Сульфуретин

Description

Sulfuretin is a natural flavonoid from the aurone group, systematically 3',4',6-trihydroxyauron. Aurones are biogenetically related to chalcones, which explains the inclusion of the product in the “Chalcones” section. The main source of excretion is the heartwood of the lacquer sumac (Rhus verniciflua); the compound is also found in the flowers of dahlias and other representatives of the Asteraceae, where it is responsible for the yellow color.

Basic Attributes

• CAS No: 120-05-8
• Chemical formula: C15H10O5
• English name: Sulfuretin (Sulphuretin)
• Systematic name: (2Z)-2-[(3,4-dihydroxyphenyl)methylene]-6-hydroxy-3(2H)-benzofuranone
• Molecular weight: 270.24
• Exact weight: 270.24
• EU number: 204-366-4

Physico-chemical characteristics

• PSA: 87
• XLogP3: 1.98
• Density: 1.6 ± 0.1 g/cm³ (calculated value)
• Melting point: 303 °C
• Boiling point: 585.0 ± 50.0 °C at 760 mm Hg. Art. (calculated value)
• Flash point: 228.8 ± 23.6 °C (estimated value)
• Refractive index: 1.793

The values ​​given with plus-minus intervals were obtained by calculation methods and serve as a guide, and not as passport characteristics of the batch.

Structure

The molecule is built on a 3(2H)-benzofuranone (auron) skeleton with an exocyclic double bond of the Z-configuration, which connects the heterocycle to a 3,4-dihydroxyphenyl (catechol) moiety. Hydroxyl groups are located at positions 6, 3' and 4'. The catechol fragment is responsible for antioxidant properties and for interaction with metal-containing enzymes.

Described biological activity

• Anti-inflammatory effect: suppression of NF-κB transcriptional activity through inhibition of IKKβ phosphorylation
• Decreased expression of inducible NO synthase and cyclooxygenase-2 in lipopolysaccharide-stimulated RAW 264.7 macrophages
• Dose-dependent reduction in the production of nitric oxide, prostaglandin E2, tumor necrosis factor alpha and interleukin-1β
• Induction of heme oxygenase-1 in macrophages
• Inhibition of fungal tyrosinase, IC50 = 13.64 µM
• Reduced oxidative stress, platelet aggregation and mutagenesis
• In a mouse model of ovalbumin-induced asthma, there was a decrease in infiltration of eosinophils, macrophages and lymphocytes and a decrease in the levels of TNF-α, IL-5, IL-13 and CCL11
• Reducing the manifestations of experimental arthritis in mice

Scope of application

• Analytical standard for control of identity and quantitation in extracts of Rhus verniciflua and related plant materials
• Reference substance in phytochemical and pharmacological studies
• Object for the development of cosmetic formulations as a tyrosinase inhibitor

Synonyms

• 3',4',6-Trihydroxyauron; 3',4',6-trihydroxybenzalcoumaranone
• 3(2H)-Benzofuranone, 2-(3,4-dihydroxybenzylidene)-6-hydroxy-
• 2-(3,4-Dihydroxybenzylidene)-6-hydroxy-3(2H)-benzofuranone
• Sulphuretin

Storage and handling

Storage conditions and hazard class are not indicated in the original product card. Handling is the same as with a standard sample of a polyphenolic compound: sealed containers, protected from light and moisture, handling samples with gloves. The catechol fragment is sensitive to oxidation by atmospheric oxygen, especially in an alkaline environment and in solutions.