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

Name
DIGITOXIGENIN
EINECS
CAS No. 143-62-4
Article Data63
CAS DataBase
Density 1.231g/cm³
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
Appearance
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
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
PSA 66.76000
LogP 3.60430

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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
at 245℃; other temp., other substrates;	A 4% B 2% C 6%

...Expand

: 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

Conditions	Yield
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

Conditions	Yield
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

...Expand

: 71-63-6, 11054-89-0, 23394-08-3
digitoxin

: 143-62-4
(+)-digitoxigenin

Conditions

Conditions	Yield
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

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

: 71-63-6
digitoxin

A: 16479-50-8
digitoxigen O-[2',6'-dideoxy-β-D-ribo-hexopyranosyl]-(1->4)-(2,6-dideoxy-β-D-ribo-hexopyranoside)

B: 18404-43-8
evatromonoside

C: 143-62-4
(+)-digitoxigenin

Conditions

Conditions	Yield
In propan-1-ol at 125℃; for 1.16667h;
at 275℃;
at 275℃;

...Expand

: 71-63-6
digitoxin

A: 16479-50-8
digitoxigen O-[2',6'-dideoxy-β-D-ribo-hexopyranosyl]-(1->4)-(2,6-dideoxy-β-D-ribo-hexopyranoside)

B: 2053-00-1, 17050-70-3, 22899-74-7, 25029-50-9, 45742-39-0, 45742-40-3, 49871-87-6, 51020-42-9, 62413-93-8, 71328-50-2, 74112-04-2, 74112-05-3, 74112-09-7, 74112-10-0, 74112-11-1, 74112-14-4, 78185-01-0, 78185-02-1, 89253-95-2, 89253-96-3, 89253-97-4, 97276-35-2, 102850-49-7, 102850-50-0, 110043-58-8, 138458-66-9, 138458-67-0, 139630-51-6, 139683-22-0
β-D-digitoxopyranose

C: 18404-43-8
evatromonoside

D: 143-62-4
(+)-digitoxigenin

Conditions

Conditions	Yield
With water In 1,4-dioxane at 100℃; for 35h; Further byproducts given;	A 41 mg B n/a C 33 mg D 80 mg

...Expand

: 71-63-6
digitoxin

A: 16479-50-8
digitoxigen O-[2',6'-dideoxy-β-D-ribo-hexopyranosyl]-(1->4)-(2,6-dideoxy-β-D-ribo-hexopyranoside)

B: 90762-99-5, 90763-00-1, 90763-10-3, 90790-04-8
β-D-digitoxosyl-(1<*>4)-β-D-digitoxose

C: 18404-43-8
evatromonoside

D: 143-62-4
(+)-digitoxigenin

Conditions

Conditions	Yield
With water In 1,4-dioxane at 100℃; for 35h; Further byproducts given;	A 41 mg B n/a C 33 mg D 80 mg

...Expand

: 13238-31-8
14-hydroxy-3β-(tetra-O-acetyl-lin-tri[1β=>4]-D-ribo-2,6-dideoxy-hexopyranosyloxy)-5β,14β-card-20(22)-enolide

A: 4321-20-4
3β-hydroxy-5β-carda-14,20(22)-dienolide

B: 143-62-4
(+)-digitoxigenin

Conditions

Conditions	Yield
With hydrogenchloride In methanol at 50℃; for 0.5h; Mechanism;	A n/a B 15 mg

: 3946-61-0
3β,14β,21-trihydroxy-5β-pregnane-20-one

: malonyl coenzyme A

: 143-62-4
(+)-digitoxigenin

Conditions

Conditions	Yield
With 21-hydroxy-malonyltransferase enzyme; Hepes-KOH buffer In dimethyl sulfoxide at 90℃; for 1h;

