Булатантриол

Description

Bulatanetriol is a natural sesquiterpenoid first isolated from the plant Annona bullata; the substance is also found in the rhizome of the common calamus (Acorus calamus) and in various species of the genus Homalomena. In structure, it belongs to bicyclic octahydroindene sesquiterpenoids: the carbobicyclic core carries a 2-hydroxy-2-methylpropyl substituent in one position, methyl groups in the other two and hydroxyl groups, giving the molecule the status of a triol - hence the name of the substance. The structure and relative configuration were established by X-ray diffraction analysis, the absolute configuration was determined by chiroptical examination of the corresponding 7-keto derivative.

Basic Attributes

• CAS No.: 99933-32-1
• Chemical formula: C15H28O3
• Molecular Weight: 256.386
• Exact weight: 256.204
• DSSTox ID: DTXSID50244351
• PSA specifications: 60.7
• XLogP3: 1.8

Chemical classification

A sesquiterpenoid, a secondary alcohol and a tertiary alcohol at the same time (two different types of hydroxyl groups in the molecule), a carbobicyclic compound. The molecule differs from the more well-known acetogenin bullatacin from the same plant source (CAS 123123-32-0) - both substances are isolated from Annona bullata, but belong to different structural classes of natural compounds: bullatacin is a sesquiterpenoid, bullatacin is an acetogenin.

Scope of application

No practical commercial use has been described; the substance is of interest for the chemistry of natural compounds as an object for studying the biosynthesis of sesquiterpenoids and structural analysis. Plant sources - Annona bullata, Acorus calamus and species of the genus Homalomena - are traditionally used in folk medicine in the regions where they grow.

Storage and transportation

There are no data on toxicity, hazard class and UN transport codes in the sources - the substance is distributed as a research reagent. Store in an airtight container in a cool, dry place, protected from light; work using standard laboratory personal protective equipment.

Sesquiterpenoids as a structural class

Sesquiterpenoids are a group of natural C15 compounds formed from three isoprene units; in the plant world they perform protective and signaling functions and often determine the aroma and taste of plant materials. Bicyclic sesquiterpenoids of the octahydroindene type, which include bulathantriol, are characteristic of several unrelated plant families - araceae (Homalomena, Acorus) and annonaceae (Annona), which indicates the independent, convergent emergence of similar biosynthetic pathways in these taxa, and not the common evolutionary origin of the trait.

Analytical role of structural analysis

Determination of the absolute configuration through chiroptical examination of a 7-keto derivative is a standard technique in the stereochemistry of natural compounds, used when direct X-ray diffraction analysis provides only the relative, but not the absolute, configuration of the chiral centers of the molecule. This two-step approach to structure determination is typical of complex polycyclic terpenoids isolated in small quantities from plant materials.