3685-55-0

Basic information

• Product Name: 2-hydroxymuconic acid
• Synonyms: 2-hydroxymuconic acid
• CAS NO: 3685-55-0
• Molecular Formula: C₆H₆O₅
• Molecular Weight: 0
• Mol File: 3685-55-0.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 332.6°Cat760mmHg
• Flash Point: 169.2°C
• Appearance: /
• Density: 1.559g/cm³
• Vapor Pressure: 2.77E-05mmHg at 25°C
• Refractive Index: 1.595
• CAS DataBase Reference: 2-hydroxymuconic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-hydroxymuconic acid(3685-55-0)
• EPA Substance Registry System: 2-hydroxymuconic acid(3685-55-0)

Safety Data

• Hazardous Substances Data: 3685-55-0(Hazardous Substances Data)

Usage

General Description

2-hydroxymuconic acid is a chemical compound that is a derivative of muconic acid, which is an intermediate in the degradation of aromatic compounds such as benzene and toluene. It is produced in the body as a metabolite of the aromatic amino acid tyrosine, and it can also be found as a byproduct of microbial metabolism in the environment. 2-hydroxymuconic acid has been studied for its potential use as a biomarker for exposure to benzene and other aromatic hydrocarbons, as well as for its role in the formation of harmful reactive oxygen species. Additionally, it has also been investigated for its potential as a building block for the synthesis of polymers and other organic compounds.

InChI:InChI=1/C6H6O5/c7-4(6(10)11)2-1-3-5(8)9/h1-3,8-9H,(H,10,11)/b2-1+

Upstream product

• 783334-77-0 2-hydroxymuconic 6-semialdehyde 

Downstream Products

• 20406-62-6 2-oxopent-4-enoic acid 
• 41453-55-8 4-hydroxy-2-oxopentanoic acid 

Relevant articles and documents

Metabolism of 4-amino-3-hydroxybenzoic acid by Bordetella sp. strain 10d: A different modified meta-cleavage pathway for 2-aminophenols

Bordetella sp. strain 10d metabolizes 4-amino-3-hydroxybenzoic acid via 2-hydroxymuconic 6-semialdehyde. Cell extracts from 4-amino-3-hydroxybenzoate- grown cells showed high NAD+-dependent 2-hydroxymuconic 6-semialdehyde dehydrogenase, 4-oxalocrotonate tautomerase, 4-oxalocrotonate decarboxylase, and 2-oxopent-4-enoate hydratase activities, but no 2-hydroxymuconic 6-semialdehyde hydrolase activity. These enzymes involved in 4-amino-3-hydroxybenzoate metabolism were purified and characterized. When 2-hydroxymuconic 6-semialdehyde was used as substrate in a reaction mixture containing NAD+ and cell extracts from 4-amino-3-hydroxybenzoate-grown cells, 4-oxalocrotonic acid, 2-oxopent-4-enoic acid, and 4-hydroxy-2-oxovaleric acid were identified as intermediates, and pyruvic acid was identified as the final product. A complete pathway for the metabolism of 4-amino-3-hydroxybenzoic acid in strain 10d is proposed. Strain 10d metabolized 2-hydroxymuconic 6-semialdehyde derived from 4-amino-3-hydroxybenzoic acid via a dehydrogenative route, not via a hydrolytic route. This proposed metabolic pathway differs considerably from the modified meta-cleavage pathway of 2-aminophenol and those previously reported for methyl- and chloroderivatives.