20426-12-4

Basic information

• Product Name: 4-HYDROXYCHALCONE
• Synonyms: HYDROXYCHALCONE, 4-;(E)-3-(4-HYDROXYPHENYL)-1-PHENYLPROP-2-EN-1-ONE;BENZYLIDENE-4-HYDROXYACETOPHENONE;2-(4-HYDROXYBENZAL)ACETOPHENONE;2-(4-HYDROXYBENZYLIDENE)ACETOPHENONE;4-HYDROXYBENZYLIDENEACETOPHENONE;4-HYDROXYCHALCONE;1-Phenyl-3-(4-hydroxyphenyl)-2-propene-1-one
• CAS NO: 20426-12-4
• Molecular Formula: C₁₅H₁₂O₂
• Molecular Weight: 224.25
• EINECS: -0
• Product Categories: Aromatic Acetophenones & Derivatives (substituted);Biochemistry;Flavonoids;Inhibitors
• Mol File: 20426-12-4.mol
• Article Data: 105

Chemical Properties

• Melting Point: 180-184 °C
• Boiling Point: 394.9 °C at 760 mmHg
• Flash Point: 168.6 °C
• Appearance: /
• Density: 1.191 g/cm³
• Vapor Pressure: 8.41E-07mmHg at 25°C
• Refractive Index: 1.653
• PKA: 9.76±0.26(Predicted)
• Water Solubility: Insoluble in water.
• BRN: 2049155
• CAS DataBase Reference: 4-HYDROXYCHALCONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-HYDROXYCHALCONE(20426-12-4)
• EPA Substance Registry System: 4-HYDROXYCHALCONE(20426-12-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26
• RIDADR: UN 3077 9/PG III
• RTECS: UD1675000
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 20426-12-4(Hazardous Substances Data)

Usage

Description

4-Hydroxychalcone, a member of the chalcone class, is a trans-chalcone derivative with a hydroxy group at the 4th position. It is characterized by its yellow powder appearance and is known for its potential applications in various fields due to its chemical properties.

Uses

Used in Pharmaceutical Industry:
4-Hydroxychalcone is used as an anti-angiogenesis agent for inhibiting the formation of new blood vessels, which is a critical process in the growth and metastasis of tumors. This property makes it a valuable compound in the development of cancer treatments.
4-Hydroxychalcone is also used as an antineoplastic agent, which means it has the ability to inhibit or prevent the growth and spread of neoplasms (abnormal growths), particularly cancerous cells. Its antineoplastic properties contribute to its potential use in the development of cancer therapies.
Used in Chemical Synthesis:
4-Hydroxychalcone serves as an organic intermediate in the synthesis of various chemical compounds. Its unique structure allows it to be a versatile building block for creating a range of molecules with different applications in various industries, including pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C15H12O2/c16-14-9-6-12(7-10-14)8-11-15(17)13-4-2-1-3-5-13/h1-11,16H/b11-8+

Upstream product

• 123-08-0 4-hydroxy-benzaldehyde 
• 98-86-2 acetophenone 
• 1122-54-9 methyl (4-pyridyl) ketone 
• 6515-21-5 4-methoxymethoxy-benzaldehyde 
• 100-52-7 benzaldehyde 
• 99-93-4 4-Hydroxyacetophenone 
• 3235-02-7 p-methylbenzaldehyde oxime 
• 1774-66-9 3-(4-bromophenyl)-1-phenylprop-2-en-1-one 
• 70-11-1 α-bromoacetophenone 
• 22252-15-9 trans-4-methoxychalcone 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 7400-08-0 p-Coumaric Acid 
• 611-73-4 Benzoylformic acid 
• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 1268853-29-7 4-(4-hydroxyphenyl)-2-phenylpyrido[2,3-b]indolizine-10-carbonitrile 
• 121146-38-1 [4-(1,2-Dibromo-3-oxo-3-phenyl-propyl)-phenoxy]-acetic acid ethyl ester 
• 121146-37-0 [4-(1,2-Dibromo-3-oxo-3-phenyl-propyl)-phenoxy]-acetic acid methyl ester 

