13323-66-5

Basic information

• Product Name: 1-(2-HYDROXYPHENYL)-3-(4-HYDROXYPHENYL)-2-PROPEN-1-ONE
• Synonyms: 4,2'-DIHYDROXYCHALCONE;1-(2-HYDROXYPHENYL)-3-(4-HYDROXYPHENYL)-2-PROPEN-1-ONE;1-(2-HYDROXYPHENYL)-3-(4-HYDROXYPHENYL)PROP-2-EN-1-ONE;2',4-DIHYDROXYCHALCONE;3-(2-HYDROXYPHENYL)-4-HYDROXYACRYLOPHENONE
• CAS NO: 13323-66-5
• Molecular Formula: C₁₅H₁₂O₃
• Molecular Weight: 240.25
• Mol File: 13323-66-5.mol
• Article Data: 58

Chemical Properties

• Melting Point: 167 °C(Solv: ethanol (64-17-5))
• Boiling Point: 445.5°C at 760 mmHg
• Flash Point: 237.4°C
• Appearance: /
• Density: 1.286g/cm³
• Vapor Pressure: 1.49E-08mmHg at 25°C
• Refractive Index: 1.684
• PKA: 7.72±0.30(Predicted)
• CAS DataBase Reference: 1-(2-HYDROXYPHENYL)-3-(4-HYDROXYPHENYL)-2-PROPEN-1-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-HYDROXYPHENYL)-3-(4-HYDROXYPHENYL)-2-PROPEN-1-ONE(13323-66-5)
• EPA Substance Registry System: 1-(2-HYDROXYPHENYL)-3-(4-HYDROXYPHENYL)-2-PROPEN-1-ONE(13323-66-5)

Safety Data

• Hazardous Substances Data: 13323-66-5(Hazardous Substances Data)

Usage

General Description

1-(2-Hydroxyphenyl)-3-(4-hydroxyphenyl)-2-propen-1-one, also known as curcumin, is a natural phenolic compound found in the rhizome of the turmeric plant. It is well-known for its vibrant yellow color and has been used for centuries as a spice, food preservative, and traditional medicine in various cultures. Curcumin is believed to exhibit antioxidant, anti-inflammatory, and anti-cancer properties, and has been the subject of extensive research for its potential health benefits. It is also commonly used as a dye in foods, cosmetics, and textiles due to its intense color. Overall, 1-(2-Hydroxyphenyl)-3-(4-hydroxyphenyl)-2-propen-1-one has diverse applications and is of significant interest in the fields of medicine, nutrition, and chemistry.

InChI:InChI=1/C15H12O3/c16-12-8-5-11(6-9-12)7-10-15(18)13-3-1-2-4-14(13)17/h1-10,16-17H/b10-7+

Upstream product

• 118-93-4 o-hydroxyacetophenone 
• 123-08-0 4-hydroxy-benzaldehyde 
• 130600-79-2 (E)-1-(2-Hydroxy-phenyl)-3-[4-(tetrahydro-pyran-2-yloxy)-phenyl]-propenone 
• 6515-21-5 4-methoxymethoxy-benzaldehyde 
• 6515-18-0 1-[2-(methoxymethoxy)phenyl]ethanone 
• 100-52-7 benzaldehyde 
• 928634-31-5 (E)-1-(2-hydroxyphenyl)-3-[4-(methoxymethoxy)phenyl]-2-propen-1-one 
• 111391-32-3 (E)-3-(4-(benzyloxy)phenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one 
• 4397-53-9 p-benzyloxybenzaldehyde 
• 74189-56-3 4-(tetrahydropyran-2-yloxy)benzaldehyde 
• 204703-70-8 1-(2-(tetrahydro-2H-pyran-2-yloxy)phenyl)ethanone 
• 18962-05-5 4-isopropoxybenzaldehyde 
• 100-83-4 meta-hydroxybenzaldehyde 
• 70201-54-6 1-(2-(1-methylethoxy)phenyl)ethanone 