: 7647-01-0
hydrogenchloride

: 71-63-6
digitoxin

: 143-62-4
(+)-digitoxigenin

Conditions

Conditions	Yield
at 30℃; Rate constant; Hydrolysis;

digilanide-A: digilanide-A

: 143-62-4
(+)-digitoxigenin

Conditions

Conditions	Yield
With ethanol; sulfuric acid; water

evomonoside: evomonoside

: 143-62-4
(+)-digitoxigenin

Conditions

Conditions	Yield
With hydrogenchloride; water; acetone

purpureaglucoside-A: purpureaglucoside-A

: 143-62-4
(+)-digitoxigenin

Conditions

Conditions	Yield
With hydrogenchloride; ethanol; water

: 19855-40-4
digitoxigen (β-D-glucopyranosyl)-(1→4)-(2,6-dideoxy-β-D-ribohexopyranosyl)-(1→4)-(2,6-dideoxy-β-D-ribohexopyranosyl)-(1→4)-2,6-dideoxy-β-D-ribohexopyranoside

aqueous methanol. sulfuric acid: aqueous methanol. sulfuric acid

A: 527-52-6
D-digitxose

B: 143-62-4
(+)-digitoxigenin

C digilanidobiose: digilanidobiose

...Expand

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

diluted aq.-ethanolic sulfuric acid: diluted aq.-ethanolic sulfuric acid

A: 527-52-6
D-digitxose

B: 143-62-4
(+)-digitoxigenin

C digilanidobiose: digilanidobiose

Conditions

Conditions	Yield
at 40℃; anschliessendes Behandeln mit verd. wss. Schwefelsaeure;

...Expand

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

diluted aqueous methanol. hydrochloric acid: diluted aqueous methanol. hydrochloric acid

A: 527-52-6
D-digitxose

B: 143-62-4
(+)-digitoxigenin

C O3-acetyl-digilanidobiose: O3-acetyl-digilanidobiose

Conditions

Conditions	Yield
anschliessendes Behandeln mit verd. wss. Salzsaeure;

...Expand

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

: 143-62-4
(+)-digitoxigenin

Conditions

Conditions	Yield
With water

: 932024-66-3
C27H36OSi

: 143-62-4
(+)-digitoxigenin

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: 63 percent / K2CO3; org. peroxide / benzene / 20 °C 2.1: t-BuLi; lithium 2-thienylcyanocuprate / diethyl ether; tetrahydrofuran / -78 - -10 °C 2.2: 91 percent / diethyl ether; tetrahydrofuran / -78 - -30 °C 3.1: 99 percent / aq. TsOH / acetone / Heating 4.1: 82 percent / Cs2CO3 / acetonitrile / Heating 5.1: DIBAL-H / CH2Cl2 / -78 °C 5.2: KH; CS2; MeI / tetrahydrofuran / 20 °C 5.3: n-Bu3SnH; AIBN / benzene / Heating 6.1: 98 percent / TBAF / tetrahydrofuran / Heating 7.1: O2; Rose bengal; DIPEA / CH2Cl2 / -78 °C / Irradiation 7.2: 61 percent / NaBH4; H2O / CH2Cl2 / 20 °C View Scheme

Yield

Multi-step reaction with 7 steps
1.1: 63 percent / K2CO3; org. peroxide / benzene / 20 °C
2.1: t-BuLi; lithium 2-thienylcyanocuprate / diethyl ether; tetrahydrofuran / -78 - -10 °C
2.2: 91 percent / diethyl ether; tetrahydrofuran / -78 - -30 °C
3.1: 99 percent / aq. TsOH / acetone / Heating
4.1: 82 percent / Cs2CO3 / acetonitrile / Heating
5.1: DIBAL-H / CH2Cl2 / -78 °C
5.2: KH; CS2; MeI / tetrahydrofuran / 20 °C
5.3: n-Bu3SnH; AIBN / benzene / Heating
6.1: 98 percent / TBAF / tetrahydrofuran / Heating
7.1: O2; Rose bengal; DIPEA / CH2Cl2 / -78 °C / Irradiation
7.2: 61 percent / NaBH4; H2O / CH2Cl2 / 20 °C
View Scheme

