2',5'-Dihydroxyacetophenone

2',5'-Dihydroxyacetophenone

Product Introduction

2',5'-Dihydroxyacetophenone Basic information
Product Name: 2',5'-Dihydroxyacetophenone
Synonyms: 1-(2,5-dihydroxyphenyl)-ethanon;1-Acetyl-2,5-dihydroxybenzene;2,5-Dihydroxy-1-acetylbenzene;2',5'-dihydroxy-acetophenon;Acetophenone, 2',5'-dihydroxy-;Acetylhydroquinone;QUINACETOPHENONE;2-Acetylhydroquinone Quinacetophenone
CAS: 490-78-8
MF: C8H8O3
MW: 152.15
EINECS: 207-716-4
Product Categories: Building Blocks;C7 to C8;Carbonyl Compounds;Chemical Synthesis;Ketones;Organic Building Blocks;FINE Chemical & INTERMEDIATES;Aromatic Acetophenones & Derivatives (substituted)
Mol File: 490-78-8.mol
2',5'-Dihydroxyacetophenone Structure
 
2',5'-Dihydroxyacetophenone Chemical Properties
Melting point 204-206 °C(lit.)
Boiling point 234.6°C (rough estimate)
density 1.2143 (rough estimate)
refractive index 1.4447 (estimate)
storage temp. Store below +30°C.
solubility dioxane: 50 mg/mL, clear
pka 9.86±0.18(Predicted)
form Crystals or Crystalline Powder
color Yellow to yellow-green
Water Solubility insoluble
BRN 637903
InChIKey WLDWSGZHNBANIO-UHFFFAOYSA-N
LogP 1.274 (est)
CAS DataBase Reference 490-78-8(CAS DataBase Reference)
NIST Chemistry Reference Ethanone, 1-(2,5-dihydroxyphenyl)-(490-78-8)
EPA Substance Registry System Ethanone, 1-(2,5-dihydroxyphenyl)- (490-78-8)
 
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36
WGK Germany 3
RTECS AM7700000
Hazard Note Irritant
TSCA Yes
HS Code 29145000
 
MSDS Information
Provider Language
2-Acetylhydroquinone English
ACROS English
SigmaAldrich English
ALFA English
 
2',5'-Dihydroxyacetophenone Usage And Synthesis
Description 2',5'-Dihydroxyacetophenone is a natural phenolic compound that is found in many plants. It has been shown to have anti-inflammatory properties through its ability to inhibit the production of pro-inflammatory cytokines, such as tumor necrosis factor alpha and interleukin 1 beta.
Chemical Properties yellow to yellow-green crystals or
Uses 2',5'-Dihydroxyacetophenone is an intermediate used in various synthetic preparations of pharmaceutical goods, 1-(2,5-Dihydroxyphenyl)ethanone was untilized in the synthesis of new flavonoid fatty acid esters with anti-adipogenic and glucose consumption enhancing activities.
Uses 1-(2,5-Dihydroxyphenyl)ethanone is an intermediate used in various synthetic preparations of pharmaceutical goods, 1-(2,5-Dihydroxyphenyl)ethanone was untilized in the synthesis of new flavonoid fatty acid esters with anti-adipogenic and glucose consumption enhancing activities.
Application 2',5'-Dihydroxyacetophenone inhibits the formation of reactive oxygen species and nitric oxide in rat neutrophils. It also has the ability to reduce oxidative stress by scavenging free radicals and inhibiting lipid peroxidation. The underlying mechanism for these effects is not fully understood but may be due to its ability to act as a substrate for matrix-assisted laser desorption ionization (MALDI). This means that it can react with protocatechuic acid molecules that are present in the sample preparation chamber, leading to polymerase chain reaction (PCR) amplification.
Definition ChEBI: 2',5'-Dihydroxyacetophenone is an aromatic ketone.
Preparation Preparation by Fries rearrangement of hydroquinone diacetate,
with aluminium chloride(91%) (76%)(63–77%) (55–60%)
with zinc chloride in refluxing acetic acid (quantitative yield)
with boron trifluoride etherate in benzene at reflux (65%).
Synthesis Reference(s) The Journal of Organic Chemistry, 18, p. 1709, 1953 DOI: 10.1021/jo50018a014
 
2',5'-Dihydroxyacetophenone Preparation Products And Raw materials
Raw materials Aluminium chloride hexahydrate-->1,4-Diacetoxybenzene
Preparation Products 3,6-DIHYDROXYFLAVONE-->6-Hydroxy-4-oxo-4H-1-benzopyran-2-carboxylic acid ethyl ester

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