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CAS No.: | 71-63-6 |
---|---|
Name: | DIGITOXIN |
Article Data: | 15 |
Molecular Structure: | |
Formula: | C41H64O13 |
Molecular Weight: | 764.951 |
Synonyms: | Digitoxin(8CI);Digitoxoside (7CI);Cardidigin;Cardigin;Carditoxin;Coramedan;Cristapurat;Crystalline digitalin;Crystodigin;Digicor;Digilong;Digimerck;Digipural;Digisidin;Digitaline Nativelle;Digitophyllin;Digitoxigenin tridigitoxoside;Digitrin;Ditaven;Glucodigin;Lanatoxin;Myodigin;NSC 7529;Purodigin;Purpurid;Tradigal;Unidigin;digitoxin; |
EINECS: | 200-760-5 |
Density: | 1.33 g/cm3 |
Melting Point: | 240 °C |
Boiling Point: | 902.3 °C at 760 mmHg |
Flash Point: | 269.5 °C |
Solubility: | soluble in water |
Appearance: | odorless white or pale buff microcrystalline powder |
Hazard Symbols: | T |
Risk Codes: | 23/25-33 |
Safety: | 45 |
Transport Information: | UN 2811 |
PSA: | 182.83000 |
LogP: | 3.24730 |
digitoxigen O-[2'',6''-dideoxy-β-D-ribo-hexopyranosyl]-(1->4)-O-[3'-O-acetyl-2',6'-dideoxy-β-D-ribo-hexopyranosyl]-(1->4)-(3-O-acetyl-2,6-dideoxy-β-D-ribo-hexopyranoside
digitoxin
Conditions | Yield |
---|---|
With lithium hydroxide In methanol; water at 20℃; for 2h; | 83% |
With lithium hydroxide | 83% |
With water; lithium hydroxide In methanol at 20℃; for 3h; | 74% |
With lithium hydroxide |
digitoxin
Conditions | Yield |
---|---|
With biocellulase In water at 37℃; for 48h; | 68% |
(21',23'-epoxy-14'-hydroxy-24'-nor-5'β,14'β-chola-10',22'-dien-3'β-yl) O-<2''',6'''-dideoxy-β-D-ribo-hexopyranosyl>-(1->4)-O-<2'',6''-dideoxy-β-D-ribo-hexopyranosyl>-(1->4)-<2,6-dideoxy-β-D-ribo-hexopyranoside>
digitoxin
Conditions | Yield |
---|---|
With sodium tetrahydroborate; sodium acetate; 3-chloro-benzenecarboperoxoic acid 1.) CH2Cl2, RT, 2 h; 2.) THF/MeOH, 3h, RT; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With alkaline saponification |
Digitoxigenin 3-O-bisdigitoxosideacetyldigilanidobioside, or lanatoside A
A
D-Glucose
B
digitoxin
Conditions | Yield |
---|---|
With water; enzyme |
digitoxin
Conditions | Yield |
---|---|
mit Hilfe eines Enzym-Praeparats aus Blaettern von Digitalis purpurea; | |
mit Hilfe eines Enzym-Praeparats aus Blaettern von Digitalis lanata; |
3"',4"'-di-O-acetyl digitoxin
digitoxin
Conditions | Yield |
---|---|
With sodium methylate In methanol | |
With sodium methylate In methanol |
tert-butyl ((2S,6R)-6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl) carbonate
digitoxin
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 90 percent / PPh3 / Pd2(DBA)3*CHCl3 / CH2Cl2 / 8 h / 0 °C 2: CeCl3; NaBH4 / methanol / 3 h / -78 °C 3: 89 percent / N-methylmorpholine; Ph3P; diethyl azodicarboxylate / o-nitrobenzenesulfonyl hydrazide / -30 - 20 °C 4: 91 percent / N-methylmorpholine N-oxide; OsO4 / H2O / 3 h / 0 °C 5: 83 percent / LiOH / methanol; H2O / 2 h / 20 °C View Scheme |
digitoxigen 3-O-acetyl-2,6-dideoxy-4-O-((2'R,6'R)-3',6'-dihydro-6'-methyl-2H-pyran-2'-yl)-β-D-ribo-hexopyranoside
digitoxin
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: 91 percent / N-methylmorpholine N-oxide; OsO4 / H2O / 8 h / 0 °C 2.1: p-TsOH / benzene / 20 °C 2.2: 99 percent / p-TsOH / tetrahydrofuran; H2O 3.1: 90 percent / PPh3 / Pd2(DBA)3*CHCl3 / CH2Cl2 / 8 h / 0 °C 4.1: CeCl3; NaBH4 / methanol / 3 h / -78 °C 5.1: 89 percent / N-methylmorpholine; Ph3P; diethyl azodicarboxylate / o-nitrobenzenesulfonyl hydrazide / -30 - 20 °C 6.1: 91 percent / N-methylmorpholine N-oxide; OsO4 / H2O / 3 h / 0 °C 7.1: 83 percent / LiOH / methanol; H2O / 2 h / 20 °C View Scheme |
digitoxin
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: 82 percent / N-methylmorpholine; Ph3P; diethyl azodicarboxylate / o-nitrobenzenesulfonyl hydrazide / 6 h / -30 - 20 °C 2.1: 91 percent / N-methylmorpholine N-oxide; OsO4 / H2O / 8 h / 0 °C 3.1: p-TsOH / benzene / 20 °C 3.2: 99 percent / p-TsOH / tetrahydrofuran; H2O 4.1: 90 percent / PPh3 / Pd2(DBA)3*CHCl3 / CH2Cl2 / 8 h / 0 °C 5.1: CeCl3; NaBH4 / methanol / 3 h / -78 °C 6.1: 89 percent / N-methylmorpholine; Ph3P; diethyl azodicarboxylate / o-nitrobenzenesulfonyl hydrazide / -30 - 20 °C 7.1: 91 percent / N-methylmorpholine N-oxide; OsO4 / H2O / 3 h / 0 °C 8.1: 83 percent / LiOH / methanol; H2O / 2 h / 20 °C View Scheme |
