220430-82-0

Basic information

• Product Name: 2',4-DIHYDROXY-3-METHOXYCHALCONE
• Synonyms: 2',4-DIHYDROXY-3-METHOXYCHALCONE;4,2'-DIHYDROXY-3-METHOXYCHALCONE
• CAS NO: 220430-82-0
• Molecular Formula: C₁₆H₁₄O₄
• Molecular Weight: 270.28
• Mol File: 220430-82-0.mol
• Article Data: 8

Chemical Properties

• Melting Point: 127-129°C
• Appearance: /
• CAS DataBase Reference: 2',4-DIHYDROXY-3-METHOXYCHALCONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2',4-DIHYDROXY-3-METHOXYCHALCONE(220430-82-0)
• EPA Substance Registry System: 2',4-DIHYDROXY-3-METHOXYCHALCONE(220430-82-0)

Safety Data

• Hazardous Substances Data: 220430-82-0(Hazardous Substances Data)

Usage

Description

2',4-DIHYDROXY-3-METHOXYCHALCONE is a natural chemical compound belonging to the chalcone class of flavonoids, found in plants such as Angelica gigas and Glycyrrhiza glabra. It is recognized for its potent antioxidant and anti-inflammatory properties, and research indicates its potential therapeutic effects in various diseases, including cancer, diabetes, and cardiovascular conditions. Furthermore, it has been studied for its neuroprotective and antimicrobial activities, as well as its potential use in skincare and cosmetic products due to its ability to protect against oxidative stress and inflammation.

Uses

Used in Pharmaceutical Applications:
2',4-DIHYDROXY-3-METHOXYCHALCONE is used as a therapeutic agent for various diseases, such as cancer, diabetes, and cardiovascular conditions, due to its potential health benefits and ability to modulate biological pathways associated with these conditions.
Used in Neuroprotective Applications:
In the field of neuroscience, 2',4-DIHYDROXY-3-METHOXYCHALCONE is used as a neuroprotective agent, leveraging its potential to safeguard the nervous system against damage and degeneration.
Used in Antimicrobial Applications:
2',4-DIHYDROXY-3-METHOXYCHALCONE is utilized as an antimicrobial agent, given its capacity to combat microbial infections and contribute to overall health.
Used in Skincare and Cosmetic Industry:
In the skincare and cosmetic sector, 2',4-DIHYDROXY-3-METHOXYCHALCONE is used as an active ingredient in products designed to protect the skin against oxidative stress and inflammation, thereby promoting skin health and appearance.

Upstream product

• 65490-08-6 2-hydroxy-4-(methoxymethoxy)acetophenone 
• 6099-04-3 trans-3-methoxycinnamic acid 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 591-31-1 3-methoxy-benzaldehyde 
• 111841-07-7 2-hydroxy-4-(tetrahydropyran-2-yloxy)acetophenone 
• 1026639-10-0 (E)-1-[2-Hydroxy-4-(tetrahydro-pyran-2-yloxy)-phenyl]-3-(3-methoxy-phenyl)-propenone 

Downstream Products

• 93012-40-9 3'-methoxy-7-hydroxyflavanone 

Relevant articles and documents

Synthesis and biological evaluation of isoliquiritigenin derivatives as a neuroprotective agent against glutamate mediated neurotoxicity in HT22 cells

Glutamate-induced neurotoxicity is characterized by cellular Ca2+ uptake, which is upstream of reactive oxygen species (ROS)-induced apoptosis signaling and MAPKs activation. In the present study, we synthesized isoliquiritigenin analogs with electron-donating and electron-withdrawing functional groups. These analogs were evaluated for neuroprotective effect against glutamate-induced neurotoxicity in HT22 cells. Among these analogs, compound BS11 was selected as a potent neuroprotective agent. Cellular Ca2+ concentration, ROS level, MAPKs activation and AIF translocation to the nucleus were increased upon treatment with 5 mM glutamate. In contrast, we identified that compound BS11 reduced the cellular Ca2+ concentration and ROS level upon glutamate exposure. Western blot analysis showed that MAPK activation was decreased by treatment with compound BS11. We further identified that cotreatment of compound BS11 and glutamate inhibited translocation of AIF to the nucleus.

Fast and efficient synthesis of flavanones from cinnamic acids

A fast and efficient synthesis of flavanones from cinnamic acids in three steps has been developed. First, the cinnamic acid was converted to cinnamyol chlorides using SOCl2. The acid chlorides were then treated with substituted phenols in BF3· OEt2to furnish corresponding chalcones in 42(75% yields. Base-catalyzed cyclization of the chalcones at room temperature afforded corresponding flavones in 85–95% yields. The conversion of the cinnamic acid derivatives to corresponding chalcones was found to be sensitive to the position and nature of the substituents on the aromatic rings.

Investigation of chalcones and benzochalcones as inhibitors of breast cancer resistance protein

Breast cancer resistance protein (BCRP/ABCG2) belongs to the ATP binding cassette family of transport proteins. BCRP has been found to confer multidrug resistance in cancer cells. A strategy to overcome resistance due to BCRP overexpression is the investigation of potent and specific BCRP inhibitors. The aim of the current study was to investigate different multi-substituted chalcones for their BCRP inhibition. We synthesized chalcones and benzochalcones with different substituents (viz. OH, OCH3, Cl) on ring A and B of the chalcone structure. All synthesized compounds were tested by Hoechst 33342 accumulation assay to determine inhibitory activity in MCF-7 MX and MDCK cells expressing BCRP. The compounds were also screened for their P-glycoprotein (P-gp) and Multidrug resistance-associated protein 1 (MRP1) inhibitory activity in the calcein AM accumulation assay and were found to be selective towards inhibition of BCRP. Substituents at position 2′ and 4′ on chalcone ring A were found to be essential for activity; additionally there was a great influence of substituents on ring B. Presence of 3,4-dimethoxy substitution on ring B was found to be optimal, while presence of 2- and 4-chloro substitution also showed a positive effect on BCRP inhibition.