Downstream Products

• 112980-31-1 (2Z)-2-[(4-hydroxyphenyl)methylidene]benzofuran-3-one 
• 6515-37-3 2-(4-hydroxyphenyl)chroman-4-one 
• 421573-08-2 3-(2-hydroxyphenyl)-5-(4-hydroxyphenyl)-4,5-dihydro-1H-pyrazole 
• 1250377-70-8 4-(2-fluorophenyl)-1-[1-(2-hydroxyphenyl)-3-phenylallylidene]semicarbazide 
• 1344115-24-7 C₂₁H₁₇N₃O₃ 
• 1208112-44-0 3-(2-hydroxyphenyl)-5-(4-hydroxyphenyl)-1N-benzoyl-4,5-dihydro-1H-pyrazole 
• 1208112-46-2 3-(2-hydroxyphenyl)-5-(4-hydroxyphenyl)-1N-(benzenesulphonyl)-4,5-dihydro-1H-pyrazole 
• 1208112-48-4 3-(2-hydroxyphenyl)-5-(4-hydroxyphenyl)-1N-(4-methyl benzenesulphonyl)-4,5-dihydro-1H-pyrazole 
• 1208112-52-0 N-hydroxy-3-(2-hydroxyphenyl)-5-(4-hydroxyphenyl)-4,5-dihydro-1H-pyrazole-1-carboximidamide 
• 1344115-19-0 C₁₆H₁₅N₃O₄ 
• 1344115-22-5 C₁₆H₁₆N₄O₂ 
• 1344115-17-8 C₁₆H₁₅N₃O₃ 
• 1344115-15-6 1-(3-(2-hydroxyphenyl)-5-(4-hydroxyphenyl)-4,5-dihydro-1Hpyrazol-1-yl) ethan-1-one 
• 14919-49-4 3-hydroxy-2-(4-hydroxy-phenyl)-chromen-4-one 

Relevant articles and documents

Evaluation of the anti-inflammatory effect of chalcone and chalcone analogues in a Zebrafish model

The aim of this study was to investigate novel chalcones with potent anti-inflammatory activities in vivo. Chalcone and two chalcone analogues (compound 5 and 9) were evaluated using a caudal fin-wounded transgenic zebrafish line Tg(mpx:gfp) to visualize the effect of neutrophil recruitment dynamically. Results showed that treatment with compound 9 not only affected wound-induced neutrophil recruitment, but also affected Mpx enzymatic activity. Moreover, protein expression levels of pro-inflammatory factors (Mpx, NFκB, and TNFα) were also regulated by compound 9. Taken together, our results provide in vivo evidence of the anti-inflammatory effects of synthesized chalcone analogues on wound-induced inflammation.

Glycolytic inhibition and antidiabetic activity on synthesized flavanone scaffolds with computer aided drug designing tools

Background: Diabetes mellitus is a challengeable metabolic disorder that leads to a group of complications when the HbA1c level is not maintained. Most of the existing drugs avail-able in the market in long-term use may lead to serious adverse effects. He

A Convenient One-Pot Synthesis of Chalcones and Their Derivatives and Their Antimicrobial Activity

Abstract: A series of chalcones were synthesized by base-catalyzed Clasien-Schmidtcondensation of substituted benzaldehydes and substituted acetophenones at roomtemperature. The addition of hydrazine hydrate and hydroxylamine hydrochlorideacross the double bond of the obtained chalcones gave pyrazole and isoxazolederivatives, respectively. All the synthesized compounds were characterized by1H and 13C NMR andFT-IR spectroscopy and screened for their in vitro antimicrobial activityagainst two bacterial strains, Pseudomonasaeruginosa and Pseudomonasoryzihabitans using Ciprofloxacin as standard drug.1-(2-Methoxyphenyl)-3-phenylprop-2-en-1-one and1-(4-chlorophenyl)-3-phenylprop-2-en-1-one showed significant activity againstboth bacterial strains and hence proved to be potent antimicrobialagents.

Natural product-based design, synthesis and biological evaluation of 2′,3,4,4′-tetrahydrochalcone analogues as antivitiligo agents

A bioactive component, 2′,3,4,4′-tetrahydrochalcone (RY3-a) was first isolated from Vernohia anthelmintica (L.) willd seeds, and a set of its analogs, RY3-a-1–RY3-a-15 and RY3-c were designed and synthesized. Biological activity assays showed that RY3-c exhibited better melanogenesis and antioxidant activity and lower toxicity in comparison with RY3-a and butin. Further study tests showed that RY3-c exhibited better melanogenesis activity compared with the positive control 8-methoxypsoralan (8-MOP) in a vitiligo mouse model, suggesting that RY3-c is a good candidate antivitiligo agent. Mechanistic studies showed that RY3-c could repair cell damage induced by excessive oxidative stress and may exert melanin synthesis activity in the mouse melanoma B16F10 cell line by activating the mitogen-activated protein kinase (MAPK) pathway and the upregulation of c-kit.