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548-00-5

548-00-5 Structure

548-00-5 Structure
IdentificationBack Directory
[Name]

Ethyl Biscoumacetate
[CAS]

548-00-5
[Synonyms]

Trombil
Pelentan
Trombarin
Trombolysan
Ethyl Biscoumacetate
DI(4-oxi-cymarinyl-3)
Ethyl Biscoumacetate USP/EP/BP
ethyl bis(4-hydroxy-2-oxo-2H-chromen-3-yl)acetate
ethyl 2,2-bis(2-hydroxy-4-oxochromen-3-yl)acetate
ethyl 2,2-bis(2-hydroxy-4-oxo-chromen-3-yl)ethanoate
2,2-bis(2-hydroxy-4-keto-chromen-3-yl)acetic acid ethyl ester
2H-1-Benzopyran-3-acetic acid, 4-hydroxy-α-(4-hydroxy-2-oxo-2H-1-benzopyran-3-yl)-2-oxo-, ethyl ester
[EINECS(EC#)]

208-940-5
[Molecular Formula]

C22H16O8
[MOL File]

548-00-5.mol
[Molecular Weight]

408.36
Chemical PropertiesBack Directory
[Definition]

A synthetic derivative of bishydroxycoumarin.
[Appearance]

White, crystalline solid; odorless; bitter taste.Soluble in acetone and benzene; slightly soluble in alcohol and ether; insoluble in water.
[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)
[pka]

pKa 7.5 (Uncertain)
[Water Solubility ]

54.31mg/L(temperature not stated)
Hazard InformationBack Directory
[Chemical Properties]

White, crystalline solid; odorless; bitter taste.Soluble in acetone and benzene; slightly soluble in alcohol and ether; insoluble in water.
[Uses]

Medicine (anticoagulant).
[Originator]

Tromexan,Geigy,US,1950
[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.

Synthesis_548-00-5

Safety DataBack Directory
[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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