58749-23-8

Basic information

• Product Name: LICOCHALCONEB
• Synonyms: LICOCHALCONEB;(E)-3-(3,4-Dihydroxy-2-methoxyphenyl)-1-(4-hydroxyphenyl)-2-propen-1-one;3,4,4'-Trihydroxy-2-methoxy-trans-chalcone;3,4,4'-Trihydroxy-2-Methoxychalcone;2-Propen-1-one,3-(3,4-dihydroxy-2-methoxyphenyl)-1-(4-hydroxyphenyl)-, (2E)-;Licoagrochalcone B
• CAS NO: 58749-23-8
• Molecular Formula: C₁₆H₁₄O₅
• Molecular Weight: 286.28
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 58749-23-8.mol
• Article Data: 5

Chemical Properties

• Melting Point: 196-197℃
• Boiling Point: 550.5°Cat760mmHg
• Flash Point: 208.5°C
• Appearance: /
• Density: 1.369±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 9.95E-13mmHg at 25°C
• Refractive Index: 1.684
• PKA: 7.80±0.15(Predicted)
• CAS DataBase Reference: LICOCHALCONEB(CAS DataBase Reference)
• NIST Chemistry Reference: LICOCHALCONEB(58749-23-8)
• EPA Substance Registry System: LICOCHALCONEB(58749-23-8)

Safety Data

• Hazardous Substances Data: 58749-23-8(Hazardous Substances Data)

Usage

Chemical Properties

Licochalcone B is a yellow crystalline powder, soluble in methanol, ethanol, DMSO and other organic solvents,and it is derived from licorice rhizomes.

Uses

Licochalcone B has anti-tumor, anti-inflammatory, and antioxidant effects.It can be used for content determination, identification, pharmacological experiments, etc.

Biological Activity

Licochalcone B is extracted from Glycyrrhizainflate root. LICOCHALCONEB inhibits the self-aggregation of amyloid β (Aβ420) (IC50=2.16 μM) and disintegrates pre-formed Aβ42 fibrils, reducing metal-induced Aβ42 aggregation by chelating metal ions.

InChI:InChI=1/C16H14O5/c1-21-16-11(5-9-14(19)15(16)20)4-8-13(18)10-2-6-12(17)7-3-10/h2-9,17,19-20H,1H3/b8-4+

Upstream product

• 99-93-4 4-Hydroxyacetophenone 
• 1528738-93-3 3-[3,4-bis (ethoxymethoxy)-2-methoxyphenyl]-1-[(4-tetrahydro-2H-pyran-2-yloxy)phenyl]prop-2-en-1-one 
• 16162-69-9 1-(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)ethanone 
• 85699-01-0 2-hydroxy-3,4,4'-tri(methoxymethoxy)chalkone 
• 85698-99-3 2-hydroxy-3,4-bis(methoxymethoxy)benzaldehyde 
• 85699-00-9 1-[4-(methoxymethoxy)phenyl]-1-ethanone 
• 2144-08-3 2,3,4-trihydroxybenzylaldehyde 
• 85699-02-1 (E)-3-(2-Methoxy-3,4-bis-methoxymethoxy-phenyl)-1-(4-methoxymethoxy-phenyl)-propenone 

Relevant articles and documents

Microbial conjugation studies of licochalcones and xanthohumol

Microbial conjugation studies of licochalcones (1–4) and xanthohumol (5) were performed by using the fungi Mucor hiemalis and Absidia coerulea. As a result, one new glucosylated metabolite was produced by M. hiemalis whereas four new and three known sulfated metabolites were obtained by transformation with A. coerulea. Chemical structures of all the metabolites were elucidated on the basis of 1D-, 2D-NMR and mass spectroscopic data analyses. These results could contribute to a better understanding of the metabolic fates of licochalcones and xanthohumol in mammalian systems. Although licochalcone A 4′-sulfate (7) showed less cytotoxic activity against human cancer cell lines compared to its substrate licochalcone A, its activity was fairly retained with the IC50 values in the range of 27.35–43.07 μM.

Synthesis of licochalcone analogues with increased anti-inflammatory activity

Licohalcones have been reported to have various biological activities. However, most of licochalcones also showed cytotoxicity even though their versitile utilities. Licochalcones B and D, which have common substituents at aromatic ring B, are targeted to

Synthesis of 3,4,4'-Trihydroxy-2-methoxychalkone (Licochalkone-B)

Licochalkone-B has been synthesised starting from pyrogallol aldehyde (I) which is partially methoxymethylated and condensed with p-methoxymethoxyacetophenone (III) under alkaline conditions.The resulting chalkone (IV) on methylation followed by demethoxy