4-Pyridoxic acid Chemical Properties

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)

pka

0.47±0.25(Predicted)

form 

Solid

color 

Pale Beige to Light Brown

Merck 

13,8071

Stability:

Hygroscopic

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

2

RTECS 

NS1800000

4-Pyridoxic acid Usage And Synthesis

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.

Uses

4-Pyridoxic Acid, a catabolite of vitamin B6 (P991735), is a water-soluble B-group vitamin that can be used as a urinary diagnostic biomarker for determining the nutritional status of these vitamins.

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.

4-Pyridoxic acid(82-82-6)Related Product Information

• 4-Pyridylcarbinol
• Pyridoxine
• 3-METHYL-4-PYRIDINECARBOXYLIC ACID
• 2,5-Dimethylpyridine
• 2-METHYL-4-HYDROXYMETHYLPYRIDINE
• 3-Hydroxy-2-methylpyridine
• 3,4-Lutidine
• 2-FORMYL-5-PICOLINE
• 4-Pyridoxic acid
• 3-HYDROXY-4-METHYLPYRIDINE
• 3-Pyridinemethanol
• 3-Hydroxypyridine
• 2-Methylisonicotinic acid
• 4-Pyridinecarboxaldehyde
• 3-Hydroxypyridine-4-carboxaldehyde
• 3-HYDROXY-5-METHYLPYRIDINE
• Isonicotinic acid
• 3-HYDROXY-4-PYRIDINECARBOXYLIC ACID