Pyridoxal hydrochloride Chemical Properties

Melting point:

173 °C (dec.)(lit.)

storage temp. 

2-8°C

solubility 

DMSO (Slightly), Methanol (Slightly), Water (Slightly)

form 

Powder

color 

White

Water Solubility 

Soluble in water and ethanol.

Sensitive 

Hygroscopic

Merck 

14,7978

BRN 

3656994

InChIKey

FCHXJFJNDJXENQ-UHFFFAOYSA-N

CAS DataBase Reference

65-22-5(CAS DataBase Reference)

EPA Substance Registry System

Pyridoxal hydrochloride (65-22-5)

Safety Information

Hazard Codes 

Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

24/25-22-36-26

WGK Germany 

2

RTECS 

UV1225000

F 

8

TSCA 

Yes

HS Code 

29362500

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Pyridoxal hydrochloride Usage And Synthesis

Description

Pyridoxal hydrochloride is a hydrochloride salt formed by combining pyridoxal with hydrochloric acid. It is also a derivative of pyridinium salt and vitamin B6. It has important roles in E. coli metabolites, Saccharomyces cerevisiae metabolites, cofactors, human metabolites and mouse metabolites. It can be used as a calibrator for liquid chromatography of food samples, a component of culture media for lactic acid bacteria (LAB) and foodborne pathogens (FBP) (component of arginine decarboxylase and lysine decarboxylase).

Chemical Properties

White to off-white crystalline powder

Uses

For the labeling of amino acids and their detection in picomolar amounts1; Coenzymes and Cofactors, vol. 1: Vitamin B6, Pyridoxal Phosphate2

Uses

Pyridoxal hydrochloride is used in labeling of amino acids for their detection. It finds application in neurotransmitters, sphingolipids and aminolevulinic acid. It is also used as a nutritional agent. It is also applied in research studies like biochemical, drugs and in media supplements.

Uses

Pyridoxal hydrochloride is one of the three natural forms of vitamin B6, along with pyridoxamine and pyridoxine. All of these forms are converted in the human body into a single biologically active form, Pyridoxal 5-phosphate (P991715). Green plants are a natural source of Pyridoxal, and its deficiency in the human body can lead to serious complications such as epilepsy and seizures.

Definition

ChEBI: Pyridoxal hydrochloride is a hydrochloride obtained by combining pyridoxal with one molar equivalent of hydrochloric acid. It has a role as an Escherichia coli metabolite, a Saccharomyces cerevisiae metabolite, a cofactor, a human metabolite and a mouse metabolite. It is a hydrochloride, a pyridinium salt and a vitamin B6. It contains a pyridoxal(1+).

General Description

Pyridoxal is a heterocyclic compound, weighing 167.2 Da. It is one of the natural forms of vitamin B₆. Pyridoxal is found to be less stable than pyridoxine, hence heating might result in the loss of its action. Pyridoxal has a wide variety of sources and is present in both plants and animals. Pyridoxal serves as an efficient precursor for coenzymes : pyridoxal phosphate and pyridoxamine phosphate.

Biological Activity

Pyridoxal hydrochloride，the 4-carboxyaldehyde form of vitamin b6 which is converted to pyridoxal phosphate which is a coenzyme for synthesis of amino acids, neurotransmitters (serotonin, norepinephrine), sphingolipids, aminolevulinic acid.

Biochem/physiol Actions

Vitamin B6 plays a key role in metabolism of both carbohydrates and amino acids. It is implicated in the synthesis of neurotransmitters like dopamine from L-DOPA, serotonin from 5-HTP, and γaminobutyric acid (GABA) from glutamate. Vitamin B6 plays a major role in maintenance of a healthy nervous system.

Safety Profile

Poison by intramuscular, intravenous, and intraperitoneal routes. Moderately toxic by ingestion and subcutaneous routes. When heated to decomposition it emits very toxic fumes of NOx and HCl. See also ALDEHYDES.

Synthesis

In the 25mL reaction flask with agitator and thermometer, add successively 0.085g (0.5mmol) 2,2,6,6-tetramethyl piperidine-nitrogen-oxyradical, 0.29g (2mmol) cupric bromide, 0.40g (5mmol) pyridine and 2.06g (10mmol) pyridoxinehydrochloride. Add water 5mL, temperature is controlled at 30 DEG C, opens and stirs.Then drip 2.0g (18mmol) 30% hydrogen peroxide, control temperature of reaction at 30～35 DEG C simultaneously.After dropwising, insulation continues to stir 1～2 hour at 30～35 DEG C, and gained reaction solution reaches 99% (liquid-phase condition: chromatographic column is XDB-G8 250 × 4.6 mm 5um through Liquid Detection pyridoxol transformation efficiency.Moving phase is methyl alcohol: buffer=15: 85; Buffer:0.04% sodium pentanesulfonate is adjusted PH to 3 with Glacial acetic acid; Detection wavelength is 284nm), reaction preference is 98%.
In addition, get about 5mL reaction solution and directly go up silicagel column, eluent is methylene dichloride: methyl alcohol=20: 1, obtain final elutriant through gradient elution, and be concentrated into dryly, can obtain white solidpyridoxalhydrochloride, fusing point 164.1-164.8 DEG C, nuclear-magnetism characterizes as follows: 1hNMR (400MHz, DMSO), δ: 8.27 (s, 1H, CHO), 6.63 (d, 1H, CH), 5.00-5.16 (m, 2H, CH2), 2.62 (s, 3H, CH3).
Because pyridoxalhydrochloride is unstable, difficult separation, reaction solution then adds p-ethoxyaniline 1.37g (10mmol), treated yellow Schiff alkali (IX) 2.10g that obtains without separating.The total recovery of two-step reaction is 88%.

Purification Methods

Dissolve it in water and adjust the pH to 6 with NaOH. Set aside overnight to crystallise. The crystals are washed with cold water, dried in a vacuum desiccator over P2O5 and stored in a brown bottle at room temperature. The free base is then converted to the hydrochloride with one equivalent of HCl. [Fleck & Alberty J Phys Chem 66 1678 1962, Beilstein 21/13 V 44.]

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