molecular formula C8H11NO3 B162805 Piridoxina CAS No. 65-23-6

Piridoxina

Número de catálogo: B162805
Número CAS: 65-23-6
Peso molecular: 169.18 g/mol
Clave InChI: LXNHXLLTXMVWPM-UHFFFAOYSA-N
Atención: Solo para uso de investigación. No para uso humano o veterinario.
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Descripción

La piridoxina, comúnmente conocida como vitamina B6, es una vitamina soluble en agua que juega un papel crucial en diversas funciones biológicas. Se encuentra naturalmente en muchos alimentos y también está disponible como suplemento dietético. La this compound es esencial para el metabolismo de los aminoácidos, los carbohidratos y los lípidos, y apoya la salud del cerebro, la función inmunitaria y la síntesis de neurotransmisores .

Métodos De Preparación

Rutas sintéticas y condiciones de reacción: La piridoxina se puede sintetizar mediante varios métodos. Un enfoque común implica la condensación de cianoacetamida con compuestos 1,3-dicarbonílicos. Otro método utiliza la condensación de derivados de 1,3-oxazol con dienófilos, seguida de hidrogenación catalítica . Estos métodos se caracterizan por altos rendimientos y condiciones de reacción suaves.

Métodos de producción industrial: La producción industrial de this compound generalmente implica el método "oxazol", que es un proceso de dos etapas. La primera etapa involucra la condensación de dienos para formar compuestos intermedios, que luego se convierten en this compound mediante hidrogenación catalítica . Este método se usa ampliamente debido a su eficiencia y rentabilidad.

Análisis De Reacciones Químicas

Tipos de reacciones: La piridoxina experimenta varias reacciones químicas, incluida la oxidación, la reducción y la sustitución. Se puede oxidar selectivamente para formar piridoxal o clorhidrato de piridoxal utilizando un sistema de oxidación catalítica .

Reactivos y condiciones comunes: Los reactivos comunes utilizados en la oxidación de la this compound incluyen fuentes de oxígeno, catalizadores, sales inorgánicas y ligandos de amina. Las reacciones generalmente se llevan a cabo en agua como disolvente en condiciones suaves .

Productos principales: Los principales productos formados a partir de la oxidación de la this compound son el piridoxal y el clorhidrato de piridoxal, que son intermediarios clave en la síntesis de piridoxal 5'-fosfato, la forma activa de coenzima de la vitamina B6 .

Comparación Con Compuestos Similares

La piridoxina es parte del grupo de la vitamina B6, que incluye piridoxal y piridoxamina, junto con sus derivados fosforilados. Estos compuestos son químicamente similares y pueden interconvertirse en sistemas biológicos . El piridoxal 5'-fosfato tiene la mayor actividad biológica entre estos compuestos, pero todas las formas son esenciales para varias reacciones enzimáticas .

Compuestos similares:

  • Piridoxal
  • Piridoxamina
  • This compound 5'-fosfato
  • Piridoxal 5'-fosfato
  • Piridoxamina 5'-fosfato

La this compound es única en su estabilidad y es la forma más utilizada en los suplementos dietéticos .

Propiedades

IUPAC Name

4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol
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InChI

InChI=1S/C8H11NO3/c1-5-8(12)7(4-11)6(3-10)2-9-5/h2,10-12H,3-4H2,1H3
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InChI Key

LXNHXLLTXMVWPM-UHFFFAOYSA-N
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Description Data deposited in or computed by PubChem

Canonical SMILES

CC1=NC=C(C(=C1O)CO)CO
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Molecular Formula

C8H11NO3
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Related CAS

58-56-0 (hydrochloride)
Record name Pyridoxine [INN:BAN]
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DSSTOX Substance ID

DTXSID4023541
Record name Pyridoxine
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Molecular Weight

169.18 g/mol
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Physical Description

White powder; [Alfa Aesar MSDS], Solid
Record name Pyridoxine
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Solubility

79 mg/mL
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Vapor Pressure

0.00000028 [mmHg]
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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).
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CAS No.

65-23-6
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Melting Point

159-162 °C, 159 - 162 °C
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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%.
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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).
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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.

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

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

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

ANone: Pyridoxine, 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 pyridoxine in specific biological formulations.

ANone: The study on 4'-deoxypyridoxine provides insights into the structure-activity relationship of pyridoxine. This compound, a pyridoxine 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 pyridoxine structure can significantly alter its biological effects.

ANone: While specific formulation strategies were not discussed in the provided abstracts, research involving pyridoxine often focuses on its administration and bioavailability. For instance, in the treatment of pyridoxine-dependent epilepsy, the timing of pyridoxine supplementation, including antenatal administration, has been explored to optimize its therapeutic efficacy. [] This highlights the ongoing efforts to improve the delivery and effectiveness of pyridoxine 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 pyridoxine metabolism. [] Patients on chronic levodopa treatment exhibited higher plasma and erythrocyte PLP concentrations after receiving intravenous pyridoxine compared to levodopa-naive controls. [] This finding suggests an adaptive alteration in pyridoxine 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 pyridoxine uptake is a carrier-mediated process, suggesting the existence of specific transporters for pyridoxine absorption in the colon. [] Similarly, research on pancreatic acinar cells demonstrated a regulatable and specific carrier-mediated mechanism for pyridoxine uptake, indicating that different cell types may possess unique mechanisms for pyridoxine transport and utilization. []

ANone: Research in rats indicates that pyridoxine might offer protection against the toxic effects of linezolid, an antibiotic. [] Co-administration of pyridoxine with linezolid attenuated hematological toxicity, hepatotoxicity, and oxidative stress markers in rats, suggesting a potential role for pyridoxine 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 pyridoxine 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 pyridoxine supplementation can enhance disease resistance and immune responses in fish. [] Fish fed diets containing pyridoxine exhibited higher survival rates after bacterial challenge, along with improvements in various immune parameters. [] These findings highlight the potential of pyridoxine 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 pyridoxine.

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

ANone: While specific drug delivery strategies for pyridoxine 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 pyridoxine glucosides. [] This research suggests that the form in which pyridoxine 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 pyridoxine treatment and adjust dosages as needed.

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

ANone: Researchers prioritize the validation of analytical methods used in pyridoxine research. A study validating an HPLC method for simultaneous analysis of metamizole, thiamine, and pyridoxine 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 pyridoxine.

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

ANone: Pyridoxine research extends beyond the realm of nutrition science and demonstrates significant overlap with other disciplines. For instance, the investigation of pyridoxine-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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