42059-48-3

Basic information

• Product Name: 4-ACETYL-3-HYDROXYPHENYL ACETATE
• Synonyms: ACETIC ACID 4-ACETYL-3-HYDROXY-PHENYL ESTER;4-ACETYL-3-HYDROXYPHENYL ACETATE;4'-ACETOXY-2'-HYDROXYACETOPHENONE;4-Acetyl-3-hydroxyphenyl acetate, 95+%
• CAS NO: 42059-48-3
• Molecular Formula: C₁₀H₁₀O₄
• Molecular Weight: 194.18
• Mol File: 42059-48-3.mol
• Article Data: 13

Chemical Properties

• Melting Point: 73,5-74,5°C
• Boiling Point: 331.2 °C at 760 mmHg
• Flash Point: 131.4 °C
• Appearance: /
• Density: 1.236 g/cm³
• Vapor Pressure: 8.2E-05mmHg at 25°C
• Refractive Index: 1.543
• Solubility: soluble in Methanol
• PKA: 9.40±0.10(Predicted)
• CAS DataBase Reference: 4-ACETYL-3-HYDROXYPHENYL ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-ACETYL-3-HYDROXYPHENYL ACETATE(42059-48-3)
• EPA Substance Registry System: 4-ACETYL-3-HYDROXYPHENYL ACETATE(42059-48-3)

Safety Data

• Hazard Codes: Xi:Irritant
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 42059-48-3(Hazardous Substances Data)

Usage

Preparation

Preparation by reaction of acetic anhydride on resaceto-phenone, ? at reflux ? with sodium acetate; ? with pyridine (95%).

Synthesis Reference(s)

Synthetic Communications, 24, p. 1151, 1994 DOI: 10.1080/00397919408011711

InChI:InChI=1/C10H10O4/c1-6(11)9-4-3-8(5-10(9)13)14-7(2)12/h3-5,13H,1-2H3

Upstream product

• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 127-09-3 sodium acetate 
• 108-24-7 acetic anhydride 
• 108-05-4 vinyl acetate 
• 90-33-5 7-hydroxy-4-methyl-chromen-2-one 
• 64-19-7 acetic acid 
• 108-46-3 recorcinol 
• 72712-19-7 2,4-diacetoxy acetophenone 
• 75-36-5 acetyl chloride 

Downstream Products

• 56133-02-9 2-acetyl-5-(benzyloxy)phenyl acetate 
• 493-33-4 1-(4-hydroxy-2-methoxy-phenyl)ethanone 
• 2163-12-4 2,4-diacetylresorcinol 
• 2161-85-5 1-(5-acetyl-2,4-dihydroxyphenyl)-1-ethanone 
• 2896-60-8 4-ethyl-1,3-benzenediol 
• 99186-47-7 4-ethyl resorcinol monoacetate 
• 127265-10-5 4-ethylresorcinol acetate 
• 52751-42-5 2'-acetoxy-4'-hydroxyacetophenone 
• 1201816-77-4 1-cyclohexyl-5-(2-hydroxy-4-methoxybenzoyl)pyridin-2(1H)-one 
• 1201816-79-6 1-butyl-5-(2-hydroxy-4-methoxybenzoyl)pyridin-2(1H)-one 
• 1388221-20-2 1-butyl-5-(2,4-dihydroxybenzoyl)pyridin-2(1H)-one 

Relevant articles and documents

Design, synthesis and QSAR study of 2′-hydroxy-4′-alkoxy chalcone derivatives that exert cytotoxic activity by the mitochondrial apoptotic pathway

Eleven 4′-alkoxy chalcones were synthesized and biologically evaluated for their antiproliferative activity against four human tumor cell lines (PC-3, MCF-7, HF-6, and CaSki). Compounds 3a-3d and 3f were selective against PC-3, with IC50 values ranging from 8.08 to 13.75 μM. In addition, chalcones 3a-3c did not affect the normal fibroblasts BJ cells. The most active and selective compounds were further evaluated for their effect on the progression of cell cycle in PC-3 cells, and chalcones 3a and 3c induced a G2/M phase arrest. Furthermore, it was found that these three chalcones induced the mitochondrial apoptotic pathway by regulating Bax and Bcl-2 transcripts and by increasing caspase 3/7 activation. Otherwise, the QSAR model indicates that the double bond of the α,β-unsaturated carbonyl, as well as the planar structure geometry, are important to the biological activity of the synthetized chalcones. Based on these studies, it was concluded that withdrawing substituents in ring A, decrease the antiproliferative activity. This is related to the possible mechanism of action of these compounds, where a Michael addition needs to take place in order to be a potent anticancer agent.

Method for preparing 2', 4'-resacetophenone-2'-carboxylic ester

The invention relates to the field of small organic molecule synthesis and particularly provides a synthetic process of 2', 4'-resacetophenone-2'-carboxylic ester. The synthetic process comprises the following steps that 1, 2', 4'-resacetophenone serves as a substrate, acyl chloride serves as acylation reagent, and 2', 4'-resacetophenone-4'-carboxylic ester is synthesized; 2, an acid binding agent with the same equivalent is added to the 2', 4'-resacetophenone-2'-carboxylic ester synthesized in step 1, and a reaction is conducted in polar non-protonic solvent at the room temperature; 3, silica gel column chromatography separation and purification are conducted, target components are collected, and the 2', 4'-resacetophenone-2'-carboxylic ester is obtained. By means of the acyl transfer reaction, the 2', 4'-resacetophenone-2'-carboxylic ester which is difficult to construct through common chemical methods can be synthesized, the reaction is high in atom economy, easy and convenient to operate and ideal in yield, and potential industrial application value is achieved.

Inhibition of Alzheimer's BACE-1 by 2,6-dialkyl-4-chromon-3-yl-1,4-dihydropyridine-3,5-dicarboxylates

Alzheimer's disease is the most common cause of dementia in the elderly, and no disease-modifying therapy is yet available for this devastating pathology. Deposition of different physicochemical forms of amyloid-β peptides is a critical phase in the patho