31405-69-3

Basic information

• Product Name: 2’-hydroxy-5’-(methoxymethoxy)acetophenone
• Synonyms: 2’-hydroxy-5’-(methoxymethoxy)acetophenone
• CAS NO: 31405-69-3
• Molecular Weight: 196.203
• Mol File: 31405-69-3.mol

Chemical Properties

• CAS DataBase Reference: 2’-hydroxy-5’-(methoxymethoxy)acetophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 2’-hydroxy-5’-(methoxymethoxy)acetophenone(31405-69-3)
• EPA Substance Registry System: 2’-hydroxy-5’-(methoxymethoxy)acetophenone(31405-69-3)

Safety Data

• Hazardous Substances Data: 31405-69-3(Hazardous Substances Data)

Upstream product

• 131341-58-7 2,5'-dihydroxy acetophenone 
• 107-30-2 chloromethyl methyl ether 
• 490-78-8 2,5-Dihydroxyacetophenone 

Downstream Products

• 353239-45-9 6,4'-di(methoxymethoxy)flavanone 
• 1134396-10-3 2'-hydroxy-5'-methoxymethoxy-3-bromo-chalcone 
• 1234351-55-3 (Z)-2-(3-methoxybenzylidene)-5-hydroxybenzo[b]furan-3-one 
• 1234351-58-6 (Z)-5-hydroxy-2-(4-methoxybenzylidene)benzofuran-3(2H)-one 
• 1234351-42-8 (Z)-2-(3-chlorobenzylidene)-5-hydroxybenzo[b]furan-3-one 
• 1261274-04-7 (Z)-5-hydroxy-2-(4-fluorobenzylidene)benzofuran-3(2H)-one 
• 1261274-05-8 (Z)-5-hydroxy-2-(4-bromobenzylidene)benzofuran-3(2H)-one 
• 1311272-26-0 (Z)-2-(4-methoxybenzylidene)-5-(methoxymethoxy)benzo[b]furan-3-one 
• 1311272-27-1 (Z)-2-(3-methoxybenzylidene)-5-(methoxymethoxy)benzo[b]furan-3-one 
• 1311272-28-2 (Z)-2-(3,4-dimethoxybenzylidene)-5-(methoxymethoxy)benzo[b]furan-3-one 
• 1311272-29-3 (Z)-2-(4-fluorobenzylidene)-5-(methoxymethoxy)benzo[b]furan-3-one 
• 1311272-30-6 (Z)-2-(4-bromobenzylidene)-5-(methoxymethoxy)benzo[b]furan-3-one 
• 1311272-31-7 (Z)-2-(3-chlorobenzylidene)-5-(methoxymethoxy)benzo[b]furan-3-one 
• 1311272-32-8 (Z)-2-(3-nitrobenzylidene)-5-(methoxymethoxy)benzo[b]furan-3-one 

Relevant articles and documents

Design, synthesis and metabolic regulation effect of farnesoid X receptor (FXR) antagonistic benzoxepin-5-ones

A series of benzoxepin-5-ones were designed and synthesized by the cyclization of chalcones which were previously found as FXR antagonists. The cellular FXR antagonism of benzoxepines was investigated, among which the most potent compound 10l was able to reduce the plasma and hepatic triglyceride and plasma ALT levels in mice.

Extensive structure modification on luteolin-cinnamic acid conjugates leading to BACE1 inhibitors with optimal pharmacological properties

BACE1 inhibitory conjugates derived from two natural products, luteolin (1) and p-hydroxy-cinnamic acid (2), were subjected to systematic structure modifications, including various positions in luteolin segment for conjugation, different linkers (length, bond variation), as well as various substitutions in cinnamic acid segment (various substituents on benzene, and replacement of benzene by heteroaromatics and cycloalkane). Optimal conjugates such as 7c and 7k were chosen on the basis of a series of bioassay data for further investigation.

Design, synthesis, and evaluation of a water soluble C5-monoketone type curcumin analogue as a potent amyloid β aggregation inhibitor

A structure activity relationship study of curcumin analogues for the inhibition of amyloid β aggregation is described. Optimization of the o-phenol and olefin spacer resulted in the identification of the C5-monoketone type curcumin analogue AY1319, which

5′-Chloro-2,2′-dihydroxychalcone and related flavanoids as treatments for prostate cancer

Several flavonoids and their biosynthetic precursor chalcones were designed and synthesized to improve the biological effects of the lead compound 2′-hydroxyflavonone against androgen receptor (AR)-dependent transcriptional stimulation. Newly synthesized chalcones 19 and 26 suppressed AR-dependent transcription as well as DHT-dependent growth stimulation at a low micromolar level. These compounds were also effective against ligand-independent constitutively active mutant AR derived from castration-resistant PCa (CRPC). Compounds 19 and 26 showed broad spectrum antiproliferative activity at 5–10 μM against multiple tumor cell lines including androgen-independent and taxane-resistant prostate cancer as well as a multidrug-resistant subline. Mode of action studies suggested that 19 induced sub-G1 accumulation in PC-3 cells by disrupting the microtubule network without affecting cell cycle progression. Furthermore, the in vivo effectiveness of chalcone 19 was confirmed in a xenograft model antitumor assay. Thus, chalcone 19 has the potential to be a bifunctional lead for treatment of AR-dependent PCa at lower doses as well as AR-independent PCa, including CRPC, at higher doses.

