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

• Language:English Provider:2-Acetylhydroquinone
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

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

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.

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.

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%).

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.

Synthesis Reference(s)

The Journal of Organic Chemistry, 18, p. 1709, 1953 DOI: 10.1021/jo50018a014

2',5'-Dihydroxyacetophenone(490-78-8)Related Product Information

• 2',4'-Dichloroacetophenone
• 4'-Hydroxyacetophenone
• 3-Nitroacetophenone
• PIPERACETAZINE (250 MG)
• DIHYDROXYACETOPHENONE,DIHYDROXYACETOPHENONE,3,4-,3',4'-DIHYDROXYACETOPHENONE,3,4-DIHYDROXYACETOPHENONE,3,4-Dihydroxyacetophenone 3',4'-Dihydroxyacetophenone
• 3-Aminoacetophenone
• 4-Nitroacetophenone
• 2-HYDROXYACETOPHENONE
• 2-Bromoacetophenone
• Acetophenone
• 2'-Hydroxyacetophenone
• 3'-Hydroxyacetophenone
• 4'-Bromoacetophenone
• 2'-Hydroxy-5'-methoxyacetophenone
• 5,8-Dihydroxy-1,4-naphthoquinone
• 3',5'-Dihydroxyacetophenone 3,5-Dihydroxyacetophenone,3',5'-DIHYDROXYACETOPHENONE,3,5-DIHYDROXYACETOPHENONE MONOHYDRATE,3,5-DIHYDROXYACETOPHENONE
• 2',6'-Dihydroxyacetophenone
• 2-BROMO-2',5'-DIMETHOXYACETOPHENONE