Gigactonine
From Wikipedia, the free encyclopedia
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| Names | |
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| IUPAC name
(1α,6β,14α,16β)-20-Ethyl-4-(hydroxymethyl)-6,14,16-trimethoxyaconitane-1,7,8-triol | |
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3D model (JSmol) |
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| ChemSpider | |
PubChem CID |
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CompTox Dashboard (EPA) |
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| Properties[1] | |
| C24H39NO7 | |
| Molar mass | 453.576 g·mol−1 |
| Melting point | 168 °C (334 °F; 441 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Gigactonine is a naturally occurring diterpene alkaloid first isolated from Aconitum gigas. It occurs widely in the Ranunculaceae plant family. The polycyclic ring system of this chemical compound contains nineteen carbon atoms and one nitrogen atom, which is the same as in aconitine and this is reflected in its preferred IUPAC name.
Gigactonine was reported in 1978 after its isolation from Aconitum gigas. Although a novel structure at that time, it was recognised to be related to known diterpene alkaloids including delsoline, which is methylated on its 4-hydroxymethyl primary alcohol sidechain.[1]
Synthesis
Although individual members of this class of alkaloids have been extensively studied, their chemical complexity has limited the number which have been individually synthesised. Similarly, their full biosynthetic pathway is only known in outline in most cases.[2]