508-88-3

Basic information

• Product Name: (17α)-3α,14-Dihydroxy-5β-card-20(22)-enolide
• Synonyms: (17α)-3α,14-Dihydroxy-5β-card-20(22)-enolide;3-epi-17βH-Digitoxigenin;17α-Digitoxigenin;17βH-Digitoxigenin
• CAS NO: 508-88-3
• Molecular Formula: C₂₃H₃₄O₄
• Molecular Weight: 374.51
• Mol File: 508-88-3.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 549.3°C at 760 mmHg
• Flash Point: 188.2°C
• Appearance: /
• Density: 1.231g/cm³
• Vapor Pressure: 2.36E-14mmHg at 25°C
• Refractive Index: 1.59
• CAS DataBase Reference: (17α)-3α,14-Dihydroxy-5β-card-20(22)-enolide(CAS DataBase Reference)
• NIST Chemistry Reference: (17α)-3α,14-Dihydroxy-5β-card-20(22)-enolide(508-88-3)
• EPA Substance Registry System: (17α)-3α,14-Dihydroxy-5β-card-20(22)-enolide(508-88-3)

Safety Data

• Hazardous Substances Data: 508-88-3(Hazardous Substances Data)

Usage

General Description

(17α)-3α,14-Dihydroxy-5β-card-20(22)-enolide, also known as Digoxigenin, is a steroid derived from the plant Digitalis purpurea, commonly known as foxglove. It is a cardiac glycoside that has been used in the treatment of congestive heart failure and arrhythmias. Digoxigenin works by inhibiting the sodium-potassium pump in the cell membrane, leading to increased intracellular calcium levels, which in turn improves cardiac contractility and reduces heart rate. It also has anti-inflammatory and anti-cancer properties, and has been used as a tool in molecular biology for detection and localization of nucleic acids. However, it carries a risk of toxicity and overdose, so it should be used with caution under medical supervision.

InChI:InChI=1/C23H34O4/c1-21-8-5-16(24)12-15(21)3-4-19-18(21)6-9-22(2)17(7-10-23(19,22)26)14-11-20(25)27-13-14/h11,15-19,24,26H,3-10,12-13H2,1-2H3/t15-,16+,17+,18+,19-,21+,22-,23+/m1/s1

Upstream product

• 143-62-4 (+)-digitoxigenin 
• 143-62-4 digitoxigenin 
• 14364-89-7 Gitoxigenin 3-O-monodigitalosideglucoside, or digitalinum verum 
• 71-63-6 digitoxin 
• 1111-39-3 acetyldigitoxin 
• 17575-20-1 Digitoxigenin 3-O-bisdigitoxosideacetyldigilanidobioside, or lanatoside A 
• 41628-29-9 Uzarigenin 3-O-β-D-Glucopyranosyl (1-4)-β-D-Glucopyranoside 
• 6877-82-3 Desglucouzarin 
• 114590-46-4 17α-digitoxigenin β-D-apiosyl-(1*6)-β-D-glucosyl-(1*4)-α-L-thevetoside 
• 114590-45-3 17α-digitoxigenin β-Cellobiosyl-(1*4)-α-L-thevetoside 
• 27127-79-3 17α-digitoxigenin β-Gentiobiosyl-(1*4)-α-L-thevetoside 

Downstream Products

• 143-62-4 3-epidigitoxigenin 
• 128701-09-7 digitoxigenin myristate 
• 128701-08-6 digitoxigenin palmitate 
• 128701-07-5 digitoxigenin stearate 
• 514-39-6 periplogenin 
• 514-39-6 3-epiperiplogenin 
• 6877-82-3 3-epidigitoxigenin β-D-glucoside 
• 18531-44-7 periplogenin β-D-glucoside 
• 6877-82-3 digitoxigenin β-D-glucoside 
• 20231-81-6 3-epidigitoxigenin β-D-gentiobioside 
• 2287-95-8 3β,14-dihydroxy-5β,14β-card-20(22)-enolide 3-(3-carboxypropanoate) 

Relevant articles and documents

BIOTRANSFORMATION OF DIGITOXIGENIN BY CELL SUSPENSION CULTURES OF STROPHANTHUS DIVARICATUS

Eight compounds, including a new compound (3-epi-17βH-gitoxigenin) were isolated as biotransformation products of digitoxigenin by cell suspension cultures of Strophanthus divaricatus.At the same time, three products were identified by TLC and HPLC. 16β-Hydroxylation and isomerization of the 17β-butenolide ring of digitoxigenin molecule were demonstrated using this cell suspension culture. Key Word Index - Strophanthus divaricatus; Apocynaceae; biotransformation; 16β-hydroxylation; isomerization of 17β-butenolide ring; cardenolides; digitoxigenin; 17βH-gitoxigenin; 3-epi-17βH-gitoxigenin.

Studies on Cerbera. V. Minor glycosides of 17α-digitoxigenin from the stems of genus Cerbera

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Potential anticancer agents. V. Cardiac glycosides of Asclepias albicans (Asclepiadaceae)

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