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ピリドキシン

Pyridoxine

HCID 1054
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基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
65-23-6
標準SMILES
Cc1ncc(CO)c(CO)c1O
InChIKey
LXNHXLLTXMVWPM-UHFFFAOYSA-N
分子式
C8H11NO3
平均分子量
169.18 g/mol
単同位体質量
169.07389321

概要

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.

名称と識別子

優先名称
Pyridoxine
IUPAC
4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol
現地名
ピリドキシン
英語名
Pyridoxine
分子式
C8H11NO3
分子量
169.18

名称と別名

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
名称をさらに表示
2-メチル-3-ヒドロキシピリジン-4,5-ジメタノール3-ヒドロキシ-2-メチルピリジン-4,5-ジメタノールピリビトール4,5-ビス(ヒドロキシメチル)-2-メチルピリジン-3-オールビーシックスピリドキシン5-ヒドロキシ-6-メチルピリジン-3,4-ジメタノールピリドキソール5-ヒドロキシ-6-メチル-3,4-ピリジンジメタノールヒドキシンピリドキソルアデルミン5-ヒドロキシ-6-メチルピリジン-3,4-ビスメタノールベザチン5-ヒドロキシ-6-メチルピリジン-3,4-ビス(メタノール)グラビドックス3-ヒドロキシ-2-メチル-4,5-ピリジンジメタノールピリドキシンＨＣｌビタミンB6(ピリドキシン)PYRIDOXINE HCLPyridoxine (Vitamin B6)(5-hydroxy-6-Methylpyridine-3,4-diyl)diMethanol

物性

構造計算による物性補完中

XLogP
-0.8
極性表面積
73.6 Ų
水素結合供与体数
3
水素結合受容体数
4
回転可能結合数
2
重原子数
12
形式電荷
0
複雑度
142

実験および物理化学的性質

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

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals

CosmeticsHair conditioning; Antistatic; Skin conditioning
LogP-0.77
Food AdditivesUse unspecified -> FDA Substance added to food
Solubility79 mg/mL
Human Drugs · 5 件

Breast Feeding; Lactation; Milk, Human; Vitamins

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Vitamins and minerals

Melting Point · 2 件

159-162 °C

159 - 162 °C

Vapor Pressure0.00000028 [mmHg]
Physical Description · 3 件

Dry Powder

White powder; [Alfa Aesar MSDS]

Solid

安全と法規制

安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 5 件

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.

危険有害性情報

Regulatory Information · 4 件

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 件

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%)

毒性情報

化学と産業

薬理情報

ATC Code · 4 件

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 件

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 件

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).

関連反応

5 件
反応記録を作成
HRID 198087 の反応式
HRID 198087反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 839525 の反応式
HRID 839525反応物としてuspto-grants-1978_06
HRID 1350549 の反応式
HRID 1350549生成物としてuspto-grants-2007_05
HRID 1972117 の反応式
HRID 1972117生成物としてuspto-grants-2013_04
HRID 2222062 の反応式
HRID 2222062生成物としてuspto-grants-2008_05

化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
その他の操作
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PYRIDOXIN HYDROCHLORIDE
5-HYDROXY-6-METHYL-3,4-PYRIDINEDIMETHANOL HYDROCHLORIDE
B6-HCL
Pridoxine
ADEMINE 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

データベース識別子

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
Ionization Efficiency · 6 件

Positive

3.28

2.7

Agilent XCT

Electrospray ionization

formic acid (5.3nM)

Collision Cross Section · 6 件

133.7 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: APCI+; Dataset: TOXCAST; Source Identifier: DTXSID1040792]

134.4 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

132.3 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

134.6 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

126.18 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

135.69 Ų [M+H]+ [CCS Type: DT; Method: stepped-field]

物理化学的性質

融点
214 · 214-215 °C(lit.)
沸点
298.46 °C · 298.46°C (rough estimate)
比重(密度)
1.2435 · 1.2435 (rough estimate)
屈折率
1.51 · 1.5100 (estimate)
貯蔵温度
2 · Inert atmosphere,2-8°C
溶解性
2 O: · H2O: 0.1g/mL at20℃ 無色透明
酸解離定数(Pka)
5 · pKa 5.00(H2O t = 25.0 I = 0.15 (mixed)) (Uncertain)
外見
個体
色
ホワイトからオフホワイト
臭い (Odor)
無臭
BCS Class
1 · 1,3
安定性
安定。強力な酸化剤とは相容れない。
化粧品成分の機能
ヘアコンディショニング帯電防止スキンコンディショニング
InChI
1S/C8H11NO3/c1-5-8(12)7(4-11)6(3-10)2-9-5/h2,10-12H,3-4H2,1H3
InChIKey
LXNHXLLTXMVWPM-UHFFFAOYSA-N
SMILES
Cc1ncc(CO)c(CO)c1O
LogP
-0.77 · -0.770
CAS データベース
65 · 65-23-6(CAS DataBase Reference)
NISTの化学物質情報
2 · 2-Methyl-3-hydroxy-4,5-dihydroxymethylpyridine(65-23-6)
EPAの化学物質情報
3 · 3,4-Pyridinedimethanol, 5-hydroxy-6-methyl- (65-23-6)

化学的性質

化学的特性crystalline solid

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 件

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 件

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

pyridoxine

DILI Negative

Intravenous

DOI:10.1016/j.drudis.2019.09.022

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Toxicity DataLD50: 4 gm/kg (oral, rat)

安全データ

F
8-10
wgk
3
tsca
TSCA listed
rtecs
UV1350000
hs_code
29362500
risk_code
36/37/38
hazard_code
Xi
safety_code
26-36
ストレージクラス
11 - Combustible Solids
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 件

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

FDA Pharmacological Classification · 6 件

KV2JZ1BI6Z

PYRIDOXINE

Established Pharmacologic Class [EPC] - Vitamin B6 Analog

Chemical/Ingredient structural concept [Chemical/Ingredient] - Vitamin B 6

Chemical/Ingredient structural concept [Chemical/Ingredient] - Analogs/Derivatives

Pyridoxine is a Vitamin B6 Analog. The chemical classification of pyridoxine is Vitamin B 6 and Analogs/Derivatives.

