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Pyridoxal phosphate

CAS No.
54-47-7
Chemical Name:
Pyridoxal phosphate
Synonyms
Pyridoxal-5-phosphat;P-5-P;PYRIDOXINEPHOSPHATE;PYRIDOXAL 5'-MONOPHOSPHATE;pal-p;piodel;Pydoxa;Aderol;pydoxal;Navisal
CBNumber:
CB0257385
Molecular Formula:
C8H10NO6P
Molecular Weight:
247.14
MDL Number:
MFCD00006333
MOL File:
54-47-7.mol
MSDS File:
SDS
TDS File:
TDS
Last updated:2026-09-07 16:58:08

Pyridoxal phosphate Properties

Melting point 140-143 °C
Boiling point 565.7±60.0 °C(Predicted)
Density 1.638±0.06 g/cm3(Predicted)
storage temp. Inert atmosphere,Store in freezer, under -20°C
solubility DMSO (Slightly, Heated), Methanol (Slightly), Water (Slightly)
pka 1.56±0.10(Predicted)
form powder
color Off-white to yellow
Stability Hygroscopic
Major Application clinical testing
Cosmetics Ingredients Functions SKIN CONDITIONING
InChI InChI=1S/C8H10NO6P/c1-5-8(11)7(3-10)6(2-9-5)4-15-16(12,13)14/h2-3,11H,4H2,1H3,(H2,12,13,14)
InChIKey NGVDGCNFYWLIFO-UHFFFAOYSA-N
SMILES C1(C)=NC=C(COP(O)(O)=O)C(C=O)=C1O
LogP -1.921 (est)
CAS DataBase Reference 54-47-7(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII F06SGE49M6
NCI Drug Dictionary pyridoxal phosphate
ATC code A11HA06
EPA Substance Registry System 4-Pyridinecarboxaldehyde, 3-hydroxy-2-methyl-5-[(phosphonooxy)methyl]- (54-47-7)
UNSPSC Code 41116107
NACRES NA.24

SAFETY

Risk and Safety Statements

Symbol(GHS)  Exclamation Mark (GHS07)
GHS07
Signal word  Warning
Hazard statements  H315-H319
Precautionary statements  P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313
Safety Statements  22-24/25
WGK Germany  3
8-10-23
TSCA  TSCA listed
HS Code  29362500
Storage Class 3 - Flammable liquids
Hazard Classifications Eye Irrit. 2
Flam. Liq. 2

Pyridoxal phosphate price More Price(60)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Biosynth FP59593 Pyridoxal-5-phosphate 54-47-7 0.025kg $164.91 2026-06-04 Buy
Biosynth FP59593 Pyridoxal-5-phosphate 54-47-7 0.05kg $247.37 2026-06-04 Buy
Biosynth FP59593 Pyridoxal-5-phosphate 54-47-7 0.1kg $412.28 2026-06-04 Buy
Biosynth FP59593 Pyridoxal-5-phosphate 54-47-7 0.25kg $577.19 2026-06-04 Buy
Biosynth FP59593 Pyridoxal-5-phosphate 54-47-7 0.5kg $907.02 2026-06-04 Buy
Product number Packaging Price Buy
FP59593 0.025kg $164.91 Buy
FP59593 0.05kg $247.37 Buy
FP59593 0.1kg $412.28 Buy
FP59593 0.25kg $577.19 Buy
FP59593 0.5kg $907.02 Buy

Pyridoxal phosphate Chemical Properties, Uses, Production

Description

Pyridoxal phosphate is an organic compound formed by the combination of vitamin B6 and phosphoric acid, including pyridoxal, pyridoxamine, and pyridoxine, which exist in the form of phosphate esters in the body. Among them, pyridoxal phosphate and pyridoxamine phosphate can be converted into each other, and they are all active types. Pyridoxal phosphate is the active form of vitamin B6. Several reactions catalyzed by pyridoxal phosphate are: transamination, α-decarboxylation, β-decarboxylation, β-elimination, γ-elimination, racemization and aldol reaction.

Chemical Properties

Pyridoxal phosphate is a white, odourless crystalline powder that turns bright yellow in alkaline solutions. Its aqueous solution remains stable at low temperatures and in the absence of light but decomposes gradually when exposed to light. It is soluble in formic acid, aqueous pyridine, and dilute alkaline solutions, with limited solubility in organic solvents such as water, ethanol, acetone, chloroform, and ether. The oral LD50 in rats is 5900 mg/kg.

Uses

Vitamin (enzyme co-factor).

Definition

Pyridoxal Phosphate also known as PLP, pyridoxal 5'-phosphate or P5P, is the active form of vitamin B6 and a coenzyme for many pyridoxal phosphate (PLP)-dependent enzymes. PLP is involved in numerous enzymatic transamination, decarboxylation and deamination reactions; it is necessary for the synthesis of amino acids and amino acid metabolites, and for the synthesis and/or catabolism of certain neurotransmitters, including the conversion of glutamate into gamma-aminobutyric acid (GABA) and levodopa into dopamine. PLP can be used as a dietary supplement in cases of vitamin B6 deficiency. Reduced levels of PLP in the brain can cause neurological dysfunction.

Preparation

Synthesis of Pyridoxal Phosphate: Pyridoxal phosphate is synthesized from pyridoxine. Initially, pyridoxamine dihydrochloride is reacted with anhydrous phosphoric acid to produce pyridoxamine phosphate. This intermediate is then oxidized with manganese dioxide to yield pyridoxal phosphate.

