507-60-8

Basic information

• Product Name: 6-beta-acetoxy-3-beta(beta-D-glucopyranosyloxy)-8,14-dihydroxybufa-4,20,22-trienolide
• Synonyms: 6-beta-acetoxy-3-beta(beta-D-glucopyranosyloxy)-8,14-dihydroxybufa-4,20,22-trienolide;Bufa-4,20,22-trienolide, 6-(acetyloxy)-3-(.beta.-D-glucopyranosyloxy)-8,14-dihydroxy-, (3.beta.,6.beta.)-;scilliroside;bufa-4,20,22-trienolide, 6-(acetyloxy)-3-(β-D-glucopyranosyloxy)-8,14-dihydroxy-, (3β, 6β)- red squill scilliroside;3β-(β-D-Glucopyranosyloxy)-6β-acetoxy-8,14-dihydroxy-14β-bufa-4,20,22-trienolide;6β-(Acetoxy)-3β-(β-D-glucopyranosyloxy)-8,14-dihydroxybufa-4,20,22-trienolide;Silmurin
• CAS NO: 507-60-8
• Molecular Formula: C32H44O12
• Molecular Weight: 620.68456
• EINECS: 208-077-4
• Mol File: 507-60-8.mol
• Article Data: 0

Chemical Properties

• Melting Point: 168-170°
• Boiling Point: 581.69°C (rough estimate)
• Flash Point: 252.3 °C
• Appearance: /
• Density: 1.1882 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.6390 (estimate)
• CAS DataBase Reference: 6-beta-acetoxy-3-beta(beta-D-glucopyranosyloxy)-8,14-dihydroxybufa-4,20,22-trienolide(CAS DataBase Reference)
• NIST Chemistry Reference: 6-beta-acetoxy-3-beta(beta-D-glucopyranosyloxy)-8,14-dihydroxybufa-4,20,22-trienolide(507-60-8)
• EPA Substance Registry System: 6-beta-acetoxy-3-beta(beta-D-glucopyranosyloxy)-8,14-dihydroxybufa-4,20,22-trienolide(507-60-8)

Safety Data

• Hazard Codes: T+
• Statements: 28
• Safety Statements: 36/37-45
• RIDADR: 2810
• HazardClass: 6.1(a)
• PackingGroup: I
• Hazardous Substances Data: 507-60-8(Hazardous Substances Data)

Usage

Description

Red squill (Urginea maritima) is a large onionlike plant that grows in coastal regions along the Mediterranean Sea and in the United States; it contains a variety of cardiac glycosides, including scilliroside. All parts of the plant contain scilliroside but it is most concentrated in the bulb. There is also a white squill whose bulbs are white. Red squill has long been known and used medicinally. The earliest reference to red squill is in the Ebers Papyrus as treatment for dropsy (heart failure). Use as treatment for cough, arthritis, general diuretic, and emetic has also been described. Medicinal use declined during the nineteenth century because foxglove (digitalis) was revealed to be safer and more efficacious in the treatment of heart failure. However, use of red squill as a folk medicinal remedy continues, and deaths and serious illness may occur. Red squill is one of the oldest rodenticides and has been in use since the thirteenth century. However, scilliroside has extremely poor palatability, and many rats learn to avoid the bait. Since 1989, rodenticides containing red squill are not approved for use in the United States.

Uses

Rat poisonings containing scilliroside continue to be available and used worldwide. Technical-grade red squill powders can contain up to 28% scilliroside, and baits typically contain 0.01–0.07% of the toxicant.

Toxicity evaluation

Red squill has a multitude of toxic effects. It is directly irritating to the gastric mucosa, contributing to nausea, vomiting, abdominal pain, diarrhea, and anorexia. Rats are not able to vomit, contributing to the perceived selectivity of toxicity in rats. Scilliroside and scillaren A are both cardiac glycosides, and, like digoxin, inhibit Na+/K+ ATPase, block AV conduction, and may cause a slowed or rapid heart rate and abnormal heart rhythms.

InChI:InChI=1/C33H46O11/c1-17(35)42-22-14-32(4)24(9-11-31(3)20(8-12-33(31,32)40)18-5-6-25(36)41-16-18)30(2)10-7-19(13-21(22)30)43-29-28(39)27(38)26(37)23(15-34)44-29/h5-6,13,16,19-20,22-24,26-29,34,37-40H,7-12,14-15H2,1-4H3/t19-,20+,22+,23+,24+,26+,27-,28+,29+,30-,31+,32+,33+/m0/s1