: 932024-72-1
C41H54O5Si

: 143-62-4
(+)-digitoxigenin

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: 99 percent / aq. TsOH / acetone / Heating 2.1: 82 percent / Cs2CO3 / acetonitrile / Heating 3.1: DIBAL-H / CH2Cl2 / -78 °C 3.2: KH; CS2; MeI / tetrahydrofuran / 20 °C 3.3: n-Bu3SnH; AIBN / benzene / Heating 4.1: 98 percent / TBAF / tetrahydrofuran / Heating 5.1: O2; Rose bengal; DIPEA / CH2Cl2 / -78 °C / Irradiation 5.2: 61 percent / NaBH4; H2O / CH2Cl2 / 20 °C View Scheme

Yield

Multi-step reaction with 5 steps
1.1: 99 percent / aq. TsOH / acetone / Heating
2.1: 82 percent / Cs2CO3 / acetonitrile / Heating
3.1: DIBAL-H / CH2Cl2 / -78 °C
3.2: KH; CS2; MeI / tetrahydrofuran / 20 °C
3.3: n-Bu3SnH; AIBN / benzene / Heating
4.1: 98 percent / TBAF / tetrahydrofuran / Heating
5.1: O2; Rose bengal; DIPEA / CH2Cl2 / -78 °C / Irradiation
5.2: 61 percent / NaBH4; H2O / CH2Cl2 / 20 °C
View Scheme

: 932024-73-2
C39H50O4Si

: 143-62-4
(+)-digitoxigenin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: DIBAL-H / CH2Cl2 / -78 °C 1.2: KH; CS2; MeI / tetrahydrofuran / 20 °C 1.3: n-Bu3SnH; AIBN / benzene / Heating 2.1: 98 percent / TBAF / tetrahydrofuran / Heating 3.1: O2; Rose bengal; DIPEA / CH2Cl2 / -78 °C / Irradiation 3.2: 61 percent / NaBH4; H2O / CH2Cl2 / 20 °C View Scheme

: 932024-60-7
C39H52O3Si

: 143-62-4
(+)-digitoxigenin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 98 percent / TBAF / tetrahydrofuran / Heating 2.1: O2; Rose bengal; DIPEA / CH2Cl2 / -78 °C / Irradiation 2.2: 61 percent / NaBH4; H2O / CH2Cl2 / 20 °C View Scheme

: 932024-61-8
C39H50O4Si

: 143-62-4
(+)-digitoxigenin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 82 percent / Cs2CO3 / acetonitrile / Heating 2.1: DIBAL-H / CH2Cl2 / -78 °C 2.2: KH; CS2; MeI / tetrahydrofuran / 20 °C 2.3: n-Bu3SnH; AIBN / benzene / Heating 3.1: 98 percent / TBAF / tetrahydrofuran / Heating 4.1: O2; Rose bengal; DIPEA / CH2Cl2 / -78 °C / Irradiation 4.2: 61 percent / NaBH4; H2O / CH2Cl2 / 20 °C View Scheme

: 932024-62-9
C27H34O2Si

: 143-62-4
(+)-digitoxigenin

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: t-BuLi; lithium 2-thienylcyanocuprate / diethyl ether; tetrahydrofuran / -78 - -10 °C 1.2: 91 percent / diethyl ether; tetrahydrofuran / -78 - -30 °C 2.1: 99 percent / aq. TsOH / acetone / Heating 3.1: 82 percent / Cs2CO3 / acetonitrile / Heating 4.1: DIBAL-H / CH2Cl2 / -78 °C 4.2: KH; CS2; MeI / tetrahydrofuran / 20 °C 4.3: n-Bu3SnH; AIBN / benzene / Heating 5.1: 98 percent / TBAF / tetrahydrofuran / Heating 6.1: O2; Rose bengal; DIPEA / CH2Cl2 / -78 °C / Irradiation 6.2: 61 percent / NaBH4; H2O / CH2Cl2 / 20 °C View Scheme

