| Identification | Back Directory | [Name]
4-PYRIDOXIC ACID | [CAS]
82-82-6 | [Synonyms]
4-Pyridoxic
Pyridoxic Acid
4-PYRIDOXIC ACID
4-pyridoxinicacid
4-pyridoxinsaeure
4-pyridoxylicacid
4-Pyridoxic acid >=98%
4-pyridoxinecarboxylicacid
4-Pyridoxicacidcrystalline
3-hydroxy-2-methyl-5-methylol-isonicotinic acid
3-hydroxy-5-(hydroxymethyl)-2-methyl-isonicotinicaci
3-hydroxy-5-(hydroxymethyl)-2-methylisonicotinicacid
2-METHYL-3-HYDROXY-4-CARBOXY-5-HYDROXYMETHYLPYRIDINE
3-hydroxy-5-(hydroxymethyl)-2-methyl-4-pyridinecarboxylicaci
3-hydroxy-5-(hydroxymethyl)-2-methyl-4-pyridinecarboxylicacid
2-Methyl-3-hydroxy-5-(hydroxymethyl)pyridine-4-carboxylic acid
3-hydroxy-5-(hydroxymethyl)-2-methyl-pyridine-4-carboxylic acid
4-Pyridinecarboxylic acid, 3-hydroxy-5-(hydroxymethyl)-2-methyl-
2-Methyl-3-hydroxy-4-carboxy-5-hydroxymethylpyridine, 3-Hydroxy-5-(hydroxymethyl)-2-methyl-4-pyridinecarboxylic acid | [EINECS(EC#)]
201-440-8 | [Molecular Formula]
C8H9NO4 | [MDL Number]
MFCD00006334 | [MOL File]
82-82-6.mol | [Molecular Weight]
183.16 |
| Chemical Properties | Back Directory | [Melting point ]
258-261 °C (dec.) (lit.) | [Boiling point ]
584.5±50.0 °C(Predicted) | [density ]
1.480±0.06 g/cm3(Predicted) | [storage temp. ]
-20°C | [solubility ]
Aqueous Base (Slightly), Water (Very Slightly) | [form ]
Solid | [pka]
0.47±0.25(Predicted) | [color ]
Pale Beige to Light Brown | [Merck ]
13,8071 | [Stability:]
Hygroscopic |
| Questions And Answer | Back Directory | [Description]
4-pyridoxic acid is a methylpyridine that is 2-methylpyridine substituted by a hydroxy group at C-3, a carboxy group at C-4, and a hydroxymethyl group at C-5. It is the catabolic product of vitamin B6 and is excreted in the urine. It has a role as a human metabolite and a mouse metabolite. It is a member of methylpyridines, a hydroxymethylpyridine, a monohydroxypyridine and a vitamin B6. It derives from an isonicotinic acid. It is a conjugate acid of a 4-pyridoxate.
https://pubchem.ncbi.nlm.nih.gov/compound/4-Pyridoxic-acid | [Biotechnological Production]
4-Pyridoxic acid is an inactive metabolite of pyridoxine.It is formed from pyridoxine via pyridoxal 5'-phosphate and pyridoxal intermediates by pyridoxine kinase or pyridoxamine phosphate oxidase, as well as pyridoxine-5'-phosphate oxidase, aldehyde dehydrogenase, or aldehyde oxidase.
4-Pyridoxic acid is the catabolic product of vitamin B6 (also known as pyridoxine, pyridoxal and pyradoxamine) which is excreted in the urine. Urinary levels of 4-pyridoxic acid are lower in females than in males and will be reduced in persons with riboflavin deficiency. 4-Pyridoxic acid is formed by the action of aldehyde oxidase I (an endogenous enzyme) and by microbial enzymes (pyridoxal 4-dehydrogenase), an NAD-dependent aldehyde dehydrogenase. 4-pyridoxic acid can be further broken down by the gut microflora via 4-pyridoxic acid dehydrogenase. This enzyme catalyzes the four electron oxidation of 4-pyridoxic acid to 3-hydroxy-2-methylpyridine-4,5-dicarboxylate, using nicotinamide adenine dinucleotide as a cofactor. | [Uses]
4-Pyridoxic acid is a catabolite of vitamin B6. It has been used as a standard in the clinical spectrometric analysis of metabolites. |
| Hazard Information | Back Directory | [Definition]
ChEBI: 4-pyridoxic acid is a methylpyridine that is 2-methylpyridine substituted by a hydroxy group at C-3, a carboxy group at C-4, and a hydroxymethyl group at C-5. It is the catabolic product of vitamin B6 and is excreted in the urine. It has a role as a mouse metabolite and a human urinary metabolite. It is a member of methylpyridines, a hydroxymethylpyridine, a monohydroxypyridine and a vitamin B6. It is functionally related to an isonicotinic acid. It is a conjugate acid of a 4-pyridoxate. | [Synthesis Reference(s)]
Journal of Heterocyclic Chemistry, 4, p. 625, 1967 DOI: 10.1002/jhet.5570040427 | [Enzyme inhibitor]
This oxidized derivative (FW = 171.15 g/mol) of pyridoxal is the chief catabolic product of pyridoxine, pyridoxal, and pyridoxamine degradation; it can be isolated from human urine. The carboxyl group has a pKa value of 5.50 while the phenolic OH has a value of 9.75. 4-Pyridoxic acid has a blue fluorescence which is maximal between pH 3 and 4. Heating 4-pyridoxic acid in 0.5 N acid will convert the metabolite to its lactone, which has an even stronger fluorescence. Target(s): dextransucrase; glucose dehydrogenase; pyridoxal dehydrogenase; and pyridoxaminephosphate oxidase. |
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