Секоизоларицирезинол диглюкозид

Description

Secoisolariciresinol diglucoside (abbreviation SDG) is a plant lignan, more precisely secoisolariciresinol diglucoside: the aglycone is linked by two β-D-glucose residues at the hydroxyl groups of the butanediyl fragment. The richest source is flax seeds, where the content reaches 370 mg SDG per 100 g of seeds; The substance is present in smaller quantities in other oilseeds and nuts, legumes, whole grains, certain fruits and vegetables, coffee, tea and wine.

Metabolism

After ingestion, SDG is hydrolyzed to the aglycone secoisolariciresinol (SECO), which is converted by intestinal microflora into the enterolignans enterodiol (ED) and enterolactone (EL). It is these metabolites that are classified as phytoestrogens and are considered active forms when taken orally.

Properties studied

• antioxidant activity - indicated for SDG itself, its aglycone and metabolites enterodiol and enterolactone, including in relation to DNA damage and lipid peroxidation
• Lowering lipid and glucose levels, influencing blood pressure, reducing oxidative stress and inflammation are areas of research into the effects of SDG metabolites in relation to cardiovascular disease and metabolic syndrome.
• the relationship between SDG and enterolactone and the course of tumor processes in the mammary gland is being studied

Identification

• CAS No.: 158932-33-3 (Additional No. 382135-57-1)
• Formula: C32H46O16
• Systematic name: (2R,3R)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]-1,4-butanediyl bis-β-D-glucopyranoside
• Synonyms: SDG, secoisolariciresinol diglucoside, (R,R)-secoisolariciresinol diglucoside
• Class: lignans (lignan glycosides)

Physico-chemical indicators

• Molecular weight: 686.69800
• Exact weight: 686.70
• Density: 1.523 g/cm³
• Boiling point: 989.171 °C at 760 mm Hg. Art.
• Flash point: 552.031 °C
• Refractive index: 1.655
• Steam pressure: 0 mmHg Art. at 25 °C
• PSA Specifications: 257.68000
• XLogP3: −2.23440

The values ​​of boiling, flash, density and refractive index are calculated by software methods: the substance decomposes long before the indicated boiling point. Zero vapor pressure at 25 °C and XLogP3 −2.23 reflect the non-volatility and high hydrophilicity of the product.

Application

• standardization of flaxseed extracts and lignan complexes for SDG content
• analytical standard for HPLC and LC-MS for the control of raw materials and finished forms
• raw materials for nutraceutical compositions based on flax lignans
• research reagent in work on lignan metabolism and phytoestrogens

Storage and handling

The powder is hygroscopic, glycosidic bonds are sensitive to moisture and acids. Store in an airtight container, in a dry and dark place, at a low temperature. Work with gloves, no dust.