ChemicalBook Product Catalog Chemical Reagents Organic reagents Aromatic ketones 2',5'-Dihydroxyacetophenone

2',5'-Dihydroxyacetophenone

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
form Crystals or Crystalline Powder
pka9.86±0.18(Predicted)
color Yellow to yellow-green
Water Solubility insoluble
BRN 637903
InChIKeyWLDWSGZHNBANIO-UHFFFAOYSA-N
LogP1.274 (est)
CAS DataBase Reference490-78-8(CAS DataBase Reference)
NIST Chemistry ReferenceEthanone, 1-(2,5-dihydroxyphenyl)-(490-78-8)
EPA Substance Registry SystemEthanone, 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
ProviderLanguage
2-Acetylhydroquinone English
SigmaAldrich English
ACROS English
ALFA English
2',5'-Dihydroxyacetophenone Usage And Synthesis
Description2',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 Propertiesyellow to yellow-green crystals or
Uses1-(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.
Uses2',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.
PreparationPreparation 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%).


Application2',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.
DefinitionChEBI: 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 Preparation Products And Raw materials
Raw materialsAluminium chloride hexahydrate-->1,4-Diacetoxybenzene
Preparation Products3,6-DIHYDROXYFLAVONE-->6-Hydroxy-4-oxo-4H-1-benzopyran-2-carboxylic acid ethyl ester
2-BROMO-2',4'-DIHYDROXYACETOPHENONE 6,7-DICHLORO-1,4-DIHYDROXYANTHRAQUINONE, 97 2,4,6-dihydroxyacetophenone 2-BROMO-2',5'-DIMETHOXYACETOPHENONE 1,4-DIHYDROXY-2,3-DIMETHYLANTHRAQUINONE ACID GREEN 41 1,2,5,8-TETRAHYDROXYANTHRAQUINONE alpha-Dimethylamino-3',4'-dihydroxyacetophenone,ALPHA-DIMETHYLAMINO-3',4'-DIHYDROXYACETOPHENONE HYDROCHLORIDE 2-Bromoacetophenone 2,3-DIHYDRO-9,10-DIHYDROXY-1,4-ANTHRACENEDIONE DIHYDROXYACETOPHENONE,DIHYDROXYACETOPHENONE,3,4-,3',4'-DIHYDROXYACETOPHENONE,3,4-DIHYDROXYACETOPHENONE,3,4-Dihydroxyacetophenone 3',4'-Dihydroxyacetophenone 4'-(Allyloxy)-2',6'-dihydroxyacetophenone 2-AMINO-3,4-DIHYDROXYACETOPHENONE 2-chloro-2-5-dihydroxyacetophenone 1-(2,4-Bis(benzoyloxy)phenyl)ethanone 5,8-Dihydroxy-1,4-naphthoquinone 6,7-DIMETHOXY-2,2-DIMETHYL-4-CHLOROMANONE PIPERACETAZINE (250 MG)
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