65-22-5

Basic information

• Product Name: Pyridoxal hydrochloride
• Synonyms: 3-hydroxy-2-methyl-5-methylol-pyridin-1-ium-4-carbaldehyde chloride;3-hydroxy-5-(hydroxymethyl)-2-methyl-4-pyridin-1-iumcarboxaldehyde chloride;3-hydroxy-5-(hydroxymethyl)-2-methyl-pyridin-1-ium-4-carbaldehyde chloride;3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-1-ium-4-carbaldehyde chloride;3-hydroxy-5-(hydroxymethyl)-2-methylpyridine-4-carbaldehyde hydrochloride;Pyridoxal hydrochloride, >=98%;Pyridoxal hydrochloride(PLC);PYRIDOXAL HCL SIGMA GRADE CRYSTALLIN
• CAS NO: 65-22-5
• Molecular Formula: C₈H₁₀NO₃*Cl
• Molecular Weight: 203.62
• EINECS: 200-602-5
• Product Categories: Biochemistry;Vitamin Derivatives;Vitamins;Aldehydes;Building Blocks;C8;Carbonyl Compounds;Chemical Synthesis;Nutrition Research;Organic Building Blocks;Vitamin B;Vitamin B6;Companion Products and Reagents;Insect Platform;Biochemicals and Reagents;Cell Culture;Fluorescent Labels;Fluorescent Probes;Labels;Other Fluorescent Labels;Particles and Stains;Serum-free Media;and Substrates;Cofactors;Enzymes;Inhibitors;Other Cofactors;Isolabel
• Mol File: 65-22-5.mol
• Article Data: 5

Chemical Properties

• Melting Point: 173 °C (dec.)(lit.)
• Boiling Point: 412.8 °C at 760 mmHg
• Flash Point: 203.5 °C
• Appearance: White/Powder
• Vapor Pressure: 1.48E-07mmHg at 25°C
• Storage Temp.: −20°C
• Solubility: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• Water Solubility: Soluble in water and ethanol.
• Sensitive: Hygroscopic
• Merck: 14,7978
• BRN: 3656994
• CAS DataBase Reference: Pyridoxal hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Pyridoxal hydrochloride(65-22-5)
• EPA Substance Registry System: Pyridoxal hydrochloride(65-22-5)

Safety Data

• Hazard Codes: Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 24/25-22-36-26
• WGK Germany: 2
• RTECS: UV1225000
• F: 8
• TSCA: Yes
• Hazardous Substances Data: 65-22-5(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white crystalline powder

Uses

Different sources of media describe the Uses of 65-22-5 differently. You can refer to the following data:
1. For the labeling of amino acids and their detection in picomolar amounts1; Coenzymes and Cofactors, vol. 1: Vitamin B6, Pyridoxal Phosphate2
2. Pyridoxal 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.
3. 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.

Definition

ChEBI: A hydrochloride obtained by combining pyridoxal with one molar equivalent of hydrochloric acid.

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

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.

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.]

InChI:InChI=1/C8H9NO3.ClH/c1-5-8(12)7(4-11)6(3-10)2-9-5;/h2,4,10,12H,3H2,1H3;1H

Synthetic route

Nα-(3-hydroxy-5-hydroxymethyl-2-methyl-pyridin-4-ylmethylene)-histidine (14029-59-5) → pyridoxal hydrochloride (65-22-5) + L-histidine (71-00-1)

Conditions	Yield
With buffer solution In various solvent(s) at 25℃; Rate constant;

pyridoxal (66-72-8) → pyridoxal hydrochloride (65-22-5)

Conditions	Yield
With hydrogenchloride In water at 20℃; for 72h;

pyridoxal hydrochloride (58-56-0) → pyridoxal hydrochloride (65-22-5)

