5462-27-1

Basic information

• Product Name: (2,5-diacetyloxy-4-methyl-phenyl) acetate
• Synonyms: (2,5-diacetyloxy-4-methyl-phenyl) acetate
• CAS NO: 5462-27-1
• Molecular Formula: C₁₃H₁₄O₆
• Molecular Weight: 266.2467
• Mol File: 5462-27-1.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 359.6 °C at 760 mmHg
• Flash Point: 157.8 °C
• Appearance: /
• Density: 1.218 g/cm³
• Vapor Pressure: 2.34E-05mmHg at 25°C
• Refractive Index: 1.507
• CAS DataBase Reference: (2,5-diacetyloxy-4-methyl-phenyl) acetate(CAS DataBase Reference)
• NIST Chemistry Reference: (2,5-diacetyloxy-4-methyl-phenyl) acetate(5462-27-1)
• EPA Substance Registry System: (2,5-diacetyloxy-4-methyl-phenyl) acetate(5462-27-1)

Safety Data

• Hazardous Substances Data: 5462-27-1(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Canadian Journal of Chemistry, 45, p. 1975, 1967 DOI: 10.1139/v67-314

InChI:InChI=1/C13H14O6/c1-7-5-12(18-9(3)15)13(19-10(4)16)6-11(7)17-8(2)14/h5-6H,1-4H3

Upstream product

• 108-24-7 acetic anhydride 
• 553-97-9 2-Methyl-1,4-benzoquinone 
• 3131-54-2 4-methylbenzo-1,2-quinone 
• 7664-93-9 sulfuric acid 
• 7601-90-3 perchloric acid 
• 64-19-7 acetic acid 
• 452-86-8 4-methyl-1,2-dihydroxybenzene 

Downstream Products

• 1124-09-0 1,2,4-tri-hydroxy-5-methylbenzene 
• 615-91-8 2-hydroxy-5-methyl-1,4-benzoquinone 

Relevant articles and documents

Oxidative chemistry of the natural antioxidant hydroxytyrosol: Hydrogen peroxide-dependent hydroxylation and hydroxyquinone/o-quinone coupling pathways

Oxidation of the natural antioxidant hydroxytyrosol (1) with peroxidase/H2O2 in phosphate buffer at pH 7.4 led to the formation of two main ethyl acetate-extractable products. These could be isolated by preparative TLC after reduction and acetylation, and were identified as the tetraacetyl derivative of 2-(2,4,5-trihydroxyphenyl)ethanol (3) and the heptaacetyl derivative of the pentahydroxybiphenyl 4 by 2D NMR and MS analysis. Similar oxidation of 4-methylcatechol gave, after the same work-up, the acetylated derivatives of 1,2,4-trihydroxy-5-methylbenzene (5) and the pentahydroxybiphenyl 6. Mechanistic experiments suggested that hydrogen peroxide affects the course of the oxidation of 1 by adding to the first formed o-quinone to give a hydroxyquinone intermediate. This could bring nucleophilic attack to the o-quinone of 1 to give the dimer 4. These results disclose novel oxidative pathways of 4-alkylcatechols and provide an improved chemical basis to enquire into the mechanism of the antioxidant action of 1.