Pyridoxine

Numéro de catalogue: B162805

Numéro CAS: 65-23-6

Poids moléculaire: 169.18 g/mol

Clé InChI: LXNHXLLTXMVWPM-UHFFFAOYSA-N

Attention: Uniquement pour un usage de recherche. Non destiné à un usage humain ou vétérinaire.

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Vue d'ensemble

1. Description

7. Propriétés

2. Applications de recherche scientifique

8. Synthesis routes and methods I

3. Méthodes de préparation

9. Synthesis routes and methods II

4. Analyse des réactions chimiques

10. Retrosynthesis analysis

5. Mécanisme d'action

11. Q & A

6. Comparaison avec des composés similaires

12. Avertissement

Description

La pyridoxine, communément appelée vitamine B6, est une vitamine hydrosoluble qui joue un rôle crucial dans diverses fonctions biologiques. Elle se trouve naturellement dans de nombreux aliments et est également disponible sous forme de complément alimentaire. La this compound est essentielle au métabolisme des acides aminés, des glucides et des lipides, et elle soutient la santé du cerveau, la fonction immunitaire et la synthèse des neurotransmetteurs .

Applications De Recherche Scientifique

Pyridoxine has a wide range of scientific research applications:

Chemistry: this compound and its derivatives are used as starting materials for the synthesis of various compounds with potential pharmacological activities.

Biology: this compound is essential for the metabolism of amino acids, carbohydrates, and lipids, and it plays a role in the synthesis of neurotransmitters.

Medicine: this compound is used to treat and prevent vitamin B6 deficiency, sideroblastic anemia, this compound-dependent epilepsy, and certain metabolic disorders.

Industry: this compound is used in the production of fortified foods and dietary supplements.

Méthodes De Préparation

Voies de synthèse et conditions réactionnelles : La pyridoxine peut être synthétisée par différentes méthodes. Une approche courante implique la condensation du cyanoacétamide avec des composés 1,3-dicarbonylés. Une autre méthode utilise la condensation de dérivés de 1,3-oxazole avec des diénophiles, suivie d’une hydrogénation catalytique . Ces méthodes se caractérisent par des rendements élevés et des conditions réactionnelles douces.

Méthodes de production industrielle : La production industrielle de la this compound implique généralement la méthode « oxazole », qui est un processus en deux étapes. La première étape implique la condensation diénique pour former des composés intermédiaires, qui sont ensuite convertis en this compound par hydrogénation catalytique . Cette méthode est largement utilisée en raison de son efficacité et de son coût-efficacité.

Analyse Des Réactions Chimiques

Types de réactions : La pyridoxine subit diverses réactions chimiques, notamment l’oxydation, la réduction et la substitution. Elle peut être oxydée sélectivement pour former du pyridoxal ou du chlorhydrate de pyridoxal en utilisant un système d’oxydation catalytique .

Réactifs et conditions courants : Les réactifs courants utilisés dans l’oxydation de la this compound comprennent les sources d’oxygène, les catalyseurs, les sels inorganiques et les ligands d’amine. Les réactions sont généralement effectuées dans l’eau comme solvant dans des conditions douces .

Produits principaux : Les produits principaux formés à partir de l’oxydation de la this compound sont le pyridoxal et le chlorhydrate de pyridoxal, qui sont des intermédiaires clés dans la synthèse du phosphate de pyridoxal 5′, la forme coenzyme active de la vitamine B6 .

4. Applications de la recherche scientifique

La this compound a un large éventail d’applications de recherche scientifique :

Chimie : La this compound et ses dérivés sont utilisés comme matières premières pour la synthèse de divers composés ayant des activités pharmacologiques potentielles.

Biologie : La this compound est essentielle au métabolisme des acides aminés, des glucides et des lipides, et elle joue un rôle dans la synthèse des neurotransmetteurs.

Médecine : La this compound est utilisée pour traiter et prévenir la carence en vitamine B6, l’anémie sidéroblastique, l’épilepsie dépendante de la this compound et certains troubles métaboliques.