Conditions	Yield
With hydrogenchloride; manganese(IV) oxide In water at 55℃; for 28h; Temperature;	88 g
With acetic acid; sodium nitrite In water at 5 - 20℃; for 2h; Reagent/catalyst; Solvent;
With hydrogenchloride; manganese(IV) oxide In water at 20℃; for 6h;

pyridoxal hydrochloride (65-22-5) + edaravone (89-25-8) → 1-(5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-6-methyl-1,3-dihydro-furo[3,4-c]pyridin-7-ol (854010-13-2)

Conditions	Yield
With sodium carbonate In water at 10 - 20℃; pH=2.04; Reagent/catalyst; pH-value;	99%
With sodium hydroxide In water at 20℃; for 0.5h;	6.8%
With sodium hydroxide In water at 20 - 30℃; for 2h; pH=6.3 - 12.1; Time;

ethanol (64-17-5) + pyridoxal hydrochloride (65-22-5) → 1-ethoxy-7-hydroxy-6-methyl-1,3-dihydrofuro[3,4-c]pyridin-5-ium chloride (6151-12-8)

Conditions	Yield
at 60℃; for 2h;	99%
at 60℃; for 2h;	99%
for 1.5h; Reflux;	93%

pyridoxal hydrochloride (65-22-5) + isopropyl alcohol (67-63-0) → 7-hydroxy-1-isopropoxy-6-methyl-1,3-dihydrofuro[3,4-c]pyridin-5-ium chloride

Conditions	Yield
at 60℃; for 2h;	99%

methanol (67-56-1) + pyridoxal hydrochloride (65-22-5) → 7-hydroxy-1-methoxy-6-methyl-1,3-dihydrofuro[3,4-c]pyridin-5-ium chloride

Conditions	Yield
for 2h; Reflux;	98%

pyridoxal hydrochloride (65-22-5) + ethylenediamine (107-15-3) → C18H22N4O4

Conditions	Yield
With potassium hydroxide In ethanol for 1h; pH=6.5; Heating;	97%

pyridoxal hydrochloride (65-22-5) + ethylenediamine (107-15-3) → N,N′-ethylenebis-(pyridoxylideneiminato) (88969-07-7)

Conditions	Yield
Stage #1: pyridoxal hydrochloride With triethylamine In methanol Stage #2: ethylenediamine In methanol for 5h;	96.5%

1-benzyl-1H-pyrrole-2,5-dione (1631-26-1) + glycine ethyl ester hydrochloride (5680-79-5) + pyridoxal hydrochloride (65-22-5) → methyl (1R*,3S*,3aR*,6aS*)-5-benzyl-3-(3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl)-4,6-dioxooctahydropyrrolo[3,4-c]pyrrole-1-carboxylate

Conditions	Yield
With silver(I) acetate; triethylamine In ethanol at 70℃; diastereoselective reaction;	96%

pyridoxal hydrochloride (65-22-5) + 4-Nitrophenylene-1,2-diamine (99-56-9) → 4-((E)-(2-amino-4-nitrophenylimino)methyl)-5-(hydroxymethyl)-2-methylpyridin-3-ol

Conditions	Yield
Stage #1: pyridoxal hydrochloride With triethylamine In methanol for 0.166667h; Stage #2: 4-Nitrophenylene-1,2-diamine In methanol for 5h;	96%

aminoguanidine bicarbonate (2582-30-1) + pyridoxal hydrochloride (65-22-5) → {[(3-hydroxy-5-(hydroxymethyl)-2-methyl-4-pyridyl)methylene]amino}guanidine (4362-86-1)

Conditions	Yield
With sodium carbonate decahydrate In water	95%
In water at 20℃; for 30h;
With sodium carbonate decahydrate In water

pyridoxal hydrochloride (65-22-5) + Trp (54-12-6) → pyridoxylidenetryptophan Schiff base (13311-34-7)

Conditions	Yield
In ethanol at 5℃;	94%
In ethanol; water at 25℃; pH=6.7 - 7.0;	75%

pyridoxal hydrochloride (65-22-5) → pyridoxal (66-72-8)

