472-26-4

Basic information

• Product Name: 3β,5,14-Trihydroxy-5β-bufa-20,22-dienolide
• Synonyms: 3β,5,14-Trihydroxy-5β,14β-bufa-20,22-dienolide;3β,5,14-Trihydroxy-5β-bufa-20,22-dienolide;Telocinobufagin;Telocinobufogenin;(3beta,5beta)-3,5,14-Trihydroxybufa-20,22-dienolide;Telobufotoxin;(3β,5β)-3,5,14-Trihydroxybufa-20,22-dienolide;NSC 119989
• CAS NO: 472-26-4
• Molecular Formula: C₂₄H₃₄O₅
• Molecular Weight: 402.52376
• Product Categories: Steroids
• Mol File: 472-26-4.mol
• Article Data: 0

Chemical Properties

• Melting Point: 208-214 °C
• Boiling Point: 589.6°Cat760mmHg
• Flash Point: 201°C
• Appearance: /
• Density: 1.311
• Vapor Pressure: 2.34E-16mmHg at 25°C
• Refractive Index: 1.624
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly, Heated), Methanol (Slightly)
• PKA: 14.62±0.70(Predicted)
• CAS DataBase Reference: 3β,5,14-Trihydroxy-5β-bufa-20,22-dienolide(CAS DataBase Reference)
• NIST Chemistry Reference: 3β,5,14-Trihydroxy-5β-bufa-20,22-dienolide(472-26-4)
• EPA Substance Registry System: 3β,5,14-Trihydroxy-5β-bufa-20,22-dienolide(472-26-4)

Safety Data

• Hazardous Substances Data: 472-26-4(Hazardous Substances Data)

Usage

Description

3β,5,14-Trihydroxy-5β-bufa-20,22-dienolide, also known as Telocinobufagin, is a naturally occurring compound that is primarily isolated from the skin secretion of the toad Bufo rubescens. It is a steroidal glycoside with a unique chemical structure characterized by the presence of three hydroxyl groups at the 3β, 5, and 14 positions, and a dienone structure at the 20,22 positions. 3β,5,14-Trihydroxy-5β-bufa-20,22-dienolide exhibits a range of biological activities, making it a potential candidate for various pharmaceutical applications.

Uses

Used in Pharmaceutical Industry:
3β,5,14-Trihydroxy-5β-bufa-20,22-dienolide is used as a novel antibiotic cardiotonic for its ability to strengthen the contraction of the heart muscle. This property makes it a valuable compound in the development of new drugs for the treatment of heart-related conditions.
Used in Anticancer Applications:
Although not explicitly mentioned in the provided materials, given its structural similarity to other bufadienolides, which are known for their cytotoxic properties, 3β,5,14-Trihydroxy-5β-bufa-20,22-dienolide could potentially be used as an anticancer agent. Further research would be required to explore its efficacy and safety in this context.
Used in Drug Delivery Systems:
As with gallotannin, the development of novel drug delivery systems could be beneficial for enhancing the applications and efficacy of 3β,5,14-Trihydroxy-5β-bufa-20,22-dienolide. Utilizing carriers such as organic and metallic nanoparticles could improve its delivery, bioavailability, and therapeutic outcomes in various medical applications.

InChI:InChI=1/C24H34O5/c1-21-9-5-16(25)13-23(21,27)11-7-19-18(21)6-10-22(2)17(8-12-24(19,22)28)15-3-4-20(26)29-14-15/h3-4,14,16-19,25,27-28H,5-13H2,1-2H3/t16-,17+,18?,19?,21+,22+,23-,24-/m0/s1

Upstream product

• 64-17-5 ethanol 
• 64-19-7 acetic acid 
• 470-42-8 marinobufagin 

Downstream Products

• 1224695-39-9 telocinobufagin-3-O-sulfite 
• 110371-55-6 (S)-2-{4-[(3S,5S,8R,9S,10R,13R,14S,17R)-5,14-Dihydroxy-10,13-dimethyl-17-(6-oxo-6H-pyran-3-yl)-hexadecahydro-cyclopenta[a]phenanthren-3-yloxycarbonyl]-butyrylamino}-5-guanidino-pentanoic acid 
• 110371-57-8 Pentanedioic acid (3S,5S,8R,9S,10R,13R,14S,17R)-5,14-dihydroxy-10,13-dimethyl-17-(6-oxo-6H-pyran-3-yl)-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester 4-nitro-phenyl ester 
• 110372-11-7 Pentanedioic acid (3S,5S,8R,9S,10R,13R,14S,17R)-5,14-dihydroxy-10,13-dimethyl-17-(6-oxo-6H-pyran-3-yl)-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester methyl ester 
• 110371-60-3 Pentanedioic acid mono-[(3S,5S,8R,9S,10R,13R,14S,17R)-5,14-dihydroxy-10,13-dimethyl-17-(6-oxo-6H-pyran-3-yl)-hexadecahydro-cyclopenta[a]phenanthren-3-yl] ester