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E1379

Sigma-Aldrich

7-Ethoxycoumarin

Synonym(s):

7-Ethoxy-1-benzopyran-2-one

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About This Item

Empirical Formula (Hill Notation):
C11H10O3
CAS Number:
31005-02-4
Molecular Weight:
190.20
Beilstein:
146200
EC Number:
250-429-4
MDL number:
MFCD00006877
UNSPSC Code:
12161501
PubChem Substance ID:
24894404
NACRES:
NA.77

Assay

≥99.45% (HPLC)

form

powder

mp

88-90 °C (lit.)

solubility

95% ethanol: 50 mg/mL, clear to slightly hazy, colorless to faintly yellow

fluorescence

λex 323 nm; λem 386 nm

SMILES string

CCOc1ccc2C=CC(=O)Oc2c1

InChI

1S/C11H10O3/c1-2-13-9-5-3-8-4-6-11(12)14-10(8)7-9/h3-7H,2H2,1H3

InChI key

LIFAQMGORKPVDH-UHFFFAOYSA-N

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Application

7-Ethoxycoumarin has been used to study the functional activity of recombinant P450. ) It has also been used as an internal standard for in vitro S-warfarin 7-hydroxylation and high performance liquid chromatography (HPLC) analysis.

Biochem/physiol Actions

7-Ethoxycoumarin is a cytochrome P450 substrate.
Substrate for CYP2B6

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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Unravelling the molecular determinants of bee sensitivity to neonicotinoid insecticides
Manjon C, et al.
Current Biology, 28(7), 1137-1143 (2018)
Tomohide Uno et al.
Comparative biochemistry and physiology. Toxicology & pharmacology : CBP, 147(3), 278-285 (2008-02-05)
We indicated that two P450s (1A9 and 1C1) from Japanese eel (Anguilla japonica) metabolized 7-ethoxycoumarin, 7-ethoxyresorufin, and flavanone. At first, we constructed expression vectors for two types of P450 (1A9 and 1C1). The reduced CO-difference spectra of Escherichia coli cells
Wataru Kuki et al.
Nutrition and cancer, 60(3), 368-372 (2008-04-30)
We previously reported that auraptene (7-geranyloxycoumarin; AUR), a coumarin that occurs widely in citrus fruit, has been shown to be a promising cancer-preventive agent in several rodent models. However, its bioavailability and metabolism have not been investigated. In this study
Paul M van Midwoud et al.
Biotechnology and bioengineering, 105(1), 184-194 (2009-09-01)
Early detection of kinetic, metabolic, and toxicity (ADME-Tox) profiles for new drug candidates is of crucial importance during drug development. This article describes a novel in vitro system for the incubation of precision-cut liver slices (PCLS) under flow conditions, based
Ying Zhou et al.
Applied microbiology and biotechnology, 87(2), 647-655 (2010-03-13)
Systematic screening of single-gene knockout collection of Escherichia coli BW25113 (the Keio collection) was performed to select mutants that could enhance the deethylation of 7-ethoxycoumarin catalyzed by CYP154A1. After 96-well plate high-throughput screening followed by test tube assays, four mutants
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