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Ethyl Biscoumacetate

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Ethyl Biscoumacetate Basic information

Product Name:
Ethyl Biscoumacetate
Synonyms:
  • DI(4-oxi-cymarinyl-3)
  • Pelentan
  • Trombarin
  • Trombil
  • Trombolysan
  • 2,2-bis(2-hydroxy-4-keto-chromen-3-yl)acetic acid ethyl ester
  • ethyl 2,2-bis(2-hydroxy-4-oxochromen-3-yl)acetate
  • ethyl 2,2-bis(2-hydroxy-4-oxo-chromen-3-yl)ethanoate
CAS:
548-00-5
MF:
C22H16O8
MW:
408.36
EINECS:
208-940-5
Product Categories:
  • Aromatics
  • Heterocycles
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
Mol File:
548-00-5.mol
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Ethyl Biscoumacetate Chemical Properties

Melting point:
177-182° and mp 154-157°
Boiling point:
448.92°C (rough estimate)
Density 
1.3259 (rough estimate)
refractive index 
1.4480 (estimate)
storage temp. 
Amber Vial, -20°C Freezer, Under inert atmosphere
solubility 
Chloroform (Slightly), DMSO (Slightly)
form 
Solid
pka
pKa 7.5 (Uncertain)
color 
White
Water Solubility 
54.31mg/L(temperature not stated)
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Safety Information

RIDADR 
2811
HazardClass 
6.1(b)
PackingGroup 
III
Toxicity
LD50 in mice, rats (g/kg): 0.88, 0.26 orally; 0.32, 1.1 i.p. (Gruber)
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Ethyl Biscoumacetate Usage And Synthesis

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

Anticoagulant.

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.

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