Record Information |
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Version | 2.0 |
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Creation Date | 2015-09-08 17:49:57 -0600 |
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Update Date | 2016-09-13 16:35:43 -0600 |
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Secondary Accession Numbers | |
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Identification |
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Name: | 2,3-Dihydroxybenzoic acid |
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Description | 2-pyrocatechuic acid, also known as 2,3-Dihydroxybenzoic acid, is a member of the chemical class known as Hydroxybenzoic Acid Derivatives. These are compounds containing an hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxylic acid. 2,3-Dihydroxybenzoic acid is a colorless solid that occurs naturally, being formed via the shikimate pathway. It is incorporated into various siderophores, which are molecules that strongly complex iron ions for absorption into bacteria. 2,3-DHB consists of a catechol group, which upon deprotonation binds iron centers very strongly, and the carboxylic acid group by which the ring attaches to various scaffolds via amide linkages. A famous high affinity siderophore is enterochelin, which contains three dihydroxybenzoyl substituents linked to the depsitripeptide of serine. (Wikipedia) In E. coli K-12, 2-pyrocatechuic acid is involved in biosynthesis of siderophore group nonribosomal peptides. (KEGG) |
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Structure | |
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Synonyms: | |
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Chemical Formula: | |
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Weight: | Average: Not Available Monoisotopic: Not Available |
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InChI Key: | Not Available |
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InChI: | Not Available |
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CAS number: | Not Available |
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IUPAC Name: | 2-carboxy-6-hydroxybenzen-1-olate |
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Traditional IUPAC Name: | 2-carboxy-6-hydroxybenzenolate |
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SMILES: | Not Available |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Benzene and substituted derivatives |
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Sub Class | Benzoic acids and derivatives |
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Direct Parent | Hydroxybenzoic acid derivatives |
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Alternative Parents | |
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Substituents | - Hydroxybenzoic acid
- Benzoic acid
- Benzoyl
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Phenoxide
- Vinylogous acid
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Hydrocarbon derivative
- Organic oxygen compound
- Organic oxide
- Organooxygen compound
- Organic anion
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Physical Properties |
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State: | Not Available |
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Charge: | -1 |
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Melting point: | Not Available |
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Experimental Properties: | |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations: | Cytoplasm |
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Reactions: | 2,3-dihydroxy-2,3-dihydrobenzoate + NAD > 2,3-Dihydroxybenzoic acid + NADH + Hydrogen ion6 Adenosine triphosphate + 3 L-Serine + 3 2,3-Dihydroxybenzoic acid + 3 L-Serine >6 Adenosine monophosphate + enterobactin +6 Pyrophosphate +3 Hydrogen ionAdenosine triphosphate + 2,3-Dihydroxybenzoic acid > Pyrophosphate + (2,3-Dihydroxybenzoyl)adenylic acidAdenosine triphosphate + 2,3-Dihydroxybenzoic acid <> (2,3-Dihydroxybenzoyl)adenylic acid + Pyrophosphate2,3-Dihydroxybenzoic acid + Adenosine triphosphate + Hydrogen ion > (2,3-Dihydroxybenzoyl)adenylic acid + Pyrophosphate |
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SMPDB Pathways: | Biosynthesis of siderophore group nonribosomal peptides | PW000760 | | Enterobactin Biosynthesis | PW002048 | |
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KEGG Pathways: | - Biosynthesis of siderophore group nonribosomal peptides ec01053
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EcoCyc Pathways: | Not Available |
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Concentrations |
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| Not Available |
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Spectra |
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Spectra: | Not Available |
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References |
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References: | Not Available |
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Synthesis Reference: | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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Links |
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External Links: | |
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