C52H58O16
ouabain
Conditions | Yield |
---|---|
With sodium carbonate In methanol at 20℃; for 1h; | 88% |
ouabain
trimethylsilyl trifluoromethanesulfonate
Conditions | Yield |
---|---|
With pyridine at 20℃; for 1h; | 95% |
ouabain
Conditions | Yield |
---|---|
With 4-methyl-morpholine; 6C6H15P*4CF3O3S(1-)*2Ru(2+); acetone at 65℃; for 3.5h; Inert atmosphere; Sealed tube; | 92% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In tetrahydrofuran at 23℃; for 16h; | 91% |
ouabain
acetone
4-((3R,3aR,5R,5aS,5bR,9aR,11S,12aS,14aR,14bS)-5,12a,14b-trihydroxy-11-(((3aR,4R,6S,7S,7aR)-7-hydroxy-2,2,6-trimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-4-yl)oxy)-3a,8,8-trimethylhexadecahydro-6H-cyclopenta[7,8]phenanthro[4,4a-d][1,3]dioxin-3-yl)furan-2(5H)-one
Conditions | Yield |
---|---|
With hydrogenchloride at 25℃; for 2h; | 89% |
With hydrogenchloride at 20℃; | 84% |
With hydrogenchloride In water at 20℃; for 2h; | 84% |
ouabain
acetic anhydride
(2R,3R,4R,5S,6S)-2-(((1R,3S,5S,10R,11R,13R,14S,17R)-1,11-diacetoxy-10-(acetoxymethyl)-5,14-dihydroxy-13-methyl-17-(5-oxo-2,5-dihydrofuran-3-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)-6-methyltetrahydro-2H-pyran-3,4,5-triyl triacetate
Conditions | Yield |
---|---|
Reflux; | 88% |
for 1.5h; Heating; | 71% |
With pyridine |
ouabain
triisopropylsilyl trifluoromethanesulfonate
3',19-di-[(triisopropylsilyl)oxy]-3β-[(α-L-rhamnopyranosyl)oxy]-1β,5,11α,14-tetrahydroxycard-20(22)-enolide
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide for 1.5h; | 88% |
With pyridine at 20℃; for 1h; | 33% |
ouabain
triisopropylsilyl trifluoromethanesulfonate
Conditions | Yield |
---|---|
With pyridine at 20℃; for 1h; | 87% |
ouabain
(Z)-4-hydroxy-3-((1R,3S,5S,8R,9S,10R,11R,13R,14S,17R)-1,5,11,14-tetrahydroxy-10-(hydroxymethyl)-13-methyl-3-((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yloxy)hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)but-2-enoic acid
Conditions | Yield |
---|---|
With lithium hydroxide In tetrahydrofuran at 20℃; Saponification; | 79% |
Conditions | Yield |
---|---|
Stage #1: ouabain With dihydroxy-methyl-borane In tetrahydrofuran; isopropyl alcohol Glovebox; Inert atmosphere; Stage #2: tert-butyl allyl carbonate With tris(dibenzylideneacetone)dipalladium chloroform complex; triphenylphosphine In tetrahydrofuran; isopropyl alcohol at 25℃; for 16.16h; Glovebox; Inert atmosphere; Sealed tube; | 74% |
ouabain
tert-butyldimethylsilyl chloride
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide for 2h; | 72% |
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen | 65% |
With water; palladium Hydrogenation; |
Conditions | Yield |
---|---|
Stage #1: tert-butyl allyl carbonate With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenylphosphine In tetrahydrofuran for 0.5h; Glovebox; Inert atmosphere; Stage #2: ouabain With 1,3-dihydro-1-hydroxy-3-phenyl-2,1-benzoxaborole In tetrahydrofuran; isopropyl alcohol at 25℃; for 16h; Inert atmosphere; Glovebox; | 64.6% |
ouabain
1-epi-ouabain
Conditions | Yield |
---|---|
With 4-methyl-morpholine; 6C6H15P*4CF3O3S(1-)*2Ru(2+) In 2,2,2-trifluoroethanol at 70℃; for 11h; | 60% |
