6338-81-4

Basic information

• Product Name: 4'-HYDROXY-4-METHOXYCHALCONE
• Synonyms: 4'-HYDROXY-4-METHOXYCHALCONE;1-(4-hydroxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one;2-Propen-1-one, 1-(4-hydroxyphenyl)-3-(4-methoxyphenyl)-;Nsc 40922
• CAS NO: 6338-81-4
• Molecular Formula: C₁₆H₁₄O₃
• Molecular Weight: 254.28
• Product Categories: Chalcones
• Mol File: 6338-81-4.mol
• Article Data: 95

Chemical Properties

• Melting Point: 217-218 °C(Solv: ethanol (64-17-5))
• Boiling Point: 467°C at 760 mmHg
• Flash Point: 176.8°C
• Appearance: /
• Density: 1.197g/cm³
• Vapor Pressure: 2.41E-09mmHg at 25°C
• Refractive Index: 1.631
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly, Sonicated)
• PKA: 7.66±0.15(Predicted)
• CAS DataBase Reference: 4'-HYDROXY-4-METHOXYCHALCONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-HYDROXY-4-METHOXYCHALCONE(6338-81-4)
• EPA Substance Registry System: 4'-HYDROXY-4-METHOXYCHALCONE(6338-81-4)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 6338-81-4(Hazardous Substances Data)

Usage

Description

4'-HYDROXY-4-METHOXYCHALCONE is a chalcone derivative characterized by its chemical structure featuring a hydroxy and methoxy group at the 4' position. It is a promising compound with potential applications in various fields due to its unique properties.

Uses

Used in Pharmaceutical Industry:
4'-HYDROXY-4-METHOXYCHALCONE is used as a key intermediate for synthesizing novel heterocyclic derivatives of chalcone. These derivatives have potential applications as antihyperglycemic agents, which can be beneficial in the development of treatments for diabetes and related conditions.

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

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 99-93-4 4-Hydroxyacetophenone 
• 41564-67-4 (E)-1,3-bis(4-methoxyphenyl)-2-propene-1-one 
• 16162-69-9 1-(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)ethanone 
• 87486-00-8 (E)-4-(3-(4-methoxyphenyl)acryloyl)phenyl acetate 
• 1010118-52-1 C₂₃H₂₀O₅S 
• 123-08-0 4-hydroxy-benzaldehyde 
• 126443-12-7 4'-bromo-4-methoxy-trans-chalcone 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 67963-68-2 t-butyldimethylsilyl-4-bromophenol 
• 830-09-1 3-(4'-methoxyphenyl)propenoic acid 
• 108-95-2 phenol 

Downstream Products

• 148404-16-4 4-methoxy-4'-(2-pyrrolidinoethoxy) chalkone 
• 148404-10-8 1-(4,5-Dihydro-3-(4-hydroxyphenyl)-5-(4-methoxyphenyl)pyrazol-1-yl)ethanone 
• 132808-71-0 4-(4-Hydroxy-phenyl)-6-(4-methoxy-phenyl)-5,6-dihydro-1H-pyrimidine-2-thione 
• 79492-54-9 3-cyano-4-(p-methoxyphenyl)-6-(p-hydroxyphenyl)-pyridine-2-ones 
• 79492-50-5 2-amino-3-cyano-4-(p-methoxyphenyl)-6-(p-hydroxyphenyl)-pyridine 
• 370590-08-2 {4-[(E)-3-(4-Methoxy-phenyl)-acryloyl]-phenoxy}-acetic acid ethyl ester 
• 132808-71-0 4-[2-mercapto-6-(4-methoxy-phenyl)-5,6-dihydro-pyrimidin-4-yl]-phenol 
• 332951-06-1 2-amino-4-(4-hydroxyphenyl)-6-(4-methoxyphenyl)pyrimidine 
• 689266-47-5 4'-(2,3-epoxypropoxy)-4-methoxychalcone 

Relevant articles and documents

Bis(4,5-dihydropyrazole) derivatives: Synthesis, characterization and antimicrobial-antioxidant evaluations

In the present work, five new bispyrazolines 3(a-e) have been prepared from the cyclization reaction of bischalcones 2(a-e) with phenyl hydrazine under alcoholic medium. The bischalcones 2(a-e) were synthesized by using the alkylation of chalcone 1 with a

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.

Chalcone-Supported Cardiac Mesoderm Induction in Human Pluripotent Stem Cells for Heart Muscle Engineering

Human pluripotent stem cells (hPSCs) hold great promise for applications in cell therapy and drug screening in the cardiovascular field. Bone morphogenetic protein 4 (BMP4) is key for early cardiac mesoderm induction in hPSC and subsequent cardiomyocyte derivation. Small-molecular BMP4 mimetics may help to standardize cardiomyocyte derivation from hPSCs. Based on observations that chalcones can stimulate BMP4 signaling pathways, we hypothesized their utility in cardiac mesoderm induction. To test this, we set up a two-tiered screening strategy, (1) for directed differentiation of hPSCs with commercially available chalcones (4’-hydroxychalcone [4’HC] and Isoliquiritigen) and 24 newly synthesized chalcone derivatives, and (2) a functional screen to assess the propensity of the obtained cardiomyocytes to self-organize into contractile engineered human myocardium (EHM). We identified 4’HC, 4-fluoro-4’-methoxychalcone, and 4-fluoro-4’-hydroxychalcone as similarly effective in cardiac mesoderm induction, but only 4’HC as an effective replacement for BMP4 in the derivation of contractile EHM-forming cardiomyocytes.

Development of pH-activatable fluorescent probes for rapid visualization of metastatic tumours and fluorescence-guided surgeryviatopical spraying

A series of pH-activatable aza-BODIPY-based fluorescent probes were developed for rapid cancer visualization and real-time fluorescence-guided surgery by harnessing topical spraying. These probes exhibited good water-solubility, a tunable pKafrom 5.0 to 7.9, and stable intense NIR emission at ～725 nm under acidic conditions.AzaB5with a pKavalue of 6.7 was able to rapidly and clearly visualize pulmonary and abdominal metastatic tumours including tiny metastases less than 2 mmviatopical spraying, further improving intraoperative fluorescence-guided resection. We believe thatAzaB5is promising as a powerful tool to rapidly delineate a broad range of malignancies and assist surgical tumour resection.