41743-56-0

Basic information

• Product Name: LUTEONE
• Synonyms: LUTEONE;5,7,2',4'-TETRAHYDROXY-6-PRENYLISOFLAVONE;6-PRENYL-2'-HYDROXYGENISTEIN;Luteone (isoflavone);3-(2,4-Dihydroxyphenyl)-5,7-dihydroxy-6-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one
• CAS NO: 41743-56-0
• Molecular Formula: C₂₀H₁₈O₆
• Molecular Weight: 354.35
• Product Categories: Iso-Flavones
• Mol File: 41743-56-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 635.7 °C at 760 mmHg
• Flash Point: 230.8 °C
• Appearance: /
• Density: 1.424 g/cm³
• Vapor Pressure: 9.39E-17mmHg at 25°C
• Refractive Index: 1.69
• CAS DataBase Reference: LUTEONE(CAS DataBase Reference)
• NIST Chemistry Reference: LUTEONE(41743-56-0)
• EPA Substance Registry System: LUTEONE(41743-56-0)

Safety Data

• Hazardous Substances Data: 41743-56-0(Hazardous Substances Data)

Usage

General Description

Luteone is a bioactive substance found in certain types of plants and herbs. It exhibits a number of medicinal properties including the ability to influence hormonal activity, act as an anti-inflammatory agent, and potentially prevent tumor growth. In nature, it plays a role in plant defense mechanisms against pathogens or predators. Some laboratory studies suggest that luteone may also be beneficial in the treatment of serious conditions such as cancer and Alzheimer's disease, but further research is needed in this area.

InChI:InChI=1/C20H18O6/c1-10(2)3-5-13-16(23)8-17-18(19(13)24)20(25)14(9-26-17)12-6-4-11(21)7-15(12)22/h3-4,6-9,21-24H,5H2,1-2H3

Upstream product

• 358-72-5 dimethylallyl diphosphate 
• 1156-78-1 2',4',5,7-tetrahydroxyisoflavone 
• 115-19-5 2-methyl-but-3-yn-2-ol 
• 844868-34-4 6'-acetoxy-2,4,2',4'-tetrakis(benzyloxy)-3'-iodochalcone 
• 321570-04-1 2',4',7-tris(benzoyloxy)-6-(3-hydroxy-3-methylbutyl)-5-tosyloxyisoflavone 
• 321570-10-9 2',4',7-tris(benzoyloxy)-6-(3-methyl-2-butenyl)-5-tosyloxyisoflavone 
• 321569-92-0 1-[6-benzoyloxy-2,4-bis(benzyloxy)-3-iodophenyl]-2-[2,4-bis(benzyloxy)phenyl]-3,3-dimethoxypropan-1-one 
• 321569-89-5 2,4,2',4'-tetrakis(benzyloxy)-6'-benzoyloxy-3'-iodochalcone 
• 321570-01-8 2',4',7-tris(benzoyloxy)-5-hydroxy-6-(3-hydroxy-3-methylbutyl)isoflavone 
• 321569-86-2 2,4,2',4'-tetrakis(benzyloxy)-6'-hydroxy-3'-iodochalcone 
• 321569-95-3 2',4',5,7-tetrakis(benzyloxy)-6-iodoisoflavone 
• 321569-81-7 2',4'-bis(benzyloxy)-3'-iodo-6'-(methoxymethoxy)acetophenone 
• 321569-79-3 2',4'-dihydroxy-3'-iodo-6'-(methoxymethoxy)acetophenone 
• 91681-62-8 2',4',5,7-tetrahydroxy-6-(3-hydroxy-3-methylbutyl)isoflavone 

Downstream Products

• 91681-64-0 6-(2,4-Dihydroxy-phenyl)-4-hydroxy-2-(1-hydroxy-1-methyl-ethyl)-2,3-dihydro-furo[3,2-g]chromen-5-one 
• 91681-63-9 6-(2,3-Dihydroxy-3-methyl-butyl)-3-(2,4-dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-one 
• 41628-68-6 2',4',5,7-tetraacetoxy-6-(3-methyl-2-butenyl)isoflavone 
• 136337-79-6 3-(2,4-Dihydroxy-phenyl)-5,7-dihydroxy-6-(4-hydroxy-3-hydroxymethyl-but-2-enyl)-chromen-4-one 
• 136337-76-3 (E)-4-[3-(2,4-Dihydroxy-phenyl)-5,7-dihydroxy-4-oxo-4H-chromen-6-yl]-2-methyl-but-2-enoic acid 
• 136337-75-2 (Z)-hydroxyluteone 
• 136337-77-4 2,6,8-Trihydroxy-7-((E)-4-hydroxy-3-methyl-but-2-enyl)-10,11-dioxa-benzo[b]fluoren-5-one 

Relevant articles and documents

Molecular Characterization and Phylogenetic Analysis of Two Novel Regio-specific Flavonoid Prenyltransferases from Morus alba and Cudrania tricuspidata

Prenylated flavonoids are attractive specialized metabolites with a wide range of biological activities and are distributed in several plant families. The prenylation catalyzed by prenyltransferases represents a Friedel-Crafts alkylation of the flavonoid skeleton in the biosynthesis of natural prenylated flavonoids and contributes to the structural diversity and biological activities of these compounds. To date, all identified plant flavonoid prenyltransferases (FPTs) have been identified in Leguminosae. In the present study two new FPTs, Morus alba isoliquiritigenin 3′-dimethylallyltransferase (MaIDT) and Cudrania tricuspidata isoliquiritigenin 3′-dimethylallyltransferase (CtIDT), were identified from moraceous plants M. alba and C. tricuspidata, respectively. MaIDT and CtIDT shared low levels of homology with the leguminous FPTs. MaIDT and CtIDT are predicted to be membrane-bound proteins with predicted transit peptides, seven transmembrane regions, and conserved functional domains that are similar to other homogentisate prenyltransferases. Recombinant MaIDT and CtIDT were able to regioselectively introduce dimethylallyl diphosphate into the A ring of three flavonoids with different skeleton types (chalcones, isoflavones, and flavones). Phylogenetic analysis revealed thatMaIDT and CtIDT are distantly related to their homologs in Leguminosae, which suggests that FPTs in Moraceae and Leguminosae might have evolved independently. MaIDT and CtIDT represent the first two non-Leguminosae FPTs to be identified in plants and could thus lead to the identification of additional evolutionarily varied FPTs in other non-Leguminosae plants and could elucidate the biosyntheses of prenylated flavonoids in various plants. Furthermore, MaIDT and CtIDT might be used for regiospecific prenylation of flavonoids to produce bioactive compounds for potential therapeutic applications due to their high efficiency and catalytic promiscuity.

Regioselective synthesis of prenylisoflavones: Syntheses of luteone and luteone hydrate

The palladium-catalyzed coupling reaction of 6-iodoisoflavone, prepared from 3′-iodoacetophenone derivative, with 2-methyl-3-butyn-2-ol gave the 6-alkynylisoflavone derivative, which was hydrogenaied to give the 6-alkylhydroxyisoflavone (luteone hydrate)