Multi-step reaction with 2 steps 1: 6C6H15P*4CF3O3S(1-)*2Ru(2+); 4-methyl-morpholine; acetone / 3.5 h / 65 °C / Inert atmosphere; Sealed tube 2: 6C6H15P*4CF3O3S(1-)*2Ru(2+); 4-methyl-morpholine; isopropyl alcohol / 2,2,2-trifluoroethanol / 1 h / 65 °C View Scheme |
ouabain
acetone
4-((3R,3aR,5R,5aS,5bR,9aR,11S,12aS,14aR,14bS)-5,11,12a,14b-tetrahydroxy-3a,8,8-trimethylhexadecahydro-6H-cyclopenta[7,8]phenanthro[4,4a-d][1,3]dioxin-3-yl)furan-2(5H)-one
Conditions | Yield |
---|---|
With hydrogenchloride at 20℃; | 55% |
With hydrogenchloride at 20℃; for 120h; Inert atmosphere; | 55% |
With hydrogenchloride |
Conditions | Yield |
---|---|
With copper(II) sulfate | 54% |
ouabain
triisopropylsilyl trifluoromethanesulfonate
B
3',19-di-[(triisopropylsilyl)oxy]-3β-[(α-L-rhamnopyranosyl)oxy]-1β,5,11α,14-tetrahydroxycard-20(22)-enolide
Conditions | Yield |
---|---|
With pyridine at 20℃; for 1h; | A 50% B 14% |
Conditions | Yield |
---|---|
With hydrogenchloride In methanol; water | 43% |
Multi-step reaction with 3 steps 1: HCl / 23 °C 2: 97 percent / imidazole / acetonitrile; dimethylformamide / 12 h / 23 °C 3: 72 percent / aq. HCl / methanol / 4 h / 23 °C View Scheme |
Conditions | Yield |
---|---|
With hydrogenchloride |
Conditions | Yield |
---|---|
With perchloric acid; acetic acid 1β,11α,19-triacetoxy-5-hydroxy-3β-O-acetyl-α-L-rhamnopyranosyloxy>-5β-carda-14,20(22)-dienolide; |
Conditions | Yield |
---|---|
With zinc(II) chloride |
Conditions | Yield |
---|---|
With copper(II) sulfate | |
With hydrogenchloride |
Conditions | Yield |
---|---|
With hydrogenchloride |
ouabain
Conditions | Yield |
---|---|
With water; oxygen; platinum β-dehydro-g-stropanthin; |
ouabain
Conditions | Yield |
---|---|
With methanol; potassium hydroxide Ansaeuern der Reaktionsloesung mit wss. Salzsaeure; |
ouabain
Conditions | Yield |
---|---|
With water; oxygen; platinum α-dehydro-g-stropanthin; |
Conditions | Yield |
---|---|
15 min; |
Conditions | Yield |
---|---|
With perchloric acid; acetic acid |
EPA Extremely Hazardous Substances List. Reported in EPA TSCA Inventory.
The Ouabain, with the CAS registry number 630-60-4, is also known as G-Strophanthin. It belongs to the product categories of Biochemistry; Glycosides; Rhamnose; Steroidglycosides; Steroids; Sugars. Its EINECS number is 211-139-3. This chemical's molecular formula is C29H44O12 and molecular weight is 584.65. What's more, its systematic name is (1β,3β,5β,11α)-3-[(6-Deoxy-α-L-mannopyranosyl)oxy]-1,5,11,14,19-pentahydroxycard-20(22)-enolide. Its classification codes are: (1)Cardiotonic agents; (2)Cardiovascular Agents; (3)Drug / Therapeutic Agent; (4)Enzyme inhibitors; (5)Mutation data; (6)Natural Product; (7)Protective Agents. This chemical is used to produce rapid digitalization in acute congestive heart failure, and it is also recommended in treatment of atrial or nodal paroxysmal tachycardia and atrial flutter. It is a cardioactive glycoside consisting of rhamnose and ouabagenin, obtained from the seeds of Strophanthus gratus and other plants of the Apocynaceae. It should be sealed and stored in a cool and dry place. Moreover, it should be protected from oxides.
