| Identification | Back Directory | [Name]
meproscillarin | [CAS]
33396-37-1 | [Synonyms]
KY18
KY-18
Clift
KY 18
Rambufaside
Meprosillarin
meproscillarin
Methyl proscillaridin
Methyl proscillaridin A
Proscillaridin 4'-methyl ether
3β-[(4-O-Methyl-6-deoxy-α-L-mannopyranosyl)oxy]-14-hydroxybufa-4,20,22-trienolide
3β-[(6-Deoxy-4-O-methyl-α-L-mannopyranosyl)oxy]-14-hydroxybufa-4,20,22-trienolide
Bufa-4,20,22-trienolide, 3-[(6-deoxy-4-O-methyl-α-L-mannopyranosyl)oxy]-14-hydroxy-, (3β)- | [EINECS(EC#)]
251-493-6 | [Molecular Formula]
C31H44O8 | [MDL Number]
MFCD00869433 | [MOL File]
33396-37-1.mol | [Molecular Weight]
544.681 |
| Chemical Properties | Back Directory | [Melting point ]
213-217℃ | [alpha ]
D20 -94° (CH3OH) | [Boiling point ]
538.46°C (rough estimate) | [density ]
1.29 | [refractive index ]
1.4900 (estimate) |
| Safety Data | Back Directory | [Safety Profile]
Poison by ingestion and
intravenous routes. Experimental reproductive effects. When heated to
decomposition it emits acrid smoke and
irritating fumes. | [Toxicity]
LD50 oral in rat: 79mg/kg |
| Hazard Information | Back Directory | [Originator]
Clift,Knoll | [Definition]
ChEBI: Meproscillarin is a steroid lactone. It is functionally related to a bufanolide. | [Manufacturing Process]
100 g proscillaridin (from Scilla maritima L., enzymatic hydrolysis) was dissolved in 500 ml dry tetrahydrofuran, mixed with 100 ml of triethyl ortoformiate and 50 mg p-tholuene sulfonic acid and stirred for 15 minutes at 20°C.
It was put into a separating funnel and shook with 1 L ethyl acetate and 200 ml of 5% sodium hydroxide. The an organic layer was separated, with 2-3 L water washed (portions 400-500 ml), dried over sodium sulfate and distilled in vacuum to dryness at about 60°C. 121.2 g crude proscillaridin-2,3-ethyl ortoformiate yielded. It was dissolved in 1 L dimethylformamide, mixed with 200 ml methyl iodide and stirred with 20 g 55-60% suspension of sodium hydride at 20°C for 1 hour. 14 L ethyl acetate was added, 5 times with 1-2 L water shook and the organic layer was distilled to 1/4 of volume. The solution of proscillaridin-2,3-ethyl ortho-formiate-4-methyl ester obtained (about 1 L) was mixed with 2 L 0.002 N HCl and stood for 2 hours at 20°C. Then it was neutralized with 0.1 N sodium hydroxide and distilled in vacuum to about 1 L. The solution was shook with 2 L chloroform and 1 L water, organic layer was separated, water layer was 2 times was extracted with still 1 L chloroform and the pooled organic phase dried over sodium sulfate. Then the solvent was removed and 147 g of obtained product was purified by chromatography on silica gel in system chloroform/acetone 4:1.
63 g of crude amorphic 4-O-methylproscillaridin was isolated and recrystallized from methylene chloride/ethyl acetate to give 49.3 g (53% yield) the desired product; MP: 213°-217°C. | [Therapeutic Function]
Cardiotonic |
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