544329
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:
Molecular Weight:
204.22
EC Number:
201-721-5
UNSPSC Code:
12352100
PubChem Substance ID:
Beilstein/REAXYS Number:
169998
MDL number:
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
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
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Regulatory Information
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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