Relevant articles and documents

Design, in silico and in?vitro evaluation of curcumin analogues against Plasmodium falciparum

The polyphenolic compound curcumin has been reported for its antimalarial properties in various scientific studies. Plasmodium falciparum ATP6, the parasite orthologue of mammalian sarcoplasmic Ca2+ ATPase (SERCA) has been identified as a key molecular target of both artemisinin and curcumin. The work was thereby undertaken to study the anti-malarial properties of two different series of curcumin analogues based on their docking interactions with PfATP6 and correlating the results with their anti-malarial activity. The compounds were designed retaining similar functional groups as that of the parent curcumin nucleus while incorporating changes in the carbon chain length, unsaturated groups and the number of ketone groups. The compounds (1E, 4E)-1,5-bis(4-methylphenyl)penta-1,4-dien-3-one (CD-9), (1E, 4E)-1,5-bis(4-methoxyphenyl)penta-1,4-dien-3-one (CD-8) and (E)-1,3-bis(4-hydroxylphenyl)prop-2-en-1-one (CD-1) showed IC50 values of 1.642?μM, 1.764?μM and 2.59?μM in 3D7 strain and 3.039?μM, 7.40?μM and 11.3?μM in RKL-2 strain respectively. Detailed structure-activity relationship studies of the compounds showed that CD-9 and CD-8 had a common hydrophobic interaction with the residue Leu268 of the PfATP6 protein and has been postulated through our study to be the reason for their antimalarial activity as seen after corroborating the results with the in?vitro study. The study provided valuable insight about the ligand-protein interaction of the various functional groups of curcumin and its analogues against the PfATP6 protein and their importance in imparting antimalarial action.

Chalcone based aryloxypropanolamines as potential antihyperglycemic agents

A series of chalcone based aryloxypropanolamines were synthesized and evaluated for their antihyperglycemic activity in SLM and STZ rat models. Most of the compounds exhibited moderate to good activity ranging from 6.5% to 31.1% in SLM and 8.3% to 22.6% i

Aldoxime- and hydroxy-functionalized chalcones as highly potent and selective monoamine oxidase-B inhibitors

A panel of 30 chalcone derivatives, including 19 aldoxime-chalcone ethers (ACE), and 11 hydroxyl?chalcones (HC), previously synthesized using a Pd-catalyzed C–O cross-coupling method were evaluated for their inhibitory activities against monoamine oxidases (MAOs), cholinesterases (ChEs), and β-secretase (BACE-1). HC6 was the most potent inhibitor of MAO-B with an IC50 value of 0.0046 μM and a selectivity index (SI) of 1,113. HC3 also potently inhibited MAO-B (IC50 = 0.0067 μM) and had the highest SI (1,455). ACE7 and ACE15 were also potent MAO-B inhibitors (IC50 = 0.012 and 0.018 μM, respectively), with SIs of 260 and 1,161, respectively. HC3 and HC6 were reversible competitive inhibitors of MAO-B, with Ki values of 0.0036 and 0.0013 μM, respectively. A structure–activity relationship revealed that methyl and fluorine substituents contributed to increasing both inhibition and selectivity. ACE7 was the most effective inhibitor of MAO-A (IC50 = 1.49 μM), followed by ACE3 (IC50 = 3.75 μM). No compounds effectively inhibited AChE, BChE, or BACE-1. A docking simulation showed that the ligand efficiency and docking scores of HC3 and HC6 toward MAO-B were consistent with the experimental IC50 values. These results suggest that HC3 and HC6 can be considered promising candidates for the treatment of neurological disorders.

Acrylate-substituted pyrazoline derivative, photocurable composition and preparation method

The present application relates to an acrylate-substituted pyrazoline derivative represented by formula (I), a photocurable composition, and a preparation method and application of the acrylate-substituted pyrazoline derivative represented by formula (I).

Phenazine-chalcone hybrid compound as well as preparation method and application thereof

The invention discloses a phenazine-chalcone hybrid compound, a preparation method thereof and application thereof in preparation of anti-brain glioma drugs. The structure of the phenazine-chalcone hybrid compound is shown as a formula (I). Compared with