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

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

Uses

Used in Pharmaceutical Industry:
Bavachalcone is used as a therapeutic agent for its anti-inflammatory, antioxidant, and hepatoprotective properties, making it beneficial in the treatment of various health conditions.
Used in Cancer Treatment:
Bavachalcone is used as an anti-cancer agent, targeting a range of cancers due to its ability to exhibit biological activities that inhibit tumor growth and progression.
Used in Skin Disorder Treatment:
Bavachalcone is used as a treatment for skin disorders, leveraging its anti-inflammatory and anti-viral properties to improve skin health and address specific dermatological conditions.
Used in Neurodegenerative Disease Management:
Bavachalcone is used as a potential treatment for neurodegenerative diseases, with research indicating its capacity to mitigate the effects of such conditions through its neuroprotective properties.
Used in Metabolic Disorder Treatment:
Bavachalcone is used as a therapeutic intervention for metabolic disorders, given its demonstrated potential to address and manage these health issues.
Used in Inflammatory Condition Management:
Bavachalcone is used as an anti-inflammatory agent for the treatment of inflammatory conditions, capitalizing on its natural ability to reduce inflammation and alleviate symptoms.

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

• 1092462-95-7 4'-methoxy-4-methoxymethoxy-2'-prenyloxychalcone 
• 552-41-0 1-(2-hydroxy-4-methoxyphenyl)ethanone 
• 6515-21-5 4-methoxymethoxy-benzaldehyde 
• 128961-25-1 1-(4-methoxy-2-((3-methylbut-2-en-1-yl)oxy)phenyl)ethan-1-one 
• 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 
• 123-08-0 4-hydroxy-benzaldehyde 
• 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 
• 870-63-3 prenyl bromide 
• 28437-37-8 5-C-prenylresacetophenone 
• 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 
• 13745-20-5 2',4,4'-trihydroxychalcone 

Downstream Products

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

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

Microbial Transformation of Broussochalcones A and B by Aspergillus niger

Broussochalcones A (BCA, 1) and B (BCB, 2) are major bioactive constituents isolated from Broussonetia papyrifera, a polyphenol-rich plant belonging to the family Moraceae. Due to their low yields from natural sources, BCA (1) and BCB (2) were prepared sy

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.

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.

Synthesis and antibacterial activity of chalcones bearing prenyl or geranyl groups from Angelica keiskei

Chalcones bearing prenyl or geranyl groups from Angelica keiskei, such as 4-hydroxyderricin (1a), xanthoangelol (1e), xanthoangelol F (1f), xanthoangelol H (2), deoxyxanthoangelol H (3), and deoxydihydroxanthoangelol H (4) and their derivatives were synthesized. From the evaluation of antibacterial activity of the synthesized chalcones, 1a, isobavachalcone (1b), 1e, 1f, bavachalcone (5a), and broussochalcone B (5b) were found to inhibit Gram-positive bacteria.