Пентаацетат сирингина

Description

Syringin pentaacetate is a fully acetylated derivative of syringin, a phenylpropanoid glycoside also known as eleutheroside B. The original syringin molecule consists of a sinapyl alcohol linked by a glycosidic bond to glucose and contains five free hydroxyl groups: four on the glucose moiety and one primary on the allylic side chain of the aglycone. Acetylation of all five positions gives the product of composition C27H34O14 - syringin C17H24O9 plus five acetyl residues.

Basic Attributes

• CAS No: 92233-55-1
• Chemical formula: C27H34O14
• Molecular weight: 582.55046
• Exact weight: 582.194885
• PSA Specifications: 168
• XLogP3: 3.00

Physico-chemical properties

• Density: 1.3 ± 0.1 g/cm³
• Boiling point: 646.0 ± 55.0 °C at 760 mm Hg. Art.
• Flash point: 270.0 ± 31.5 °C
• Refractive index: 1.530

Unlike most positions in this group, the exact mass value of 582.194885 is consistent with the formula C27H34O14 and is suitable for mass spectrometric identification. The boiling and flash points are marked with the estimated error and are obtained by the estimation method.

Why are glycosides acetylated?

Peracetylation is a standard technique in the chemistry of carbohydrates and glycosides that solves three problems.

• Solubility and chromatography. Free hydroxyls make the glycoside highly polar and prone to peak smearing. After acetylation, the substance enters the organic phase, and XLogP3 rises to 3.00 against negative values ​​for the original glycoside - this allows analysis in the normal phase and work in non-polar solvents
• Protection. Acetyl groups block hydroxyls during subsequent transformations at other positions of the molecule and are removed by mild alkaline hydrolysis
• Crystallization and structural analysis. Glycoside peracetates, as a rule, crystallize better and give NMR spectra that are easier to interpret, which is traditionally used in determining the structure

About the original connection

Syringin (eleutheroside B) is a characteristic component of lilac bark and plants of the genus Eleutherococcus. Pentaacetate retains the carbon skeleton of the original glycoside and serves as its derivative for analytical and preparative purposes.

Scope of application

Open reference databases for specific applications do not contain CAS for this particular purpose: the application and production sections of PubChem for the position are not filled out. The product is offered as a research reagent and reference substance. The intended purpose of a specific batch should be clarified in the manufacturer’s documentation; It is incorrect to transfer the biological properties of free syringin to pentaacetate - acetylation changes both solubility and the ability to interact with biological targets.

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 and especially alkaline environment, so the product is stored in a tightly closed container without access to moisture, in a cool place; solutions are prepared immediately before use and are not left in contact with bases. Weighing should be carried out under a hood, wearing gloves and safety glasses.