Pyridoxal 5'-phosphate monohydrate Chemical Properties

Melting point:

140-143 °C(lit.)

storage temp. 

2-8°C

solubility 

Acetonitrile (Slightly), DMSO (Slightly)

form 

Crystalline Powder

color 

Pale yellow

Water Solubility 

5 g/L (20 ºC)

Sensitive 

Light Sensitive

Merck 

14,7979

BRN 

234749

Stability:

Air Sensitive, Moisture Sensitive

InChI

InChI=1S/C8H10NO6P.H2O/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);1H2

InChIKey

CEEQUQSGVRRXQI-UHFFFAOYSA-N

SMILES

C1(COP(=O)(O)O)=CN=C(C)C(O)=C1C=O.O

CAS DataBase Reference

41468-25-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

24/25-36-26

WGK Germany 

2

RTECS 

UV1208000

F 

8-10-23

TSCA 

Yes

HS Code 

29333990

MSDS

• Language:English Provider:3-Hydroxy-2-methyl-5-([phosphonooxy]methyl)-4-pyridinecarboxaldehyde
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Pyridoxal 5'-phosphate monohydrate Usage And Synthesis

Chemical Properties

Pyridoxal Phosphate Hydrate occurs as a pale yellow-white to light yellow crystalline powder.
It is slightly soluble in water, and practically insoluble in ethanol (99.5).
It dissolves in dilute hydrochloric acid and in sodium hydroxide TS.
The pH of a solution prepared by dissolving 0.1 g of Pyridoxal Phosphate Hydrate in 200 mL of water is between 3.0 and 3.5.
Pyridoxal Phosphate Hydrate is colored to light red by light.

Uses

Pyridoxal 5-phosphate (PLP) (active form of Vitamin B6) is an enzyme prosthetic group that acts as a coenzyme in transamination, decarboxylation and deamination reactions such as the conversion of dopa into dopamine; of glutamate into GABA; of histidine to histamine. PLP works mechanistically through formation of a Schiff-base.

Application

Pyridoxal 5′-phosphate (PLP), an active form of vitamin B6/ pyridoxine is the coenzyme of amino acid metabolism.
Pyridoxal 5′-phosphate monohydrate has been used:
as a component in the reaction mixture for ornithine decarboxylase (ODC) activity assay
as a standard to quantify the concentration of pyridoxal 5′-phosphate (PLP) in cerebrospinal fluid (CSF) of children
as a dietary supplement to study its effects on the lethal phenotype of mutant flies.

Definition

ChEBI: Pyridoxal 5-phosphate monohydrate is a pyridinecarbaldehyde.

Biosynthesis

Two distinct pathways for Pyridoxal 5′-phosphate (PLP) biosynthesis are known. 1.The 'DXP dependent' pathway is found in Escherichia coli and a few members of the γ subdivision of proteobacteria and has been extensively characterized. In this pathway deoxyxylulose 5-phosphate (DXP) is condensed with 3-hydroxy-1-aminoacetone phosphate to give PNP. PNP is oxidized to PLP by PdxH. The DXP dependent pathway is not widely distributed and is surprisingly complex requiring seven enzymes (GapB, PdxB, PdxF (SerC), PdxA, DXS, PdxJ and PdxH). This pathway was the first discovered and it has been extensively reviewed. 2. The second pathway uses Pdx1 and Pdx2 to catalyze the condensation of d-ribose 5-phosphate (R5P), glutamine and glyceraldehyde 3-phosphate to form PLP. The mechanistic and structural characterization of both pathways is at an advanced stage.

General Description

Pyridoxal 5'-phosphate (PLP, vitamin B6) is an essential cofactor in all living systems. It is one of the most versatile cofactors and participates in transamination, decarboxylation, racemization, Cα-Cβ cleavage and α-β elimination reactions. PLP plays an important role in amino acid and carbohydrate metabolism and has been implicated in singlet oxygen resistance. 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. By inhibiting AGE formation and working as a coenzyme in chemical reactions, pyridoxal 5’-phosphate can support healthy nerve, eye, cardiovascular and kidney function.

Biological Activity

Pyridoxine participates in the production of lipid and neurotransmitters. Pyridoxal 5′-phosphate (PLP) serves as a cofactor to stabilize carbanions at Cα of amino acids. Pyridoxine deficiency results in peripheral neuropathy. Absence of PLP leads to neonatal epileptic encephalopathy. PLP acts as a coenzyme in transamination, decarboxylation and deamination reactions such as the conversion of dopa into dopamine; of glutamate into γ aminobutyric acid (GABA); of histidine to histamine. PLP works mechanistically through formation of a Schiff-base.

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