Yield

Multi-step reaction with 6 steps
1.1: t-BuLi; lithium 2-thienylcyanocuprate / diethyl ether; tetrahydrofuran / -78 - -10 °C
1.2: 91 percent / diethyl ether; tetrahydrofuran / -78 - -30 °C
2.1: 99 percent / aq. TsOH / acetone / Heating
3.1: 82 percent / Cs2CO3 / acetonitrile / Heating
4.1: DIBAL-H / CH2Cl2 / -78 °C
4.2: KH; CS2; MeI / tetrahydrofuran / 20 °C
4.3: n-Bu3SnH; AIBN / benzene / Heating
5.1: 98 percent / TBAF / tetrahydrofuran / Heating
6.1: O2; Rose bengal; DIPEA / CH2Cl2 / -78 °C / Irradiation
6.2: 61 percent / NaBH4; H2O / CH2Cl2 / 20 °C
View Scheme

: 108-24-7
acetic anhydride

: 143-62-4
(+)-digitoxigenin

: 808-19-5
digitoxigenin 3-acetate

Conditions

Conditions	Yield
With pyridine; dmap at 20 - 30℃; Inert atmosphere;	100%
In pyridine at 24℃; for 28h;	98%
With sodium acetate
In pyridine
With pyridine

: 110-87-2
3,4-dihydro-2H-pyran

: 143-62-4
(+)-digitoxigenin

: 809-98-3
14-hydroxy-3β-tetrahydropyranyloxy-5β-card-20(22)-enolide

Conditions

Conditions	Yield
polymer bound diphenylphosphane hydrobromide In dichloromethane at 20℃; for 3h;	99%
With ethyl acetate; trichlorophosphate
With pyridinium p-toluenesulfonate In dichloromethane

: 1268341-16-7
C14H22O5

: 143-62-4
(+)-digitoxigenin

: 1268341-20-3
C32H46O6

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine In dichloromethane; chloroform at 0℃;	98%

: 69739-34-0
t-butyldimethylsiyl triflate

: 143-62-4
(+)-digitoxigenin

: 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

Conditions

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 1h;	96%

: 1268341-15-6
C13H20O5

: 143-62-4
(+)-digitoxigenin

: 1268341-19-0
C31H44O6

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine In dichloromethane; chloroform at 0℃;	94%

: 143-62-4
(+)-digitoxigenin

: 1102-88-1
digitoxigenone

Conditions

Conditions	Yield
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide for 3h; Ambient temperature;	92%
With N-methyl-2-indolinone; tetrapropylammonium perruthennate In dichloromethane at 20℃; Oxidation;	89%
Stage #1: (+)-digitoxigenin With chromium(VI) oxide; sulfuric acid In water; acetone at 0℃; for 0.333333h; Stage #2: In methanol; water; acetone at 0℃; for 0.333333h;	84%

: 1268341-13-4
C12H18O5

: 143-62-4
(+)-digitoxigenin

: 1268341-17-8
C30H42O6

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine In dichloromethane; chloroform at 0℃;	90%

: 7693-46-1
4-Nitrophenyl chloroformate

: 143-62-4
(+)-digitoxigenin

: 4-nitrophenyl carbamate-3-O-digitoxigenin

Conditions

Conditions	Yield
With pyridine In 1,2-dichloro-ethane for 16h; Molecular sieve;	88.56%

: 679412-06-7
tert-butyl ((2R,6R)-6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl) carbonate

: 143-62-4
(+)-digitoxigenin

: 1256497-85-4
(2R,6S)-2-methyl-6-(digitoxigenoxy)-2H-pyran-3(6H)-one

Conditions

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenylphosphine In tetrahydrofuran; dichloromethane at 0℃; for 8h; Inert atmosphere;	88%
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenylphosphine In dichloromethane at 0℃; for 8h;	88%
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenylphosphine In dichloromethane at 0℃; for 12h;	83%

