Digitoxigenin

Suppliers

Names

[ CAS No. ]:
143-62-4

[ Name ]:
Digitoxigenin

[Synonym ]:
Digitoxigenin
4-[(3S,5R,8R,9S,10S,13R,14S,17R)-3,14-Dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2(5H)-furanone
EINECS 205-603-4
Echujetin
Thevetigenin
3b,14-Dihydroxy-5b-card-20(22)-enolide
(3β,5β)-3,14-Dihydroxycard-20(22)-ènolide
card-20(22)-enolide, 3,14-dihydroxy-, (3b,5b)-
Cerberigenin
D20:22-3,14,21-Trihydroxynorcholenic Acid Lactone
4-[(3S,5R,8R,9S,10S,13R,14S,17R)-3,14-Dihydroxy-10,13-diméthylhexadécahydro-1H-cyclopenta[a]phénanthrén-17-yl]-2(5H)-furanone
(3β,5β)-3,14-Dihydroxycard-20(22)-enolide
Card-20(22)-enolide, 3,14-dihydroxy-, (3β,5β)-
(3b,5b)-3,14-dihydroxycard-20(22)-enolide
3-[(3S,5R,8R,9S,10S,13R,14S,17R)-3,14-dihydroxy-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
MFCD00003687
δ20:22-3,14,21-Trihydroxynorcholenic acid lactone
4-[(3S,5R,8R,9S,10S,13R,14S,17R)-3,14-Dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2(5H)-furanon
Evonogenin

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
549.3±50.0 °C at 760 mmHg

[ Melting Point ]:
253-255 °C (dec.)(lit.)

[ Molecular Formula ]:
C₂₃H₃₄O₄

[ Molecular Weight ]:
374.514

[ Flash Point ]:
188.2±23.6 °C

[ Exact Mass ]:
374.245697

[ PSA ]:
66.76000

[ LogP ]:
2.79

[ Vapour Pressure ]:
0.0±3.4 mmHg at 25°C

[ Index of Refraction ]:
1.591

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: FH4975000

CHEMICAL NAME :: 5-beta-Card-20(22)-enolide, 3-beta,14-dihydroxy-

CAS REGISTRY NUMBER :: 143-62-4

BEILSTEIN REFERENCE NO. :: 0095448

LAST UPDATED :: 199612

DATA ITEMS CITED :: 10

MOLECULAR FORMULA :: C23-H34-O4

MOLECULAR WEIGHT :: 374.57

WISWESSER LINE NOTATION :: L E5 B666TJ A1 E1 F- DT5OV CUTJ IQ OQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1600 ug/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 11,848,1961

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 26170 ug/kg

TOXIC EFFECTS :: Brain and Coverings - recordings from specific areas of CNS Behavioral - convulsions or effect on seizure threshold Cardiac - other changes

REFERENCE :: AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 153,436,1965

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 11820 ug/kg

TOXIC EFFECTS :: Brain and Coverings - recordings from specific areas of CNS Behavioral - convulsions or effect on seizure threshold Cardiac - other changes

REFERENCE :: AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 153,436,1965

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1131 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: LIFSAK Life Sciences. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.1-8, 1962-69; V.14- 1974- Volume(issue)/page/year: 37,775,1985

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intracerebral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 187 ug/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 11,908,1961

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 254 ug/kg

TOXIC EFFECTS :: Gastrointestinal - nausea or vomiting

REFERENCE :: JPHAA3 Journal of the American Pharmaceutical Association. (Washington, DC) V.1-28, 1912-39; New series: V.1-17, 1961-77. Volume(issue)/page/year: 27,189,1938

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 1419 ug/kg

TOXIC EFFECTS :: Brain and Coverings - recordings from specific areas of CNS Behavioral - convulsions or effect on seizure threshold Cardiac - other changes