Biological Functions

Pyridoxal phosphate is the coenzyme form of vitamin B6. In the catalytic reaction, the intramolecular aldehyde group of pyridoxal phosphate is combined with the amino group of α-amino acid to form an aldimine, also known as Schiffbase, and then the amino acid undergoes transamination, decarboxylation or racemization according to the characteristics of different enzymes and proteins. . As a coenzyme of amino acid transaminase, decarboxylase and racemase, it plays a very important role in amino acid metabolism.

Synthesis Reference(s)

Journal of the American Chemical Society, 73, p. 4693, 1951 DOI: 10.1021/ja01154a062

Mechanism of action

Pyridoxal phosphate(PLP) acts as a coenzyme in all transamination reactions, and in certain decarboxylation, deamination, and racemization reactions of amino acids. The aldehyde group of PLP forms a Schiff-base linkage (internal aldimine) with the ε-amino group of a specific lysine group of the aminotransferase enzyme. The α-amino group of the amino acid substrate displaces the ε-amino group of the active-site lysine residue in a process known as transaldimination. The resulting external aldimine can lose a proton, carbon dioxide, or an amino acid sidechain to become a quinoid intermediate, which in turn can act as a nucleophile in several reaction pathways.

Purification Methods

PLP has been purified by dissolving 2g in H2O (10-15mL, in a dialysis bag a third full) and dialysing with gentle stirring against 1L of H2O (+ two drops of toluene) for 15hours in a cold room. The dialysate is evaporated to 80-100mL, then lyophilised. Lemon yellow microscopic needles of the monohydrate remain when all the ice crystals have been removed. The purity is checked by paper chromatography (in EtOH or n-PrOH/NH3) and the spot(s) visualised under UV light after reaction with a spray of p-phenylene diamine, NH3 and molybdate. Solutions stored in a freezer are 2-3% hydrolysed in 3weeks. At 25o, only 4-6% hydrolysis occurs even in N NaOH or HCl, and 2% is hydrolysed at 37o in 1day-but is complete at 100o in 4hours. It is best stored as a dry solid at -20o. In aqueous acid the solution is colourless but is yellow in alkaline solutions. It has UV max at 305nm ( 1100) and 380nm ( 6550) in 0.1 N NaOH; 330nm ( 2450) and 388nm ( 4,900) in 0.05M phosphate buffer pH 7.0 and 295nm ( 6700) in 0.1N HCl. [Peterson et al. Biochemical Preparations 3 34, 119 1953.] The oxime decomposes at 229-230o and is practically insoluble in H2O, EtOH and Et2O. The O-methyloxime decomposes at 212-213o. [Heyl et al. J Am Chem Soc 73 3430 1951.] It has also been purified by column chromatography through Amberlite IRC-50 (H+) [Peterson & Sober J Am Chem Soc 76 169 1954]. [Beilstein 21/13 V 46.]

65-22-5
54-47-7
Synthesis of Pyridoxal phosphate from Pyridoxal hydrochloride
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1Kg/Bag 98.5% up / EP 20 tons Sinoway Industrial co., ltd.
PYRIDOXAL-5-PHOSPHORIC ACID PYRIDOXAL 5'-MONOPHOSPHATE CODECARBOXYLASE 3-hydroxy-2-methyl-5-((phosphonooxy)methyl)-4-pyridinecarboxaldehyd 3-hydroxy-2-methyl-5-[(phosphonooxy)methyl]-4-pyridinecarboxaldehyd apolonb(sub6) apolonb6 biosechs hairoxal hexerminp hiadelon hi-pyridoxin pal-p phosphopyridoxal phosphoridoxalcoenzyme piodel pydoxal pyridoxaldehydephosphate pyridoxalmonophosphate pyridoxalp pyridoxylphosphate pyromijin sechvitan vitahexinp vitazechs Pyridoxal-5-phosphat PYRIDOXAL-5-PHOSPHATE(P) (3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl)methyl phosphate Pyridoxal-5'-Phosphate~99% Pyridoxal-5-Phosphate99.0%Min. VitaminB6phosphate Pyridoxal 5'-(dihydrogen phosphate) Pyridoxal phosphate Codecarboxylase PLP 2-Methyl-3-hydroxy-4-formyl-5-pyridylmethylphosphoric acid 3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde 5-phosphate 4-Pyridinecarboxaldehyde, 3-hydroxy-2-methyl-5-[(phosphonooxy)methyl]- Coenzyme B6 Pydoxa Aderol Navisal Neoaderol Pyridoxal-5-phosphate(P5P) 3-Hydroxy-2-methyl-5-[(phosphonooxy)methyl]-4-pyridinecarboxaldehyde (4-formyl-5-hydroxy-6-methyl-pyridin-3-yl)methoxyphosphonic acid PYRIDOXINEPHOSPHATE Pyridoxal 5-phosphate (methyl-D3) Pyridoxal phosphate(PLP) 5-Pyridoxal phosphate Pyridoxal phosphate USP/EP/BP Pyridoxal phosphate/P5P Pyridoxal phosphate API Pyridoxal5′-phosphate 5 Pyridoxal 5'-phosphate(P5P) Cymoxanil Impurity 1 Pyridoxal 5-Phosphate in Water:Acetonitrile=8:2 Pyridoxal 5′-phosphate solution Pyridoxal phosphate, 98%