Industrie : La this compound est utilisée dans la production d’aliments enrichis et de compléments alimentaires.

Mécanisme D'action

La pyridoxine est convertie en phosphate de pyridoxal 5′ dans l’organisme, qui agit comme coenzyme dans diverses réactions biochimiques. Elle est impliquée dans le métabolisme des acides aminés, du glycogène et des lipides, et elle aide à la synthèse des neurotransmetteurs tels que la sérotonine, la dopamine, la norépinéphrine et l’acide gamma-aminobutyrique (GABA). Le phosphate de pyridoxal 5′ joue également un rôle dans la synthèse de l’hémoglobine et des sphingolipides .

Comparaison Avec Des Composés Similaires

La pyridoxine fait partie du groupe de la vitamine B6, qui comprend le pyridoxal et la pyridoxamine, ainsi que leurs dérivés phosphorylés. Ces composés sont chimiquement similaires et peuvent être interconvertis dans les systèmes biologiques . Le phosphate de pyridoxal 5′ possède la plus grande activité biologique parmi ces composés, mais toutes les formes sont essentielles à diverses réactions enzymatiques .

Composés similaires :

Pyridoxal
Pyridoxamine
Phosphate de this compound 5′
Phosphate de pyridoxal 5′
Phosphate de pyridoxamine 5′

La this compound est unique par sa stabilité et est la forme la plus couramment utilisée dans les compléments alimentaires .

Propriétés

IUPAC Name	4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

InChI	InChI=1S/C8H11NO3/c1-5-8(12)7(4-11)6(3-10)2-9-5/h2,10-12H,3-4H2,1H3	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

InChI Key	LXNHXLLTXMVWPM-UHFFFAOYSA-N	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Canonical SMILES	CC1=NC=C(C(=C1O)CO)CO	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Molecular Formula	C8H11NO3	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Related CAS	58-56-0 (hydrochloride)	Source
Record name	Pyridoxine [INN:BAN]
Source	ChemIDplus
URL	https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0000065236
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DSSTOX Substance ID	DTXSID4023541	Source
Record name	Pyridoxine
Source	EPA DSSTox
URL	https://comptox.epa.gov/dashboard/DTXSID4023541
Description	DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology.

Molecular Weight	169.18 g/mol	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Physical Description	White powder; [Alfa Aesar MSDS], Solid	Source
Record name	Pyridoxine
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Record name	Pyridoxine
Source	Human Metabolome Database (HMDB)
URL	http://www.hmdb.ca/metabolites/HMDB0000239
Description	The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body.
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Solubility	79 mg/mL	Source
Record name	Pyridoxine
Source	DrugBank
URL	https://www.drugbank.ca/drugs/DB00165
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Record name	Pyridoxine
Source	Human Metabolome Database (HMDB)
URL	http://www.hmdb.ca/metabolites/HMDB0000239
Description	The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body.
Explanation	HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.

Vapor Pressure	0.00000028 [mmHg]	Source
Record name	Pyridoxine
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Mechanism of Action	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).	Source
Record name	Pyridoxine
Source	DrugBank
URL	https://www.drugbank.ca/drugs/DB00165
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CAS No.	65-23-6	Source
Record name	Pyridoxine
Source	CAS Common Chemistry
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Record name	Pyridoxine [INN:BAN]
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Record name	Pyridoxine
Source	DrugBank
URL	https://www.drugbank.ca/drugs/DB00165
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Record name	pyridoxine
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Record name	3,4-Pyridinedimethanol, 5-hydroxy-6-methyl-
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Record name	Pyridoxine
Source	EPA DSSTox
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Record name	Pyridoxine
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Record name	PYRIDOXINE
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Record name	Pyridoxine
Source	Human Metabolome Database (HMDB)
URL	http://www.hmdb.ca/metabolites/HMDB0000239
Description	The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body.
Explanation	HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.

