Артеаннуин Л

Description

Arteannuin L is a sesquiterpene isolated from Artemisia annua L. It can also be obtained by synthetically modifying artemisinin, extracted from the same plant material.

Basic Attributes

• CAS No.: 207446-89-7
• Chemical formula: C15H22O3
• Molecular Weight: 250.338
• Exact weight: 250.156891
• PSA Specifications: 46.5
• XLogP3: 2.08

Physico-chemical characteristics

• Density: 1.1±0.1 g/cm3
• Boiling point: 420.7±38.0 °C at 760 mm Hg. Art.
• Flash point: 178.0±19.5°C
• Refractive index: 1.535

Features of stereochemistry

In the initial description of arteannuins K, L, and M, an error was made in determining the stereochemical configuration, which was subsequently corrected based on derivatization studies. Accurate stereochemical identification is important for analytical control of the authenticity of the reference standard.

Plant source and related substances

Artemisia annua L. (Artemisia annua, Qing Hao) synthesizes sesquiterpenes in glandular trichomes on the surface of leaves and flower heads. From this plant raw material, a wide range of related sesquiterpenes in addition to artemisinin have been isolated - arteannuin B, dihydroartemisinic and artemisinic acids, as well as a series of compounds arteannuin K, L, M, N, which are similar in nomenclature. The possibility of obtaining arteannuin L by directed chemical modification of artemisinin itself reflects the structural relationship of these metabolites within the framework of a single terpenoid biosynthetic cascade leading from a common precursor, amphoradiene, through successive oxidative steps to the target antimalarial endoperoxide. Such structural parallels facilitate the identification of minor sesquiterpenes in the chromatographic analysis of complex plant extracts.

Scope of application

Provided as a high-purity reference standard and natural compound for the analytical and biosynthetic study of the sesquiterpene profile of Artemisia annua, including structure confirmation of related compounds by HPLC, NMR and mass spectrometry. The standard is also used in the development and validation of analytical methods for the quantitative determination of minor sesquiterpenes in plant extracts and pharmaceutical intermediates based on Artemisia annua.

Storage and transportation

Store in a dry place, protected from light at low temperatures. No special transport classification of dangerous goods has been established; it is supplied as a laboratory reagent in small quantities. Moderate boiling points (420.7±38.0 °C) and flash points (178.0±19.5 °C) when stored in closed containers do not create additional requirements for the temperature regime of the warehouse beyond standard conditions for organic reagents. A hazard class is not assigned for the transportation of laboratory quantities of such research sesquiterpene.