Welcome to LookChem.com Sign In|Join Free
  • or
Home > Products >  > 

Digitoxin
Related Products

Hot Products

Basic Information Post buying leads Suppliers Cas Database
Name

Digitoxin

 EINECS 200-760-5
CAS No. 71-63-6 Density 1.33 g/cm3
PSA 182.83000 LogP 3.24730
Solubility soluble in water Melting Point 240 °C
Formula C41H64O13 Boiling Point 902.3 °C at 760 mmHg
Molecular Weight 764.951 Flash Point 269.5 °C
Transport Information UN 2811 Appearance odorless white or pale buff microcrystalline powder
Safety 45 Risk Codes 23/25-33
Molecular Structure Molecular Structure of 71-63-6 (DIGITOXIN) Hazard Symbols ToxicT
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;

Article Data 15

Digitoxin 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
ConditionsYield
With lithium hydroxide In methanol; water at 20℃; for 2h;83%
With lithium hydroxide83%
With water; lithium hydroxide In methanol at 20℃; for 3h;74%
With lithium hydroxide

Lanatoside A

71-63-6

digitoxin

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With water; enzyme
purpureaglucoside-A

purpureaglucoside-A

71-63-6

digitoxin

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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

Digitoxin Consensus Reports

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

Digitoxin 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.

Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 71-63-6