Physical properties of Ouabain are: (1)ACD/LogP: -2.205; (2)# of Rule of 5 Violations: 3; (3)ACD/LogD (pH 5.5): -2.21; (4)ACD/LogD (pH 7.4): -2.21; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 1.51; (8)ACD/KOC (pH 7.4): 1.51; (9)#H bond acceptors: 12; (10)#H bond donors: 8; (11)#Freely Rotating Bonds: 12; (12)Polar Surface Area: 206.6 Å2; (13)Index of Refraction: 1.655; (14)Molar Refractivity: 141.172 cm3; (15)Molar Volume: 384.679 cm3; (16)Polarizability: 55.965×10-24cm3; (17)Surface Tension: 83.78 dyne/cm; (18)Density: 1.52 g/cm3; (19)Flash Point: 272.893 °C; (20)Enthalpy of Vaporization: 138.556 kJ/mol; (21)Boiling Point: 838.219 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.
Uses of Ouabain: it can be used to produce 1b,3',19-tri-[(tert-butyldimethylsilyl)oxy]-3b-[(a-L-rhamnopyranosyl)oxy]-5,11a,14-trihydroxycard-20(22)-enolide. It will need reagent imidazole and solvent dimethylformamide with the reaction time of 2 hours. The yield is about 72%.
When you are using this chemical, please be cautious about it as the following:
This chemical is toxic by inhalation and if swallowed. In case of accident or if you feel unwell, you should seek medical advice immediately (show the label where possible).
You can still convert the following datas into molecular structure:
(1)SMILES: O=C\1OC/C(=C/1)[C@H]2CC[C@@]6(O)[C@]2(C)C[C@@H](O)[C@H]4[C@H]6CC[C@]5(O)C[C@@H](O[C@@H]3O[C@H]([C@H](O)[C@@H](O)[C@H]3O)C)C[C@@H](O)[C@]45CO
(2)Std. InChI: InChI=1S/C29H44O12/c1-13-22(34)23(35)24(36)25(40-13)41-15-8-19(32)28(12-30)21-17(3-5-27(28,37)9-15)29(38)6-4-16(14-7-20(33)39-11-14)26(29,2)10-18(21)31/h7,13,15-19,21-25,30-32,34-38H,3-6,8-12H2,1-2H3/t13-,15-,16+,17+,18+,19+,21+,22-,23+,24+,25-,26+,27-,28+,29-/m0/s1
(3)Std. InChIKey: LPMXVESGRSUGHW-HBYQJFLCSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
cat | LD50 | intraperitoneal | 100ug/kg (.1mg/kg) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 155, Pg. 165, 1965. | |
cat | LD50 | intravenous | 100ug/kg (.1mg/kg) | Proceedings of the Society for Experimental Biology and Medicine. Vol. 35, Pg. 316, 1936. | |
cat | LDLo | intraduodenal | 820ug/kg (.82mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 8, Pg. 557, 1958. | |
cat | LDLo | oral | 5mg/kg (5mg/kg) | Farmacognosia. Vol. 13, Pg. 375, 1953. | |
cat | LDLo | subcutaneous | 150ug/kg (.15mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 23, Pg. 1125, 1973. | |
cat | LDLo | unreported | 90ug/kg (.09mg/kg) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 148, Pg. 471, 1964. | |
dog | LDLo | intravenous | 54ug/kg (.054mg/kg) | CARDIAC: CHANGE IN RATE | Journal of Pharmacology and Experimental Therapeutics. Vol. 179, Pg. 447, 1971. |
dog | LDLo | oral | 1500ug/kg (1.5mg/kg) | "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935. | |
dog | LDLo | subcutaneous | 100ug/kg (.1mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 23, Pg. 1125, 1973. | |
frog | LD50 | intravenous | 250ug/kg (.25mg/kg) | Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 61, Pg. 231, 1965. | |
frog | LD50 | parenteral | 370ug/kg (.37mg/kg) | Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 53, Pg. 995, 1957. | |
