39 and 210 microM, respectively. After incubation of P450
Thomas Van Leeuwen et al.
Pest management science, 62(5), 425-433 (2006-03-22)
Tetranychus urticae Koch has recently developed resistance to chlorfenapyr in Australia and Japan, but no attempt has yet been made to describe the biochemical mechanisms involved in chlorfenapyr resistance. In this study a laboratory-selected chlorfenapyr-resistant strain was investigated. Resistance to
Maori Mitsuda et al.
Protein expression and purification, 46(2), 401-405 (2005-11-29)
Improvement of CYP2B6 expression was examined by co-expression with molecular chaperones GroES/EL. Although a CO-reduced difference spectrum was not detected in Escherichia coli transformed only by the CYP2B6-expressing vector, co-expression of GroES/EL resulted in high-level expression which reached over 2000
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