76754-24-0

Basic information

• Product Name: 3',6-Di(dimethylallyl)genistein
• Synonyms: 3',6-Di(dimethylallyl)genistein;3'-γ,γ-Dimethylallylwighteone;5,7-Dihydroxy-3-[4-hydroxy-3-(3-methyl-2-butenyl)phenyl]-6-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one;Lupalbigenin;5,7,4'-Trihydroxy-6,3'-diprenylisoflavone
• CAS NO: 76754-24-0
• Molecular Formula: C₂₅H₂₆O₅
• Molecular Weight: 406.47
• Mol File: 76754-24-0.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3',6-Di(dimethylallyl)genistein(CAS DataBase Reference)
• NIST Chemistry Reference: 3',6-Di(dimethylallyl)genistein(76754-24-0)
• EPA Substance Registry System: 3',6-Di(dimethylallyl)genistein(76754-24-0)

Safety Data

• Hazardous Substances Data: 76754-24-0(Hazardous Substances Data)

Usage

General Description

3',6-Di(dimethylallyl)genistein is a chemical compound that belongs to the flavonoid group. It is derived from genistein, a natural isoflavone found in various plants, and is modified with two dimethylallyl groups at the 3' and 6' positions. 3',6-Di(dimethylallyl)genistein has been studied for its potential health benefits, including anti-inflammatory, antioxidant, and anticancer properties. It has also been investigated for its ability to modulate estrogen receptor activity, making it of interest for hormone-related conditions. 3',6-Di(dimethylallyl)genistein has shown promise in various laboratory studies and is being researched for its potential therapeutic applications.

Upstream product

• 446-72-0 5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on 
• 780724-90-5 dimethylallyl diphosphate 
• 1186-30-7 3,3-dimethylallyl diphosphate triammonium salt 
• 358-72-5 dimethylallyl diphosphate 

Downstream Products

• 76754-27-3 5-Hydroxy-3-[4-hydroxy-3-(3-methyl-but-2-enyl)-phenyl]-7-methoxy-6-(3-methyl-but-2-enyl)-chromen-4-one 

Relevant articles and documents

Molecular insights into the enzyme promiscuity of an aromatic prenyltransferase

Aromatic prenyltransferases (aPTases) transfer prenyl moieties from isoprenoid donors to various aromatic acceptors, some of which have the rare property of extreme enzymatic promiscuity toward both a variety of prenyl donors and a large diversity of acceptors. In this study, we discovered a new aPTase, AtaPT, from Aspergillus terreus that exhibits unprecedented promiscuity toward diverse aromatic acceptors and prenyl donors and also yields products with a range of prenylation patterns. Systematic crystallographic studies revealed various discrete conformations for ligand binding with donor-dependent acceptor specificity and multiple binding sites within a spacious hydrophobic substrate-binding pocket. Further structure-guided mutagenesis of active sites at the substrate-binding pocket is responsible for altering the specificity and promiscuity toward substrates and the diversity of product prenylations. Our study reveals the molecular mechanism underlying the promiscuity of AtaPT and suggests an efficient protein engineering strategy to generate new prenylated derivatives in drug discovery applications.

Flavanone 8-dimethylallyltransferase in Sophora flavescens cell suspension cultures

Dimethylallyl diphosphate: naringenin 8-dimethylallyltransferase (EC 2.5.1) was characterized. The enzyme was enantiospecific for (-)-(2S)-naringenin and utilized 3,3-dimethylallyl diphosphate as sole prenyl donor. It required Mg2+ (optimum concentration, 10 mM), and has an optimum pH of 9-10. The apparent K(m) values for 3,3-dimethylallyl diphosphate and naringenin were 120 and 36 μM, respectively. The microsomal fraction prenylated several other flavanones at the C-8 position less effectively as compared with naringenin. Interestingly, when 2'-hydroxynaringenin was used as a prenyl acceptor, the 8-lavandulyl (sophoraflavanone G) and the 6-dimethylallyl derivatives were formed, together with the 8-dimethylallyl derivative, leachianone G. These results suggest that the 2'-hydroxy group of naringenin plays an important role for the formation of a lavandulyl group. (C) 2000 Elsevier Science Ltd.