28448-85-3

Basic information

• Product Name: Bavachalcone
• Synonyms: Bavachalcone;(E)-1-[2,4-Dihydroxy-5-(3-methyl-2-butenyl)phenyl]-3-(4-hydroxyphenyl)-2-propen-1-one;Broussochalcone B;(2E)-1-[2,4-Dihydroxy-5-(3-methyl-2-buten-1-yl)phenyl]-3-(4-hydroxyphenyl)-2-propen-1-one;Roussochalcone B
• CAS NO: 28448-85-3
• Molecular Formula: C₂₀H₂₀O₄
• Molecular Weight: 324.37000
• Mol File: 28448-85-3.mol
• Article Data: 6

Chemical Properties

• Melting Point: 168-169℃
• Boiling Point: 549.6oC at 760 mmHg
• Flash Point: 300.2oC
• Appearance: /
• Density: 1.243
• Vapor Pressure: 1.09E-12mmHg at 25°C
• Refractive Index: 1.658
• PKA: 7.58±0.50(Predicted)
• CAS DataBase Reference: Bavachalcone(CAS DataBase Reference)
• NIST Chemistry Reference: Bavachalcone(28448-85-3)
• EPA Substance Registry System: Bavachalcone(28448-85-3)

Safety Data

• Hazardous Substances Data: 28448-85-3(Hazardous Substances Data)

Usage

General Description

Bavachalcone is a naturally occurring chemical compound found in the seeds of Psoralea corylifolia, also known as the bavachi plant. It is a chalconoid, a type of flavonoid, and has been traditionally used in Ayurvedic medicine for its anti-inflammatory, antioxidant, and hepatoprotective properties. Research has shown that bavachalcone exhibits a range of biological activities, including anti-cancer, anti-bacterial, and anti-viral effects. It has also been studied for its potential role in treating skin disorders and neurodegenerative diseases. Additionally, bavachalcone has shown promise in the treatment of metabolic disorders and inflammatory conditions. Overall, bavachalcone is a versatile and promising natural compound with potential applications in medicine and healthcare.

InChI:InChI=1/C20H20O4/c1-13(2)3-7-15-11-17(20(24)12-19(15)23)18(22)10-6-14-4-8-16(21)9-5-14/h3-6,8-12,21,23-24H,7H2,1-2H3/b10-6+

Upstream product

• 1544322-43-1 (E)-1-(2,4-bis(methoxymethoxy)-5-(3-methylbut-2-en-1-yl)phenyl)-3-(4-(methoxymethoxy)phenyl)prop-2-en-1-one 
• 6515-05-5 2',4'-bis(methoxymethoxy)acetophenone 
• 1544322-35-1 1-(5-iodo-2,4-bis(methoxymethoxy)phenyl)ethanone 
• 1544322-28-2 (E)-1-(5-iodo-2,4-bis(methoxymethoxy)phenyl)-3-(4 (methoxymethoxy)phenyl)prop-2-en-1-one 
• 13745-20-5 2',4,4'-trihydroxychalcone 
• 870-63-3 prenyl bromide 
• 952647-84-6 (E)-1-(2-hydroxy-4-(methoxymethoxy)-5-(3-methylbut-2-en-1-yl)phenyl)-3-(4-(methoxymethoxy)phenyl)prop-2-en-1-one 
• 123-08-0 4-hydroxy-benzaldehyde 
• 28437-37-8 5-C-prenylresacetophenone 
• 128961-13-7 (E)-1-(2-hydroxy-4-methoxy-5-(3-methylbut-2-en-1-yl)phenyl)-3-(4-(methoxymethoxy)phenyl)prop-2-en-1-one 
• 128961-25-1 1-(4-methoxy-2-((3-methylbut-2-en-1-yl)oxy)phenyl)ethan-1-one 
• 6515-21-5 4-methoxymethoxy-benzaldehyde 
• 552-41-0 1-(2-hydroxy-4-methoxyphenyl)ethanone 
• 1092462-95-7 4'-methoxy-4-methoxymethoxy-2'-prenyloxychalcone 

Downstream Products

• 118267-01-9 1-(7-hydroxy-2,2-dimethylchroman-6-yl)-3-(4-hydroxyphenyl)propenone 
• 19825-37-7 (E)-1-(2,4-dimethoxy-5-(3-methylbut-2-en-1-yl)phenyl)-3-(4-methoxyphenyl)prop-2-en-1-one 

Relevant articles and documents

Magnesium dicarboxylates promote the prenylation of phenolics that is extended to the total synthesis of icaritin

The prenylation of phenolic substrates promoted by magnesium dicarboxylates was developed. An investigation of the scope demonstrated that substrates with electron-donating group(s) gave better yields than those with electron-withdrawing group(s). Althoug

Synthesis and anti-cancer activity evaluation of novel prenylated and geranylated chalcone natural products and their analogs

Four natural chalcones bearing prenyl or geranyl groups, i.e., bavachalcone (1a), xanthoangelol (1b), isobavachalcone (1c), and isoxanthoangelol (1d) were synthesized by using a regio-selective iodination and the Suzuki coupling reaction as key steps. The first total synthesis of isoxanthoangelol (1d) was achieved in 36% overall yield. A series of diprenylated and digeranylated chalcone analogs were also synthesized by alkylation, regio-selective iodination, aldol condensation, Suzuki coupling and [1,3]-sigmatropic rearrangement. The structures of the 11 new derivatives were confirmed by 1H NMR, 13C NMR and HRMS. The anticancer activity of these new chalcone derivatives against human tumor cell line K562 were evaluated by MTT assay in vitro. SAR studies suggested that the 50-prenylation/geranylation of the chalcones significantly enhance their cytotoxic activity. Among them, Bavachalcone (1a) displayed the most potent cytotoxic activity against K562 with IC50 value of 2.7 mM. The morphology changes and annexin-V/PI staining studies suggested that those chalcone derivatives inhibited the proliferation of K562 cells by inducing apoptosis.

Concise synthesis of prenylated and geranylated chalcone natural products by regiospecific iodination and Suzuki coupling reactions

Four natural chalcones bearing prenyl or geranyl groups, i.e., isobavachalcone (1), bavachalcone (2), xanthoangelol (3), and 2′,4′,4-trihydroxy-5′-geranylchalcone (isoxanthoangelol, 4) were synthesized by using a regio-selective iodination and the Suzuki coupling reaction as key steps. Among them, the first total synthesis of 2′,4′,4-trihydroxy-5′-geranylchalcone was achieved in 36% overall yield. Comparing with the reported methods based on C-alkylation or O-alkylation followed by Claisen rearrangement to introduce the side chain, this new strategy capitalizes on a precious regiochemical control during iodination. The overall yields for the synthesis of the first three chalcones were improved from 17% to 53%, 12% to 35%, and 28% to 50%, respectively.