2134-91-0

Usage

General Description

5-Carboxyvanillic acid is a chemical compound that belongs to the family of vanillic acids, and it is formed by the addition of a carboxylic acid group to the parent compound vanillic acid. It is a white crystalline solid that is slightly soluble in water and possesses a sweet taste. 5-Carboxyvanillic acid has been identified as a potential biomarker for the diagnosis of various types of cancer, and it has also been studied for its potential antioxidant and anti-inflammatory properties. Additionally, 5-CARBOXYVANILLIC ACID has been investigated for its role in the metabolism of dietary compounds and its potential as a precursor for the synthesis of various pharmaceuticals and bioactive molecules.

InChI:InChI=1/C9H8O6/c1-15-6-3-4(8(11)12)2-5(7(6)10)9(13)14/h2-3,10H,1H3,(H,11,12)(H,13,14)

Upstream product

• 2931-90-0 5-formylvanillin 
• 712-53-8 3-formyl-4-hydroxy-5-methoxybenzoic acid 
• 3507-08-2 3-carboxy-4-hydroxy-5-methoxybenzaldehyde 
• 7647-01-0 hydrogenchloride 
• 83130-34-1 5-cyano-2,3-dimethoxy-benzoic acid 
• 7152-89-8 5-allyl-2-hydroxy-3-methoxy-benzoic acid ethyl ester 
• 38480-94-3 2,3-dimethoxyacetophenone 
• 703-98-0 1-(2-hydroxy-3-methoxyphenyl)ethanone 
• 34809-90-0 3-acetyl-4-hydroxy-3-methoxybenzaldehyde 
• 121-33-5 vanillin 
• 2092-49-1 6,6'-dihydroxy-5,5'-dimethoxy-biphenyl-3,3'-dicarbaldehyde 
• 121-34-6 3-methoxy-4-hydroxybenzoic acid 
• 298-14-6 potassium hydrogencarbonate 
• 87743-10-0 3-((dimethylamino)methyl)-4-hydroxy-5-methoxybenzaldehyde 

Downstream Products

• 50522-16-2 4-hydroxy-5-methoxy-isophthalic acid dimethyl ester 
• 4707-77-1 4,5-dihydroxy-1,3-benzenedisulfonic acid 

Relevant academic research and scientific papers

Selective carboxylation of substituted phenols with engineered Escherichia coli whole-cells

Selective carboxylation of substituted phenols is realized in the presence of bicarbonate under ambient pressure by engineered Escherichia coli whole-cells expressing various hydroxybenzoate decarboxylases, leading to their corresponding ortho-hydroxybenzoates. This process may be further developed as an efficient route to upgrade lignin-derived phenolic compounds as valuable building blocks.

Sphingobacterium sp. T2 Manganese Superoxide Dismutase Catalyzes the Oxidative Demethylation of Polymeric Lignin via Generation of Hydroxyl Radical

Sphingobacterium sp. T2 contains two extracellular manganese superoxide dismutase enzymes which exhibit unprecedented activity for lignin oxidation but via an unknown mechanism. Enzymatic treatment of lignin model compounds gave products whose structures were indicative of aryl-Cα oxidative cleavage and demethylation, as well as alkene dihydroxylation and alcohol oxidation. 18O labeling studies on the SpMnSOD-catalyzed oxidation of lignin model compound guiaiacylglycerol-β-guaiacyl ether indicated that the an oxygen atom inserted by the enzyme is derived from superoxide or peroxide. Analysis of an alkali lignin treated by SpMnSOD1 by quantitative 31P NMR spectroscopy demonstrated 20-40% increases in phenolic and aliphatic OH content, consistent with lignin demethylation and some internal oxidative cleavage reactions. Assay for hydroxyl radical generation using a fluorometric hydroxyphenylfluorescein assay revealed the release of 4.1 molar equivalents of hydroxyl radical by SpMnSOD1. Four amino acid replacements in SpMnSOD1 were investigated, and A31H or Y27H site-directed mutant enzymes were found to show no lignin demethylation activity according to 31P NMR analysis. Structure determination of the A31H and Y27H mutant enzymes reveals the repositioning of an N-terminal protein loop, leading to widening of a solvent channel at the dimer interface, which would provide increased solvent access to the Mn center for hydroxyl radical generation.