Дитиглоилтелоидин

Description

Ditigloylteloidine is a tropane alkaloid, a diester of the amino alcohol teloidin and tiglinic acid (at both hydroxyl groups of the 3α,6β positions), CAS 7159-86-6, formula C18H27NO5. Belongs to the section of alkaloids, structurally related to the group of tropane alkaloids of the Solanaceae (Solanaceae) along with atropine and scopolamine.

Basic Attributes

• CAS No.: 7159-86-6
• Chemical formula: C18H27NO5
• Molecular weight: 337.41068
• Exact weight: 337.41
• PSA Specifications: 76.07
• XLogP3: 1.5176

Physico-chemical characteristics

• Density: 1.17 ± 0.1 g/cm3 (predicted)

Scope of application

Tropane alkaloid of the teloidine group: teloidin differs from tropine by an additional hydroxyl group at the 7-position of the bicyclo[3.2.1]octane framework, and esterification of two hydroxyls with tiglinic acid (a fragment characteristic of plants of the genus Datura and Duboisia) gives ditigloylteloidin. Such esters are isolated from plants of the Solanaceae family when studying the biosynthesis of tropane alkaloids and the chemotaxonomy of the genus; Teloidine esters themselves are of primarily research interest as markers of metabolic pathways leading to the more well-known alkaloids of this group - atropine, scopolamine, hyoscyamine.

Synonyms

Tiglinic acid, 7-hydroxy-3α,6β-tropandiyl ester; 3α,6β-ditigloyloxytropan-7β-ol; Teloidine, 3,6-ditiglate.

Place in the product classifier

In the table, the product is classified in the “Alkaloids” section - a broad category of nitrogen-containing natural compounds with pronounced physiological activity, which, in addition to nightshade tropane esters, also includes other structural classes (pyridine, isoquinoline, indole alkaloids). Within this category, ditigloylteloidin is distinguished by its narrow natural abundance and almost complete lack of studied pharmacological activity compared to the more well-known representatives of the section.

Biosynthetic context

Tropane alkaloids are biosynthesized in plants from ornithine via putrescine and N-methylputrescine to form the characteristic bicyclic tropane scaffold. Teloidin, which carries an additional hydroxyl group compared to tropine, and tiglinic acid (2-methyl-2-butenoic acid) are both typical intermediate metabolic products of plants of the genus Datura and Duboisia, which are characterized by acylation of the hydroxyls of tropane alcohols precisely with tigloyl groups (unlike, for example, tropine, which is often esterified with tropic acid to form atropine). The presence of two tigloyl residues in the molecule distinguishes dithigloylteloidin from related monoesters and makes it a convenient chemical marker for chemotaxonomic comparison of Solanaceae species and populations.

What is not transferred from the sources

The product dump only shows the molecular weight, exact weight, PSA, XLogP3 and predicted density; no data on melting/boiling points, solubility, toxicity and transport codes were found in the dump or in available open sources - the substance is of highly specialized research interest and is poorly described in the public literature.