548-00-5 Usage
Chemical Properties
White, crystalline solid; odorless; bitter
taste.Soluble in acetone and benzene; slightly soluble in alcohol and ether; insoluble in water.
Originator
Tromexan,Geigy,US,1950
Uses
Medicine (anticoagulant).
Definition
A synthetic derivative of bishydroxycoumarin.
Manufacturing Process
7 g of benzotetronic acid are dissolved in 750 cc of water at boiling
temperature and there after 10.5 g of glyoxylic acid ethyl ester ethyl
alcoholate are added. After a short while the liquid becomes turbid and
gradually a white deposit is separated. The deposit is filtrated and dried in
vacuo. The melting point is 172°C to 174°C; after recrystallization from
methyl alcohol 153°C to 154°C.The crude product is dissolved in sodium lye, filtrated by means of animal
charcoal precipitated by means of hydrochloric acid, and recrystallized from
methyl alcohol. The melting point is 153°C to 154°C.
Therapeutic Function
Anticoagulant
Synthesis
Ethyl biscoumacetate, the ethyl ester of bis-(4-hydroxy-
3-coumarinyl)-acetic acid (24.1.9), is synthesized analogously from 4-hydroxycoumarine,
but using ethylglyoxylate, its semiacetal or glyoxylic acid instead of formaldehyde.
Check Digit Verification of cas no
The CAS Registry Mumber 548-00-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,4 and 8 respectively; the second part has 2 digits, 0 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 548-00:
(5*5)+(4*4)+(3*8)+(2*0)+(1*0)=65
65 % 10 = 5
So 548-00-5 is a valid CAS Registry Number.
InChI:InChI=1/C22H16O8/c1-2-28-20(25)15(16-18(23)11-7-3-5-9-13(11)29-21(16)26)17-19(24)12-8-4-6-10-14(12)30-22(17)27/h3-10,15,23-24H,2H2,1H3
548-00-5Relevant articles and documents
Synthesis and biological evaluation of coumarin-based inhibitors of NAD(P)H: Quinone oxidoreductase-1 (NQO1)
Nolan, Karen A.,Doncaster, Jeremy R.,Dunstan, Mark S.,Scott, Katherine A.,Frenkel, A. David,Siegel, David,Ross, David,Barnes, John,Levy, Colin,Leys, David,Whitehead, Roger C.,Stratford, Ian J.,Bryce, Richard A.
experimental part, p. 7142 - 7156 (2010/07/20)
The synthesis is reported here of two novel series of inhibitors of human NAD(P)H quinone oxidoreductase-1 (NQO1), an enzyme overexpressed in several types of tumor cell. The first series comprises substituted symmetric dicoumarol analogues; the second series contains hybrid compounds where one 4-hydroxycoumarin systemis replaced by a different aromatic moiety. Several compounds show equivalent or improved NQO1 inhibition over dicoumarol, both in the presence and in the absence of added protein. Further, correlation is demonstrated between the ability of these agents to inhibit NQO1 and computed binding affinity. We have solved the crystal structure of NQO1 complexed to a hybrid compound and find good agreement with the in silico model. For both MIA PaCa-2 pancreatic tumor cells and HCT116 colon cancer cells, dicoumarol shows the greatest toxicity of all compounds. Thus, we provide a computational, synthetic, and biological platform to generate competitive NQO1 inhibitors with superior pharmacological properties to dicoumarol. This will allow a more definitive study of NQO1 activity in cells, in particular, its drug activating/detoxifying properties and ability to modulate oncoprotein stability. 2009 American Chemical Society.
