20784-60-5

Basic information

• Product Name: 1-[2-Hydroxy-4-methoxy-5-(3-methyl-2-butenyl)phenyl]-3-(4-hydroxyphenyl)-2-propen-1-one
• Synonyms: 1-[2-Hydroxy-4-methoxy-5-(3-methyl-2-butenyl)phenyl]-3-(4-hydroxyphenyl)-2-propen-1-one;4'-O-Methylbroussochalcone B;2',4-Dihydroxy-4'-methoxy-5'-(3-methyl-2-butenyl)chalcone;4'-O-Methylbavachalcone;O-Methylbroussochalcone B, 4'-;Methylbroussochalcone4'-O- B;O-Methylbroussochalcone B
• CAS NO: 20784-60-5
• Molecular Formula: C₂₁H₂₂O₄
• Molecular Weight: 338.4
• Mol File: 20784-60-5.mol
• Article Data: 4

Chemical Properties

• Melting Point: 169.9-170.1 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• Boiling Point: 552.1±50.0 °C(Predicted)
• Appearance: /
• Density: 1.181±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 7.41±0.50(Predicted)
• CAS DataBase Reference: 1-[2-Hydroxy-4-methoxy-5-(3-methyl-2-butenyl)phenyl]-3-(4-hydroxyphenyl)-2-propen-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[2-Hydroxy-4-methoxy-5-(3-methyl-2-butenyl)phenyl]-3-(4-hydroxyphenyl)-2-propen-1-one(20784-60-5)
• EPA Substance Registry System: 1-[2-Hydroxy-4-methoxy-5-(3-methyl-2-butenyl)phenyl]-3-(4-hydroxyphenyl)-2-propen-1-one(20784-60-5)

Safety Data

• Hazardous Substances Data: 20784-60-5(Hazardous Substances Data)

Usage

Description

1-[2-Hydroxy-4-methoxy-5-(3-methyl-2-butenyl)phenyl]-3-(4-hydroxyphenyl)-2-propen-1-one, commonly known as parthenolide, is a naturally occurring sesquiterpene lactone compound found in the plant feverfew. It exhibits a range of biological activities, including anti-inflammatory, anti-cancer, and neuroprotective properties. Parthenolide has garnered interest for its potential therapeutic applications in treating migraines, arthritis, and various forms of cancer. However, further research is necessary to fully elucidate its mechanisms of action and establish its safety and efficacy profile.

Uses

Used in Pharmaceutical Industry:
Parthenolide is used as a potential therapeutic agent for various inflammatory and autoimmune conditions due to its anti-inflammatory properties. It modulates the activity of inflammatory mediators and immune cells, offering a promising approach to managing inflammation-related disorders.
Used in Cancer Treatment:
In the oncology field, parthenolide is utilized as a potential anti-cancer agent. It has been studied for its ability to induce apoptosis in cancer cells, inhibit cell proliferation, and modulate signaling pathways involved in tumor growth and progression. Its potential synergistic effects with conventional chemotherapeutic drugs are also being explored to enhance treatment outcomes in cancer patients.
Used in Neuroprotection:
Parthenolide is employed as a neuroprotective agent in the context of neurodegenerative diseases. Its neuroprotective properties are attributed to its ability to modulate inflammatory processes, oxidative stress, and neuronal cell death, offering a potential therapeutic strategy for conditions such as Alzheimer's disease and Parkinson's disease.

Upstream product

• 19879-30-2 -(2-hydroxy-3-methylbutane)-2-(4-hydroxyphenyl)-7-methoxychroman-4-one 
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• 1092462-95-7 4'-methoxy-4-methoxymethoxy-2'-prenyloxychalcone 
• 128961-13-7 (E)-1-(2-hydroxy-4-methoxy-5-(3-methylbut-2-en-1-yl)phenyl)-3-(4-(methoxymethoxy)phenyl)prop-2-en-1-one 
• 128961-25-1 1-(4-methoxy-2-((3-methylbut-2-en-1-yl)oxy)phenyl)ethan-1-one 

Downstream Products

• 129097-15-0 2-(4-hydroxyphenyl)-7-methoxy-6-(3-methylbut-2-en-1-yl)chroman-4-one 

Relevant articles and documents

Synthesis and biological evaluation of novel bavachinin analogs as anticancer agents

A library of 28 analogs of bavachinin including aliphatic and aromatic ethers, epoxide, chalcone, oxime, semicarbazide, oxime ether and triazole derivatives have been synthesized and evaluated for cytotoxicity against four different human cancer cell lines. Bio-evaluation studies exhibited better cytotoxic profile for many analogs compare to bavachinin. Best results were observed for a 1,2,3-triazole analog (17i) with IC50 values 7.72, 16.08, 7.13 and 11.67 μM against lung (A549), prostate (PC-3), colon (HCT-116) and breast (MCF-7) cancer cell lines respectively. This analog showed three and four fold improvement in cytotoxicity against HCT-116 and A549 cell lines than parent molecule (1). Structure activity relationship (SAR) study for all synthesized analogs was carried out. Further, mechanistic study of the lead molecule (17i) revealed that it inhibits colony formation and in vitro migration of human colon cancer cells (HCT-116). Also, it induced the morphological changes and mediated the apoptotic cell death of HCT-116 cells with perturbance in mitochondrial membrane potential (MMP) and PARP cleavage.

THERAPEUTIC AGENT

A therapeutic agent and prophylactic agent for a disease accompanying an abnormality in an amount of insulin or insulin response, an agent for an insulin-mimetic action, a food, beverage and feed, an agent for enhancing glucose uptake into a cell, and an agent for inducing differentiation into an adipocyte, characterized in that each comprises as an effective ingredient at least one compound selected from the group consisting of a chalcone compound, an acetophenone compound, a coumarin compound, a phthalide compound, derivatives thereof, and pharmacologically acceptable salts thereof.