Pyridoxal (HCID 1050)

Overview

Pyridoxal is a pyridinecarbaldehyde that is pyridine-4-carbaldehyde bearing methyl, hydroxy and hydroxymethyl substituents at positions 2, 3 and 5 respectively. The 4-carboxyaldehyde form of vitamin B6, it is converted into pyridoxal phosphate, a coenzyme for the synthesis of amino acids, neurotransmitters, sphingolipids and aminolevulinic acid. It has a role as a cofactor, a mouse metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a human metabolite. It is a member of methylpyridines, a vitamin B6, a monohydroxypyridine, a pyridinecarbaldehyde and a hydroxymethylpyridine. It is a conjugate base of a pyridoxal(1+).

Names & identifiers

Preferred name: Pyridoxal
IUPAC: 3-hydroxy-5-(hydroxymethyl)-2-methylpyridine-4-carbaldehyde
English name: pyridoxal
Molecular formula: C8H9NO3
Molecular weight: 167.16

Names & synonyms

pyridoxal66-72-8Pyridoxaldehyde3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde3-hydroxy-5-(hydroxymethyl)-2-methylpyridine-4-carbaldehydePiridoxalDTXSID40460204-Pyridinecarboxaldehyde, 3-hydroxy-5-(hydroxymethyl)-2-methyl-CHEBI:173103THM379K8A3-hydroxy-5-(hydroxymethyl)-2-methyl-4-pyridinecarboxaldehyde3-Hydroxy-5-(hydroxymethyl)-2-methylpyridine-4-carboxaldehyde

Show more names

PYRIDOXALEPyridoxal Labeled d3Metazachlor Impurity 8(Triflumizole)3-hydroxy-2-methyl-5-methylol-isonicotinaldehyde3-Hydroxy-5-hydroxymethyl-2-methylpyridine-4-carbaldehyde3-Hydroxy-5-(hydroxymethyl)-2-methyl-4-pyridinecarbaldehyde3-(Hydroxymethyl)-5-hydroxy-6-methylpyridine-4-carbaldehyde

DTXCID20260202-methyl-3-hydroxy-4-formyl-5-hydroxymethylpyridineRefChem:177705200-630-8MFCD00464806EINECS 200-630-8NSC 196133-hydroxy-5-(hydroxymethyl)-2-methyl-pyridine-4-carbaldehyde

Database identifiers

CAS: 66-72-8
PubChem CID: 1050
DTXSID: DTXSID4046020
ChEMBL: CHEMBL102970
ChEBI: CHEBI:17310
UNII: 3THM379K8A
EC Number: 200-630-8
Nikkaji: J2.361B

Properties

Computed structural properties

XLogP: 0
Topological polar surface area: 70.4 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 4
Rotatable bonds: 2
Heavy atoms: 12
Formal charge: 0
Complexity: 162

Experimental & physicochemical properties

Chemical ClassesBiological Agents -> Vitamins and Derivatives

DrugsPharmaceuticals -> Listed in ZINC15

LogP-0.82

Solubility500.0 mg/mL

Melting Point165 °C

Vapor Pressure0.00000162 [mmHg]

Physicochemical properties

Melting point: 165 °C · 165 °C
Boiling point: 412.8 · 412.8±40.0 °C(Predicted)
Density: 1.36 · 1.360±0.06 g/cm3(Predicted)
storage temp.: 2 · under inert gas (nitrogen or Argon) at 2-8°C
form: Solid
pka: 4.2 · pKa 4.20 (H2O t = 25 I = 0.1)(Approximate)
color: White to off-white
EWG's Food Scores: 1 · 1
FDA UNII: 3 THM379K8A · 3THM379K8A
EPA Substance Registry System: 4 · 4-Pyridinecarboxaldehyde, 3-hydroxy-5-(hydroxymethyl)-2-methyl- (66-72-8)
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302
Precautionary statements: 264 · P264-P270-P301+P312-P330-P501

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 39 reports by companies from 1 notifications to the ECHA C&L Inventory.

Hazard information

Hazards SummaryCauses rigidity and convulsions in oral and intraperitoneal lethal-dose studies of mice; [RTECS] See Pyridoxine hydrochloride.

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Safety data

Signal word: Warning
Symbol(GHS): GHS07
Hazard statements: H302
Precautionary statements: P264-P270-P301+P312-P330-P501

Chemistry & industry

Pharmacology

Pharmacodynamics · 1 item

Pyridoxal principally in the form of the coenzyme pyridoxal 5'-phosphate, is involved in a wide range of biochemical reactions, including the metabolism of amino acids and glycogen, the synthesis of nucleic acids, hemogloblin, sphingomyelin and other sphingolipids, and the synthesis of the neurotransmitters serotonin, dopamine, norepinephrine and gamma-aminobutyric acid (GABA).

Mechanism of Action · 1 item

Pyridoxal is the precursor to pyridoxal phosphate. Pyridoxal 5'-phosphate is involved in a wide range of biochemical reactions, including the metabolism of amino acids and glycogen, the synthesis of nucleic acids, hemogloblin, sphingomyelin and other sphingolipids, and the synthesis of the neurotransmitters serotonin, dopamine, norepinephrine and gamma-aminobutyric acid (GABA).

MeSH Pharmacological ClassificationA group of water-soluble vitamins, some of which are COENZYMES.

Tissue LocationsErythrocyte

Cellular LocationsCytoplasm

Metabolite Pathways2-Methyl-3-Hydroxybutryl CoA Dehydrogenase Deficiency

Uses & manufacturing

UsesThe 4-carboxyaldehyde form of vitamin B6 that is converted to the coenzyme pyridoxal phosphate; [ChemIDplus]

Applications · 1 item

UsesPyridoxal is a neuroprotectant. Pyridoxal is one of the main forms of vitamin B6. Pyridoxal is phosphorylated by pyridoxal kinase to pyridoxal phosphate (HY-B1744). Pyridoxal is oxidized by the liver to 4-pyridoxic acid (HY-113493) and excreted in the urine. Pyridoxal has shown promise in the study of carpal tunnel syndrome (CTS)[1][2][3].

Upstream & downstream products

Downstream products

Suppliers26 total

毕佳索（上海毕得医药科技股份有限公司）400-6005915 · [email protected]

成都彼样生物科技有限公司18108052721 · [email protected]

北京索莱宝科技有限公司010-50973130 17801761073 · [email protected]

安耐吉化学&3A（安徽泽升科技有限公司）021-58432009 400-005-6266 · [email protected]

韶关市启程生物科技有限公司18122215013 · [email protected]

Additional notes

DefinitionChEBI: A pyridinecarbaldehyde that is pyridine-5-carbaldehyde bearing methyl, hydroxy and hydroxymethyl substituents at positions 2, 3 and 4 respectively.