Птерозин В

Description

Pterosin B is a sesquiterpenoid of a number of pterosins, a derivative of 1-indanone, the commercial form corresponds to the (2R) isomer. Systematic name: (2R)-2,3-dihydro-6-(2-hydroxyethyl)-2,5,7-trimethyl-1H-inden-1-one. The compound occupies a special position in this group: it is the main breakdown product of ptaquiloside, the iludan glycoside of bracken, which is associated with the toxicity and carcinogenicity of the plant for farm animals. That is why pterosin B is more often used than other pterosins in the analysis of feed, soil and natural waters.

Basic Attributes

• CAS No.: 34175-96-7
• Chemical formula: C14H18O2
• Molecular weight: 218.296
• Exact weight: 218.29
• HS code: 2914400090
• PSA specifications: 37.3
• XLogP3: 2.65
• Designation: BI2

Physico-chemical indicators

• Density: 1.1 ± 0.1 g/cm³
• Boiling point: 396.5 ± 41.0 °C at 760 mm Hg. Art.
• Flash point: 169.3 ± 20.2 °C
• Refractive index: 1.560

Density, boiling point and flash point were obtained by calculation. Real distillation at 396 °C is impossible: the compound decomposes earlier. HS code 2914400090 classifies the product as a ketone alcohol, which corresponds to the structure - carbonyl group of indanone and primary hydroxyl side chain.

Structure

Bicyclic indan-1-one system. The five-membered ring carries a ketone at C-1 and a methyl group at C-2 - this is the only stereocenter of the molecule, the commercial form corresponds to configuration R. The aromatic ring is replaced by methyls at C-5 and C-7 and a 2-hydroxyethyl group at C-6. The values ​​of PSA 37.3 and XLogP3 2.65 indicate moderate lipophilicity: dissolution occurs in methanol, ethanol, acetonitrile, DMSO, and weakly in water.

Association with ptaquiloside

Ptaquiloside in an aqueous environment loses glucose and turns into an unstable dienone intermediate, an alkylating agent responsible for DNA damage. The end product of this chain is pterosin B, a stable compound. The ratio of the contents of two substances is used to assess the degree of decomposition of the toxin in selected samples, and the quantitative determination of pterosin B is used as an indirect indicator of the initial content of ptaquiloside in the raw material.

Purpose

• analytical standard for the determination of ptaquiloside and its degradation products by HPLC and LC-MS methods
• control of the safety of feed and pastures infested with bracken
• studies of the migration of bracken toxins into soil and groundwater
• biological screening: effects on glucose consumption by cells have been described for pterosins

Storage

Sub-zero temperature, darkness, tightly closed container. Solutions in DMSO are stored in frozen portions. The product card does not list specific hazard phrases; handling - wear gloves and glasses, work with powder in a fume hood. The product is intended for research purposes.