Melting Point	159-162 °C, 159 - 162 °C	Source
Record name	Pyridoxine
Source	DrugBank
URL	https://www.drugbank.ca/drugs/DB00165
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Record name	Pyridoxine
Source	Human Metabolome Database (HMDB)
URL	http://www.hmdb.ca/metabolites/HMDB0000239
Description	The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body.
Explanation	HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.

Synthesis routes and methods I

Procedure details

In a second alternative and preferred workup, the reaction mixture (following complete conversion to compound (C)) is cooled to 20° C. and diluted with water (approximately 2.80 L of water for every 1 kg of starting pyridoxine HCl). After phase separation the organic phase is washed with water. The combined aqueous phases are reextracted twice with TBME. The combined TBME phases are washed once with saturated NaHCO3-solution and once with diluted brine. The MTBE-product solution is concentrated to a concentration of about 50% and stored at room temperature until it is further converted. If this second alternative workup is used, the volume of MTBE in the synthetic step is preferably reduced by about 26%.

[Compound]

Name

compound ( C )

Quantity

0 (± 1) mol

Type

reactant

Reaction Step One

Name

pyridoxine HCl

Quantity

1 kg

Type

reactant

Reaction Step Two

Name

water

Quantity

0 (± 1) mol

Type

solvent

Reaction Step Two

Name

water

Quantity

2.8 L

Type

solvent

Reaction Step Two

Name

Pyridoxine

Details

Synthesis routes and methods II

Procedure details

In a similar manner as described in Example 3, S. meliloti PY-C341K1 was cultured in a flask containing LBMCG containing 10 μg/ml of Tc for 16 hours at 30° C., and the cell suspension of the strain was prepared. A tube containing 5 ml of the reaction mixtures composed of 0, 30, and 50 μg/ml of NTG and 1.6×109 cells per ml in 50 mM Tris-HCl buffer (pH 8.0) was incubated with a reciprocal shaking (275 rpm) for 30 min at 30° C. The cells of each reaction mixture were washed twice with sterile saline and suspended in saline. 100 μl of the cell suspension was spread onto agar plates containing LBMCG containing 10 μg/ml of Tc, and then the plates were incubated for 2-3 days at 30° C. The cells grown on the plates were recovered by suspending in sterile saline. After centrifugation of the suspension, the cell suspension was diluted to give a turbidity of OD600=1.6, and finally to 10−5. Each 100 μl of the diluents was spread onto five agar plates containing LBMCG containing 10 μg/ml of Tc and 0, 0.125, 0.15, or 0.175% glycine because 0.15% glycine completely inhibited the growth of S. meliloti PY-C341K1 on LBMCG plate, and then the plates were incubated for 4 days at 30° C. Ten colonies treated with 50 μg/ml of NTG grown on plates LBMCG containing 10 μg/ml of Tc and 0.175% glycine were picked up on LBMCG agar containing 10 μg/ml of Tc. After incubation for 2 days at 30° C., the productivity of vitamin B6 in ten colonies together with the parent strain (S. meliloti PY-C341K1) was examined by flask fermentation. One loopful cells was inoculated to tubes containing 8 ml of SM medium, and then the tubes were shaken on a reciprocal shaker (275 rpm) at 30° C. After shaking for 19 hours, each 4 ml of culture broth was transferred to a 500-ml flask with two baffles containing 200 ml of PM medium modified to 0.175% NH4Cl, and shaken on a rotary shaker (180 rpm) at 30° C. After shaking for 4 days, sterile solution of urea was added to the each flask at 0.125%, and the shaking were further continued for 3 days. The contents of vitamin B6 in the supernatant of 7-day culture broth were quantified by HPLC method as described in Example 3. As a result, S. meliloti PY-EGC1 produced 362 mg of pyridoxol per liter and was about 2.11 times higher than strain PY-341K1 (the parent).

