29477-54-1

Basic information

• Product Name: Ethanone,1-(3,4-dihydroxyphenyl)-2-hydroxy-
• Synonyms: Acetophenone,2,3',4'-trihydroxy- (6CI,8CI); 2-Hydroxy-3',4'-dihydroxyacetophenone
• CAS NO: 29477-54-1
• Molecular Formula: C8H8 O4
• Molecular Weight: 168.149
• Mol File: 29477-54-1.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Ethanone,1-(3,4-dihydroxyphenyl)-2-hydroxy-(CAS DataBase Reference)
• NIST Chemistry Reference: Ethanone,1-(3,4-dihydroxyphenyl)-2-hydroxy-(29477-54-1)
• EPA Substance Registry System: Ethanone,1-(3,4-dihydroxyphenyl)-2-hydroxy-(29477-54-1)

Safety Data

• Hazardous Substances Data: 29477-54-1(Hazardous Substances Data)

Usage

General Description

Ethanone,1-(3,4-dihydroxyphenyl)-2-hydroxy- is a chemical compound with the molecular formula C8H8O4. It is also known by its common name, dihydroxyacetophenone. Ethanone,1-(3,4-dihydroxyphenyl)-2-hydroxy- is a derivative of acetophenone and contains two hydroxyl groups on the phenyl ring. It is commonly used in the synthesis of pharmaceuticals and natural products due to its potential pharmacological properties. This chemical has been studied for its antioxidant and anti-inflammatory activities, making it a promising candidate for medicinal applications. Additionally, its structure and properties make it an important intermediate in the production of other organic compounds.

Upstream product

• 76734-99-1 2-(3',4'-dihydroxyphenyl)-3-acetylamino-6-(N-acetyl-2''-aminoethyl)-2,3-dihydro-1,4-benzodioxin 
• 120-80-9 benzene-1,2-diol 
• 122121-92-0 4-(2-hydroxyethyl)cyclohexa-3,5-diene-1,2-dione 
• 10597-60-1 hydroxytyrosol 
• 28822-73-3 3,4-dihydroxyphenylethyleneglycol 
• 99-40-1 2-chloro-3',4'-dihydroxyacetophenone 

Downstream Products

• 10597-60-1 hydroxytyrosol 
• 28822-73-3 3,4-dihydroxyphenylethyleneglycol 

Relevant articles and documents

A three-step, gram-scale synthesis of hydroxytyrosol, hydroxytyrosol acetate, and 3,4-dihydroxyphenylglycol

Hydroxytyrosol and two other polyphenols of olive tree, hydroxytyrosol acetate and 3,4-dihydroxyphenylglycol, are known for a wide range of beneficial activities in human health and prevention from diseases. The inability to isolate high, pure amounts of these natural compounds and the difficult and laborious procedures for the synthesis of them led us to describe herein an efficient, easy, cheap, and scaling up synthetic procedure, from catechol, via microwave irradiation.

The metabolic fate of ortho-quinones derived from catecholamine metabolites

ortho-Quinones are produced in vivo through the oxidation of catecholic substrates by enzymes such as tyrosinase or by transition metalions. Neuromelanin, a dark pigment present in the substantia nigra and locus coeruleus of the brain, is produced from dopamine (DA) and norepinephrine (NE) via an interaction with cysteine, but it also incorporates their alcoholic and acidic metabolites. In this study we examined the metabolic fate of ortho-quinones derived from the catecholamine metabolites, 3,4-dihydroxyphenylethanol (DOPE), 3,4-dihydroxyphenylethylene glycol (DOPEG), 3,4-dihydroxyphenylacetic acid (DOPAC) and 3,4-dihydroxyphenylmandelic acid (DOMA). The oxidation of catecholic substrates by mushroom tyrosinase was followed by UV-visible spectrophotometry. HPLC analysis after reduction with NaBH4 or ascorbic acid enabled measurement of the half-lives of ortho-quinones and the identification of their reaction products. Spectrophotometric examination showed that the ortho-quinones initially formed underwent extensive degradation at pH 6.8. HPLC analysis showed that DOPE-quinone and DOPEG-quinone degraded with half-lives of 15 and 30 min at pH 6.8, respectively, and >100 min at pH 5.3. The major product from DOPE-quinone was DOPEG which was produced through the addition of a water molecule to the quinone methide intermediate. DOPEG-quinone yielded a ketone, 2-oxo-DOPE, through the quinone methide intermediate. DOPAC-quinone and DOMA-quinone degraded immediately with decarboxylation of the ortho-quinone intermediates to form 3,4-dihydroxybenzylalcohol (DHBAlc) and 3,4-dihydroxybenzaldehyde (DHBAld), respectively. DHBAlc-quinone was converted to DHBAld with a half-life of 9 min, while DHBAld-quinone degraded rapidly with a half-life of 3 min. This study confirmed the fact that ortho-quinones from DOPE, DOPEG, DOPAC and DOMA are converted to quinone methide tautomers as common intermediates, through proton rearrangement or decarboxylation. The unstable quinone methides afford stable alcoholic or carbonyl products.

Studies of the sclerotization of insect cuticle. The structure of a dimeric product formed by incubation of N-acetyldopamine with locust cuticle

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