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Pyridoxal-5'-(dihydrogenphosphat)

(4-Formyl-5-hydroxy-6-methylpyridin-1-ium-3-yl)methyl hydrogen phosphate

HCID 177532046
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Grundinformationen

CAS
54-47-7
Standard-SMILES
Cc1[nH+]cc(COP(=O)([O-])O)c(C=O)c1O
InChIKey
NGVDGCNFYWLIFO-UHFFFAOYSA-N
Summenformel
C8H10NO6P
Durchschnittliche Molmasse
247,14 g/mol
Monoisotopische Masse
247,02457404

Überblick

This is the active form of vitamin B6 serving as a coenzyme for synthesis of amino acids, neurotransmitters (serotonin, norepinephrine), sphingolipids, aminolevulinic acid. During transamination of amino acids, pyridoxal phosphate is transiently converted into pyridoxamine phosphate (pyridoxamine).

Namen und Bezeichner

Bevorzugter Name
(4-Formyl-5-hydroxy-6-methylpyridin-1-ium-3-yl)methyl hydrogen phosphate
IUPAC
(4-formyl-5-hydroxy-6-methylpyridin-1-ium-3-yl)methyl hydrogen phosphate
Lokaler Name
Pyridoxal-5'-(dihydrogenphosphat)
Englischer Name
Pyridoxal phosphate
Summenformel
C8H10NO6P
Molmasse
247.14

Namen und Synonyme

Pyridoxal-5-phosphatP-5-PPYRIDOXINEPHOSPHATEPYRIDOXAL 5'-MONOPHOSPHATEpal-ppiodelPydoxaAderolpydoxalNavisal

Datenbank-Bezeichner

CAS
54-47-7
PubChem CID
177532046
Nikkaji
J3.767.213K

Eigenschaften

Berechnete Struktureigenschaften

XLogP
-1
Polarare Oberfläche (TPSA)
121 Ų
H-Brücken-Donoren
3
H-Brücken-Akzeptoren
6
Frei drehbare Bindungen
4
Schwere Atome
16
Formalladung
0
Komplexität
290

Experimentelle und physikochemische Eigenschaften

Solubility · 2 Einträge

Appreciable

28 mg/mL

Melting Point255 °C
Physical DescriptionSolid

Physikochemische Eigenschaften

Schmelzpunkt
140 · 140-143 °C
Siedepunkt
565.7 · 565.7±60.0 °C(Predicted)
Dichte
1.638 · 1.638±0.06 g/cm3(Predicted)
storage temp.
-20 °C · Inert atmosphere,Store in freezer, under -20°C
Löslichkeit
DMSO (Slightly, Heated), Methanol (Slightly), Water (Slightly)
pka
1.56 · 1.56±0.10(Predicted)
Aggregatzustand
powder
Farbe
Off-white to yellow
Geruch (Odor)
Odorless
Stabilität
Hygroscopic

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

Sicherheitsdaten

F
8-10-23
wgk
3
tsca
TSCA listed
hs_code
29362500
safety_code
22-24/25
Speicherklasse
3 - Flammable liquids
Hazard Classifications
Eye Irrit. 2Flam. Liq. 2

Chemie und Industrie

Pharmakologische Informationen

Pharmacodynamics · 1 Eintrag

The two major forms of vitamin B6 are pyridoxine and pyridoxamine. In the liver they are converted to pyridoxal phosphate (PLP) which is a cofactor in many reactions of amino acid metabolism. PLP also is necessary for the enzymatic reaction governing the release of glucose from glycogen. Pyroluria is one potential cause of vitamin B6 deficiency.

Mechanism of Action · 1 Eintrag

Pyridoxal Phosphate is a coenzyme of many enzymatic reactions. It is the active form of vitamin B6 which comprises three natural organic compounds, pyridoxal, pyridoxamine and pyridoxine. Pyridoxal phosphate acts as a coenzyme in all transamination reactions, and in some oxylation and deamination reactions of amino acids. The aldehyde group of pyridoxal phosphate forms a Schiff-base linkage with the epsilon-amino group of a specific lysine group of the aminotransferase enzyme. The alpha-amino group of the amino acid substrate displaces the epsilon-amino group of the active-site lysine residue. The resulting aldimine becomes deprotonated to become a quinoid intermediate, which in turn accepts a proton at a different position to become a ketimine. Ketimine becomes hydrolyzed so that the amino group remains on the protein complex.

Tissue LocationsErythrocyte
Cellular LocationsMitochondria
Metabolite Pathways2-aminoadipic 2-oxoadipic aciduria

Anwendungen

VerwendenVitamin (enzyme co-factor).

Darstellung · 1 Eintrag

synthetischeSynthesis 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.

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Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
Major Application
clinical testing
Kosmetik-Inhaltsstoffe Funktionen
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 · -1.921 (est)
CAS Datenbank
54 · 54-47-7(CAS DataBase Reference)
EPA chemische Informationen
4 · 4-Pyridinecarboxaldehyde, 3-hydroxy-2-methyl-5-[(phosphonooxy)methyl]- (54-47-7)

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

MangandioxidPyridoxinDiphosphorpentaoxidPyridoxamindihydrochloridSulphosuccinic acid ester3-Pyridinemethanol, 4-[[(4-ethoxyphenyl)imino]methyl]-5-hydroxy-6-methyl-, α-(dihydrogen phosphate) (9CI)Pyridoxaminphosphat5-Hydroxy-4-(hydroxymethyl)-6-methyl-3-pyridylmethyldihydrogenphosphatPyridoxalhydrochlorid2-Amino-2-methylpropionsurePyridoxinhydrochloridDL-Alanin

Nachgelagerte Produkte

3-Hydroxy-5-hydroxymethyl-2,4-dimethylpyridiniumchloridPropanedioic acid, aminomethyl- (9CI)DL-Serindihydrogenphosphat2-Aminoethyldihydrogenphosphat
Ergänzende Hinweise · 1 Eintrag

DefinitionPyridoxal 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.