Benzoxy tropylium compound, preparation method of benzoxy tropylium compound, pharmaceutical composition and usages of pharmaceutical composition and benzoxy tropylium compound

The invention discloses a benzoxy tropylium compound shown as a formula I, a preparation method of the benzoxy tropylium compound, a composition containing the compound, and usage of the compound in the preparation of farnesoid ester X receptor antagonists, liver protective agents and medicaments for preventing hyperlipidemia and preventing type 2 diabetes mellitus. The formula I is shown in the description.

Synthesis and biological evaluations of chalcones, flavones and chromenes as farnesoid x receptor (FXR) antagonists

Farnesoid X receptor (FXR), a nuclear receptor mainly distributed in liver and intestine, has been regarded as a potential target for the treatment of various metabolic diseases, cancer and infectious diseases related to liver. Starting from two previously identified chalcone-based FXR antagonists, we tried to increase the activity through the design and synthesis of a library containing chalcones, flavones and chromenes, based on substitution manipulation and conformation (ring closure) restriction strategy. Many chalcones and four chromenes were identified as microM potent FXR antagonists, among which chromene 11c significantly decreased the plasma and hepatic triglyceride level in KKay mice.

Ferrocenyl-appended aurone and flavone: Which possesses higher inhibitory effects on DNA oxidation and radicals?

The aim of the present work was to compare the antioxidative effect of the ferrocenyl-appended aurone with that of ferrocenyl-appended flavone; therefore, nine aurones together with the flavone-type analogues were synthesized by using chalcone as the reactant. The radical-scavenging property was evaluated by reacting with the 2,2β-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS+·), 2,2β-diphenyl-1-picrylhydrazyl radical (DPPH), and galvinoxyl radical, respectively. The cytotoxicity was estimated by inhibiting 2,2β-azobis(2-amidinopropane hydrochloride) (AAPH)-induced oxidation of DNA. It was found that the introduction of the ferrocenyl group remarkably increased the radical-scavenging activities of aurone and flavone. Especially, the ferrocenyl group in flavones can quench radicals even in the absence of the phenolic hydroxyl group, while ferrocenyl-appended aurones can efficiently protect DNA against AAPH-induced oxidation. Therefore, the antioxidative effect was generated by the ferrocenyl group and enhanced by the electron-donating group attaching to the para-position of the ferrocenyl group. Introducing the ferrocenyl group into natural compounds may be a useful strategy for increasing the antioxidative effectiveness.

Synthesis and biological evaluation of new flavonoid fatty acid esters with anti-adipogenic and enhancing glucose consumption activities

Oleoyl Formononetin (OF) has good weight loss activity and hypolipidemic activity, could improve insulin sensitivity and suppress adipogenesis. To acquire better biological activities, three series of flavonoid fatty acid esters were designed and synthesized by optimizing the structure of OF. Their bioactivities were assayed in vitro. Some of these novel compounds could effectively inhibit preadipocyte proliferation and adipogenesis. Moreover, they could enhance glucose consumption in adipocytes notably.

Synthesis, biological evaluation and quantitative structure-activities relationship of flavonoids as vasorelaxant agents

A series of flavonoid derivatives were designed, synthesized. Their vasorelaxant activities were evaluated experimentally against rat aorta rings pretreated with phenylephrine (PE). Among them, 6-hydroxy-8-allyl-4′-chloro-flavanone 8q exhibited the highes

Preparative monohydroxyflavanone syntheses and a protocol for gas chromatography-mass spectrometry analysis of monohydroxyflavanones

We describe a facile efficient, and preparative approach for monohydroxyflavanone syntheses. Using this protocol, a hydroxyl is regio-selectively introduced at one carbon of a flavanone A- or B-ring per synthesis. The seven possible isomers were each synthesized from the corresponding monomethoxymethoxylated 2′-hydroxychalcones in acidic solution. These monohydroxyflavanones were characterized using a gas chromatography-mass spectrometry (GC-MS) system that incorporated a DB-5 capillary column. Ours is the first report of a preparative synthetic method during which a single hydroxyl can be selectively added to a flavanone A- or B-ring at any position. We are also the first to develop a procedure that separates the seven isomers by GC and characterizes the mass spectra of the isomers. Both the synthetic method and the GC-MS conditions may become important tools during future flavanone metabolism and oxidation studies.