Эврикарпин А

Description

Eurycarpine A is a prenylated isoflavone, 3-[2,4-dihydroxy-3-(3-methyl-2-buten-1-yl)phenyl]-7-hydroxy-4H-1-benzopyran-4-one. Isolated from the roots of Glycyrrhiza eurycarpa P.C. Li - plants of the genus Licorice (Fabaceae).

Basic Attributes

• CAS No: 166547-20-2
• Chemical formula: C20H18O5
• Molecular weight: 338.35392
• Exact weight: 338.115
• PSA Specifications: 87
• XLogP3: 4
• Catalog section: flavonoids

Physico-chemical characteristics

• Density: 1.351±0.06 g/cm3 (predicted value)
• Boiling point: 601.0±55.0°C (predicted value)

Synonyms

• Eurycarpin A
• 3-[2,4-Dihydroxy-3-(3-methyl-2-buten-1-yl)phenyl]-7-hydroxy-4H-1-benzopyran-4-one

Structural features

The molecule is built on the skeleton of 4H-1-benzopyran-4-one (chromone) with an aromatic substituent in position 3, characteristic of isoflavones, in contrast to flavones with the same substituent in position 2. Hydroxyl groups in ring A (position 7) and ring B (positions 2, 4) in combination with the prenyl (3-methyl-2-butenyl) group form a typical genus Glycyrrhiza substitution profile for prenylated isoflavones, distinguishing eurycarpine A from simple, non-prenylated isoflavones of the same series.

Substance class and biological activity

Prenylated isoflavones are a subclass of flavonoids with an isopentenyl substituent in the aromatic ring, characteristic of plants of the genus Glycyrrhiza. The presence of a 3-methyl-2-butenyl (prenyl) group increases the lipophilicity of the molecule (XLogP3 4) compared to non-prenylated isoflavones.

• described as a peroxisome proliferator-activated receptor (PPAR) ligand antagonist
• found together with eurycarpine B in the roots of Glycyrrhiza eurycarpa
• refers to prenylated flavonoids, for which the anti-inflammatory and antioxidant effects characteristic of the class are described in the literature

Scope of application

Used as an analytical standard for phytochemical studies of the genus Glycyrrhiza and as a reagent for studying the interaction of prenylated flavonoids with nuclear PPAR receptors in pharmacological models. The genus Glycyrrhiza (licorice) is a well-known source of biologically active flavonoids and triterpene saponins used as an object of comparative phytochemical profiling; Eurycarpine A is used in this context as a marker compound for the species Glycyrrhiza eurycarpa.

Storage and transportation

Store in tightly closed original container, in a cool, dry place, away from direct light and sources of moisture. No special transport codes or toxicological data are provided in the dump; When working with the substance, it is recommended to use gloves and avoid dust when weighing samples. Supplied in the form of a technical substance of laboratory purity, without medical or food purposes, in batches of laboratory packaging.