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

Description

Licochalcone B is a yellow crystalline compound derived from licorice rhizomes, known for its anti-tumor, anti-inflammatory, and antioxidant properties. It is soluble in organic solvents such as methanol, ethanol, and DMSO, making it a versatile compound for various applications in the pharmaceutical and related industries.

Uses

Used in Pharmaceutical Applications:
Licochalcone B is used as an active pharmaceutical ingredient for its anti-tumor, anti-inflammatory, and antioxidant effects. It can be employed in the development of drugs targeting various types of cancer and inflammatory conditions.
Used in Research and Development:
Licochalcone B serves as a valuable compound for content determination, identification, and pharmacological experiments. Its properties make it a useful tool in the study of various biological processes and the development of new therapeutic strategies.
Used in Antioxidant Formulations:
Due to its antioxidant properties, Licochalcone B can be used as an additive in the formulation of antioxidant supplements and skincare products, providing protection against oxidative stress and promoting overall health and well-being.
Used in Drug Delivery Systems:
Similar to gallotannin, Licochalcone B can be incorporated into drug delivery systems to enhance its bioavailability and therapeutic outcomes. This application can involve the use of organic and metallic nanoparticles as carriers for improved delivery to target cells and tissues.

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

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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