630-60-4

Basic information

• Product Name: G-STROPHANTHIN
• Synonyms: QUABAIN;PUROSTROPHAN;STROPHANTHIN, G-;OUABAIN;(1beta,3beta,5beta,11alpha)-ahydroxy;(1beta,3beta,5beta,11alpha)-hydroxy;3-((6-deoxy-alpha-l-mannopyranosyl)oxy)-1,5,11alpha,14,19-pentahydroxycard-20(;3-[(6-deoxy-.alpha.-L-mannopyranosyl)oxy]-1,5,11,14,19-pentahydroxy-,(1.beta.,3.beta.,5.beta.,11.aCard-20(22)-enolide
• CAS NO: 630-60-4
• Molecular Formula: C₂₉H₄₄O₁₂
• Molecular Weight: 584.65
• EINECS: 211-139-3
• Product Categories: Biochemistry;Glycosides;Rhamnose;Steroidglycosides;Steroids;Sugars;Inhibitors
• Mol File: 630-60-4.mol
• Article Data: 1

Chemical Properties

• Melting Point: 200°C
• Boiling Point: 561.69°C (rough estimate)
• Flash Point: 272.893 °C
• Appearance: white/powder
• Density: 1.1941 (rough estimate)
• Vapor Pressure: 7.63E-08mmHg at 25°C
• Refractive Index: -32 ° (C=1, H2O)
• Storage Temp.: Desiccate at -20°C
• Solubility: H2O: 10 mg/mL cold
• PKA: 13.04±0.70(Predicted)
• Water Solubility: 13g/L(25 oC)
• Merck: 6901
• CAS DataBase Reference: G-STROPHANTHIN(CAS DataBase Reference)
• NIST Chemistry Reference: G-STROPHANTHIN(630-60-4)
• EPA Substance Registry System: G-STROPHANTHIN(630-60-4)

Safety Data

• Hazard Codes: T
• Statements: 23/25-33
• Safety Statements: 45
• RIDADR: UN 1544 6.1/PG 1
• WGK Germany: 3
• RTECS: RN3850000
• F: 8
• Hazardous Substances Data: 630-60-4(Hazardous Substances Data)

Usage

Description

One of several cardiac glycosides that have been used clinically as cardiotonic agents and diuretics. Ouabain is obtained from the seeds of Strophanthus gratus, Acokanthera ouabaio, and related species. It was formerly prescribed under the name strophanthuis as the purified seed extract.

General Description

Odorless, white crystals or crystalline powder as an octahydrate. Used to produce rapid digitalization in acute congestive heart failure. Also recommended in treatment of atrial or nodal paroxysmal tachycardia and atrial flutter.

Reactivity Profile

When heated to decomposition, G-STROPHANTHIN emits acrid smoke and fumes. Hydrolysis yields one mole ouabagenin and one mole rhamnose. Stable in air, but affected by light (G-STROPHANTHIN octahydrate) [EPA, 1998].

Health Hazard

G-STROPHANTHIN is classified as extremely toxic. Probable oral lethal dose in humans is less than 5 mg/kg or a taste (less than 7 drops) for 70 kg (150-lb.) person. Exposure may result in respiratory and cardiac failure, and/or hyperalkemia. Patients with frequent premature ventricular heart beats or who have received any preparation of digitalis during preceding three weeks are prone to toxicity.

Fire Hazard

When heated to decomposition, G-STROPHANTHIN emits acrid smoke and fumes. Hydrolysis yields one mole ouabagenin and one mole rhamnose. Stable in air, but affected by light (G-STROPHANTHIN octahydrate)

Biological Activity

Selective Na + , K + -ATPase inhibitor.

Safety Profile

Poison by ingestion, intramuscular, intraperitoneal, intravenous, subcutaneous, and parented routes. Moderately toxic by intraduodenal route. A cardac stimulant. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes

InChI:InChI=1/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h12,14H,2-11,15-17H2,1H3,(H,19,20)

Synthetic route

C52H58O16 (1018988-68-5) → ouabain (630-60-4)

Conditions	Yield
With sodium carbonate In methanol at 20℃; for 1h;	88%

ouabain (630-60-4) + trimethylsilyl trifluoromethanesulfonate (27607-77-8) → 1α,2',3',11α,19-hexa-[(trimethylsilyl)oxy]-3β-[(α-L-rhamnopyranosyl)oxy]-5,14-dihydroxycard-20(22)-enolide

