58749-22-7

Basic information

• Product Name: LICOCHALCONE-A
• Synonyms: LICOCHALCONE-A;(E)-3-[5-(1,1-DIMETHYL-2-PROPENYL)-4-HYDROXY-2-METHOXYPHENYL]-1-(4-HYDROXYPHENYL)-2-PROPEN-1-ONE;4′,4-Dihydroxy-3-α,α-dimethylallyl-6-methoxychalcone;7-Dimethoxycoumarin;Licochalcone A, >=98%;2-Propen-1-one, 3-[5-(1,1-dimethyl-2-propen-1-yl)-4-hydroxy-2-methoxyphenyl]-1-(4-hydroxyphenyl)-, (2E)-;(2E)-3-[4-Hydroxy-2-methoxy-5-(2-methylbut-3-en-2-yl)phenyl]-1-(4-hydroxyphenyl)prop-2-en-1-one
• CAS NO: 58749-22-7
• Molecular Formula: C₂₁H₂₂O₄
• Molecular Weight: 338.4
• EINECS: 1592732-453-0
• Product Categories: The group of Liquorice;sy;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 58749-22-7.mol

Chemical Properties

• Melting Point: 100°
• Boiling Point: 532.554 °C at 760 mmHg
• Flash Point: 186.946 °C
• Appearance: White crystalline powder
• Density: 1.171 g/cm³
• Vapor Pressure: 5.88E-12mmHg at 25°C
• Refractive Index: 1.61
• Storage Temp.: ?20°C
• PKA: 7.82±0.15(Predicted)
• BRN: 4534154
• CAS DataBase Reference: LICOCHALCONE-A(CAS DataBase Reference)
• NIST Chemistry Reference: LICOCHALCONE-A(58749-22-7)
• EPA Substance Registry System: LICOCHALCONE-A(58749-22-7)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36/37
• WGK Germany: 3
• RTECS: UB8755000
• Hazardous Substances Data: 58749-22-7(Hazardous Substances Data)

Usage

Uses

Used in Cancer Treatment:
Licochalcone A is used as an anti-cancer agent for its ability to induce apoptosis in multiple types of cancer cells. It modulates various cellular pathways and enhances the efficacy of conventional chemotherapy drugs, making it a promising candidate for cancer treatment.
Used in Bone Marrow Mesenchymal Stem Cells (BMSC) Applications:
Licochalcone A is used as a promoter of osteogenetic differentiation when applied to BMSC-aggregates. This application provides a promising strategy for treating osteoporotic weight-bearing bone fractures with defects, as it can stimulate the differentiation of stem cells into bone-forming cells.
Used in Pharmaceutical Industry:
Licochalcone A is used as a pharmaceutical candidate due to its anti-tumor and anti-parasitic properties. Its ability to interfere with the mitochondrial electron transport chain and energy metabolism of parasites makes it a potential agent for treating parasitic infections.
Used in Drug Development:
Licochalcone A is used in the development of new drugs that target cancer cells and parasites. Its multifaceted effects on cellular pathways and its ability to enhance the efficacy of chemotherapy drugs make it a valuable compound for drug development efforts.

Biochem/physiol Actions

Inhibits vegetative growth of spore-forming bacteria, B. subtilis and other food-contaminating microorganisms.

InChI:InChI=1/C21H22O4/c1-5-21(2,3)17-12-15(20(25-4)13-19(17)24)8-11-18(23)14-6-9-16(22)10-7-14/h5-13,22,24H,1H2,2-4H3/b11-8+