Conditions	Yield
With sodium hydrogencarbonate In water for 1h;	94%
With sodium hydrogencarbonate In water	80%

oxalamic acid hydrazide (515-96-8) + pyridoxal hydrochloride (65-22-5) → 2-[2-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methylene]hydrazinyl]-2-oxoacetamide

Conditions	Yield
With potassium hydroxide In methanol; water for 3h; pH=6.5 - 7;	94%

pyridoxal hydrochloride (65-22-5) + di(n-butyl)tin oxide (818-08-6) + 2-Amino-5-nitrophenol (121-88-0) → C22H29N3O5Sn

Conditions	Yield
With potassium hydroxide In methanol; toluene for 8h; Reflux;	94%

pyridoxal hydrochloride (65-22-5) + di(n-butyl)tin oxide (818-08-6) + 2-hydroxy-5-nitroaniline (99-57-0) → C22H29N3O5Sn

Conditions	Yield
With potassium hydroxide In methanol; toluene for 8h; Reflux;	94%

pyridoxal hydrochloride (65-22-5) + 1,3-dimethyl-5-pyrazolone (2749-59-9) → 4-[bis(5-hydroxy-1,3-dimethyl-1H-pyrazol-4-yl)-methyl]-3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-1-ium chloride

Conditions	Yield
With hydrogenchloride In ethanol; water for 6h; Heating;	94%

pyridoxal hydrochloride (65-22-5) + 5-methyl-2-phenyl-2H-pyrazol-3-ol (942-32-5) → 7-hydroxy-1-(5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-6-methyl-1,3-dihydrofuro[3,4-c]pyridin-5-ium chloride

Conditions	Yield
With hydrogenchloride In ethanol; water for 10h; Reflux;	93%

pyridoxal hydrochloride (65-22-5) + di(n-butyl)tin oxide (818-08-6) + 2-amino-4-methoxyphenol (20734-76-3) → C23H32N2O4Sn

Conditions	Yield
With potassium hydroxide In methanol; toluene for 8h; Reflux;	93%

1-(3-sulfoamido)-1 phenyl-3-methyl-5-pyrazolone (89-29-2) + pyridoxal hydrochloride (65-22-5) → 7-hydroxy-1-[5-hydroxy-3-methyl-1-(3-sulfamoylphenyl)-1H-pyrazol-4-yl]-6-methyl-1,3-dihydrofuro-[3,4-c]pyridin-5-ium chloride

Conditions	Yield
With hydrogenchloride In ethanol; water for 6h; Reflux;	93%

pyridoxal hydrochloride (65-22-5) + 3-methylthio-4-methyl semicarbazide hydroiodide → 3-hydroxy-5-hydroxymethyl-2-methylpyridin-4-ylmethylene(4-methyl-S-methyl)isothiosemicarbazide

Conditions	Yield
In water at 20℃; for 2h;	93%

pyridoxal hydrochloride (65-22-5) + 2-Amino-2-methylpropane-1,3-diol (115-69-5) → 2-[(7-hydroxy-6-methyl-1,3-dihydrofuro[3,4-c]-pyridin-1-yl)amino]-2-methylpropane-1,3-diol hydrochloride

Conditions	Yield
In ethanol at 20℃; for 12h;	93%

pyridoxal hydrochloride (65-22-5) + 4-hydroxybenzoic acid hydrazide (5351-23-5) → C16H17N3O4*ClH

Conditions	Yield
In methanol at 50℃; for 2h; Inert atmosphere;	93%

2-phenylethanol (60-12-8) + pyridoxal hydrochloride (65-22-5) → 7-hydroxy-6-methyl-1-phenethoxy-1,3-dihydrofuro[3,4-c]pyridin-5-ium chloride

Conditions	Yield
at 60℃; for 2h;	92%

pyridoxal hydrochloride (65-22-5) + 4-methyl-1,2-diaminobenzene (496-72-0) → N,N′-dipyridoxyl(4-methyl-1,2-phenylenediamine)

Conditions	Yield
Stage #1: pyridoxal hydrochloride With triethylamine In methanol for 0.166667h; Stage #2: 4-methyl-1,2-diaminobenzene In methanol at 20℃; for 5h;	92%