Conditions	Yield
With pyridine at 20℃; for 1h;	95%

ouabain (630-60-4) → C29H42O12

Conditions	Yield
With 4-methyl-morpholine; 6C6H15P*4CF3O3S(1-)*2Ru(2+); acetone at 65℃; for 3.5h; Inert atmosphere; Sealed tube;	92%

ouabain (630-60-4) + 1,1-dimethoxycyclopentane (931-94-2) → C34H50O12

Conditions	Yield
With toluene-4-sulfonic acid In tetrahydrofuran at 23℃; for 16h;	91%

ouabain (630-60-4) + acetone (67-64-1) → 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 (326805-71-4)

Conditions	Yield
With hydrogenchloride at 25℃; for 2h;	89%
With hydrogenchloride at 20℃;	84%
With hydrogenchloride In water at 20℃; for 2h;	84%

ouabain (630-60-4) + acetic anhydride (108-24-7) → (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 (57198-85-3)

Conditions	Yield
Reflux;	88%
for 1.5h; Heating;	71%
With pyridine

ouabain (630-60-4) + triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → 3',19-di-[(triisopropylsilyl)oxy]-3β-[(α-L-rhamnopyranosyl)oxy]-1β,5,11α,14-tetrahydroxycard-20(22)-enolide (292068-65-6)

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide for 1.5h;	88%
With pyridine at 20℃; for 1h;	33%

ouabain (630-60-4) + triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → 1β,3',19-tri-[(triisopropylsilyl)oxy]-3β-[(α-L-rhamnopyranosyl)oxy]-5,11α,14-trihydroxycard-20(22)-enolide

Conditions	Yield
With pyridine at 20℃; for 1h;	87%

ouabain (630-60-4) → (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 (1042149-56-3)

Conditions	Yield
With lithium hydroxide In tetrahydrofuran at 20℃; Saponification;	79%

ouabain (630-60-4) + tert-butyl allyl carbonate (70122-89-3) → C32H48O12

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 (630-60-4) + tert-butyldimethylsilyl chloride (18162-48-6) → 1β,3',19-tri-[(tert-butyldimethylsilyl)oxy]-3β-[(α-L-rhamnopyranosyl)oxy]-5,11α,14-trihydroxycard-20(22)-enolide

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide for 2h;	72%

ouabain (630-60-4) → dihydro-ouabain (1183-35-3)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen	65%
With water; palladium Hydrogenation;

ouabain (630-60-4) + tert-butyl allyl carbonate (70122-89-3) → (E)-3'-allyl-ouabain

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 (630-60-4) → 1-epi-ouabain (191158-93-7)

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 (630-60-4) + acetone (67-64-1) → 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 (1178-61-6)

Conditions	Yield
With hydrogenchloride at 20℃;	55%
With hydrogenchloride at 20℃; for 120h; Inert atmosphere;	55%
With hydrogenchloride

ouabain (630-60-4) + acetone (67-64-1) → C32H48O12

Conditions	Yield
With copper(II) sulfate	54%

ouabain (630-60-4) + triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → 19-[(triisopropylsilyl)oxy]-3β-[(α-L-rhamnopyranosyl)oxy]-1β,3',5,11α,14-pentahydroxycard-20(22)-enolide + 3',19-di-[(triisopropylsilyl)oxy]-3β-[(α-L-rhamnopyranosyl)oxy]-1β,5,11α,14-tetrahydroxycard-20(22)-enolide (292068-65-6)

Conditions	Yield
With pyridine at 20℃; for 1h;	A 50% B 14%

ouabain (630-60-4) → ouabagenin (508-52-1)

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

ouabain (630-60-4) + cyclohexanone (108-94-1) → 1β,19-cyclohexyLiDenedioxy-3β,5,11α,14-tetrahydroxy-5β,14β-card-20(22)-enolide

Conditions	Yield
With hydrogenchloride

ouabain (630-60-4) + acetic anhydride (108-24-7) → 1,11,19-triacetoxy-5-hydroxy-3-(tri-O-acetyl-rhamnopyranosyloxy)-carda-14,20(22)-dienolide + 1β,5,11α,19-tetraacetoxy-3β-(tri-O-acetyl-α-L-rhamnopyranosyloxy)-5β-carda-14,20(22)-dienolide

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;

ouabain (630-60-4) + acetic anhydride (108-24-7) → 1β,5,11α,19-tetraacetoxy-3β-(tri-O-acetyl-α-L-rhamnopyranosyloxy)-5β-carda-14,20(22)-dienolide

