33396-37-1 Usage
Originator
Clift,Knoll
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
Safety Profile
Poison by ingestion and
intravenous routes. Experimental reproductive effects. When heated to
decomposition it emits acrid smoke and
irritating fumes.
Check Digit Verification of cas no
The CAS Registry Mumber 33396-37-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,3,3,9 and 6 respectively; the second part has 2 digits, 3 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 33396-37:
(7*3)+(6*3)+(5*3)+(4*9)+(3*6)+(2*3)+(1*7)=121
121 % 10 = 1
So 33396-37-1 is a valid CAS Registry Number.
InChI:InChI=1/C31H44O8/c1-17-27(36-4)25(33)26(34)28(38-17)39-20-9-12-29(2)19(15-20)6-7-23-22(29)10-13-30(3)21(11-14-31(23,30)35)18-5-8-24(32)37-16-18/h5,8,15-17,20-23,25-28,33-35H,6-7,9-14H2,1-4H3/t17?,20-,21+,22?,23?,25?,26?,27-,28+,29-,30+,31-/m0/s1