: 1268341-14-5
C13H20O5

: 143-62-4
(+)-digitoxigenin

: 1268341-18-9
C31H44O6

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine In dichloromethane; chloroform at 0℃;	88%

: 69483-67-6
3,4-Di-O-acetyl-1,5-anhydro-2,6-didesoxy-D-ribo-hex-1-enit

: 143-62-4
(+)-digitoxigenin

: 83025-21-2, 99694-28-7, 99694-29-8
(Digitoxigenin-3-yl)-3,4-di-O-acetyl-2,6-didesoxy-2-iod-α-D-altropyranosid

Conditions

Conditions	Yield
With N-iodo-succinimide In acetonitrile	86%
With N-iodo-succinimide In dichloromethane; acetonitrile for 168h;	86%

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

: 143-62-4
(+)-digitoxigenin

: (2R,6R)-2-methyl-6-(digitoxygenoxy)-2H-pyran-3(6H)-one

Conditions

Conditions	Yield
With triphenylphosphine; tris(dibenzylideneacetone)dipalladium (0) In tetrahydrofuran; dichloromethane; chloroform at 0℃; for 8h;	86%
With triphenylphosphine; tris(dibenzylideneacetone)dipalladium(0) chloroform complex In dichloromethane at 0℃; for 8h;	86%
With palladium; triphenylphosphine	86%
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenylphosphine In tetrahydrofuran; dichloromethane at 0℃; for 8h; Inert atmosphere;	86%

: tert-butyl-5,6-dihydro-6-methyl-5-oxo-2H-pyran-2-yl carbonate

: 143-62-4
(+)-digitoxigenin

: 1256497-88-7
C29H40O6

Conditions

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenylphosphine In tetrahydrofuran; dichloromethane at 0℃; for 8h; Inert atmosphere;	85%

: 476469-65-5
1,5-anhydro-3,4-bis(triethylsilyl)-2,6-dideoxy-L-lyxo-hex-1-enitol

: 143-62-4
(+)-digitoxigenin

: 476469-66-6
4-[(3S,5R,8R,9S,10S,13R,14S,17R)-14-Hydroxy-10,13-dimethyl-3-((2R,4S,5R,6S)-6-methyl-4,5-bis-triethylsilanyloxy-tetrahydro-pyran-2-yloxy)-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-5H-furan-2-one

Conditions

Conditions	Yield
With camphor-10-sulfonic acid In dichloromethane; toluene at 20℃; for 12h;	84%

: 39110-68-4
2,3,5-tri-O-acetyl-D-ribofuranosyl bromide

: 143-62-4
(+)-digitoxigenin

: 99617-50-2
3-O-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)digitoxigenin

Conditions

Conditions	Yield
With mercury(II) cyanide In acetonitrile at 60℃; for 2h;	83%

: 1207607-99-5
α/β-1-trichloroacetaimidate-2,3,4-tribenzoyl-L-ribose

: 143-62-4
(+)-digitoxigenin

: 1207607-91-7
C49H54O11

Conditions

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 0℃; for 0.333333h; Molecular sieve; Inert atmosphere;	82%

: 865484-73-7
tert-butyl ((2S,6S)-6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl) carbonate

: 143-62-4
(+)-digitoxigenin

: 1256497-84-3
C29H40O6

Conditions

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenylphosphine In tetrahydrofuran; dichloromethane at 0℃; for 6h; Inert atmosphere;	82%
With tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine In dichloromethane; chloroform at 0℃;	82%
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenylphosphine In dichloromethane at 0℃; for 8h;	82%
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenylphosphine In dichloromethane

: 865484-73-7
tert-butyl ((2S,6S)-6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl) carbonate

: 143-62-4
(+)-digitoxigenin

: (2S,6R)-2-methyl-6-(digitoxigenoxy)-2H-pyran-3(6H)-one

Conditions

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenylphosphine In tetrahydrofuran; dichloromethane at 0℃; for 6h;	82%