The IUPAC name of Digitoxin is 3-[(3S,5R,8R,9S,10S,13R,14S,17R)-3-[(2R,4S,5S,6R)-5-[(2S,4S,5S,6R)-5-[(2S,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-14-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one. With the CAS registry number 71-63-6, it is also named as Acedoxin. The product's categories are Biochemistry; Glycosides; Steroidglycosides; Steroids; Sugars; Intermediates & Fine Chemicals; Pharmaceuticals; AT Pase, and the other registry numbers are 1339-93-1; 1367-39-1; 1391-34-0; 82476-56-0. Besides, it is odorless white or pale buff microcrystalline powder, which should be sealed in brown glass bottle and stored in a dark, dry place. In addition, its molecular formula is C41H64O13 and molecular weight is 764.94.
The other characteristics of this product can be summarized as: (1)EINECS: 200-760-5; (2)ACD/LogP: 2.44; (3)# of Rule of 5 Violations: 3; (4)ACD/LogD (pH 5.5): 2.44; (5)ACD/LogD (pH 7.4): 2.44; (6)ACD/BCF (pH 5.5): 41.88; (7)ACD/BCF (pH 7.4): 41.88; (8)ACD/KOC (pH 5.5): 504.28; (9)ACD/KOC (pH 7.4): 504.28; (10)#H bond acceptors: 13; (11)#H bond donors: 5; (12)#Freely Rotating Bonds: 12; (13)Index of Refraction: 1.593; (14)Molar Refractivity: 194.87 cm3; (15)Molar Volume: 574.5 cm3; (16)Surface Tension: 61.2 dyne/cm; (17)Density: 1.33 g/cm3; (18)Flash Point: 269.5 °C; (19)Melting Point: 240 °C; (20)Enthalpy of Vaporization: 148.93 kJ/mol; (21)Boiling Point: 902.3 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25 °C.
Preparation and Uses of Digitoxin: this chemical can be extract from digitalis leaf. Additionally, as this chemical can enhance myocardial contractility, slower heart rate and inhibit conduction, it is used as a cardiotonic drug.
When you are using this chemical, please be cautious about it as the following: it is toxic by inhalation and if swallowed. And it is danger of cumulative effects. In case of accident or if you feel unwell, please seek medical advice immediately (show the label whenever possible.)
People can use the following data to convert to the molecule structure.
(1)SMILES: O=C\1OC/C(=C/1)[C@H]2CC[C@@]8(O)[C@]2(C)CC[C@H]7[C@H]8CC[C@H]6[C@]7(C)CC[C@H](O[C@@H]5O[C@H](C)[C@@H](O[C@@H]4O[C@@H]([C@@H](O[C@@H]3O[C@@H]([C@@H](O)[C@@H](O)C3)C)[C@@H](O)C4)C)[C@@H](O)C5)C6
(2)InChI: InChI=1/C41H64O13/c1-20-36(46)29(42)16-34(49-20)53-38-22(3)51-35(18-31(38)44)54-37-21(2)50-33(17-30(37)43)52-25-8-11-39(4)24(15-25)6-7-28-27(39)9-12-40(5)26(10-13-41(28,40)47)23-14-32(45)48-19-23/h14,20-22,24-31,33-38,42-44,46-47H,6-13,15-19H2,1-5H3/t20-,21-,22-,24-,25+,26-,27+,28-,29+,30+,31+,33+,34+,35+,36-,37-,38-,39+,40-,41+/m1/s1
(3)InChIKey: WDJUZGPOPHTGOT-XUDUSOBPBI
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
cat | LD50 | intraperitoneal | 170ug/kg (0.17mg/kg) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 155, Pg. 165, 1965. | |
cat | LD50 | oral | 180ug/kg (0.18mg/kg) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 159, Pg. 1, 1966. | |
cat | LDLo | intraarterial | 440ug/kg (0.44mg/kg) | Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 141, Pg. 329, 1929. | |
cat | LDLo | intraduodenal | 315ug/kg (0.315mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 20, Pg. 1765, 1970. | |
cat | LDLo | intravenous | 180ug/kg (0.18mg/kg) | Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 184, Pg. 181, 1937. | |
cat | LDLo | unreported | 325mg/kg (325mg/kg) | "Die Herzwirksamen Glykoside," Baumgarten, G., and W. Forster, Leipzig, Ger. Dem. Rep., VEB Georg Thieme, 1963Vol. -, Pg. 33, 1963. | |
dog | LDLo | intravenous | 500ug/kg (0.5mg/kg) | "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1343, 1935. | |
frog | LD50 | intravenous | 730ug/kg (0.73mg/kg) | Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 61, Pg. 231, 1965. | |
frog | LD50 | oral | 3050ug/kg (3.05mg/kg) | Japanese Journal of Pharmacology. Vol. 9, Pg. 91, 1960. | |
