Pyridoxal

Structural formula
General
Common name	Pyridoxal
other names	3-hydroxy-5- (hydroxymethyl) -2-methylpyridine-4-carbaldehyde ( IUPAC ); Pyridoxaldehyde; Vitamin B6 hydrochloride;
Molecular formula	C 8 H 9 NO 3
CAS number	66-72-8; 65-22-5 (hydrochloride);
PubChem	1050
DrugBank	DB00147
Brief description	white solid (hydrochloride)
Occurrence	ubiquitous
physiology
function	Coenzyme in various enzymatic reactions, especially with aldehyde functions
Daily need	1.6-1.8 mg
Consequences in case of deficiency	Diarrhea and vomiting, dermatitis, convulsive states, neurological disorders, epileptic fits
Overdose	> 500 mg d −1
properties
Molar mass	167.16 g mol −1
Physical state	firmly
Melting point	173 (decomposition) ° C
solubility	500 g / L
safety instructions
GHS labeling of hazardous substances Hydrochloride;	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Pyridoxal is a solid, water-soluble chemical compound that is one of the vitamins as a vital compound .

Together with their derivatives pyridoxine and pyridoxamine (with amino group ), which are easily converted into each other in vivo , they form the group vitamin B ₆ . The active form of the vitamin B ₆ group is called pyridoxal phosphate .

Pyridoxal was first synthesized in 1944 by Karl August Folkers , who had also played a key role in the structure elucidation.

Biological importance

Pyridoxal phosphate plays a central role in amino acid metabolism (for example as a coenzyme for DOPA decarboxylase ). A deficiency occurs mainly in combination with an undersupply of other B-series vitamins. Symptoms of deficiency are similar to those of niacin and riboflavin deficiency . Due to the role of the vitamin in the amino acid metabolism, the daily requirement depends on the amount of protein supplied with the food and is therefore individually different. Vitamin B ₆ is found in almost all foods. The acute toxicity is low, chronic toxicity occurs with an amount of more than 500 mg per day taken for months or years.

Some medically relevant bacteria require pyridoxal to grow. These nutritional cravings can mean that some bacteria can only live in close proximity to other strains of bacteria that produce pyridoxal.

Pyridoxal was involved in the Great Oxygen Disaster , which meant the death of numerous anaerobic living things.

Web links

Wikibooks: Biochemistry and Pathobiochemistry: Pyridoxal Phosphate Metabolism - Learning and Teaching Materials

Individual evidence

↑ ^a ^b ^c ^d ^e data sheet Pyridoxal hydrochloride, ≥99% (HPLC) from Sigma-Aldrich , accessed on May 26, 2019 ( PDF ).
↑ Coffen, DL (1978)
^ RE Olson: Karl August Folkers (1906-1997) . In: Journal of Nutrition . 131, No. 9, September 1, 2001, pp. 2227-2230. PMID 11533258 .
^ Hans Konrad Biesalski , Stephan Bischoff, Christoph Puchstein: Nutritional medicine . 4th, completely revised and expanded edition. Georg Thieme, Stuttgart 2010, ISBN 978-3-13-100294-5 , p. 166 f .
↑ KM Kim, T. Qin, YY Jiang, LL Chen, M. Xiong, D. Caetano-Anollés, HY Zhang, G. Caetano-Anollés: Protein domain structure uncovers the origin of aerobic metabolism and the rise of planetary oxygen. In: Structure (London, England: 1993). Volume 20, number 1, January 2012, pp. 67-76, doi: 10.1016 / j.str.2011.11.003 . PMID 22244756 .

[Sigma-1] ↑ ^a ^b ^c ^d ^e data sheet Pyridoxal hydrochloride, ≥99% (HPLC) from Sigma-Aldrich , accessed on May 26, 2019 ( PDF ).

[2] Coffen, DL (1978)

[3] RE Olson: Karl August Folkers (1906-1997) . In: Journal of Nutrition . 131, No. 9, September 1, 2001, pp. 2227-2230. PMID 11533258 .

[4] Hans Konrad Biesalski , Stephan Bischoff, Christoph Puchstein: Nutritional medicine . 4th, completely revised and expanded edition. Georg Thieme, Stuttgart 2010, ISBN 978-3-13-100294-5 , p. 166 f .

[5] KM Kim, T. Qin, YY Jiang, LL Chen, M. Xiong, D. Caetano-Anollés, HY Zhang, G. Caetano-Anollés: Protein domain structure uncovers the origin of aerobic metabolism and the rise of planetary oxygen. In: Structure (London, England: 1993). Volume 20, number 1, January 2012, pp. 67-76, doi: 10.1016 / j.str.2011.11.003 . PMID 22244756 .