2198-19-8

Basic information

• Product Name: 1-(2-hydroxy-4-methoxyphenyl)-3-(4-methoxyphenyl)-2-propen-1-one
• Synonyms: 1-(2-hydroxy-4-methoxyphenyl)-3-(4-methoxyphenyl)-2-propen-1-one;1-(2-Hydroxy-4-methoxyphenyl)-3-(p-methoxyphenyl)-2-propene-1-one;4'-Methoxy-2'-hydroxy-β-(4-methoxyphenyl)acrylophenone;2-Propen-1-one, 1-(2-hydroxy-4-methoxyphenyl)-3-(4-methoxyphenyl)-;Nsc 78638
• CAS NO: 2198-19-8
• Molecular Formula: C₁₇H₁₆O₄
• Molecular Weight: 284.30654
• Product Categories: Chalcones
• Mol File: 2198-19-8.mol
• Article Data: 49

Chemical Properties

• Boiling Point: 499.6°Cat760mmHg
• Flash Point: 185.5°C
• Appearance: /
• Density: 1.203g/cm³
• Vapor Pressure: 1.32E-10mmHg at 25°C
• Refractive Index: 1.614
• CAS DataBase Reference: 1-(2-hydroxy-4-methoxyphenyl)-3-(4-methoxyphenyl)-2-propen-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-hydroxy-4-methoxyphenyl)-3-(4-methoxyphenyl)-2-propen-1-one(2198-19-8)
• EPA Substance Registry System: 1-(2-hydroxy-4-methoxyphenyl)-3-(4-methoxyphenyl)-2-propen-1-one(2198-19-8)

Safety Data

• Hazardous Substances Data: 2198-19-8(Hazardous Substances Data)

Usage

General Description

1-(2-hydroxy-4-methoxyphenyl)-3-(4-methoxyphenyl)-2-propen-1-one, also known as curcumin, is a natural compound found in the rhizome of the Curcuma longa plant, which is commonly known as turmeric. It is a polyphenolic compound with various biological activities, including antioxidant, anti-inflammatory, and anticancer properties. Curcumin has been extensively studied for its potential therapeutic effects on a wide range of conditions, including cancer, diabetes, cardiovascular disease, and neurodegenerative disorders. It is also used as a food coloring and flavoring agent, as well as in traditional medicine for its health benefits. The chemical structure of curcumin consists of two aromatic rings with methoxy and hydroxy groups, and a conjugated system of double bonds, which contributes to its pharmacological properties.

InChI:InChI=1/C17H16O4/c1-20-13-6-3-12(4-7-13)5-10-16(18)15-9-8-14(21-2)11-17(15)19/h3-11,19H,1-2H3/b10-5+

Upstream product

• 552-41-0 1-(2-hydroxy-4-methoxyphenyl)ethanone 
• 123-11-5 4-methoxy-benzaldehyde 
• 150-19-6 O-methylresorcine 
• 128961-25-1 1-(4-methoxy-2-((3-methylbut-2-en-1-yl)oxy)phenyl)ethan-1-one 
• 25826-69-1 4',7-dimethoxyflavanone 
• 829-20-9 2',4'-dimethoxyacetophenone 
• 30925-62-3 metochalcone 
• 108-46-3 recorcinol 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 961-29-5 isoliquirtigenin 
• 74-88-4 methyl iodide 

Downstream Products

• 6515-26-0 (+/-)-2,3-trans-7,4'-dimethoxyflavanonol 
• 25826-69-1 4',7-dimethoxyflavanone 
• 85475-72-5 2,5-Dihydro-8-methoxy-3-(4'-methoxyphenyl)-1-benzoxepin 
• 114439-83-7 bi-(4',4-dimethoxy-chalconyl-2'-oxy)methane 
• 20979-50-4 4,7-dimethoxyflavone 
• 4537-35-3 2'-benzyloxy-4,4'-dimethoxychalcone 
• 38493-28-6 6,8-dibromo-4',7-dimethoxyflavone 
• 41682-53-5 2'-hydroxy-5'-prenyl-4,4'-dimethoxychalcone 
• 66549-80-2 2'-hydroxy-3'-prenyl-4,4'-dimethoxychalcone 
• 1292793-52-2 2'-prenyloxy-4,4'-dimethoxychalcone 
• 5128-44-9 5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one 
• 89059-54-1 6-acetyl-3-(2-hydroxy-4-methoxyphenyl)-5-(4-methoxyphenyl)cyclohex-2-en-1-one 
• 89059-53-0 3-acetyl-2-methyl-4-(4-methoxyphenyl)-6-(2-hydroxy-4-methoxyphenyl)-4H-pyran 
• 89059-52-9 3-(2-hydroxy-4-methoxyphenyl)-5-(4-methoxyphenyl)cyclohex-2-en-1-one 

Relevant articles and documents

Crystal-packing modes determine the solid-state ESIPT fluorescence in highly dipolar 2′-hydroxychalcones

This work describes the systematic study of the structure-luminescence relationship of 15 hydroxy-chalcones directly in the crystal state. Chalcones are easily assembled at the gram scale allowing for efficient variation of their substitution motifs. Our molecule variants combine two modes of fluorescence generation, ESIPT and ICT, both known for their potential to achieve significant quantum yields even with emission in the red to near infrared, a region preferred for technologies as diverse as optoelectronics and chemical sensing. Quantum yields as high as 48% (at 665 nm) and emission wavelengths in the deep red region (710 nm, 5%) were achieved with variants equipped with a strained amino substituent in the donor portion (azetidinyl). Systematic XRD analysis of large monocrystals allowed for the identification of the subtle interplay of several inter- and intra-molecular parameters in achieving such performances, be it intramolecular planarity, non-classical H-bonds, and stacking modes.

Development of a novel nitric oxide (NO) production inhibitor with potential therapeutic effect on chronic inflammation

Inflammation is a complex biological response to stimuli. Activated macrophages induced excessively release of pro-inflammatory cytokines and mediators such as endogenous radical nitric oxide (NO) play a significant role in the progression of multiple inflammatory diseases. Both natural and synthetic chalcones possess a wide range of bioactivities. In this work, thirty-nine chalcones and three related compounds, including several novel ones, based on bioactive kava chalcones were designed, synthesized and their inhibitory effects on NO production in RAW 264.7 cells were evaluated. The novel compound (E)-1-(2′-hydroxy-4′,6′-dimethoxyphenyl)-3-(3-methoxy-4-(3-morpholinopropoxy)phenyl)prop-2-en-1-one (53) exhibited a better inhibitory activity (84.0%) on NO production at 10 μM (IC50 = 6.4 μM) with the lowest cytotoxicity (IC50 > 80 μM) among the tested compounds. Besides, western blot analysis indicated that compound 53 was a potent down-regulator of inducible nitric oxide synthase (iNOS) protein. Docking study revealed that compound 53 also can dock into the active site of iNOS. Furthermore, at the dose of 10 mg/kg/day, compound 53 could both significantly suppress the progression of inflammation on collagen-induced arthritis (CIA) and adjuvant-induced arthritis (AIA) models. In addition, the structure-activity relationship (SAR) of the kava chalcones based analogs was also depicted.

NOTCH INHIBITORS FOR USE IN THE TREATMENT OF T-CELL ACUTE LYMPHOBLASTIC LEUKEMIA

Compounds of formula (I) in the capacity of compounds with anti-tumor activity for the treatment of T-cell acute lymphoblastic leukemia (T-ALL).