Pyridoxin

Pyridoxine

HCID 1054CAS 65-23-6

Grundinformationen

Standard-SMILES
Cc1ncc(CO)c(CO)c1O
InChIKey
LXNHXLLTXMVWPM-UHFFFAOYSA-N
Summenformel
C8H11NO3
Durchschnittliche Molmasse
169,18 g/mol
Monoisotopische Masse
169,07389321

Überblick

Pyridoxine is a hydroxymethylpyridine with hydroxymethyl groups at positions 4 and 5, a hydroxy group at position 3 and a methyl group at position 2. The 4-methanol form of vitamin B6, it is converted intoto pyridoxal phosphate which is a coenzyme for 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 and a hydroxymethylpyridine.

Namen und Bezeichner

Bevorzugter Name
Pyridoxine
IUPAC
4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol
Lokaler Name
Pyridoxin
Englischer Name
Pyridoxine
Summenformel
C8H11NO3
Molmasse
169.18

Namen und Synonyme

pyridoxine65-23-6PyridoxolPyridoxin3-hydroxy-4,5-bis(hydroxymethyl)-2-methylpyridineAdermineGravidoxHydoxinPyridoxolum4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol3,4-Pyridinedimethanol, 5-hydroxy-6-methyl-5-Hydroxy-6-methyl-3,4-pyridinedimethanol
Weitere Namen anzeigen
PYRIDOXINE HCLPyridoxine (Vitamin B6)(5-hydroxy-6-Methylpyridine-3,4-diyl)diMethanolPYRIDOXIN HYDROCHLORIDE5-HYDROXY-6-METHYL-3,4-PYRIDINEDIMETHANOL HYDROCHLORIDEB6-HCLPridoxineADEMINE HCL
PiridoxinaPyridoxinumPiridossina3-Hydroxy-4,5-dimethylol-alpha-picolineHexabione2-Methyl-3-hydroxy-4,5-bis(hydroxymethyl)pyridine2-Methyl-3-hydroxy-4,5-di(hydroxymethyl)pyridineVitamin V6

Datenbank-Bezeichner

CAS
65-23-6
PubChem CID
1054
DTXSID
DTXSID4023541
ChEMBL
CHEMBL1364
ChEBI
CHEBI:16709
UNII
KV2JZ1BI6Z
EC Number
200-603-0
Nikkaji
J2.095.349G、J2.356F

Eigenschaften

Berechnete Struktureigenschaften

XLogP
-0,8
Polarare Oberfläche (TPSA)
73,6 Ų
H-Brücken-Donoren
3
H-Brücken-Akzeptoren
4
Frei drehbare Bindungen
2
Schwere Atome
12

Experimentelle und physikochemische Eigenschaften

Chemical ClassesBiological Agents -> Vitamins and Derivatives
Drugs · 2 Einträge

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals

CosmeticsHair conditioning; Antistatic; Skin conditioning
LogP-0.77
Food AdditivesUse unspecified -> FDA Substance added to food
Solubility79 mg/mL

Physikochemische Eigenschaften

Schmelzpunkt
214 · 214-215 °C(lit.)
Siedepunkt
298.46 °C · 298.46°C (rough estimate)
Dichte
1.2435 · 1.2435 (rough estimate)
Brechungsindex
1.51 · 1.5100 (estimate)
storage temp.
2 · Inert atmosphere,2-8°C
Löslichkeit
2 O: · H2O: 0.1 g/mL at 20 °C, clear, colorless

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 5 Einträge

This chemical does not meet GHS hazard criteria for 3.8% (2 of 52) of reports.

Warning

H315 (96.2%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 52 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory Information · 4 Einträge

Chemical: 3,4-Pyridinedimethanol, 5-hydroxy-6-methyl-

3,4-Pyridinedimethanol, 5-hydroxy-6-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 3,4-Pyridinedimethanol, 5-hydroxy-6-methyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 28-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/25773

Pyridoxine: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Hazards Summary · 1 Eintrag

Has been tested in humans to relieve nausea and vomiting during pregnancy; Chronic ingestion of gram quantities can cause ataxia and sensory neuropathy; Has demonstrated testicular toxicity in rats; [REPROTOX] An irritant; May have cumulative adverse effects; [Alfa Aesar MSDS] See Pyridoxine hydrochloride.

Hazard Classes and CategoriesSkin Irrit. 2 (96.2%)

Toxikologische Informationen

TreatmentAdminister charcoal as a slurry. (T273)
Exposure RoutesOral; parenteral (intramuscular). The B vitamins are readily absorbed from the gastrointestinal tract, except in malabsorption syndromes. Pyridoxine is absorbed mainly in the jejunum.
Toxicity Summary · 1 Eintrag

Vitamin B6 is the collective term for a group of three related compounds, pyridoxine (PN), pyridoxal (PL) and pyridoxamine (PM), and their phosphorylated derivatives, pyridoxine 5'-phosphate (PNP), pyridoxal 5'-phosphate (PLP) and pyridoxamine 5'-phosphate (PMP). Although all six of these compounds should technically be referred to as vitamin B6, the term vitamin B6 is commonly used interchangeably with just one of them, pyridoxine. Vitamin B6, principally in its biologically active coenzyme form 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).

