| Identification | More | [Name]
Pyridoxal 5'-phosphate | [CAS]
41468-25-1 | [Synonyms]
3-HYDROXY-2-METHYL-5-[(PHOSPHONOOXY)-METHYL]-4-PYRIDINECARBOXALDEHYDE, MONOHYDRATE
CODECARBOXYLASE
CODECARBOXYLASE MONOHYDRATE
PLP
pyridoxal 5'-(dihydrogen phosphate)
PYRIDOXAL-5-PHOSPHATE H2O
PYRIDOXAL 5'-PHOSPHATE MONOHYDRATE
PYRIDOXAL 5-PHOSPHATE MONOHYDRATE
PYRIDOXAL-5-PHOSPHORIC ACID H2O
PYRIDOXAL-5-PHOSPHORIC ACID, MONOHYDRATE
Pyridoxal phosphate
PYRIDOXAL PHOSPHATE MONOHYDRATE
3-hydroxy-2-methyl-5-((phosphonooxy)methyl)-4-pyridinecarboxaldehydemonohydr
3-hydroxy-2-methyl-5-((phosphonooxy)methyl)-4-pyridinecarboxaldehydmonoh
3-hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde5-phosphatemonohydrat
phosphopyridoxalmonohydrate
pyridoxal,5-(dihydrogenphosphate),monohydrate
pyridoxal-5-monophosphoricacidestermonohydrate
pyridoxylphosphatemonohydrate
Pyridoxal 5'-phosphate hydrate | [EINECS(EC#)]
200-208-3 | [Molecular Formula]
C8H12NO7P | [MDL Number]
MFCD00149414 | [Molecular Weight]
265.16 | [MOL File]
41468-25-1.mol |
| Chemical Properties | Back Directory | [Appearance]
Pale yellowish white crystalline powder | [Melting point ]
140-143 °C(lit.)
| [storage temp. ]
2-8°C
| [solubility ]
Acetonitrile (Slightly), DMSO (Slightly) | [form ]
Crystalline Powder | [color ]
Pale yellow | [biological source]
synthetic | [Water Solubility ]
5 g/L (20 ºC) | [Sensitive ]
Light Sensitive | [Merck ]
14,7979 | [BRN ]
234749 | [Stability:]
Air Sensitive, Moisture Sensitive | [Major Application]
cell analysis | [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) | [Storage Precautions]
Light sensitive |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H302-H315-H319-H335 | [Precautionary statements ]
P261-P305+P351+P338 | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
2
| [RTECS ]
UV1208000
| [F ]
8-10-23 | [TSCA ]
Yes | [HS Code ]
29333990 | [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [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 B6,41468-25-1) 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. | [Synthesis]
A method for synthesizing pyridoxal phosphate, comprising at least the steps of:
Step 1. oxidizing pyridoxal hydrochloride to pyridoxal hydrochloride using activated manganese dioxide as a catalyst;
Step 2, condensation reaction of said | [Solubility in water]
The solubility of Pyridoxal 5'-phosphate monohydrate in binary mixed solvents of ethanol + water, isopropanol + water and acetone + water in the temperature range of 278.15K to 318.15K at normal atmospheric pressure increased with increasing temperature and molar fraction of water. It is exothermic in organic solvents and binary mixed solvents, where the mixing process is exothermic, whereas it is endothermic in water. |
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