Шприцетин

Description

Syringetin is a natural flavonol, a dimethoxy derivative of myricetin: hydroxyl groups in positions 3' and 5' of the side ring are replaced by methoxy groups. According to the ChEBI structural classification, the compound simultaneously belongs to tetrahydroxyflavones, dimethoxyflavones, 7-hydroxyflavonols, as well as to the subgroups of 3'-methoxyflavones and 3',5'-dimethoxyflavones; Functionally, it is derived from myricetin and is the conjugate acid of the syringetin(1−) anion. Found in grapes and wine, as well as in pomegranate Punica granatum and pepper Capsicum annuum.

The product name “Spricetin” is the result of an erroneous machine translation of the English Syringetin. The correct Russian name for the substance is syringetin, due to the lilac (syringyl) type of substitution of the aromatic ring.

Basic Attributes

• CAS No.: 4423-37-4
• Chemical formula: C17H14O8
• Molecular weight: 346.291
• Exact weight according to card: 346.29
• DSSTox ID: DTXSID60196074
• HS code: 2914509090
• PSA Specifications: 126
• XLogP3: 2.29960

Physico-chemical properties

• Density: 1.591 g/cm³
• Melting point: 288–289 °C
• Boiling point: 622.4 °C at 760 mm Hg. Art.
• Refractive index: 1.707

The line “Flash point: 1.591 °C” in the original card is incorrect: the specified value duplicates the density of 1.591 g/cm³ and is not the flash point. The indicator is not included in the description. The given exact mass of 346.29 also coincides with the rounded molecular mass and does not correspond to the monoisotopic mass of the formula C17H14O8 - it should be recalculated for mass spectrometry.

Biological activity

• platelet aggregation inhibitor
• metabolite
• According to studies of grapes and wine, it induces differentiation of human osteoblasts

Metabolism in humans

The known metabolites of syringetin in the human body are two glucuronide conjugates, differing in the position of glucuronic acid attachment:

• (2S,3S,4S,5R)-6-[3,5-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4-oxochromen-7-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid - conjugation at position 7
• (2S,3S,4S,5R)-6-[5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid - conjugation at position 3

Glucuronidation is a typical pathway of the second phase of flavonol biotransformation: the addition of a glucuronic acid residue sharply increases water solubility and ensures excretion in urine and bile.

Scope of application

• analytical standard for the determination of flavonols in grapes, wine and other plant materials
• reference substance in studies of the metabolism of flavonoids and their glucuronides
• object of research on antiplatelet activity and influence on bone cell differentiation

Storage and handling

GHS classification, transport codes, labels, hazard class codes and toxicological data are not included in the card - they are taken from the batch’s safety data sheet. Flavonols are oxidized by atmospheric oxygen and destroyed by light, especially in solutions and in alkaline environments: store in a dark glass container, tightly closed, in a cool place; Prepare working solutions immediately before analysis. The high melting point, 288–289 °C, ensures the stability of the dry powder under normal conditions. Weighing should be carried out under a hood, wearing gloves and safety glasses, without dust.