: 93790-78-4
4-oxo-4-(2-(trimethylsilyl)ethoxy)butanoic acid

: 143-62-4
(+)-digitoxigenin

: 107938-48-7
14-hydroxy-5β,14β-card-20(22)-enolid-3β-yl 2-(trimethylsilyl)ethyl butanedioate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In benzene for 3h; Ambient temperature;	78%

: 143-62-4
(+)-digitoxigenin

: 508-88-3
Menabegenin

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 50℃; for 16h;	76%
With sodium acetate; sodium p-hydroxybenzenesulfonate; N,N-dimethyl-formamide at 125℃;

: 129823-37-6
C46H46NO7PS

: 143-62-4
(+)-digitoxigenin

A: 103368-07-6, 103368-08-7
(3β,5β,14β,17β)-3β-<(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)oxy>-14-hydroxycard-20(22)-enolide

B: 103368-07-6, 103368-08-7
(3β,5β,14β,17β)-3β-<(2,3,4-tri-O-benzyl-β-L-rhamnopyranosyl)oxy>-14-hydroxycard-20(22)-enolide

Conditions

Conditions	Yield
With 4 A molecular sieve; boron trifluoride diethyl etherate In dichloromethane at -10℃; for 1h;	A 76% B 8%

...Expand

: 476469-56-4
Acetic acid (2S,3R,4S,6S)-6-[(2S,3R,4S)-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-3,4-dihydro-2H-pyran-3-yloxy]-3-((2S,4S,5R,6S)-4,5-diacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-methyl-tetrahydro-pyran-4-yl ester

: 143-62-4
(+)-digitoxigenin

: 476469-57-5
C53H84O16Si

Conditions

Conditions	Yield
With camphor-10-sulfonic acid In dichloromethane; toluene at 20℃; for 10h;	75%

: 1464-44-4
phenyl-β-D-glucopyranoside

: 143-62-4
(+)-digitoxigenin

: 17059-16-4
digitoxigenin 3-O-β-D-glucoside

Conditions

Conditions	Yield
In water; acetonitrile at 10℃; for 12h; β-galactosidase (obt. from Asp. oryzae), phosphate buffer pH=5;	74.1%
With β-galactosidase In water; acetonitrile at 10℃; for 12h; phosphate buffer (pH 5);	74.1%

: 143-62-4
(+)-digitoxigenin

: 1919-02-4
3β,14-dihydroxy-17β-(furan-3-yl)-5β,14β-androstane

Conditions

Conditions	Yield
Stage #1: (+)-digitoxigenin With diisobutylaluminium hydride In tetrahydrofuran at -5℃; Stage #2: With manganese(IV) oxide In 1,4-dioxane; water; acetic acid	74%

: 143-62-4
(+)-digitoxigenin

A: 1919-02-4
3β,14-dihydroxy-17β-(furan-3-yl)-5β,14β-androstane

B: 116499-22-0
24-Nor-5β,14β-chol-20(22)-en-3β,14,21,23-tetraol

C: 13957-85-2
17β-(Fur-3-yl)-5β-androst-14-en-3β-yl-acetat

Conditions

Conditions	Yield
With diisobutylaluminium hydride In tetrahydrofuran 1.) -30 deg C - -35 deg C, 1 h, 2.) up to 0 deg C during 30 min;	A 71% B 14.6% C 370 mg
With diisobutylaluminium hydride In tetrahydrofuran 1.) -30 deg C to -35 deg C, 1 h, 2.) up to 0 deg C during 30 min;	A 71% B 14.6% C 370 mg

...Expand

: 53611-24-8
4-isothiocyanato benzoyl chloride

: 143-62-4
(+)-digitoxigenin

: 14-hydroxy-3β-(4-isothiocyanatobenzoyloxy)-5β,14β-card-20(22)-enolide

Conditions

Conditions	Yield
With dmap In pyridine at 20℃; for 3h; Esterification;	68%

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 Toxic T
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

Product Name

DIGITOXIGENIN

Synthetic route

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

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

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

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

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