Диацетат Сирингаресила

Description

Syringaresinol diacetate is a derivative of the natural furofuran lignan syringaresinol, in which both free phenolic hydroxyl groups are esterified with acetic acid. Calculation of the composition confirms the structure: syringaresinol C22H26O8 plus two acetyl residues gives C26H30O10, and the exact mass 502.183899 given in the card corresponds to this formula.

The position is classified in the catalog under the “Polymers” section, which is not true: we are talking about a low molecular weight natural compound with a molecular weight of about 503, and not a polymer.

Basic Attributes

• CAS No.: 1990-77-8
• Chemical formula: C26H30O10
• Molecular Weight: 502.516
• Exact mass: 502.183899
• PSA Specifications: 107.98000
• XLogP3: 1.33

Physico-chemical properties

• Density: 1.2 ± 0.1 g/cm³
• Boiling point: 556.4 ± 50.0 °C at 760 mm Hg. Art.
• Flash point: 236.2 ± 30.2 °C
• Refractive index: 1.541

Boiling and flash points are marked with estimated error and obtained by estimation; The card does not contain the experimental melting temperature. The exact mass, on the contrary, is calculated correctly and is suitable for mass spectrometric identification.

What does acetylation give?

The original syringaresinol contains two free phenolic hydroxyls - they are responsible for the antioxidant properties and oxidative instability of the compound. Their acetylation changes the product in several ways.

• Stability. Closed hydroxyls are not oxidized by atmospheric oxygen, therefore diacetate is noticeably more stable than the original lignan during storage
• Polarity. Lipophilicity increases from XLogP3 0.71 for syringaresinol to 1.33 for diacetate, the polar surface increases from 95.8 to 108.0 due to the addition of ester groups. In practice, this changes the behavior in chromatography and makes it easier to work in organic media
• Reversibility. Acetyl groups are removed by mild alkaline hydrolysis returning to the original lignan, so diacetate is used as a protected form
• Crystallization and characterization. Phenol acetates tend to crystallize better, and the signals of acetyl methyl groups in NMR spectra serve as a convenient marker for the number of esterified hydroxyls

Scope of application

Public reference databases do not contain specific applications for this CAS. The product is offered as a research reagent: a derivative for structural studies of lignans, a protected form of syringaresinol in preparative work, a reference substance for chromatographic analysis of acetylated derivatives. It is incorrect to transfer the biological properties of free syringaresinol to diacetate - the antioxidant activity of phenolic lignans is directly related to free hydroxyls, which are esterified here.

Storage and handling

GHS classification, transport codes, labels, hazard class codes and toxicity data are not included in the card - they are taken from the batch’s safety data sheet. Acetyl esters hydrolyze in a humid environment and especially quickly in an alkaline environment, so the product is stored in an airtight container without access to moisture, in a cool place; solutions are prepared immediately before use and contact with bases is not allowed. Weighing should be carried out under a hood, wearing gloves and safety glasses.