1672-46-4

Basic information

• Product Name: DIGOXIGENIN
• Synonyms: Digoxigenin Lanadigigenin;(3beta,5beta,12beta)-3,12,14-trihydroxycard-20(22)-enolide;3β,12β,14β,21-tetrahydroxy-20(22)-norcholenic acid lactone;3β,12β,14-Trihydroxy-5β,20(22)-cardenolide, 5β,20(22)-Cardenolide-3β,12β,14-triol, Lanadigigenin, 3β,12β,14β,21-Tetrahydroxy-20(22)-norcholenic acid lactone;3β,12β,14-Trihydroxy-5β,14β-card-20(22)-enolide;3β,12β,14β-Trihydroxy-5β-carda-20(22)-enolide;δ20:22-3β,12β,14,21-tetrahydroxynorcholenic acid lactone;3-[(3S,5R,8R,9S,10S,12R,13S,14S,17R)-3,12,14-trihydroxy-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
• CAS NO: 1672-46-4
• Molecular Formula: C₂₃H₃₄O₅
• Molecular Weight: 390.51
• EINECS: 216-806-2
• Mol File: 1672-46-4.mol
• Article Data: 10

Chemical Properties

• Melting Point: 222 °C(lit.)
• Boiling Point: 435.71°C (rough estimate)
• Flash Point: 203 °C
• Appearance: white solid
• Density: 1.0639 (rough estimate)
• Vapor Pressure: 2.4E-16mmHg at 25°C
• Refractive Index: 1.6120 (estimate)
• Storage Temp.: room temp
• PKA: 14.44±0.70(Predicted)
• Merck: 13,3188
• BRN: 96479
• CAS DataBase Reference: DIGOXIGENIN(CAS DataBase Reference)
• NIST Chemistry Reference: DIGOXIGENIN(1672-46-4)
• EPA Substance Registry System: DIGOXIGENIN(1672-46-4)

Safety Data

• Hazard Codes: T+
• Statements: 26/27/28
• Safety Statements: 36/37/39-45
• RIDADR: UN 2811 6.1/PG 1
• WGK Germany: 3
• RTECS: FH5390000
• HazardClass: 6.1(a)
• PackingGroup: II
• Hazardous Substances Data: 1672-46-4(Hazardous Substances Data)

Usage

Chemical Properties

Off-White to Pale Yellow Solid

Uses

Different sources of media describe the Uses of 1672-46-4 differently. You can refer to the following data:
1. DIGOXIGENIN is a steroid used as a probe in the detection of different viruses,it is also used as a non-isotopic label for DNA.
2. cardiotonic, positive inotropic activity
3. 'Diagnosis;Mainly used as a non-isotopic label for DNA

General Description

Digoxigenin is a therapeutic drug belonging to the group of cardiac glycosides, widely used in the management of congestive heart failure and other cardiac diseases.

InChI:InChI=1/C23H34O5/c1-21-7-5-15(24)10-14(21)3-4-17-18(21)11-19(25)22(2)16(6-8-23(17,22)27)13-9-20(26)28-12-13/h9,14-19,24-25,27H,3-8,10-12H2,1-2H3

Upstream product

• 20830-75-5 digoxin 
• 5355-48-6 beta-Acetyldigoxin 
• 5511-98-8 3'''-acetyldigoxin 
• 17575-22-3 lanatoside C 
• 5352-63-6 Digoxigenin mono-digitoside 
• 71-63-6 digitoxin 
• 1111-39-3 acetyldigitoxin 
• 2842-86-6 3β-Acetoxy-14-hydroxy-12-oxo-5β,14β-card-20(22)-enolid 
• 84532-09-2 (20R,S)-20,21-Epoxy-20-methyl-5β-pregnan-3β,12α-diol-diacetat 
• 84532-08-1 20-Methylen-5β-pregnan-3β,12α-diol-diacetat 
• 87335-40-8 (3S,5R,8R,9S,10S,12S,13S,14S,17R)-17-(6-Methoxy-3,6-dihydro-[1,2]dioxin-4-yl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthrene-3,12-diol 
• 84532-18-3 3β,12α-Dihydroxy-5β,14α-card-20(22)-enolid 
• 87335-39-5 (3S,5R,8R,9S,10S,12S,13S,14S,17R)-17-((E)-3-Methoxy-1-methylene-allyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthrene-3,12-diol 
• 84532-14-9 3β,12α-Dihydroxy-20-methylen-5β-pregnan-21-al 

