Сирингарезинол

Description

Syringaresinol is a furofuran-type lignan. Structurally, it is a 7,9':7',9-diepoxylignan, which has hydroxyl groups in positions 4 and 4', and methoxy groups in positions 3, 3', 5 and 5'. In other words, two syringyl aromatic rings are connected by a rigid bicyclic furofuran bridge. According to the classification, the compound belongs to lignans, polyphenols, aromatic esters, polyesters and furofurans; functional role - plant metabolite.

The substance is widespread in the plant world: its presence is reported in 87 species from 40 families. The main sources are the genera Acanthopanax (Eleutherococcus) and Albizia; also isolated from Cinnamomum cassia and Panax ginseng, from Sarcopyramis nepalensis, Raphanus sativus var. sativus, Passerina vulgaris. Under the name lirioresinol A, it is described in Dendrobium crystallinum. Syringaresinol diglucoside is known as eleutheroside E, one of the main biologically active components of Eleutherococcus.

Basic Attributes

• CAS No: 1177-14-6
• Chemical formula: C22H26O8
• Molecular Weight: 418.442
• Exact weight: 418.162781
• PSA Specifications: 95.8
• XLogP3: 0.71

Physico-chemical properties

• Appearance: solid
• Density: 1.282 ± 0.06 g/cm³ (predicted)
• Melting point: 210–211 °C
• Boiling point: 594.7 ± 50.0 °C (predicted)
• Flash point: 313.5 ± 30.1 °C
• Refractive index: 1.578
• Vapor pressure: 9.68 × 10⁻¹⁵ mm Hg. Art. at 25 °C

The exact mass of 418.162781 is consistent with the formula C22H26O8 and is suitable for mass spectrometric identification without conversion. Melting point 210–211 °C is an experimental value; density and boiling point are marked as predicted, that is, calculated. Vapor pressure is about 10⁻¹⁵ mmHg. Art. means almost complete absence of volatility - no losses occur during evaporation of extracts.

Biological activity

Syringaresinol is classified as a dietary lignan with extensively studied biological effects.

• Anti-inflammatory. Several mechanisms are involved: suppression of inducible NO synthase (iNOS) and cyclooxygenase-2 (COX-2), reduction of NF-κB activity and levels of nitric oxide, prostaglandin E2, tumor necrosis factor alpha, interleukins 1-beta and 6
• Antiproliferative. In tumor models, it causes cell cycle arrest, increases the expression of inhibitors of cyclin-dependent kinases p21waf1/cip1 and p27kip1 and reduces the levels of cyclins and cyclin-dependent kinases themselves
• Antioxidant. General property of lignans and their metabolites, due to the phenolic nature of the structure
• Effect on pigmentation. Attenuates alpha-melanocyte-stimulating hormone-induced generation of reactive oxygen species and melanogenesis

Scope of application

• analytical standard for the control of raw materials of eleutherococcus, ginseng, cinnamon and other sources of lignans
• reference substance for chromatographic methods for determining lignans
• object of research on anti-inflammatory, antioxidant and antiproliferative activity
• parent compound in the study of eleutheroside E and other syringaresinol glycosides

Storage and handling

GHS classification, transport codes, labels and toxicity data are not included in the card - they are taken from the batch’s safety data sheet. Free phenolic hydroxyls make the compound sensitive to oxidation, so the product is stored in a tightly closed dark glass container in a cool place; solutions are prepared immediately before use; an alkaline environment is avoided. There is no volatility, the dry powder with a melting point of about 210 °C is stable under normal conditions. Weighing should be carried out under a hood, wearing gloves and safety glasses.