6-chloro-2-[1-methyl-2-(2-thienylmethylene)hydrazino]quinoxaline-4-oxide (126983-41-3) + pyridoxal hydrochloride (65-22-5) → 6-chloro-2-<2-(3-hydroxy-5-hydroxymethyl-2-methyl-4-pyridylmethylene)-1-methylhydrazino>quinoxaline 4-oxide hydrochloride

Conditions	Yield
In N,N-dimethyl-formamide at 160℃; for 0.5h;	91%

pyridoxal hydrochloride (65-22-5) + 2-amino-5-chlorophenol (28443-50-7) + di(n-butyl)tin oxide (818-08-6) → C22H29ClN2O3Sn

Conditions	Yield
With potassium hydroxide In methanol; toluene for 8h; Reflux;	91%

4-(1-benzylpiperidin-4-yl)thiosemicarbazide + pyridoxal hydrochloride (65-22-5) → C21H27N5O2S*ClH

Conditions	Yield
With acetic acid In ethanol for 2h; Schiff Reaction; Reflux;	91%

C5H12N4O (31106-56-6) + pyridoxal hydrochloride (65-22-5) → 3-hydroxy-5-hydroxymethyl-2-methylpyridin-4-ylmethylene(3-morpholino) semicarbazide

Conditions	Yield
In water at 20℃; for 1h;	91%

pyridoxal hydrochloride (65-22-5) + 4-Aminomethylpiperidine (7144-05-0) → 3-hydroxy-5-(hydroxymethyl)-2-methyl-4-{[(piperidin-4-ylmethyl)imino]methyl}pyridin-1-ium chloride

Conditions	Yield
In ethanol for 8h;	91%

pyridoxal hydrochloride (65-22-5) + 4-aminobenzohydrazide (5351-17-7) → C15H16N4O3

Conditions	Yield
In methanol at 50℃; for 3h; Inert atmosphere;	91%

pyridoxal hydrochloride (65-22-5) + 2-amino-benzenethiol (137-07-5) → 5-Hydroxymethyl-4-{[(E)-2-mercapto-phenylimino]-methyl}-2-methyl-pyridin-3-ol

Conditions	Yield
With potassium hydroxide In methanol	90%
With sodium acetate 1.) EtOH, 5 min, 2.) reflux, 30 min; Yield given. Multistep reaction;
In ethanol Reflux;

Upstream product

• 58-56-0 pyridoxal hydrochloride 
• 66-72-8 pyridoxal 
• 14029-59-5 N^α-(3-hydroxy-5-hydroxymethyl-2-methyl-pyridin-4-ylmethylene)-histidine 

Downstream Products

• 57755-34-7 (E)-5-(hydroxymethyl)-2-methyl-4-((2-phenylhydra zono)methyl)pyridin-3-ol 
• 61-67-6 4-deoxypyridoxine 
• 82-82-6 4-pyridoxic acid 
• 72343-06-7 (E)-N'-((3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl)methylene)benzohydrazide 
• 31539-75-0 5-hydroxymethyl-4-[(4-methoxy-benzylimino)-methyl]-2-methyl-pyridin-3-ol 
• 21665-11-2 4-pyridoxylideneamino-2-trityl-isoxazolidin-3-one 
• 117088-39-8 2-benzyl-4-(3-hydroxy-5-hydroxymethyl-2-methylpyridin-4-yl)-6,8-dioxo-7-phenyl-3,7-diazabicyclo<3.3.0>octane 
• 117088-38-7 2-benzyl-4-(3-hydroxy-5-hydroxymethyl-2-methylpyridin-4-yl)-6,8-dioxo-7-phenyl-3,7-diazabicyclo<3.3.0>octane-2-carboxylic acid 
• 117088-38-7 2-benzyl-4-(3-hydroxy-5-hydroxymethyl-2-methylpyridin-4-yl)-6,8-dioxo-7-phenyl-3,7-diazabicyclo<3.3.0>octane-2-carboxylic acid 
• 117088-35-4 4'-(3-hydroxy-5-hydroxymethyl-2-methylpyridin-4-yl)-6',8'-dioxo-7'-phenylspiro(cyclohexane-1,2'-<3',7'>diazabicyclo-<3.3.0>octane) 
• 117088-34-3 4'-(3-hydroxy-5-hydroxymethyl-2-methylpyridin-4-yl)-6',8'-dioxo-7'-phenylspiro(cyclopentane-1,2'-<3',7'>diazabicyclo<3.3.0>octane) 
• 876515-89-8 N'-[1-(3-Hydroxy-5-hydroxymethyl-2-methyl-pyridin-4-yl)-meth-(E)-ylidene]-hydrazinecarbodithioic acid benzyl ester 
• 122908-64-9 Schiff base pyridoxal-pyridoxamine 
• 122886-29-7 N-pyridoxylidenephenylglycine methyl ester 