frog | LDLo | subcutaneous | 400ug/kg (.4mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 23, Pg. 1125, 1973. | |
guinea pig | LD50 | intraperitoneal | 210ug/kg (.21mg/kg) | Acta Biologica et Medica Germanica. Vol. 12, Pg. 434, 1964. | |
guinea pig | LD50 | intravenous | 228ug/kg (.228mg/kg) | Acta Biologica et Medica Germanica. Vol. 12, Pg. 434, 1964. | |
guinea pig | LD50 | oral | 8280ug/kg (8.28mg/kg) | United States Patent Document. Vol. #4230702, | |
guinea pig | LD95 | intraduodenal | 3340ug/kg (3.34mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 8, Pg. 557, 1958. | |
guinea pig | LDLo | intraarterial | 40ug/kg (.04mg/kg) | Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 131, Pg. 171, 1928. | |
guinea pig | LDLo | intramuscular | 220ug/kg (.22mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 52, Pg. 1, 1934. | |
guinea pig | LDLo | subcutaneous | 100ug/kg (.1mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 23, Pg. 1125, 1973. | |
monkey | LDLo | intravenous | 102ug/kg (.102mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 13, Pg. 412, 1963. | |
mouse | LD50 | intracrebral | 69ug/kg (.069mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Pharmacological Research Communications. Vol. 6, Pg. 417, 1974. |
mouse | LD50 | intraperitoneal | 11mg/kg (11mg/kg) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 155, Pg. 165, 1965. | |
mouse | LD50 | intravenous | 2200ug/kg (2.2mg/kg) | Proceedings of the Society for Experimental Biology and Medicine. Vol. 118, Pg. 756, 1965. | |
mouse | LD50 | oral | 5mg/kg (5mg/kg) | Japanese Journal of Toxicology. Vol. 4, Pg. 105, 1991. | |
mouse | LD50 | subcutaneous | 5mg/kg (5mg/kg) | Japanese Journal of Toxicology. Vol. 4, Pg. 105, 1991. | |
pigeon | LDLo | intramuscular | 330ug/kg (.33mg/kg) | Comptes Rendus Hebdomadaires des Seances, Academie des Sciences. Vol. 149, Pg. 306, 1909. | |
pigeon | LDLo | intravenous | 183ug/kg (.183mg/kg) | CARDIAC: CHANGE IN RATE GASTROINTESTINAL: NAUSEA OR VOMITING CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 126, Pg. 412, 1960. |
pigeon | LDLo | oral | 14mg/kg (14mg/kg) | Comptes Rendus Hebdomadaires des Seances, Academie des Sciences. Vol. 149, Pg. 306, 1909. | |
rabbit | LD50 | intravenous | 252ug/kg (.252mg/kg) | Pharmacological Research Communications. Vol. 13, Pg. 571, 1981. | |
rabbit | LDLo | intramuscular | 1mg/kg (1mg/kg) | Comptes Rendus Hebdomadaires des Seances, Academie des Sciences. Vol. 149, Pg. 306, 1909. | |
rabbit | LDLo | oral | 7mg/kg (7mg/kg) | Comptes Rendus Hebdomadaires des Seances, Academie des Sciences. Vol. 149, Pg. 306, 1909. | |
rabbit | LDLo | subcutaneous | 100ug/kg (.1mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 23, Pg. 1125, 1973. | |
rat | LD50 | intravenous | 14mg/kg (14mg/kg) | Toxicology and Applied Pharmacology. Vol. 20, Pg. 44, 1971. | |
rat | LD50 | unreported | 125mg/kg (125mg/kg) | Toxicology and Applied Pharmacology. Vol. 22, Pg. 336, 1972. | |
rat | LDLo | subcutaneous | 50mg/kg (50mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 23, Pg. 1125, 1973. |
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