104691-86-3

Basic information

• Product Name: 8-PRENYLGENISTEIN
• Synonyms: 8-PRENYLGENISTEIN;3-(4-Hydroxyphenyl)-5,7-dihydroxy-8-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one;4',5,7-Trihydroxy-8-isopentenylisoflavone;4',5,7-Trihydroxy-8-prenylisoflavone;8-Isopentenylgenistein;Lupiwighteone;5,7-Dihydroxy-3-(4-hydroxyphenyl)-8-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one
• CAS NO: 104691-86-3
• Molecular Formula: C₂₀H₁₈O₅
• Molecular Weight: 338.35
• Product Categories: Miscellaneous Natural Products
• Mol File: 104691-86-3.mol
• Article Data: 8

Chemical Properties

• Melting Point: 133-135℃
• Boiling Point: 583.5°C at 760 mmHg
• Flash Point: 211.8°C
• Appearance: /
• Density: 1.351g/cm³
• Vapor Pressure: 3.25E-14mmHg at 25°C
• Refractive Index: 1.667
• CAS DataBase Reference: 8-PRENYLGENISTEIN(CAS DataBase Reference)
• NIST Chemistry Reference: 8-PRENYLGENISTEIN(104691-86-3)
• EPA Substance Registry System: 8-PRENYLGENISTEIN(104691-86-3)

Safety Data

• Hazardous Substances Data: 104691-86-3(Hazardous Substances Data)

Usage

Description

8-PRENYLGENISTEIN is a natural product derivative of Genistein, which is a bioactive compound found in various plants, particularly in the legume family. It possesses a unique chemical structure that allows it to exhibit a range of biological activities, making it a promising candidate for various applications in the pharmaceutical and cosmetic industries.

Uses

Used in Pharmaceutical Applications:
8-PRENYLGENISTEIN is used as a bioactive compound for its inhibitory activity against tyrosine kinases, including the autophosphorylation of epidermal growth factor receptor kinase. This property makes it a potential therapeutic agent for various diseases, including cancer. It also inhibits other protein kinases through competitive inhibition of ATP, leading to cell-cycle arrest and apoptosis in certain cancer cell lines.
Used in Cosmetic Applications:
8-PRENYLGENISTEIN is used as an active ingredient in the cosmetic industry for its potential anti-aging and skin protective properties. Its ability to inhibit certain enzymes and modulate cellular processes may contribute to improved skin health and appearance.
Used in Research Applications:
8-PRENYLGENISTEIN is also used as a research tool for studying the mechanisms of various biological processes, such as cell signaling, cell proliferation, and apoptosis. Its unique chemical structure and biological activities make it a valuable compound for understanding the complex interactions within cellular systems.

InChI:InChI=1/C20H18O5/c1-11(2)3-8-14-16(22)9-17(23)18-19(24)15(10-25-20(14)18)12-4-6-13(21)7-5-12/h3-7,9-10,21-23H,8H2,1-2H3

Upstream product

• 65388-04-7 4-(7-acetoxy-5-hydroxy-4-oxo-4H-chromen-3-yl)phenyl acetate 
• 446-72-0 5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on 
• 556-82-1 3-methyl-2-buten-1-ol 
• 210166-27-1 Acetic acid 3,5-bis-benzyloxy-2-[2-(4-benzyloxy-phenyl)-3,3-dimethoxy-propionyl]-6-iodo-phenyl ester 
• 210166-30-6 4',5,7-tris(benzoyloxy)-8-(3-hydroxy-3-methylbutyl)isoflavone 
• 210166-29-3 5,7-Bis-benzyloxy-3-(4-benzyloxy-phenyl)-8-(3-hydroxy-3-methyl-but-1-ynyl)-chromen-4-one 
• 210166-26-0 Acetic acid 3,5-bis-benzyloxy-2-[(E)-3-(4-benzyloxy-phenyl)-acryloyl]-6-iodo-phenyl ester 
• 210166-28-2 5,7-Bis-benzyloxy-3-(4-benzyloxy-phenyl)-8-iodo-chromen-4-one 
• 210166-25-9 (E)-3-(4-Benzyloxy-phenyl)-1-(4,6-bis-benzyloxy-2-hydroxy-3-iodo-phenyl)-propenone 
• 160154-81-4 4',6'-bis(benzyloxy)-3'-iodo-2'-(methoxymethoxy)acetophenone 
• 104691-92-1 lupiwighteone hydrate 
• 95165-66-5 3-Iod-2-hydroxy-4,6-dibenzyloxy-acetophenon 
• 18065-05-9 1-[2,4-bis(benzyloxy)-6-hydroxyphenyl]ethanone 
• 583037-95-0 4-(7-acetyloxy-5-((3-methylbut-2-en-l-yl))-4-oxo-4H-chromen-3-yl)phenyl acetate 

Downstream Products

• 76166-59-1 atalantoflavone 

Relevant articles and documents

Induction of enantio-selective apoptosis in human leukemia HL-60 cells by (S)-erypoegin K, an isoflavone isolated from Erythrina poeppigiana

Erypoegin K, an isoflavone isolated from the stem bark of Erythrina poeppigiana, has potent apoptosis-inducing effect on human leukemia HL-60 cells. Erypoegin K has a chiral carbon at the C-2′′ position of its furan ring and naturally occurs as a racemic mixture of (S)- and (R)-isomers. In the present study, we semi-synthesized (RS)-erypoegin K from genistein and separated the optical isomers by HPLC using a chiral column to characterize its apoptosis-inducing activity. Apoptotic cell death was assessed by analyzing caspase-3 and caspase-9 activation, nuclear fragmentation, and genomic DNA ladder formation. (S)-erypoegin K showed exclusive anti-proliferative and apoptosis-inducing activity, with an IC50 value of 90 nM, about 50% lower than that of its racemic mixture (175 nM). By contrast, no apoptosis-inducing activity was shown by the (R)-isomer. In addition, methylglyoxal accumulation in the culture medium was observed only in cells treated with (S)-erypoegin K. These results demonstrated that (S)-erypoegin K is a unique bioactive component that has potent apoptosis-inducing activity on HL-60 cells.

GLYOXALASE I INHIBITOR AND USE THEREOF

PROBLEM TO BE SOLVED: To provide a glyoxalase I inhibitor that is a compound showing antitumor activity. SOLUTION: The present invention provides a glyoxalase I inhibitor comprising a compound represented by the following formula, and an antitumor agent. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT

Anti-AGEs and antiparasitic activity of an original prenylated isoflavonoid and flavanones isolated from Derris ferruginea

A new isoflavonoid, 5-hydroxy-3-(4-hydroxyphenyl)-8-isopropenyl-8,9- dihydro-4H-furo-[2,3-h]-chromen-4-one named derrisisoflavone G (1), four known prenylated flavanones (2-5), four known isoflavonoids (6-9) and two phenolic derivatives (10, 11) have been