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3,β,14-Dihydroxy-5,β-card-20(22)enolide
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Name

3,β,14-Dihydroxy-5,β-card-20(22)enolide

 EINECS N/A
CAS No. 143-62-4 Density 1.231g/cm3
PSA 66.76000 LogP 3.60430
Solubility 11.24mg/L(30 oC) Melting Point 253-255oC (dec.)(lit.)
Formula C23H34 O4 Boiling Point 549.3°C at 760 mmHg
Molecular Weight 374.521 Flash Point 188.1°C
Transport Information N/A Appearance N/A
Safety Poison by ingestion, subcutaneous, intravenous, and parenteral routes. When heated to decomposition it emits acrid smoke and irritating fumes. Risk Codes 25
Molecular Structure Molecular Structure of 143-62-4 (DIGITOXIGENIN) Hazard Symbols T
Synonyms

5b-Card-20(22)-enolide, 3b,14-dihydroxy- (6CI,7CI,8CI);(+)-Digitoxigenin; Cerberigenin; Digitoxigenin; NSC 407806; D20:22-3,14,21-Trihydroxynorcholenicacid lactone

Article Data 63

3,β,14-Dihydroxy-5,β-card-20(22)enolide Synthetic route

182573-64-4

4-[(3S,5R,8R,9S,10S,13R,14S,17R)-3-(tert-Butyl-dimethyl-silanyloxy)-14-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-5H-furan-2-one

143-62-4

(+)-digitoxigenin

Conditions
ConditionsYield
With toluene-4-sulfonic acid In methanol for 24h; Ambient temperature;97%
With sulfuric acid In methanol; water for 1h; Heating;95%
71-63-6

digitoxin

143-62-4

(+)-digitoxigenin

Conditions
ConditionsYield
With sulfuric acid In methanol at 0℃; for 5h;95%
With toluene-4-sulfonic acid In methanol at 20℃;79%
With hydrogenchloride; ethanol; water
809-98-3

14-hydroxy-3β-tetrahydropyranyloxy-5β-card-20(22)-enolide

143-62-4

(+)-digitoxigenin

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In ethanol at 60℃; for 1h;85%
29742-88-9, 33156-31-9, 99780-82-2

(Digitoxigenin-3-yl)-4-O-acetyl-2,3,6-tridesoxy-α-L-erythro-hex-2-enopyranosid

143-62-4

(+)-digitoxigenin

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethanol for 2h; Product distribution;69%
1919-02-4

3β,14-dihydroxy-17β-(furan-3-yl)-5β,14β-androstane

143-62-4

(+)-digitoxigenin

Conditions
ConditionsYield
Stage #1: 3β,14-dihydroxy-17β-(furan-3-yl)-5β,14β-androstane With oxygen; rose bengal; N-ethyl-N,N-diisopropylamine In dichloromethane at -78℃; Irradiation;
Stage #2: With sodium tetrahydroborate; water In dichloromethane at 20℃; Further stages.;		61%
18810-25-8

3β-O-(β-D-digitalosyl)-14-hydroxy-5β,14β-card-20(22)-enolide

A

14364-82-0

14-dehydrodigitoxigenin 3-O-β-D-digitaloside

B

4321-20-4

3β-hydroxy-5β-carda-14,20(22)-dienolide

C

143-62-4

(+)-digitoxigenin

Conditions
ConditionsYield
at 245℃; other temp., other substrates;A 4%
B 2%
C 6%
12738-19-1, 31087-87-3, 31087-88-4, 58407-69-5, 59284-73-0, 59284-75-2, 69461-00-3, 12708-27-9

3β-O-(β-D-diginosyl)-14-hydroxy-5β,14β-card-20(22)-enolide

143-62-4

(+)-digitoxigenin

Conditions
ConditionsYield
With methanol; sulfuric acid; water
18810-25-8

3β-O-(β-D-digitalosyl)-14-hydroxy-5β,14β-card-20(22)-enolide

A

14364-82-0

14-dehydrodigitoxigenin 3-O-β-D-digitaloside

B

484-37-7, 523-75-1, 25672-81-5, 78185-80-5, 78185-81-6, 118333-77-0, 484-36-6

6-deoxy-3-O-methyl-D-galactopyranose

C

4321-20-4

3β-hydroxy-5β-carda-14,20(22)-dienolide

D

143-62-4

(+)-digitoxigenin

Conditions
ConditionsYield
With water In 1,4-dioxane at 140℃; for 8h;A 17 mg
B 11 mg
C 8 mg
D 23 mg
With water In 1,4-dioxane at 140℃; for 8h; other cardenolide and flavonoid glycosides;A 17 mg
B 11 mg
C 8 mg
D 23 mg
71-63-6, 11054-89-0, 23394-08-3

digitoxin

143-62-4

(+)-digitoxigenin

Conditions
ConditionsYield
With sulfuric acid In methanol at 20℃; for 4h;4 g
78614-49-0, 99604-84-9, 105761-94-2, 119323-62-5