[Compound]

Name

reaction

Quantity

5 mL

Type

reactant

Reaction Step One

Name

glycine

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Two

Name

glycine

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Two

Name

glycine

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Three

Name

vitamin B6

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Four

Name

NH4Cl

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Five

Name

urea

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Six

Name

vitamin B6

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Seven

Name

Tris-HCl

Quantity

0 (± 1) mol

Type

solvent

Reaction Step Eight

Name

pyridoxol

Details

Retrosynthesis Analysis

AI-Powered Synthesis Planning: Our tool employs the Template_relevance Pistachio, Template_relevance Bkms_metabolic, Template_relevance Pistachio_ringbreaker, Template_relevance Reaxys, Template_relevance Reaxys_biocatalysis model, leveraging a vast database of chemical reactions to predict feasible synthetic routes.

One-Step Synthesis Focus: Specifically designed for one-step synthesis, it provides concise and direct routes for your target compounds, streamlining the synthesis process.

Accurate Predictions: Utilizing the extensive PISTACHIO, BKMS_METABOLIC, PISTACHIO_RINGBREAKER, REAXYS, REAXYS_BIOCATALYSIS database, our tool offers high-accuracy predictions, reflecting the latest in chemical research and data.

Strategy Settings

Precursor scoring	Relevance Heuristic
Min. plausibility	0.01
Model	Template_relevance
Template Set	Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis
Top-N result to add to graph	6

Feasible Synthetic Routes

Reactant of Route 1

Pyridoxine

Reactant of Route 2

Pyridoxine

Reactant of Route 3

Pyridoxine

Reactant of Route 4

Pyridoxine

Reactant of Route 5

Pyridoxine

Reactant of Route 6

Pyridoxine

Customer

Q & A

ANone: Pyridoxine is a precursor to pyridoxal 5'-phosphate (PLP), the active form of vitamin B6. PLP functions as a crucial coenzyme for over 100 enzymes involved in various metabolic pathways. [] This includes the metabolism of amino acids, carbohydrates, lipids, neurotransmitters, and heme. [, , ]

ANone: this compound, through its conversion to PLP, plays a vital role in the biosynthesis of several neurotransmitters, including serotonin, dopamine, gamma-aminobutyric acid (GABA), and histamine. [, , ] It participates in decarboxylation and transamination reactions essential for their production.

ANone: this compound deficiency can disrupt the synthesis of neurotransmitters. For instance, inadequate this compound levels can lead to reduced GABA synthesis, potentially contributing to seizures. [, ] This highlights the critical role of this compound in maintaining normal neurological function.

ANone: The molecular formula of this compound is C8H11NO3, and its molecular weight is 169.18 g/mol.

ANone: While the provided research papers focus primarily on the biological effects of this compound, several analytical techniques have been employed. UV spectrophotometry is one such method used to quantify this compound in pharmaceutical formulations, utilizing its absorption characteristics. [, , ]

ANone: this compound, when incorporated into soybean lecithin-based extenders for goat semen, demonstrated beneficial effects on sperm quality after the freeze-thawing process. [] This suggests the compatibility and potential stabilizing properties of this compound in specific biological formulations.

ANone: The study on 4'-deoxythis compound provides insights into the structure-activity relationship of this compound. This compound, a this compound analog, demonstrated the ability to both inhibit and stimulate the growth of an Escherichia coli mutant, depending on the concentration of pyridoxal. [] This suggests that even subtle modifications to the this compound structure can significantly alter its biological effects.

ANone: While specific formulation strategies were not discussed in the provided abstracts, research involving this compound often focuses on its administration and bioavailability. For instance, in the treatment of this compound-dependent epilepsy, the timing of this compound supplementation, including antenatal administration, has been explored to optimize its therapeutic efficacy. [] This highlights the ongoing efforts to improve the delivery and effectiveness of this compound in clinical settings.

ANone: Information pertaining to SHE regulations was not covered in the provided research.