Conditions	Yield
With zinc(II) chloride

ouabain (630-60-4) + acetone (67-64-1) → 1β,5,11α,14,19-pentahydroxy-3β-(O2,O3-isopropylidene-α-L-rhamnopyranosyloxy)-5β,14β-card-20(22)-enolide

Conditions	Yield
With copper(II) sulfate
With hydrogenchloride

ouabain (630-60-4) + butanone (78-93-3) → 1β,19-((Ξ)-sec-butylidenedioxy)-3β,5,11α,14-tetrahydroxy-5β,14β-card-20(22)-enolide

Conditions	Yield
With hydrogenchloride

ouabain (630-60-4) → 1,5,11,14-tetrahydroxy-19-oxo-3-rhamnopyranosyloxy-card-20(22)-enolide

Conditions	Yield
With water; oxygen; platinum β-dehydro-g-stropanthin;

ouabain (630-60-4) → (20S,21S)-14,21-epoxy-1β,5,11α,19-tetrahydroxy-3β-α-L-rhamnopyranosyloxy-5β,14β-cardanolide

Conditions	Yield
With methanol; potassium hydroxide Ansaeuern der Reaktionsloesung mit wss. Salzsaeure;

ouabain (630-60-4) → 1,5,11,14-tetrahydroxy-19-oxo-3-rhamnopyranosyloxy-card-20(22)-enolide + β-dehydro-g-stropanthin

Conditions	Yield
With water; oxygen; platinum α-dehydro-g-stropanthin;

ouabain (630-60-4) + hydrogenchloride (7647-01-0) + acetone (67-64-1) → 1β,5,11α,14,19-pentahydroxy-3β-(O2,O3-isopropylidene-α-L-rhamnopyranosyloxy)-5β,14β-card-20(22)-enolide

Conditions	Yield
15 min;

ouabain (630-60-4) + copper(II) sulfate (7758-99-8) + acetone (67-64-1) → 1β,5,11α,14,19-pentahydroxy-3β-(O2,O3-isopropylidene-α-L-rhamnopyranosyloxy)-5β,14β-card-20(22)-enolide

ouabain (630-60-4) + acetic anhydride (108-24-7) → 1β,5,11α,19-tetraacetoxy-3β-(tri-O-acetyl-α-L-rhamnopyranosyloxy)-5β-carda-14,20(22)-dienolide + 1β,11α,19-triacetoxy-5-hydroxy-3β-O-acetyl-α-L-rhamnopyranosyloxy>-5β-carda-14,20(22)-dienolide

Conditions	Yield
With perchloric acid; acetic acid

ouabain (630-60-4) + water (7732-18-5) + nitric acid (7697-37-2) → compound C23H25NO8 of mp: about 280 degree + compound C23H24O10 of mp: about 300 degree

