CAS No.71-63-6,DIGITOXIN Suppliers

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Basic Information

Molecular Structure:
CAS No.:	71-63-6
Name:	DIGITOXIN
Article Data:	15

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

Synthetic route

: 57292-22-5
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

: 71-63-6
digitoxin

Conditions

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

: Lanatoside A

: 71-63-6
digitoxin

Conditions

Conditions	Yield
With biocellulase In water at 37℃; for 48h;	68%

: 14912-58-4
(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>

: 71-63-6
digitoxin

Conditions

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;

: 1111-39-3
acetyldigitoxin

: 71-63-6
digitoxin

Conditions

Conditions	Yield
With alkaline saponification

: 17575-20-1
Digitoxigenin 3-O-bisdigitoxosideacetyldigilanidobioside, or lanatoside A

A: 2280-44-6
D-Glucose

B: 71-63-6
digitoxin

Conditions

Conditions	Yield
With water; enzyme

purpureaglucoside-A: purpureaglucoside-A

: 71-63-6
digitoxin

Conditions

Conditions	Yield
mit Hilfe eines Enzym-Praeparats aus Blaettern von Digitalis purpurea;
mit Hilfe eines Enzym-Praeparats aus Blaettern von Digitalis lanata;

: 25876-27-1
3"',4"'-di-O-acetyl digitoxin

: 71-63-6
digitoxin

Conditions

Conditions	Yield
With sodium methylate In methanol
With sodium methylate In methanol

: 912454-82-1
tert-butyl ((2S,6R)-6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl) carbonate

: 71-63-6
digitoxin

Conditions

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

: 912454-95-6
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

: 71-63-6
digitoxin

Conditions

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

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

: digitoxigen 3-O-acetyl-2,6-dideoxy-4-O-((2'R,6'R)-5',6'-dihydro-5'-hydroxy-6'-methyl-2H-pyran-2'-yl)-β-D-ribo-hexopyranoside

: 71-63-6
digitoxin

Conditions

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

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

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Consensus Reports

Reported in EPA TSCA Inventory. EPA Extremely Hazardous Substances List.

Specification

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.