Треоцирингилглицерин

Description

Treosyringylglycerol is a phenylpropanoid, 1-(4-hydroxy-3,5-dimethoxyphenyl)propane-1,2,3-triol in the threo configuration. The aromatic ring carries two methoxy groups at positions 3 and 5 and a hydroxyl at position 4—this substitution is called syringyl (S-type). Syringyl units form the basis of hardwood lignin. The compound belongs to the model substances of lignin: on the three-carbon side chain with three hydroxyls, a fragment of the arylglycerol structure is reproduced, through which β-O-4 bonds occur in the natural polymer.

Basic Attributes

• CAS No: 121748-11-6
• Chemical formula: C11H16O6
• Molecular Weight: 244.24100
• Exact weight: 244.24
• PSA Specifications: 99.38000
• XLogP3: -1.90

Physico-chemical characteristics

• Density: 1.4 ± 0.1 g/cm³
• Boiling point: 511.4 ± 50.0 °C at 760 mm Hg. Art.
• Flash point: 263.1 ± 30.1 °C
• Refractive index: 1.589

Stereochemistry

The product is a threo-diastereomer, designated in catalogs as rel-(1R,2R) or (R*,R*). The separation of erythro- and threo-forms is fundamental: the stereochemical composition of arylglycerol-β-arylester structures is used when studying the course of reactions that model lignin biosynthesis.

Scope of application

• model compound for studying the structure and degradation of lignin in deciduous wood
• standard for chromatographic analysis of lignin degradation products
• substrate in work on the enzymatic and chemical decomposition of lignin
• reference substance in phytochemistry: phenylpropanoids of this series are found in plant extracts

Storage and handling

Store in a tightly closed container, in a cool, dry place, away from light. The substance contains three hydroxyl groups and a phenolic fragment - oxidation in air and light is undesirable. Hazard classification and transport codes are not given in the product data sheet.