吡哆醇
概述
描述
吡哆醇,俗称维生素B6,是一种水溶性维生素,在各种生物功能中起着至关重要的作用。它天然存在于许多食物中,也可以作为膳食补充剂。 吡哆醇对氨基酸、碳水化合物和脂类的代谢至关重要,并且支持大脑健康、免疫功能和神经递质的合成 .
科学研究应用
吡哆醇在科学研究中具有广泛的应用:
准备方法
合成路线和反应条件: 吡哆醇可以通过多种方法合成。一种常见的方法是氰基乙酰胺与1,3-二羰基化合物缩合。 另一种方法是1,3-恶唑衍生物与亲双烯体缩合,然后进行催化加氢 。这些方法的特点是产率高,反应条件温和。
工业生产方法: 吡哆醇的工业生产通常采用“恶唑”法,这是一个两步法。 第一步涉及二烯缩合形成中间体化合物,然后通过催化加氢转化为吡哆醇 。该方法因其效率高、成本效益高而被广泛采用。
化学反应分析
反应类型: 吡哆醇会发生各种化学反应,包括氧化、还原和取代。 它可以使用催化氧化体系选择性氧化形成吡哆醛或吡哆醛盐酸盐 .
常用试剂和条件: 吡哆醇氧化反应中常用的试剂包括氧源、催化剂、无机盐和胺配体。 反应通常在水中作为溶剂进行,在温和条件下进行 .
主要产物: 吡哆醇氧化形成的主要产物是吡哆醛和吡哆醛盐酸盐,它们是合成吡哆醛5’-磷酸(维生素B6的活性辅酶形式)的关键中间体 .
作用机制
吡哆醇在体内转化为吡哆醛5’-磷酸,后者作为各种生化反应的辅酶。 它参与氨基酸、糖原和脂类的代谢,并有助于合成神经递质,如血清素、多巴胺、去甲肾上腺素和γ-氨基丁酸(GABA) . 吡哆醛5’-磷酸还在血红蛋白和鞘脂的合成中发挥作用 .
相似化合物的比较
吡哆醇是维生素B6家族的一部分,包括吡哆醛和吡哆胺,以及它们的磷酸化衍生物。 这些化合物在化学上相似,可以在生物系统中相互转化 . 在这些化合物中,吡哆醛5’-磷酸具有最高的生物活性,但所有形式对于各种酶促反应都是必需的 .
类似化合物:
- 吡哆醛
- 吡哆胺
- 吡哆醇5’-磷酸
- 吡哆醛5’-磷酸
- 吡哆胺5’-磷酸
属性
IUPAC Name |
4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol | |
---|---|---|
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 | PubChem | |
URL | https://pubchem.ncbi.nlm.nih.gov | |
Description | Data deposited in or computed by PubChem | |
InChI Key |
LXNHXLLTXMVWPM-UHFFFAOYSA-N | |
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 | PubChem | |
URL | https://pubchem.ncbi.nlm.nih.gov | |
Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C8H11NO3 | |
Source | PubChem | |
URL | https://pubchem.ncbi.nlm.nih.gov | |
Description | Data deposited in or computed by PubChem | |
Related CAS |
58-56-0 (hydrochloride) | |
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 | |
Record name | Pyridoxine | |
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Molecular Weight |
169.18 g/mol | |
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 | |
Record name | Pyridoxine | |
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Record name | Pyridoxine | |
Source | Human Metabolome Database (HMDB) | |
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Solubility |
79 mg/mL | |
Record name | Pyridoxine | |
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Record name | Pyridoxine | |
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Vapor Pressure |
0.00000028 [mmHg] | |
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). | |
Record name | Pyridoxine | |
Source | DrugBank | |
URL | https://www.drugbank.ca/drugs/DB00165 | |
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CAS No. |
65-23-6 | |
Record name | Pyridoxine | |
Source | CAS Common Chemistry | |
URL | https://commonchemistry.cas.org/detail?cas_rn=65-23-6 | |
Description | CAS Common Chemistry is an open community resource for accessing chemical information. Nearly 500,000 chemical substances from CAS REGISTRY cover areas of community interest, including common and frequently regulated chemicals, and those relevant to high school and undergraduate chemistry classes. This chemical information, curated by our expert scientists, is provided in alignment with our mission as a division of the American Chemical Society. | |
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Record name | Pyridoxine [INN:BAN] | |
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Record name | Pyridoxine | |
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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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URL | https://echa.europa.eu/substance-information/-/substanceinfo/100.000.548 | |
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Record name | PYRIDOXINE | |
Source | FDA Global Substance Registration System (GSRS) | |
URL | https://gsrs.ncats.nih.gov/ginas/app/beta/substances/KV2JZ1BI6Z | |
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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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Melting Point |
159-162 °C, 159 - 162 °C | |
Record name | Pyridoxine | |
Source | DrugBank | |
URL | https://www.drugbank.ca/drugs/DB00165 | |
Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
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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
Synthesis routes and methods II
Procedure details
Retrosynthesis Analysis
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Strategy Settings
Precursor scoring | Relevance Heuristic |
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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
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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