Гликозолинин

Identification

Glycozolinine (CAS 1226342) is a carbazole alkaloid isolated from the roots of the plant Glycosmis pentaphylla (family Rutaceae). Chemical formula C13H11NO. Synonyms: glycosolinin, 3-methyl-6-hydroxycarbazole, glycosolinol, 6-methyl-9H-carbazol-3-ol.

Physico-chemical characteristics

• Molecular weight: 197.23254
• Exact weight: 197.084061
• HS code: 2933990090
• PSA Specifications: 36.02
• XLogP3: 3.44
• Density: 1.3±0.1 g/cm3
• Boiling point: 439.0±25.0 °C at 760 mmHg.
• Flash point: 219.3±23.2°C
• Refractive index: 1.778

Substance class and origin

Glycozolinin is a carbazole alkaloid from the plant Glycosmis pentaphylla, a genus known to be a rich source of carbazoles, quinolones and quinazolones. In the literature, the structure of glycosolinin is interpreted in two ways: according to some sources it is 6-hydroxy-3-methylcarbazole (isolated from seeds), according to others it is 5-methoxy-3-methylcarbazole; the sources also mention glycozoline, which is similar in structure, 3-methyl-6-methoxycarbazole. This variability is typical of Glycosmis carbazole alkaloids, which are often isolated in small batches and structurally refined through repeated studies. A high refractive index (1.778) is characteristic of planar aromatic tricyclic carbazole systems with developed π-electron conjugation.

Scope of application

• reference standard for phytochemical analysis of Glycosmis pentaphylla extracts
• object of research on the biological activity of carbazole alkaloids of rutaceae
• material for comparative structural studies in the series of Glycosmis carbazoles (glycosolin, glycozolinin, glycozolidine)

The plant Glycosmis pentaphylla is traditionally used in folk medicine in South and Southeast Asia; carbazole alkaloids, including glycosolinine, are considered as marker compounds in the standardization of plant raw materials and as an object of search for new biologically active structures of the carbazole series.

Storage and transportation

No data found on hazard class, transport codes or GHS phrases. The crystalline substance with a flash point of 219.3±23.2 °C is recommended to be stored in a dry, dark place, in an airtight container, away from heat sources and open flames.

Carbazole alkaloids of the genus Glycosmis

In addition to glycosolinin and glycosolin, a number of related carbazole alkaloids have been isolated from the roots and other parts of Glycosmis pentaphylla, including 3-formylcarbazole and glycosinine, and dimeric carbazole structures have been isolated from the related species Glycosmis stenocarpa. This structural diversity of carbazoles makes Glycosmis a convenient model genus for studying the biosynthesis and biological activity of this class of natural heterocycles. The carbazole tricyclic ring—the dibenzopyrrole system—is characteristic of many natural rue alkaloids, and methyl and methoxy substituents in positions 3 and 5–6 determine subtle differences in the properties of individual representatives of this series.