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Sigma-Aldrich

7-Ethoxy-4-methylcoumarin

98%

Synonym(s):

Ethyl 4-methylumbelliferyl ether

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About This Item

Empirical Formula (Hill Notation):
C12H12O3
CAS Number:
87-05-8
Molecular Weight:
204.22
Beilstein/REAXYS Number:
169998
EC Number:
201-721-5
MDL number:
MFCD00016971
UNSPSC Code:
12352100
PubChem Substance ID:
24878726

assay

98%

mp

114-116 °C (lit.)

SMILES string

CCOc1ccc2C(C)=CC(=O)Oc2c1

InChI

1S/C12H12O3/c1-3-14-9-4-5-10-8(2)6-12(13)15-11(10)7-9/h4-7H,3H2,1-2H3

InChI key

NKRISXMDKXBVRJ-UHFFFAOYSA-N

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General description

7-Ethoxy-4-methylcoumarin (EtOMC), also known as ethyl 4-methylumbelliferyl ether, is a coumarin derivative. Its standard molar energy of combustion is ?5888.0 ± 3.2kJ·mol?1 and standard molar enthalpy of formation in the crystalline phase is ?545.4 ± 3.6kJ·mol?1.EtOMC can be prepared by reacting methyl acetoacetate with 3-ethoxyphenol in the presence of boron trifluoride dihydrate.The fluorescence quenching of EtOMC is more effective in the presence 4-hydroxy-TEMPO (4-hydroxy-2,2,6,6-tetramethylpiperidin-1-oxyl).

Application

7-Ethoxy-4-methylcoumarin may be used in the assay of 4-chlormethyl-7-ethoxycoumarin O-deethylase activity.

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Lot/Batch Number
04624MI

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Analysis of fluorescence quenching of coumarin derivatives by 4-hydroxy-TEMPO in aqueous solution.
Zamojc K, et al.
Journal of Fluorescence, 24(3), 713-718 (2014)
Standard molar enthalpies of formation in the crystalline phase of 7-hydroxy-4-methylcoumarin, 7-ethoxy-4-methylcoumarin, and 6-methoxy-4-methylcoumarin.
Amador P, et al.
The Journal of Chemical Thermodynamics, 43(9), 1414-1416 (2011)
U D Kuhn et al.
Experimental and toxicologic pathology : official journal of the Gesellschaft fur Toxikologische Pathologie, 50(4-6), 491-496 (1998-10-23)
7-Ethoxycoumarin (EC) is widely used as a model substrate for monooxygenase function, its O-deethylation representing cytochrome P450 (P450) activity mainly of 1A but also of 2B isoforms. Reports on investigations of its own capacity to induce or suppress P450 activities
Pechmann reaction promoted by boron trifluoride dihydrate.
Stoyanov E and Mezger J.
Molecules (Basel), 10(7), 762-766 (2005)
S Ekins et al.
The Journal of pharmacology and experimental therapeutics, 286(3), 1253-1259 (1998-09-11)
Previous studies in this laboratory have determined the lack of specificity of several antibody and substrate probes of CYP2B6. The goals of the current study were to examine the expression of CYP2B6 in a bank of human liver microsome (HLM)
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