Digitoxigenin-3β-O-α-L-arabinofuranosid

A

5328-37-0

L-arabinose

B

143-62-4

(+)-digitoxigenin

Conditions
ConditionsYield
With phosphate buffer In water; dimethyl sulfoxide at 37℃; for 0.5h; 1 IE α-L-arabinofuranosidase (Aspergillus niger K 1), enzymatic cleavage;

3,β,14-Dihydroxy-5,β-card-20(22)enolide Chemical Properties

IUPAC Name: 4-[(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]-5H-furan-2-one
Synonyms of 3,β,14-Dihydroxy-5,β-card-20(22)enolide (CAS NO.143-62-4) : (3b,5b)-3,14-Dihydroxycard-20(22)-enolide ; 4-[(3S,5R,8R,9S,10S,13R,14S,17R)-3,14-Dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2(5H)-furanon ; Card-20(22)-enolide, 3,14-dihydroxy-, (3.beta.,5.beta.)-
Product Categories: 3,β,14-Dihydroxy-5,β-card-20(22)enolide (CAS NO.143-62-4) belongs to Biochemistry;Steroids;Steroids (Others);ATPase .
CAS NO: 143-62-4
Molecular Formula :C50H49N7O10S2
Molecular Weight :374.51
Molecular Structure :
EINECS: 205-603-4
Index of Refraction: 1.59
Surface Tension: 54.4 dyne/cm
Density: 1.231 g/cm3
Flash Point: 188.1 °C
Enthalpy of Vaporization: 95.3 kJ/mol
Boiling Point: 549.3 °C at 760 mmHg
Vapour Pressure: 2.36E-14 mmHg at 25°C 
Melting point: 253-255 °C (dec.)(lit.)

3,β,14-Dihydroxy-5,β-card-20(22)enolide Uses

 3,β,14-Dihydroxy-5,β-card-20(22)enolide (CAS NO.143-62-4) ist ein Steroid aus der Hydrolyse des Herzglykosids Digitoxin, welches im Fingerhut.

3,β,14-Dihydroxy-5,β-card-20(22)enolide Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo intravenous 254ug/kg (0.254mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING Journal of the American Pharmaceutical Association. Vol. 27, Pg. 189, 1938.
guinea pig LDLo intravenous 1419ug/kg (1.419mg/kg) BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS

CARDIAC: OTHER CHANGES

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Archives Internationales de Pharmacodynamie et de Therapie. Vol. 153, Pg. 436, 1965.
mouse LD50 intracrebral 187ug/kg (0.187mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Arzneimittel-Forschung. Drug Research. Vol. 11, Pg. 908, 1961.
mouse LD50 intravenous 1131ug/kg (1.131mg/kg)   Life Sciences. Vol. 37, Pg. 775, 1985.
mouse LD50 oral 26170ug/kg (26.17mg/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.
mouse LD50 subcutaneous 11820ug/kg (11.82mg/kg) BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS
CARDIAC: OTHER CHANGES
BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Archives Internationales de Pharmacodynamie et de Therapie. Vol. 153, Pg. 436, 1965.
pigeon LDLo parenteral 600ug/kg (0.6mg/kg)   Chemical and Pharmaceutical Bulletin. Vol. 8, Pg. 18, 1960.
rat LD50 intravenous 1600ug/kg (1.6mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Arzneimittel-Forschung. Drug Research. Vol. 11, Pg. 848, 1961.

3,β,14-Dihydroxy-5,β-card-20(22)enolide Safety Profile

Poison by ingestion, subcutaneous, intravenous, and parenteral routes. When heated to decomposition it emits acrid smoke and irritating fumes.
Hazard Codes ToxicT
Risk Statements 25 
R25 : 3,β,14-Dihydroxy-5,β-card-20(22)enolide (CAS NO.143-62-4) is toxic if swallowed.
Safety Statements 45
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR UN 3462 6.1/PG 2
WGK Germany 3
RTECS FH4975000
HazardClass 6.1(a)
PackingGroup II

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