Приморский

Description

Maritimethine is a hydroxyauron, a flavonoid yellow plant pigment. The aurone backbone is formed by benzofuran-3-one, linked by a double bond to a benzylidene moiety; in maritimethine the hydroxyl groups are in positions 6, 7, 3' and 4', the double bond configuration is Z. Hence the common synonym 6,7,3',4'-tetrahydroxyauron. The compound serves as an aglycone of maritimeine, its 6-glucoside that gives the yellow color to the inflorescences of Coreopsis maritima and related species. Aurons are classified as anthochloric pigments. In the Asteraceae family, three main aglycone-glycoside pairs have been described: sulfuretin with sulfurin, maritimethin with maritimein, and leptosidin with leptosin; maritimethine-based compounds are expected for species of the genus Bidens. Biosynthesis proceeds in such a way that aurone is formed at the aglycone level, and glucosylation follows this step. According to the ChEBI classification, maritimethine is a free radical scavenger and a plant metabolite.

Basic Attributes

• CAS No: 576-02-3
• Chemical formula: C15H10O6
• Molecular weight: 286.24
• Exact weight: 286.04773803
• XLogP3: 2.2
• PubChem CID: 5281292
• Systematic name: (2Z)-2-[(3,4-dihydroxyphenyl)methylidene]-6,7-dihydroxy-1-benzofuran-3-one

Biological role and activity

• free radical scavenger (antioxidant effect)
• plant metabolite, anthochlor group pigment
• aglycone of maritimein, a yellow pigment in the inflorescences of Coreopsis maritima

Scope of application

• standard sample for identification and quantification of aurones in plant materials and extracts by HPLC and LC-MS methods
• reagent in studies of the biosynthesis of flavonoids and the color of aster inflorescences
• standard in works on the antioxidant activity of flavonoids

Synonymy

Maritimethine; 6,7,3',4'-tetrahydroxyauron; (Z)-6,7,3',4'-tetrahydroxyauron; Maritimetin; 3(2H)-benzofuranone, 2-[(3,4-dihydroxyphenyl)methylene]-6,7-dihydroxy-, (2Z)-; 3(2H)-benzofuranone, 2-(3,4-dihydroxybenzylidene)-6,7-dihydroxy-.

Note on the name in the card

In the original product card, the Russian name is given as “Primorsky”. This is a machine translation error: English Maritimetin is parsed as an adjective maritime. The correct Russian name for the substance is maritimetin.

Storage

• Physico-chemical characteristics, GHS classification, transport markings and toxicological data are not included in the product card - refer to the supplier’s safety data sheet
• Mode for polyphenolic standards: dry dark place, sealed containers, minimal contact with air oxygen
• The catechol fragment (hydroxyls 3' and 4') is easily oxidized, especially in an alkaline environment - prepare solutions immediately before analysis