Кабралеадиол

Description

Cabraleadiol (also known as 3-epiocotillol II) is a naturally occurring damaran triterpenoid isolated from several species of the Meliaceae family: the bark of Aglaia crassinervia, the fruits and leaves of Aglaia erythrosperma, the aryllus of Carapa guianensis, and the fruits and seeds of Cabralea canjerana.

Basic Attributes

• CAS No: 67253-01-4
• Chemical formula: C30H52O3
• Molecular weight: 460.7
• Exact weight: 460.391632
• PSA Specifications: 49.69
• XLogP3: 7.90

Physico-chemical properties (calculated and reference values)

• Density: 1.0±0.1 g/cm3
• Boiling point: 533.6±15.0 °C at 760 mm Hg. Art.
• Flash point: 276.5±20.4°C
• Refractive index: 1.521

Compound class and origin

Damarane triterpendiol, widely distributed in the genus Aglaia and related genera of the family Meliaceae. The high XLogP3 value (7.90) indicates a pronounced lipophilicity of the molecule, typical of triterpenoids with a large non-polar carbon skeleton and a limited number of polar hydroxyl groups.

Biosynthesis and relationship with cabralalactone

Like cabralealactone, cabraleadiol is formed in the plant by cyclization of oxidosqualene through the damarenyl cation, a common precursor to most damaran triterpenoids. The difference between the two compounds lies in the nature of the side chain functionalization: in cabraleadiol it carries two hydroxyl groups (diol), while in cabralealactone it is closed in the lactone ring. Such structural similarity with different functionalizations is typical of triterpenoid families of the same plant and facilitates their joint identification in phytochemical studies. An acetylated derivative of cabraleadiol, cabraleadiol-3-acetate, has also been isolated from plant materials and is used in structural studies, including configuration confirmation by single crystal X-ray diffraction.

Scope of application

Like other triterpenoids of the Meliaceae family, cabraleadiol is used primarily in phytochemical studies - as a reference compound in the analysis of plant extracts and as an object for studying biological activity, including studies of pentacyclic and tetracyclic triterpenoids for insecticidal and other biological activity.

Note on data sources

Hazard classification, transport codes, GHS phrases and toxicological data (LD50 and similar) for the compound were not found in available sources; There are no commercial safety data sheets available at the time of preparation of the material. When handling the substance, it is recommended to proceed from the precautionary principle, which is typical for working with little-studied natural compounds. It is recommended to store in a dry place, protected from light, to work with gloves and with exhaust ventilation, minimizing the inhalation of dust and contact with skin throughout the entire work with the sample.