Thiamine
概要
説明
チアミンは、ビタミンB1としても知られており、人間の健康に不可欠な水溶性ビタミンです。最初のBビタミンとして発見され、炭水化物、脂肪、タンパク質の代謝において重要な役割を果たします。チアミンは、全粒穀物、豆類、一部の肉や魚など、さまざまな食品に含まれています。また、食品添加物や医薬品として市販されています .
準備方法
合成経路と反応条件: チアミンは、いくつかの化学経路を通じて合成できます。 一般的な方法の1つは、4-メチル-5-(2-ヒドロキシエチル)チアゾールを塩基性条件下で2-メチル-4-アミノ-5-クロロメチルピリミジンと反応させてチアミンを生成することです . この反応は通常、メタノールなどの溶媒と水酸化ナトリウムなどの塩基を必要とします。
工業生産方法: 工業用では、塩酸チアミンは通常、硝酸チアミンと塩酸を反応させて製造されます。このプロセスには、濃塩酸を加熱し、脱着した塩化水素ガスを冷却して乾燥し、次に硝酸チアミンのメタノール溶液に導入することが含まれます。 次に、生成した塩酸チアミンをろ過、洗浄、乾燥します .
化学反応の分析
反応の種類: チアミンは、次のようなさまざまな化学反応を起こします。
酸化: チアミンは酸化されて、分析化学で用いられる蛍光化合物であるチオクロムを生成できます。
一般的な試薬と条件:
酸化: フェリシアン化カリウムは、チアミンをチオクロムに変換するための酸化剤として一般的に用いられます.
リン酸化: チアミンは、アデノシン三リン酸（ATP）の存在下で、チアミン二リン酸キナーゼによってリン酸化されます。
主な生成物:
チオクロム: チアミンの酸化によって生成されます。
チアミン二リン酸: チアミンのリン酸化によって生成されます.
科学的研究の応用
チアミンは、科学研究において幅広い用途を持っています。
化学: チアミンとそのリン酸エステルの測定のための高速液体クロマトグラフィー（HPLC）など、さまざまな分析技術における試薬として使用されます.
生物学: トランスケトラーゼやピルビン酸脱水素酵素など、炭水化物代謝に関与する酵素の正常な機能に不可欠です.
作用機序
チアミンは、その活性型であるチアミン二リン酸を通じて主に効果を発揮します。この補酵素は、ピルビン酸やα-ケト酸の脱炭酸など、いくつかの重要な代謝経路に関与しています。 チアミン二リン酸は、エネルギー産生や核酸や脂肪酸の合成に不可欠な、トランスケトラーゼ、ピルビン酸脱水素酵素、α-ケトグルタル酸脱水素酵素などの酵素の補因子として作用します .
類似化合物:
ベンフォチアミン: バイオアベイラビリティが高く、糖尿病性神経障害の治療に用いられるチアミンの脂溶性誘導体です.
チアミン一リン酸: チアミン二リン酸の合成における中間体として機能するチアミンのリン酸化型です.
チアミン三リン酸: 細胞のエネルギー代謝に関与するチアミンの別のリン酸化型です.
独自性: チアミンは、活性型補酵素であるチアミン二リン酸の主要な前駆体であるという役割において、類似化合物の中で独特です。 ベンフォチアミンやその他の誘導体は、特定の用途や利点がありますが、チアミン自体は、さまざまな代謝過程に不可欠であり、食品添加物や強化食品で最も一般的に使用される形態です .
類似化合物との比較
Benfotiamine: A lipid-soluble derivative of thiamine that has higher bioavailability and is used to treat diabetic neuropathy.
This compound Monophosphate: A phosphorylated form of this compound that serves as an intermediate in the synthesis of this compound pyrophosphate.
This compound Triphosphate: Another phosphorylated form of this compound involved in cellular energy metabolism.
Uniqueness: this compound is unique among its similar compounds due to its role as the primary precursor for this compound pyrophosphate, the active coenzyme form. While benfotiamine and other derivatives have specific applications and advantages, this compound itself is essential for a wide range of metabolic processes and is the most commonly used form in dietary supplements and fortified foods .