Signs and SymptomsToxic effects include convulsions, dyspnea, hypermotility, diarrhea, ataxia and muscle weakness.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury · 5 Einträge

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

pyridoxine

DILI Negative

Intravenous

DOI:10.1016/j.drudis.2019.09.022

Sicherheitsdaten

F
8-10
wgk
3
tsca
TSCA listed
hs_code
29362500
RTECS-Nr.
UV1350000
risk_code
36/37/38

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 4 Einträge

A11HA02

A - Alimentary tract and metabolism

QA - Alimentary tract and metabolism

A11HA02

Protein BindingPyridoxine main active metabolite, pyridoxal 5’-phosphate, is released into the circulation (accounting for at least 60% of circulating vitamin B6) and is highly protein bound, primarily to albumin.
Pharmacodynamics · 1 Eintrag

Vitamin B6 (pyridoxine) is a water-soluble vitamin used in the prophylaxis and treatment of vitamin B6 deficiency and peripheral neuropathy in those receiving isoniazid (isonicotinic acid hydrazide, INH). Vitamin B6 has been found to lower systolic and diastolic blood pressure in a small group of subjects with essential hypertension. Hypertension is another risk factor for atherosclerosis and coronary heart disease. Another study showed pyridoxine hydrochloride to inhibit ADP- or epinephrine-induced platelet aggregation and to lower total cholesterol levels and increase HDL-cholesterol levels, again in a small group of subjects. Vitamin B6, in the form of pyridoxal 5'-phosphate, was found to protect vascular endothelial cells in culture from injury by activated platelets. Endothelial injury and dysfunction are critical initiating events in the pathogenesis of atherosclerosis. Human studies have demonstrated that vitamin B6 deficiency affects cellular and humoral responses of the immune system. Vitamin B6 deficiency results in altered lymphocyte differentiation and maturation, reduced delayed-type hypersensitivity (DTH) responses, impaired antibody production, decreased lymphocyte proliferation and decreased interleukin (IL)-2 production, among other immunologic activities.

Mechanism of Action · 1 Eintrag

Vitamin B6 is the collective term for a group of three related compounds, pyridoxine (PN), pyridoxal (PL) and pyridoxamine (PM), and their phosphorylated derivatives, pyridoxine 5'-phosphate (PNP), pyridoxal 5'-phosphate (PLP) and pyridoxamine 5'-phosphate (PMP). Although all six of these compounds should technically be referred to as vitamin B6, the term vitamin B6 is commonly used interchangeably with just one of them, pyridoxine. Vitamin B6, principally in its biologically active coenzyme form 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).

Biological Half-LifeThe total adult body pool consists of 16 to 25 mg of pyridoxine. Its half-life appears to be 15 to 20 days.
Metabolism/Metabolites · 2 Einträge

Pyridoxine is a prodrug primarily metabolized in the liver. The metabolic scheme for pyridoxine is complex, with formation of primary and secondary metabolites along with interconversion back to pyridoxine. Pyridoxine's major metabolite is 4-pyridoxic acid.

Hepatic. Half Life: 15-20 days

Verwendung und Herstellung

Uses · 3 Einträge

The 4-methanol form of vitamin B6 that is converted to the coenzyme pyridoxal phosphate; [ChemIDplus] Permitted for use as an inert ingredient in non-food pesticide products; [EPA]

Use (kg; approx.) in Germany (2009): >7500

For the treatment of vitamin B6 deficiency and for the prophylaxis of isoniazid-induced peripheral neuropathy.

U.S. Production2023: 661 lb
Consumer UsesOther
Industry UsesOther
Use ClassificationCosmetics -> Hair conditioning; Antistatic; Skin conditioning
General Manufacturing Information · 2 Einträge

Soap, Cleaning Compound, and Toilet Preparation Manufacturing

3,4-Pyridinedimethanol, 5-hydroxy-6-methyl-: ACTIVE

Anwendungen · 2 Einträge

HistoryThe discovery of vitamin was tortuous and legendary. After fat-soluble A and water soluble B were discovered by the year of 1915, the discovery of vitamins entered into a rapid developed period. In separation process of riboflavin by Kuhn and his colleagues, they noticed the unusual relationship between growth-promoting activ ity and fluorescence of extracts. Then they supposed that the existence of no fluorescent substances were very necessary for growth-promoting activity of riboflavin. And they considered this phenomenon as the evidence of a second chem ical existence in the thermostable complex. At last, they named this substance as vitamin B6 .Vitamin B6 is widely distributed in foods, including meats, whole-grain products (especially wheat), vegetables, and nuts. In the cereal grains, vitamin B6 is concen trated primarily in the germ and aleuronic layer. Thus, the refining of grains in the production of flours, which removes much of these fractions, results in substantial reductions of vitamin B6 content. The chemical forms of vitamin B6 tend to vary among foods between plant and animal origin: plant tissues contain most pyridox ine (the free alcohol form, pyridoxol), whereas animal tissues contain most pyri doxal and pyridoxamine.

Verwendenpyridoxine HCL is a skin-conditioning agent that is also widely used in hair products.

Anbieter50 Anbieter

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Ergänzende Hinweise · 1 Eintrag

DefinitionChEBI: A hydroxymethylpyridine with hydroxymethyl groups at positions 4 and 5, a hydroxy group at position 3 and a methyl group at position 2. The 4-methanol form of vitamin B6, it is converted intoto pyridoxal phosphate which is a coenzyme f r synthesis of amino acids, neurotransmitters, sphingolipids and aminolevulinic acid.

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