3261-53-8

Basic information

• Product Name: gitaloxin
• Synonyms: gitaloxin;16-Formylgitoxin;3β-[[4-O-[4-O-(2,6-Dideoxy-β-D-ribo-hexopyranosyl)-2,6-dideoxy-β-D-ribo-hexopyranosyl]-2,6-dideoxy-β-D-ribo-hexopyranosyl]oxy]-16β-formyloxy-14-hydroxy-5β,14β-card-20(22)-enolide;[3-[5-[5-(4,5-dihydroxy-6-methyloxan-2-yl)oxy-4-hydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-14-hydroxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-16-yl] formate;[3-[5-[5-(4,5-dihydroxy-6-methyl-oxan-2-yl)oxy-4-hydroxy-6-methyl-oxan-2-yl]oxy-4-hydroxy-6-methyl-oxan-2-yl]oxy-14-hydroxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-16-yl] methanoate;formic acid [3-[5-[5-(4,5-dihydroxy-6-methyl-tetrahydropyran-2-yl)oxy-4-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-4-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-14-hydroxy-17-(5-keto-2H-furan-3-yl)-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-16-yl] ester
• CAS NO: 3261-53-8
• Molecular Formula: C₄₂H₆₄O₁₅
• Molecular Weight: 808.953
• EINECS: 221-864-7
• Mol File: 3261-53-8.mol
• Article Data: 0

Chemical Properties

• Melting Point: 251.5°C
• Boiling Point: 674.74°C (rough estimate)
• Flash Point: 275.9°C
• Appearance: /
• Density: 1.1231 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.5940 (estimate)
• CAS DataBase Reference: gitaloxin(CAS DataBase Reference)
• NIST Chemistry Reference: gitaloxin(3261-53-8)
• EPA Substance Registry System: gitaloxin(3261-53-8)

Safety Data

• Hazardous Substances Data: 3261-53-8(Hazardous Substances Data)

Usage

Description

Gitaloxin, a cardenolide glycoside, is a chemical compound derived from gitoxin with a formylated 16β-hydroxy group. It is a naturally occurring substance found in various plant sources, particularly in the foxglove plant (Digitalis purpurea). Gitaloxin possesses potent pharmacological properties and has been a subject of interest for its potential therapeutic applications.

Uses

Used in Pharmaceutical Industry:
Gitaloxin is used as a therapeutic agent for its cardiotonic effects, primarily in the treatment of heart failure and certain cardiac arrhythmias. It works by increasing the force of heart muscle contractions, thereby improving the heart's pumping efficiency.
Additionally, gitaloxin has shown potential in other applications, such as:
1. Used in Cancer Treatment:
Gitaloxin is being investigated for its potential as an anticancer agent, particularly in targeting cancer cells by disrupting their energy production and inducing apoptosis.
2. Used in Drug Delivery Systems:
Gitaloxin can be incorporated into drug delivery systems to enhance its bioavailability, targeting, and overall therapeutic efficacy. This may involve the use of nanoparticles or other advanced drug delivery technologies to improve the compound's stability, solubility, and targeted delivery to specific tissues or organs.

Originator

Gitaloxin,Shanghai Lansheng Corporation

Manufacturing Process

0.2 g gitoxin was dissolved in 15 ml of dimethylformamide and mixed with 2 ml of acetanhydride, 3 ml formic acid (98%) and 2 ml triethylamine or pyridine. The reaction mixture stood for 60 min. at room temperature, then it was diluted with water, a precipitated product was filtered off. A filtrate was shook with chloroform 2 times. Chloroform was distilled to dryness and the residue was added to the precipitate. 16-Formylgitoxin was isolated by fraction crystallization. MP: 250°-253°C, yield about 50%.

Therapeutic Function

Cardiotonic

InChI:InChI=1/C42H64O15/c1-20-37(48)28(44)14-34(52-20)56-39-22(3)54-35(16-30(39)46)57-38-21(2)53-33(15-29(38)45)55-25-8-10-40(4)24(13-25)6-7-27-26(40)9-11-41(5)36(23-12-32(47)50-18-23)31(51-19-43)17-42(27,41)49/h12,19-22,24-31,33-39,44-46,48-49H,6-11,13-18H2,1-5H3

Downstream Products

• 514-21-6 ditaloxigenin 16β-formate