特性
IUPAC Name |
2-[3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethanol |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C12H17N4OS/c1-8-11(3-4-17)18-7-16(8)6-10-5-14-9(2)15-12(10)13/h5,7,17H,3-4,6H2,1-2H3,(H2,13,14,15)/q+1 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
JZRWCGZRTZMZEH-UHFFFAOYSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
CC1=C(SC=[N+]1CC2=CN=C(N=C2N)C)CCO |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C12H17N4OS+ |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
DSSTOX Substance ID |
DTXSID50220251 |
Source
|
| Record name | Thiamine ion | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID50220251 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
265.36 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Physical Description |
Solid with a slight odor; [HSDB] Crystals; [Avocado Research MSDS], Solid |
Source
|
| Record name | Thiamine | |
| Source | Haz-Map, Information on Hazardous Chemicals and Occupational Diseases | |
| URL | https://haz-map.com/Agents/17375 | |
| Description | Haz-Map® is an occupational health database designed for health and safety professionals and for consumers seeking information about the adverse effects of workplace exposures to chemical and biological agents. | |
| Explanation | Copyright (c) 2022 Haz-Map(R). All rights reserved. Unless otherwise indicated, all materials from Haz-Map are copyrighted by Haz-Map(R). No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission. | |
| Record name | Thiamine | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0000235 | |
| 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. | |
Solubility |
500.0 mg/mL |
Source
|
| Record name | Thiamine | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00152 | |
| 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. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | Thiamine | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0000235 | |
| 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. | |
Mechanism of Action |
It is thought that the mechanism of action of thiamine on endothelial cells is related to a reduction in intracellular protein glycation by redirecting the glycolytic flux. Thiamine is mainly the transport form of the vitamin, while the active forms are phosphorylated thiamine derivatives. Natural derivatives of thiamine phosphate, such as thiamine monophosphate (ThMP), thiamine diphosphate (ThDP), also sometimes called thiamine pyrophosphate (TPP), thiamine triphosphate (ThTP), and thiamine triphosphate (AThTP), that act as coenzymes in addition to their each unique biological functions. |
Source
|
| Record name | Thiamine | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00152 | |
| 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. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
CAS No. |
70-16-6, 59-43-8 |
Source
|
| Record name | 3-[(4-Amino-2-methyl-5-pyrimidinyl)methyl]-5-(2-hydroxyethyl)-4-methylthiazolium | |
| Source | CAS Common Chemistry | |
| URL | https://commonchemistry.cas.org/detail?cas_rn=70-16-6 | |
| 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. | |
| Explanation | The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated. | |
| Record name | Thiamine ion | |
| Source | ChemIDplus | |
| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0000070166 | |
| Description | ChemIDplus is a free, web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases, including the TOXNET system. | |
| Record name | Thiamine | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00152 | |
| 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. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | Thiamine ion | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID50220251 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
| Record name | Thiamine | |
| Source | European Chemicals Agency (ECHA) | |
| URL | https://echa.europa.eu/substance-information/-/substanceinfo/100.000.387 | |
| Description | The European Chemicals Agency (ECHA) is an agency of the European Union which is the driving force among regulatory authorities in implementing the EU's groundbreaking chemicals legislation for the benefit of human health and the environment as well as for innovation and competitiveness. | |
| Explanation | Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page. | |
| Record name | THIAMINE ION | |
| Source | FDA Global Substance Registration System (GSRS) | |
| URL | https://gsrs.ncats.nih.gov/ginas/app/beta/substances/4ABT0J945J | |
| Description | The FDA Global Substance Registration System (GSRS) enables the efficient and accurate exchange of information on what substances are in regulated products. Instead of relying on names, which vary across regulatory domains, countries, and regions, the GSRS knowledge base makes it possible for substances to be defined by standardized, scientific descriptions. | |
| Explanation | Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required. | |
| Record name | Thiamine | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0000235 | |
| 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 |
248 °C |
Source
|
| Record name | Thiamine | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00152 | |
| 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. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | Thiamine | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0000235 | |
| 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. | |
Retrosynthesis Analysis
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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
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