REFERENCE :: AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 153,436,1965

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Parenteral

SPECIES OBSERVED :: Bird - pigeon

DOSE/DURATION :: 600 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: CPBTAL Chemical and Pharmaceutical Bulletin. (Japan Pub. Trading Co., USA, 1255 Howard St., San Francisco, CA 94103) V.6- 1958- Volume(issue)/page/year: 8,18,1960 *** REVIEWS *** TOXICOLOGY REVIEW 85ELDJ "Die Herzwirksamen Glykoside," Baumgarten, G., and W. Forster, Leipzig, Ger. Dem. Rep., VEB Georg Thieme, 1963 Volume(issue)/page/year: -,190,1963 TOXICOLOGY REVIEW CHIMAD Chimia. (Postfach 2027, CH-4001 Basel, Switzerland) V.1- 1947- Volume(issue)/page/year: 5,93,1951

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H300

[ Precautionary Statements ]:
P264-P301 + P310

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges

[ Hazard Codes ]:
T

[ Risk Phrases ]:
R25:Toxic if swallowed.

[ Safety Phrases ]:
S45

[ RIDADR ]:
UN 3462 6.1/PG 2

[ WGK Germany ]:
3

[ RTECS ]:
FH4975000

[ Packaging Group ]:
II

[ Hazard Class ]:
6.1(a)

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

Digitoxin
14-hydroxy-3β-tetrahydropyranyloxy-5β-card-20(22)-enolide
(1S,6R)-8,8-ethylenedioxy-1-methylbicyclo[4.4.0]decan-2-one

DownStream

(5beta)-14-hydroxy-3-oxocard-20(22)-enolide
(3beta,5beta)-3-[(6-deoxy-alpha-L-mannopyranosyl)oxy]-14-hydroxycard-20(22)-enolide
Tri-O-acetyl-D-glucal
Gitoxigenin
(17α)-3α,14-Dihydroxy-5β-card-20(22)-enolide
Gitoxigenin
Ramnodigin

Articles

Synthesis and evaluation of cardiac glycoside mimics as potential anticancer drugs.

Bioorg. Med. Chem. 19 , 2407-17, (2011)

The cardiac glycoside digitoxin, consisting of a steroid core linked to a labile trisaccharide, has been used for centuries for the treatment of congestive heart failure. The well known pharmacologica...

C3'/C4'-Stereochemical Effects of Digitoxigenin α-L-/α-D-Glycoside in Cancer Cytotoxicity.

ChemMedChem 8 , 63, (2013)

Sweet'n low in stereo: A Wharton reaction was employed along with a diastereoselective palladium-catalyzed glycosylation and other post-glycosylation transformations to synthesize digitoxin analogues....

Assembly of digitoxin by gold(I)-catalyzed glycosidation of glycosyl o-alkynylbenzoates.

J. Org. Chem. 76 , 9748, (2011)

Digitoxin, a clinically important cardiac trisaccharide, was assembled efficiently from digitoxigenin and 3,4-di-O-tert-butyldiphenylsilyl-d-digitoxosyl o-cyclopropylethynylbenzoate in 9 steps and 52%...

Digitoxigenin
digitoxigenin
digitoxigenin
digitoxigenin
Δ14-digitoxigenin
Digitoxigenin-3-on
N,5-dimethyl-7-(trifluoromethyl)-4H,5H,6H,7H-[1,2,4]triazolo[1,5-a]pyrimidin-2-amine
4-((Cyclohexylamino)methyl)benzoic acid hydrochloride
1-[(2,4-Dichlorophenyl)methyl]-N-(1,1-dimethylethyl)-2-methyl-1H-indole-3-methanamine
2-Methoxy-6-(pyrazol-1-yl)-benzonitrile
1H-3-Benzazepin-7-ol, 8-chloro-2,3,4,5-tetrahydro-5-(3-iodophenyl)-3-methyl-, (S)-
(4-Methyl-tetrahydro-furan-2-yl)-methanol
N-(1-cyanocyclopentyl)-2-[4-(4-fluorobenzenesulfonyl)-1,4-diazepan-1-yl]acetamide
Ethyl 4,6-dimethyl-2,3-dihydro-1H-indole-2-carboxylate
4,5,6,7-Tetrahydrobenzo[d]isoxazole-3-carbaldehyde
6-methyl-5-(2-(5-(((4-oxo-3,4-dihydroquinazolin-2-yl)methyl)thio)-1,3,4-oxadiazol-2-yl)ethyl)pyrimidine-2,4(1H,3H)-dione