Деметилвестит

Identification

Demethylvestitol (CAS 65332-45-8) is a natural isoflavonoid of the isoflavan subclass, systematically called 2',4',7-trihydroxyisoflavan. Chemical formula C15H14O4. Also appears in chemical databases under the alternative CAS number 75556-92-2 and the expanded name 4-(3,4-dihydro-7-hydroxy-2H-1-benzopyran-3-yl)-1,3-benzenediol - the same structure, described from the point of view of a benzene diol associated with a chromane ring.

Physico-chemical characteristics

• Molecular Weight: 258.273
• Exact weight: 258.27
• PSA characteristic: 69.9 Ų
• XLogP3: 2.6
• Density: 1.382±0.06 g/cm³ (predicted value)

Other parameters - melting points, boiling points, refractive index - are not given in the original dump; they were also not found in open sources during an additional search, so the section is limited to five confirmed values.

Natural springs

Demethylvestite is isolated from the root of the Ural licorice (Glycyrrhiza uralensis), from the plant Phaseolus hispidus and from the caulis Spatholobus suberectus (Spatholobi Caulis, a vine of the legume family, widely used in Chinese herbal medicine to improve blood circulation). The compound is part of the traditional Chinese recipe Baoyuan Decoction (“Baoyuan Tang”) - a complex herbal collection.

Biological activity

As a representative of isoflavan phytoalexins, demethylvestite exhibits antifungal activity in vitro, inhibiting the growth of phytopathogenic fungi, including pathogens of the genus Anthyllis. Anti-inflammatory effects have also been described in laboratory tests. Isoflavans of this structural type are synthesized by legumes in response to infection and mechanical tissue damage - a classic protective, phytoalexin response characteristic of the Fabaceae family.

Structural class

Isoflavans are a heterocycle-saturated form of isoflavonoids, differing from isoflavones in the absence of a conjugated carbonyl group in the fourth position of the chromane ring. Three hydroxyl groups in positions 2', 4' of the benzene ring B and 7 of the A ring determine the polarity of the molecule (PSA 69.9 Ų) and moderate lipophilicity (XLogP3 2.6), characteristic of flavonoid aglycones of medium molecular weight. This combination of polar and lipophilic moieties is typical of plant secondary metabolites involved in intercellular defense signaling against pathogens and pests.

Botanical context

Three sources of demethylvestite - Ural licorice, Phaseolus hispidus and Spatholobus suberectus - belong to the legume family (Fabaceae), for which the isoflavonoid biosynthesis pathway is especially developed and serves as the basis for chemical defense against pathogens and herbivores. The co-occurrence of the compound in such different genera confirms the conservation of this pathway within the family.

Storage

Like most phenolic compounds of plant origin, demethyl vestite is sensitive to oxidation by atmospheric oxygen and to light. It is recommended to store it in a package protected from light, in a cool, dry place; For long-term storage of reactive batches, an inert atmosphere is advisable, which reduces the rate of oxidative degradation of phenolic hydroxy groups.