2',5'-Dihydroxyacetophenone

Synonym(s):2′,5′-Dihydroxyacetophenone;2,5-Dihydroxyphenyl methyl ketone;2-Acetyl-1,4-dihydroxybenzene;2-Acetylhydroquinone;Acetylquinol

CAS NO.：490-78-8
Empirical Formula: C8H8O3
Molecular Weight: 152.15
MDL number: MFCD00002343
EINECS: 207-716-4
SAFETY DATA SHEET (SDS)
Update Date: 2024-11-05 19:05:58

What is 2',5'-Dihydroxyacetophenone?

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

The Uses of 2',5'-Dihydroxyacetophenone

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.

The Uses of 2',5'-Dihydroxyacetophenone

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.

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%).

What are the applications of 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

Properties of 2',5'-Dihydroxyacetophenone

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
form	Crystals or Crystalline Powder
pka	9.86±0.18(Predicted)
color	Yellow to yellow-green
Water Solubility	insoluble
BRN	637903
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 for 2',5'-Dihydroxyacetophenone

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P280:Wear protective gloves/protective clothing/eye protection/face protection. P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. P405:Store locked up.