Узаригенин

Description

Uzarigenin is a cardenolide aglycone, a steroid with an unsaturated five-membered lactone ring at C-17 and hydroxyl groups at positions 3 and 14. Systematically described as (3β,5α)-3,14-dihydroxycard-20(22)-enolide. A natural source is the roots of uzara Xysmalobium undulatum, where uzarigenin is present as a free aglycone and as a structural part of uzarin glycoside; the raw material also contains xysmalorin and xysmalogenin. Usarigenin has also been noted in species of the genus Cynanchum. The molecular target of cardenolides is Na⁺/K⁺-ATPase; for uzarigenin, in binding experiments with Na⁺,K⁺-ATPase of pig kidneys, a Kd value of 1.05 µM was obtained.

Basic Attributes

• CAS No.: 466-09-1
• Molecular Formula: C23H34O4
• Molecular Weight: 374.51
• Exact weight: 374.51
• EU number: 207-373-0
• UNII: K9ZR7LI283
• PSA specifications: 66.76000
• XLogP3: 2.79
• Density: 1.2 ± 0.1 g/cm³
• Melting point: 240–256 °C
• Boiling point: 549.3 ± 50.0 °C at 760 mm Hg. Art.
• Flash point: 188.2 ± 23.6 °C
• Refractive index: 1.591
• Specific rotation: [α]D²⁰ +10.5° (c = 1.056, alcohol)

Toxicity

• LDLo IV, cat: 1379 mcg/kg

Purpose

• standard sample for the analysis of cardenolides in Uzara raw materials and products of its processing
• biochemical research tool Na⁺/K⁺-ATPase
• starting compound for the preparation of uzarigenin glycosides and structure-activity relationship studies

Storage and handling

Information about the GHS classification is not provided in the product data sheet, but the substance is highly active physiologically: the intravenous LDLo for a cat is 1379 mcg/kg. Work with gloves and safety glasses, avoid dust and ingress. Store in a tightly closed container, away from light, at a low temperature according to the batch passport.