Upstream product

• 1018988-68-5 C₅₂H₅₈O₁₆ 

Downstream Products

• 1526915-17-2 (3S,3aR,5R,5aS,5bR,9aR,11S,12aS,14aR,14bS)-3-((1-benzyl-1H-1,2,3-triazol-4-yl)(hydroxy)methyl)-5-(methoxymethoxy)-11-(((3aR,4R,6S,7S,7aR)-7-(methoxymethoxy)-2,2,6-trimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-4-yl)oxy)-3a,8,8-trimethyltetradecahydro-6H-cyclopenta[7,8]phenanthro[4,4a-d][1,3]dioxine-12a,14b-diol 
• 1526915-19-4 (1R,3S,5S,8R,9S,10R,11R,13R,14S,17S)-17-((1-benzyl-1H-1,2,3-triazol-4-yl)(hydroxy)methyl)-10-(hydroxymethyl)-13-methyl-3-(((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetradecahydro-5H-cyclopenta[a]phenanthrene-1,5,11,14(2H)-tetraol 
• 1526915-38-7 (3S,3aR,5R,5aS,5bR,9aR,11S,12aS,14aR,14bS)-3-(1-(4-chlorobenzyl)-1H-1,2,3-triazol-4-yl)-5,11,14b-tris(methoxymethoxy)-3a,8,8-trimethyltetradecahydro-6H-cyclopenta[7,8]phenanthro[4,4a-d][1,3]dioxin-12a(1H)-ol 
• 1526915-41-2 (1R,3S,5S,8R,9S,10R,11R,13R,14S,17S)-17-(1-(4-chlorobenzyl)-1H-1,2,3-triazol-4-yl)-10-(hydroxymethyl)-13-methyltetradecahydro-5H-cyclopenta[a]phenanthrene-1,3,5,11,14(2H)-pentaol 
• 1526915-37-6 (3S,3aR,5R,5aS,5bR,9aR,11S,12aS,14aR,14bS)-3-(1-benzyl-1H-1,2,3-triazol-4-yl)-5,11,14b-tris(methoxymethoxy)-3a,8,8-trimethyltetradecahydro-6H-cyclopenta[7,8]phenanthro[4,4a-d][1,3]dioxin-12a(1H)-ol 
• 1526915-35-4 (1R,3S,5S,8R,9S,10R,11R,13R,14S,17S)-10-(hydroxymethyl)-17-((4-(4-methoxyphenyl)-1H-1,2,3-triazol-1-yl)methyl)-13-methyltetradecahydro-5H-cyclopenta[a]phenanthrene-1,3,5,11,14(2H)-pentaol 
• 1526915-34-3 (3S,3aR,5R,5bR,9aR,11S,12aS,14bS)-5,11,14b-tris(methoxymethoxy)-3-((4-(4-methoxyphenyl)-1H-1,2,3-triazol-1-yl)methyl)-3a,8,8-trimethylhexadecahydro-1H-cyclopenta[7,8]phenanthro[4,4a-d][1,3]dioxin-12a-ol 
• 1526915-32-1 ((3S,3aR,5R,5bR,9aR,11S,12aS,14bS)-12a-hydroxy-5,11,14b-tris(methoxymethoxy)-3a,8,8-trimethylhexadecahydro-1H-cyclopenta[7,8]phenanthro[4,4a-d][1,3]dioxin-3-yl)methyl-4-methylbenzenesulfonate 
• 1526915-29-6 (1R,3S,5S,10R,11R,13R,14S,17S)-17-((1-benzyl-11'-1,2,3-triazol-4-yl)(hydroxy)methyl)-10-(hydroxymethyl)-13-methylhexadecahydro-1H-cyclopenta[a]phenanthrene-1,3,5,11,14-pentaol 
• 1526915-27-4 (3S,3aR,5R,5bR,9aR,11S,12aS,14bS)-3-((1-benzyl-1H-1,2,3-triazol-4-yl)(hydroxy)methyl)-5,11,14b-tris(methoxymethoxy)-3a,8,8-trimethylhexadecahydro-1H-cyclopenta[7,8]phenanthro[4,4a-d][1,3]dioxin-12a-ol 
• 1526915-18-3 (1R,3S,5S,8R,9S,10R,11R,13R,14S,17S)-17-((1-(4-fluorobenzyl)-1H-1,2,3-triazol-4-yl)(hydroxy)methyl)-10-(hydroxymethyl)-13-methyl-3-(((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetradecahydro-5H-cyclopenta[a]phenanthrene-1,5,11,14(2H)-tetraol 
• 1526915-16-1 (3S,3aR,5R,5aS,5bR,9aR,11S,12aS,14aR,14bS)-3-((1-(4-fluorobenzyl)-1H-1,2,3-triazol-4-yl)(hydroxy)methyl)-5-(methoxymethoxy)-11-(((3aR,4R,6S,7S,7aR)-7-(methoxymethoxy)-2,2,6-trimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-4-yl)oxy)-3a,8,8-trimethyltetradecahydro-6H-cyclopenta[7,8]phenanthro[4,4a-d][1,3]dioxine-12a,14b-diol 
• 1526915-40-1 (1R,3S,5S,8R,9S,10R,11R,13R,14S,17S)-17-(1-benzyl-1H-1,2,3-triazol-4-yl)-10-(hydroxymethyl)-13-methyltetradecahydro-5H-cyclopenta[a]phenanthrene-1,3,5,11,14(2H)-pentaol 
• 508-52-1 ouabagenin 

Relevant articles and documents

Total synthesis of ouabagenin and ouabain

(Chemical Equation Presented) The highly oxygenated steroid ouabagenin (1b) and its glycoside ouabain (1a) were prepared by a strategy based on a polyanionic cyclization. Starting building blocks A and B were combined to give the key intermediate C and transformed into 1b in 27 steps. Finally, ouabagenin (1b) was converted into ouabain (1a) in six steps (see scheme).