ANone: Research suggests that chronic levodopa administration, commonly used in Parkinson's disease, might influence this compound metabolism. [] Patients on chronic levodopa treatment exhibited higher plasma and erythrocyte PLP concentrations after receiving intravenous this compound compared to levodopa-naive controls. [] This finding suggests an adaptive alteration in this compound metabolism induced by levodopa, highlighting the complex interplay between medications and nutrient metabolism.

ANone: Studies using mouse colonic epithelial cells and human colonic apical membrane vesicles revealed that this compound uptake is a carrier-mediated process, suggesting the existence of specific transporters for this compound absorption in the colon. [] Similarly, research on pancreatic acinar cells demonstrated a regulatable and specific carrier-mediated mechanism for this compound uptake, indicating that different cell types may possess unique mechanisms for this compound transport and utilization. []

ANone: Research in rats indicates that this compound might offer protection against the toxic effects of linezolid, an antibiotic. [] Co-administration of this compound with linezolid attenuated hematological toxicity, hepatotoxicity, and oxidative stress markers in rats, suggesting a potential role for this compound in mitigating drug-induced adverse effects. []

ANone: While the exact mechanisms underlying PDE are still being elucidated, research has established a strong link between mutations in the ALDH7A1 gene, responsible for encoding alpha-aminoadipic semialdehyde (AASA) dehydrogenase, and the development of PDE. [, ] These mutations can lead to a deficiency in AASA dehydrogenase activity, resulting in the accumulation of AASA and the development of seizures. [, ] Supplementation with this compound can alleviate seizures in affected individuals, although the specific mechanisms underlying its therapeutic benefits are not fully understood. []

ANone: Research on Jian carp suggests that dietary this compound supplementation can enhance disease resistance and immune responses in fish. [] Fish fed diets containing this compound exhibited higher survival rates after bacterial challenge, along with improvements in various immune parameters. [] These findings highlight the potential of this compound as a dietary supplement for promoting fish health and resilience in aquaculture settings.

ANone: The provided abstracts do not contain information about resistance or cross-resistance to this compound.

ANone: The provided abstracts do not contain information about toxicity or long-term effects of this compound.

ANone: While specific drug delivery strategies for this compound were not discussed in detail, research highlights the importance of its bioavailability and transport. For example, studies using isolated rat liver cells investigated the uptake and metabolism of this compound glucosides. [] This research suggests that the form in which this compound is present in food can affect its absorption and utilization by the body.

ANone: Urinary α-aminoadipic semialdehyde (aAASA) levels have emerged as a potential biomarker for PDE. [] Elevated aAASA levels in urine can indicate a deficiency in AASA dehydrogenase activity, which is the underlying metabolic defect in PDE. [] Monitoring aAASA levels could help clinicians assess the effectiveness of this compound treatment and adjust dosages as needed.

ANone: Researchers utilize various analytical techniques to study this compound. High-performance liquid chromatography (HPLC) coupled with UV detection is one method for quantifying this compound in multivitamin preparations. [, ] This technique allows for the separation and measurement of this compound and other vitamins in complex mixtures.

ANone: Researchers prioritize the validation of analytical methods used in this compound research. A study validating an HPLC method for simultaneous analysis of metamizole, thiamine, and this compound in tablets highlights the importance of accuracy, precision, and specificity in analytical measurements. [] By adhering to strict validation procedures, researchers ensure the quality and reliability of their data, which is crucial for making accurate interpretations and drawing meaningful conclusions.

ANone: The provided research abstracts did not focus on these aspects related to this compound.

ANone: The recognition of this compound as an essential nutrient and the subsequent characterization of this compound deficiency syndromes represent significant milestones. [, ] Early research established the link between this compound deficiency and various conditions, including dermatitis, anemia, and neurological disorders. [, ]

ANone: this compound research extends beyond the realm of nutrition science and demonstrates significant overlap with other disciplines. For instance, the investigation of this compound-dependent epilepsy involves collaboration between geneticists, neurologists, and biochemists to unravel the complex interplay between genetic mutations, metabolic pathways, and clinical manifestations. [, ]

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