frog | LD50 | subcutaneous | 1050ug/kg (1.05mg/kg) | Japanese Journal of Pharmacology. Vol. 9, Pg. 91, 1960. | |
frog | LDLo | parenteral | 1mg/kg (1mg/kg) | Chemical and Pharmaceutical Bulletin. Vol. 11, Pg. 613, 1963. | |
guinea pig | LD50 | intraduodenal | 3mg/kg (3mg/kg) | CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION) | Arzneimittel-Forschung. Drug Research. Vol. 21, Pg. 225, 1971. |
guinea pig | LD50 | intraperitoneal | 1800ug/kg (1.8mg/kg) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 242, Pg. 35, 1979. | |
guinea pig | LD50 | oral | 3700ug/kg (3.7mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 8, Pg. 557, 1958. | |
guinea pig | LDLo | intraduodenal | 7250ug/kg (7.25mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 20, Pg. 229, 1970. | |
guinea pig | LDLo | intravenous | 310ug/kg (0.31mg/kg) | Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 237, Pg. 222, 1959. | |
infant | TDLo | oral | 150ug/kg (0.15mg/kg) | CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION) GASTROINTESTINAL: NAUSEA OR VOMITING | American Journal of Diseases of Children. Vol. 130, Pg. 425, 1976. |
infant | TDLo | parenteral | 270ug/kg/1D-I (0.27mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION) CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE | Indian Pediatrics. Vol. 30, Pg. 81, 1993. |
man | LDLo | oral | 286ug/kg (0.286mg/kg) | PERIPHERAL NERVE AND SENSATION: PARESTHESIS CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP BLOOD: THROMBOCYTOPENIA | Clinical Toxicology. Vol. 18, Pg. 679, 1981. |
man | LDLo | unreported | 44ug/kg (0.044mg/kg) | "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970. | |
man | TDLo | oral | 71ug/kg (0.071mg/kg) | CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION) | American Journal of Emergency Medicine. Vol. 2, Pg. 504, 1984. |
mouse | LD50 | intracrebral | 49ug/kg (0.049mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Arzneimittel-Forschung. Drug Research. Vol. 11, Pg. 908, 1961. |
mouse | LD50 | intraperitoneal | 3900ug/kg (3.9mg/kg) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 155, Pg. 165, 1965. | |
mouse | LD50 | intravenous | 4100ug/kg (4.1mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 8, Pg. 557, 1958. | |
mouse | LD50 | oral | 4950ug/kg (4.95mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 8, Pg. 557, 1958. | |
mouse | LD50 | subcutaneous | 22180ug/kg (22.18mg/kg) | BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD CARDIAC: OTHER CHANGES | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 153, Pg. 436, 1965. |
pig | LDLo | intraduodenal | 550ug/kg (0.55mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 20, Pg. 229, 1970. | |
pig | LDLo | intravenous | 400ug/kg (0.4mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 20, Pg. 229, 1970. | |
pigeon | LD50 | intraperitoneal | 320ug/kg (0.32mg/kg) | Journal of Pharmacy and Pharmacology. Vol. 14, Pg. 96, 1962. | |
pigeon | LDLo | intravenous | 443ug/kg (0.443mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 21, Pg. 225, 1971. | |
pigeon | LDLo | parenteral | 600ug/kg (0.6mg/kg) | Chemical and Pharmaceutical Bulletin. Vol. 11, Pg. 613, 1963. | |
rabbit | LDLo | intravenous | 1mg/kg (1mg/kg) | "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1343, 1935. | |
rat | LD50 | intravenous | 3900ug/kg (3.9mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Arzneimittel-Forschung. Drug Research. Vol. 11, Pg. 848, 1961. |
rat | LD50 | oral | 23750ug/kg (23.75mg/kg) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 164, Pg. 47, 1966. | |
rat | LD50 | subcutaneous | 16430ug/kg (16.43mg/kg) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 164, Pg. 47, 1966. | |
women | TDLo | oral | 300ug/kg (0.3mg/kg) | CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION) | American Journal of Emergency Medicine. Vol. 2, Pg. 504, 1984. |
women | TDLo | oral | 400ug/kg (0.4mg/kg) | CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE GASTROINTESTINAL: NAUSEA OR VOMITING | Clinical Toxicology. Vol. 18, Pg. 679, 1981. |