69704-15-0

Basic information

• Product Name: 4-HYDROXY-4'-METHOXYCHALCONE
• Synonyms: 4-HYDROXY-4'-METHOXYCHALCONE;3-(4-HYDROXYPHENYL)-1-(4-METHOXYPHENYL)-2-PROPEN-1-ONE
• CAS NO: 69704-15-0
• Molecular Formula: C₁₆H₁₄O₃
• Molecular Weight: 254.28
• Product Categories: Chalcones
• Mol File: 69704-15-0.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 443.3 °C at 760 mmHg
• Flash Point: 166.7 °C
• Appearance: /
• Density: 1.197 g/cm³
• Vapor Pressure: 1.8E-08mmHg at 25°C
• Refractive Index: 1.631
• CAS DataBase Reference: 4-HYDROXY-4'-METHOXYCHALCONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-HYDROXY-4'-METHOXYCHALCONE(69704-15-0)
• EPA Substance Registry System: 4-HYDROXY-4'-METHOXYCHALCONE(69704-15-0)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 69704-15-0(Hazardous Substances Data)

Usage

General Description

4-Hydroxy-4'-methoxychalcone, also known as 4,4'-dihydroxy-3,3'-dimethoxychalcone, is a chemical compound that belongs to the class of organic compounds known as chalcones. It is derived from phenol and phenylpropanoid, and constitutes a type of flavonoid. It is notable for its anti-inflammatory and antitumoral properties. In many studies, this chalcone has shown potential cytotoxic effects on cancer cells and is an ingredient in various traditional medicinal practices. However, the pharmacokinetic behavior and mechanism of action of this chalcone remain mostly unknown and warrant further investigation. The molecular formula of this compound is C17H16O4.

InChI:InChI=1/C16H14O3/c1-19-15-9-5-13(6-10-15)16(18)11-4-12-2-7-14(17)8-3-12/h2-11,17H,1H3/b11-4+

Upstream product

• 92873-00-2 4-bromo-4'-methoxychalcone 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 99-96-7 4-hydroxy-benzoic acid 
• 1615249-36-9 C₁₈H₁₈O₄ 
• 74189-56-3 4-(tetrahydropyran-2-yloxy)benzaldehyde 
• 123-08-0 4-hydroxy-benzaldehyde 

Downstream Products

• 125292-17-3 4-(1-acetyl-3-4'-methoxyphenyl-2-pyrazolin-5-yl)phenol 

Relevant articles and documents

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.

Structure-activity relationship with pyrazoline-based aromatic sulfamates as carbonic anhydrase isoforms I, II, IX and XII inhibitors: Synthesis and biological evaluation

Four new series of aromatic sulfamates were synthesized and investigated for the inhibition of four human (h) isoforms of zinc enzyme carbonic anhydrase (CA, EC 4.2.1.1), hCA I, II, IX, and XII. The reported derivatives, obtained by a sulfamoylation reaction of the corresponding phenolic precursors, bear 3,5-diarylpyrazoline moieties as spacers between the benzenesulfamate fragment which binds the zinc ion from the active site, and the tail of the inhibitor. Pyrazolines are biologically privileged scaffolds, endowed with versatile biological activity, such as an anti-proliferative action. The derivatives were tested for the inhibition of the cytosolic, hCA I and II (off target isoforms) and the trans-membrane, tumor-associated hCA IX and XII enzymes (anticancer drug targets). Generally, hCA I was not effectively inhibited, whereas many low nanomolar inhibitors were evidenced against hCA II (KIs in the range of 0.42–90.1 nM), IX (KIs in the range of 0.72–63.6 nM), and XII (KIs in the range of 0.88–85.2 nM). The best substitution fragments at the pyrazoline ring included for CA II a 4-sulfamic group on the 3-aryl and halogens on the 5-aryl or a methoxy group on the 3-aryl and a 4-sulfamate group on the 5-aryl; for CA IX and CA XII they included the sulfamic group on the 3- or 4-position of the 5-aryl and an electronwithdrawing group on the 4-postion of the 3-aryl ring.

Design, synthesis and bioactivity of chalcones and its analogues

The Vernohia anthelmintica L.'s extract is one of the most popular Uygur medicines used for vitiligo. It is believed that the chalcone compounds of the plant play an important role in the treatment since they may activate tyrosinase and improve melanin production. In this study, twenty-one chalcones and nine analogues were synthesized in view of three different components of chalcone (A, B ring and α, β-unsaturated carbonyl). After biological evaluation of their activity on tyrosinase in cell-free systems, the result showed that most compounds (except polyhydroxy chalcones) possess activator effect on the tyrosinase, especially for 13a–15a, 20a and 1b, which bearing a comparable activity to the positive control 8-MOP. SAR of these tyrosinase activator was summed up for the first time as well. Finally, compound 13a was found to increase melanin contents and tyrosinase activity 1.75 and 1.3 fold, respectively, compared with that of untreated murine B16 cells at the concentration of 40?μg/mL.