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
• Article Data: 5

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

Licochalcone A is an estrogenic flavonoid that induces apoptosis in multiple types of cancer cells. Licochalcone A applied to bone marrow mesenchymal stem cells (BMSC)-aggregate has strong osteogenetic differentiation thus providing a promising strategy in treating osteoporotic weight-bearing bone fractures with defects.

General Description

An estrogenic flavanoid with anti-tumor and anti-parasitic properties. Shown to reduce Bcl-2 protein expression and induce apoptosis in several human cancer cell lines. Also induces cell differentiation and enhances the effect of paclitaxel and vinblastine chemotherapy. Reported to interfere with parasite mitochondrial electron transport chain and energy metabolism.

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

• 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 
• 95-01-2 2,4-Dihydroxybenzaldehyde 
• 87080-25-9 2-Methoxy-4-acetoxy-4'-(methoxymethoxy)-5-(α,α-dimethylallyl)chalcone 
• 87080-24-8 2-Methoxy-4-(O-prenyl)-4'-methoxymethoxychalcone 
• 85699-00-9 1-[4-(methoxymethoxy)phenyl]-1-ethanone 
• 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 
• 73569-44-5 2-methoxy-4-[(3-methylbut-2-en-1-yl)oxy]benzaldehyde 
• 61235-37-8 2-hydroxy-4-(3-methylbut-2-enyloxy)benzaldehyde 
• 73569-46-7 4,4'-diacetoxy-2-methoxy-5-(α,α-dimethylallyl)chalkone 
• 87080-26-0 4-Hydroxy-2-methoxy-4'-(methoxymethoxy)-5-(α,α-dimethylallyl)chalcone 

Downstream Products

• 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.

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 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.