Relevant articles and documents

Preparation method of pyridoxal 5-phosphate monohydrate

The invention provides a preparation method of pyridoxal 5-phosphate monohydrate. The preparation method comprises the following steps: 1, first oxidizing pyridoxine hydrochloride to pyridoxal hydrochloride, adding sodium sulfide, then dropwise adding p-ethoxyaniline to the solution, and carrying out a reaction to produce a pyridoxal hydrochloride Schiff base; 2, adding polyphosphoric acid to thepyridoxal hydrochloride Schiff base, performing a stirring reaction, first hydrolyzing polyphosphoric acid and then performing neutralization with an alkali solution to precipitate a large amount of an orange-red solid after the reaction is completed, and filtering and washing the solid to obtain a pyridoxal 5-phosphate Schiff base; and 3, hydrolyzing the pyridoxal 5-phosphate Schiff base with a 2mol/L of alkali solution, adding an organic solvent for extracting and performing liquid separation, adding a strong acid cation exchange resin into the aqueous phase, performing stirring for 1.0 h and then performing vacuum filtration, and performing freeze drying on the filtrate to obtain pyridoxal 5-phosphate monohydrate. The preparation method of pyridoxal 5-phosphate monohydrate is simple inoperation, mild in reaction conditions, relatively high in purity and yield of the final product, and suitable for industrial application, and has relatively good economic benefits.

Method for synthesizing pyridoxal phosphate

The present invention discloses a method for synthesizing pyridoxal phosphate (5'-pyridoxal phosphate). According to the method, pyridoxine hydrochloride is used as a starting material, and is oxidized under mild reaction conditions to obtain a pyridoxal acidic salt, and a phosphate esterification reaction is carried out with a phosphate esterification reagent to obtain pyridoxal phosphate. According to the present invention, the method has advantages of easily-available raw materials, simple route, low toxicity, less side-reaction, easy product separation, easy product characterizing, high yield and the like.

Kinetisch-spektroskopische Analyse komplizierterer Folgereaktionssysteme

For certain consecutive reactions with two linearly independent reaction steps a complete kinetic analysis can be performed by using exclusively absorbance-time measurements.If the first reaction step is of pseudo first order, the concentration of the excess component can be varied in different experiments.By means of the "Formal Integration" method the trace and determinant of the kinetic matrix and both eigenvalues may be calculated for each experiment.The concentration dependence of the trace and the determinant may be used to discriminate between different reaction mechanisms and to calculate all rate constants.For the "Formal Integration" method absorbance-time measurements at two or more different wavelengths are required.At these wavelengths all components of the reaction system may absorb with the exception of the excess component.Molar absorptivities do not need to be known.In contrast to other evaluation methods that use the concentration dependence of the eigenvalues, the new method may be applied even if both eigenvalues are of the same order of magnitude.By means of this method the reaction of pyridoxal with histidine in excess is kinetically analyzed.The reaction mechanism is: . - Keywords: Kinetic analysis / Pseudo first order consecutive reactions / Formal Integration / Pyridoxal / Histidine