76172-68-4

Basic information

• Product Name: 4-METHOXY-2',4',6'-TRIHYDROXYDIHYDROCHALCONE
• Synonyms: PHLORETIN-4-METHYL ETHER;3-(4-methoxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one;1-(2,4,6-Trihydroxyphenyl)-3-(4-methoxyphenyl)-1-propanone;3-(4-Methoxyphenyl)-1-(2,4,6-trihydroxyphenyl)-1-propanone;2',4',6'-TRIHYDROXY-4-METHOXYDIHYDROCHALCONE;4-METHOXY-2',4',6'-TRIHYDROXYDIHYDROCHALCONE
• CAS NO: 76172-68-4
• Molecular Formula: C₁₆H₁₆O₅
• Molecular Weight: 288.3
• EINECS: 278-386-7
• Product Categories: Chalcones
• Mol File: 76172-68-4.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 502°C at 760 mmHg
• Flash Point: 187.5°C
• Appearance: /
• Density: 1.325g/cm³
• Vapor Pressure: 1.06E-10mmHg at 25°C
• Refractive Index: 1.633
• CAS DataBase Reference: 4-METHOXY-2',4',6'-TRIHYDROXYDIHYDROCHALCONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-METHOXY-2',4',6'-TRIHYDROXYDIHYDROCHALCONE(76172-68-4)
• EPA Substance Registry System: 4-METHOXY-2',4',6'-TRIHYDROXYDIHYDROCHALCONE(76172-68-4)

Safety Data

• Hazardous Substances Data: 76172-68-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C16H16O5/c1-21-12-5-2-10(3-6-12)4-7-13(18)16-14(19)8-11(17)9-15(16)20/h2-3,5-6,8-9,17,19-20H,4,7H2,1H3

Upstream product

• 108-73-6 3,5-dihydroxyphenol 
• 137225-57-1 (E)-3-(4-methoxyphenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one 
• 480-43-3 5,7-dihydroxy-2-(4-methoxyphenyl)chroman-4-one 
• 65490-09-7 2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone 
• 123-11-5 4-methoxy-benzaldehyde 
• 18065-05-9 1-[2,4-bis(benzyloxy)-6-hydroxyphenyl]ethanone 
• 128837-25-2 1-[2,4-bis(ethoxymethoxy)-6-hydroxyphenyl]ethan-1-one 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 1929-29-9 3-(4-methoxyphenyl)propanoic acid 

Relevant articles and documents

An Efficient Regioselective Synthesis of 8-Formylhomoisoflavonoids with Neuroprotective Activity by Enhancing Autophagy

6-Formylisoophiopogonone B (7a) and 8-formylophiopogonone B (7b), two natural products isolated fromOphiopogonjaponicus, represent a subgroup of rare 6/8-formyl/methyl-homoisoflavonoid skeletons. Herein we report an efficient method for the synthesis of these formyl/methyl-homoisoflavonoids. The synthesized compounds were evaluated for their neuroprotective effects on the MPP+-induced SH-SY5Y cell injury model and showed marked activity. Exploration of the neuroprotective mechanisms of compound7bled to an increased expression of autophagy marker LC3-II and down-regulation of autophagy substrate p62/SQSTM1. Molecular docking studies showed that7bmay prevent the inhibition of the classic PI3K-AKT-mTOR signaling pathway by interfering with the human HSP90AA1.

Base-catalyzed oxidative dearomatization of multisubstituted phloroglucinols: An easy access to C-glucosyl 3,5,6-trihydroxycyclohexa-2,4-dienone derivatives

An efficient and simple method for the protecting group-free synthesis of C-glucosyl 3,5,6-trihydroxycyclohexa-2,4-dienone has been firstly established. This method is compatible with various functional groups, such as benzyl and phenethyl groups, affording a range of C-glucosyl 3,5,6-trihydroxycyclohexa-2,4-dienone derivatives.

New homoisoflavonoid analogues protect cells by regulating autophagy

As a special group of naturally occurring flavonoids, homoisoflavonoids have been discovered as active components of several traditional Chinese medicines for nourishing heart and mind. In this study, twenty homoisoflavonoid analogues, including different substitution groups on rings A and B, as well as heteroaromatic B ring, were synthesized and evaluated for their cardioprotective and neuroprotective activities. In a H2O2-induced H9c2 cardiomyocytes injury assay, nine homoisoflavonoid analogues showed promising activities in the same level as the positive control, diazoxide. Six cardioprotective compounds with representative structure diversities were then evaluated for their neuroprotective effects on MPP+ induced SH-SY5Y cell injury model. Furthermore, autophagy inducing monodansylcadaverine (MDC) fluorescence staining methods and molecular docking studies indicated the action mechanism of these compounds may involve autophagy regulating via class I PI3K signaling pathway.