Upstream product

• 87080-26-0 4-Hydroxy-2-methoxy-4'-(methoxymethoxy)-5-(α,α-dimethylallyl)chalcone 
• 73569-44-5 2-methoxy-4-[(3-methylbut-2-en-1-yl)oxy]benzaldehyde 
• 95-01-2 2,4-Dihydroxybenzaldehyde 
• 85699-00-9 1-[4-(methoxymethoxy)phenyl]-1-ethanone 
• 87080-24-8 2-Methoxy-4-(O-prenyl)-4'-methoxymethoxychalcone 
• 16162-69-9 1-(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)ethanone 
• 1292293-96-9 (2E)-3-{2-methoxy-4-[(3-methylbut-2-en-1-yl)oxy]phenyl}-1-[4-(tetrahydro-2H-pyran-2-yloxy)phenyl]prop-2-en-1-one 
• 870-63-3 prenyl bromide 
• 151410-32-1 (2E)-1-(4-hydroxyphenyl)-3-{2-methoxy-4-[(3-methylbut-2-en-1-yl)oxy]phenyl}prop-2-en-1-one 
• 61235-37-8 2-hydroxy-4-(3-methylbut-2-enyloxy)benzaldehyde 
• 73569-46-7 4,4'-diacetoxy-2-methoxy-5-(α,α-dimethylallyl)chalkone 
• 87080-25-9 2-Methoxy-4-acetoxy-4'-(methoxymethoxy)-5-(α,α-dimethylallyl)chalcone 

Downstream Products

• 189821-53-2 1-(4-hydroxyphenyl)-3-(5-(1,1-dimethylpropenyl)-4-hydroxy-2-methoxyphenyl)propan-1-one 
• 1190747-30-8 C₂₃H₂₄O₅ 
• 73569-46-7 4,4'-diacetoxy-2-methoxy-5-(α,α-dimethylallyl)chalkone 

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.

Synthetic method for licochalcone C

According to the present invention, licochalcone C is produced by performing C-prenylation using A_2O_3, position selective deprotection and methylation, and general Claisen-Schmidt condensation under a base condition. A [3,3]-sigma bond position transferring reaction promoted by water cannot be applied to licochalcone C synthesis due to a decomposition problem. According to the present invention, it has been confirmed that position selective C-prenylation using Al_2O_3 is a novel method for synthesizing licochalcone C.COPYRIGHT KIPO 2015

Concise synthesis of licochalcone a through water-accelerated [3,3]-sigmatropic rearrangement of an aryl prenyl ether

Claisen-Schmidt condensation of 4-(tetrahydropyran-2-yloxy)acetophenone with 2-methoxy-4-[(3-methylbut-2-en-1-yl)oxy]benzaldehyde gave a THP-protected chalcone ether. Removal of the THP group under mild acidic conditions gave the corresponding chalcone ether, which underwent a water-accelerated Claisen rearrangement under microwave irradiation or heating in a sealed tube in aqueous ethanol to give a good yield of licochalcone A, which has diverse biological activities; no product of deprenylation or abnormal Claisen rearrangement was formed. The abnormal Claisen rearrangement of -substituted allyl aryl ethers is known to be a problem in [3,3]-sigmatropic rearrangement reaction; this, however, was not detected in our water-accelerated system.

Synthesis of licochalkone-A

Claisen rearrangement of 4'-hydroxy-2-methoxy-4-prenyloxychalkone (III) using acetic anhydride in dimethylaniline yields four compounds, viz. 4'-acetoxy-2-methoxy-4'',4'',5''-trimethyldihydrofuranochalkone (IV), 4,4'-diacetoxy-2-methoxy-5-(α,α-dimethylallyl)chalkone (V), 4,4'-diacetoxy-2-methoxy-3-(α,α-dimethylallyl)chalkone (VI) and 4,4'-diacetoxy-2-methoxychalkone (VII).Mild alkaline hydrolysis of V affords 4,4'-dihydroxy-2-methoxy-5-(α,α-dimethylallyl)chalkone (VIII, licochalkone-A).

Synthesis of Licochalcone-A

4,4'-Dihydroxy-2-methoxy-5-(α,α-dimethylallyl)chalcone (VII) (licochalcone-A) has been synthesised starting from β-resorcylaldehyde which on partial O-prenylation followed by methylation affords the aldehyde (II).The aldehyde (II) on condensation with p-methoxymethoxyacetophenone (III) under alkaline conditions affords the chalcone (IV), which on Claisen rearrangement yields the chalcone (V).Deacetylation and then demethoxymethylation of V by methanolic HCl affords licochalcone-A (VII), identical with a natural sample.