Downstream Products

• 20830-74-4 12β-acetoxy-3β,14β-dihydroxy-5β,14β-card-20(22)-enolide 
• 6078-59-7 3,12-Diacetyl-digoxingenin 
• 26623-76-7 3β,12β-bis-benzoyloxy-14-hydroxy-5β,14β-card-20(22)-enolide 
• 79317-29-6 digoxigenin 3β-β-D-glucoside tetraacetate 
• 4427-80-9 4-[(3S,5R,8R,9S,10S,12R,13R,17R)-2,3,4,5,6,7,8,9,10,11,12,13,16,17-tetradecahydro-3,12-dihydroxy-10,13-dimethyl-1H-cyclopenta[a]phenanthren-17-yl]furan-2(5H)-one 
• 4442-17-5 3-dehydrodigoxigenin 
• 3810-94-4 digoxigenone 
• 4442-12-0 (20R)-3β,12β,14-trihydroxy-5β,14β-cardanolide 
• 85798-97-6 (20S)-3β,12β,14-trihydroxy-5β,14β-cardanolide 
• 25817-75-8 digoxigenin 3β-β-D-glucoside 

Related news

DIGOXIGENIN (cas 1672-46-4) modification of adenovirus to spatially control gene delivery from chitosan surfaces09/28/2019

To spatially control the delivery of multiple viral vectors from biomaterial scaffolds, digoxigenin (DIG) was conjugated to adenoviral capsid proteins as an antigenic determinant for antibody immobilization. The infectivity, toxicity, specificity and immobilization stability of DIG-modified aden...detailed

Notes & TipsElimination of nonspecific bands in non-radioactive electrophoretic mobility shift assays using the DIGOXIGENIN (cas 1672-46-4) system09/27/2019

In the course of detecting nuclear transcription factors by electrophoretic mobility shift assay using digoxigenin (DIG)-labeled probes, we encountered a problem with a considerable nonspecific shift band in negative control lanes from which protein extracts were omitted. This nonspecific shift ...detailed

Competitive homogeneous DIGOXIGENIN (cas 1672-46-4) immunoassay based on fluorescence quenching by gold nanoparticles09/26/2019

We report on a competitive, homogeneous immunoassay for the detection of the hapten digoxigenin. The assay is based on competitive fluorescence quenching by gold nanoparticles. Digoxigenin is indirectly labeled with the fluorophore Cy3B through bovine serum albumin and used as a marker. Gold nan...detailed

The cardenolides strophanthidin, DIGOXIGENIN (cas 1672-46-4) and dihydroouabain act as activators of the human RORγ/RORγT receptors09/25/2019

Two isoforms of a ligand-activated nuclear receptor, RORγ and RORγT, have been implicated in various physiological functions, including energy metabolism, circadian rhythm and immune system development. Using a stably transfected reporter cell line, we screened two chemical libraries and ident...detailed

Synthesis of MeON-neoglycosides of DIGOXIGENIN (cas 1672-46-4) with 6-deoxy- and 2,6-dideoxy-d-glucose derivatives and their anticancer activity09/24/2019

Cardiac glycosides show anticancer activities and their deoxy-sugar chains are vital for their anticancer effects. In order to study the structure-activity relationship (SAR) of cardiac glycosides toward cancers and get more potent anticancer agents, a series of MeON-neoglycosides of digoxigenin...detailed

Research paperSynthesis of C3-Neoglycosides of DIGOXIGENIN (cas 1672-46-4) and their anticancer activities09/10/2019

Cardiac glycosides exhibit significant anticancer effects and the glycosyl substitution at C3 position of digoxigenin is pivotal for their biological activity. In order to study the structure-activity relationship (SAR) of cardiac glycosides toward cancers and explore more potent anticancer agen...detailed

Relevant articles and documents

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Na+/K+-ATPase-Targeted Cytotoxicity of (+)-Digoxin and Several Semisynthetic Derivatives

(+)-Digoxin (1) is a well-known cardiac glycoside long used to treat congestive heart failure and found more recently to show anticancer activity. Several known cardenolides (2-5) and two new analogues, (+)-8(9)-β-anhydrodigoxigenin (6) and (+)-17-epi-20,22-dihydro-21α-hydroxydigoxin (7), were synthesized from 1 and evaluated for their cytotoxicity toward a small panel of human cancer cell lines. A preliminary structure-activity relationship investigation conducted indicated that the C-12 and C-14 hydroxy groups and the C-17 unsaturated lactone unit are important for 1 to mediate its cytotoxicity toward human cancer cells, but the C-3 glycosyl residue seems to be less critical for such an effect. Molecular docking profiles showed that the cytotoxic 1 and the noncytotoxic derivative 7 bind differentially to Na+/K+-ATPase. The HO-12β, HO-14β, and HO-3′aα hydroxy groups of (+)-digoxin (1) may form hydrogen bonds with the side-chains of Asp121 and Asn122, Thr797, and Arg880 of Na+/K+-ATPase, respectively, but the altered lactone unit of 7 results in a rotation of its steroid core, which depotentiates the binding between this compound and Na+/K+-ATPase. Thus, 1 was found to inhibit Na+/K+-ATPase, but 7 did not. In addition, the cytotoxic 1 did not affect glucose uptake in human cancer cells, indicating that this cardiac glycoside mediates its cytotoxicity by targeting Na+/K+-ATPase but not by interacting with glucose transporters.