Винорин

Description

Vinorin is a monoterpene indole alkaloid from the roots of Rauvolfia serpentina. It occupies a central place in the biosynthesis of ajmaline, an antiarrhythmic alkaloid from the same Indian medicinal culture. The systematic designation reflects the structure: (17R,19E)-1,2,19,20-tetradehydro-1-demethylajmalan-17-ol 17-acetate.

Basic Attributes

• CAS No.: 34020-07-0
• Chemical formula: C21H22N2O2
• Molecular weight: 334.4
• Exact weight: 334.168121
• PSA specifications: 41.90000
• XLogP3: 1.93
• Density: 1.5 ± 0.1 g/cm³
• Boiling point: 471.9 ± 45.0 °C at 760 mm Hg. Art.
• Flash point: 239.2 ± 28.7 °C
• Refractive index: 1.782

Natural source and biosynthesis

The alkaloid is isolated from the root of Rauvolfia serpentina. The pathway of its formation begins with tryptamine and the monoterpene secologanin and ultimately leads to the six-ring system of ajmaline with nine chiral carbon atoms. The key enzyme is vinorine synthase (EC 2.3.1.160), an acetyltransferase of the BAHD family. It catalyzes the reversible, acetyl-CoA or CoA-dependent formation of vinorin (or 11-methoxyvinorin) from 16-epi-vellosimine (or gardneral). Vinorine synthase was the first member of the BAHD superfamily to have a crystal structure obtained; The same family includes enzymes for the biosynthesis of morphine, taxol and vindoline.

Scope of application

• analytical standard and object of research in the chemistry of natural compounds
• reference compound in works on ajmaline biosynthesis and on enzymes of the BAHD family
• substrate and product in enzymological experiments with vinorine synthase

Storage and handling

There is no data on hazard classification and transport classification in the product card. Handle as a biologically active substance for laboratory use: closed container, cool, dry place without light, work with gloves and safety glasses, avoid inhalation of dust. Check the storage conditions for a specific batch using the manufacturer's documents.