MeSH Pharmacological ClassificationA group of water-soluble vitamins, some of which are COENZYMES.
Absorption, Distribution and Excretion · 3 件

The B vitamins are readily absorbed from the gastrointestinal tract, except in malabsorption syndromes. Pyridoxine is absorbed mainly in the jejunum. The Cmax of pyridoxine is achieved within 5.5 hours.

The major metabolite of pyridoxine, 4-pyridoxic acid, is inactive and is excreted in urine

Pyridoxine 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.

Tissue LocationsErythrocyte
Cellular LocationsExtracellular
Metabolite PathwaysHypophosphatasia

用途と製造

Uses · 3 件

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 件

Soap, Cleaning Compound, and Toilet Preparation Manufacturing

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

応用分野 · 5 件

解説ビタミンB6群の一つ．ピリジン環のβ-位に結合している－CH2OHを特色とする．体内でアミノ酸代謝の補酵素に変化する．略記号PN．

来歴The 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.

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

一般的な説明The discovery of vitamin B6 is generally ascribed to Paul Gyrgy who first realized there was a vitamin that was distinctly different from vitamin B2 in 1934. Pyridoxine (PN) is the C4 hydroxymethyl derivative, pyridoxal (PL) is the C4 formyl derivative and pyridoxamine (PM) is the C4 aminomethyl derivative of 5-(hydroxymethyl)- 2-methylpyridin-3-ol). Each of these are also converted to their corresponding 5'-phosphate derivatives referred to as pyridoxine 5'-phosphate (PNP), pyridoxal 5'-phosphate (PLP), and pyridoxamine 5'-phosphate (PMP), respectively . Because of their ability to interconvert, all are considered active forms of vitamin B6 in vivo. Although PLP is the major coenzyme form, PMP can also function as a coenzyme primarily in aminotransferases. The major metabolite is 4-pyridoxic acid, which is excreted in the urine.

使用用途ピリドキシンは主に下記の3つにおいて使用されています。 1. 医薬品 ピリドキシンは、医薬品としてビタミンB6欠乏症の予防及び治療の他以下のような場合に用いられます。 ビタミンB6の需要が増大し、食事からの摂取が不十分な際の補給 (消耗性疾患、妊産婦、授乳婦など) ビタミンB6依存症 (ビタミンB6反応性貧血など) ビタミンB6の欠乏又は代謝障害が関与すると推定される次のような症状 口角炎、口唇炎、舌炎、急・慢性湿疹、脂漏性湿疹、接触皮膚炎、ニキビ、末梢神経炎、放射線障害 2. 食品添加物 ピリドキシンは、塩酸ピリドキシンとして食品添加物としても使用されます。調整粉乳や小麦粉に、ビタミンB6の強化のために加えられたり、健康的なイメージを付加した菓子や飲料などの食品に使用されたりしています。 3. 化粧品 化粧品の用途には、塩酸ピリドキシンやトリスヘキシルデカン酸ピリドキシンが使用され、それぞれ用途が違います。 塩酸ピリドキシン 塩酸ピリドキシンは、皮脂抑制作用を期待されて化粧品に配合されています。過剰な皮脂分泌を抑制することから毛髪用のコンディショニング剤などや、皮膚のテカリを防止する目的で、スキンケア製品などに使用されています。 トリスヘキシルデカン酸ピリドキシン トリスヘキシルデカン酸ピリドキシンは、ピリドキシンの3個のヒドロキシ基にイソパルミチン酸が結合したビタミンB6誘導体です。液状の油溶性の物質で、皮膚への浸透力が高いです。 フィラグリンとは角質層にあるたんぱく質ですが、皮膚に水分が不足すると、角質層の骨格となるたんぱく質「ケラチン」を集め、保湿力のある角質層をつくるはたらきの中心的役割を果たしています。トリスヘキシルデカン酸ピリドキシンはフィラグリンの産生を促進し、皮膚の保湿へ作用していると考えられています。

上流・下流製品情報

上流原料

D-(+)-サッカロース3-amino-4,5-bis(aminomethyl)2-methylpyridine trihydrochloride1,5-ジヒドロ-8-メチル-3-(1-メチルエチル)-[1,3]ジオキセピノ[5,6-c]ピリジン-9-オール酢酸[1,5-ジヒドロ-8-メチル-3-(1-メチルエチル)[1,3]ジオキセピノ[5,6-c]ピリジン]-9-イルdimethyl 5-hydroxy-6-methylpyridine-3,4-dicarboxylatediethyl 5-hydroxy-6-methylpyridine-3,4-dicarboxylate3-ヒドロキシ-2-メチル-4,5-ピリジンジカルボン酸Glycine, N-[[3-hydroxy-5-(hydroxymethyl)-2-methyl-4-pyridinyl]methyl]-3-ヒドロキシ-5-(ヒドロキシメチル)-2-メチルピリジン-4-カルボン酸D-アルトロースピリドキサールD-(+)-アロースピリドキサミン

下流製品

りん酸(4-ホルミル-5-ヒドロキシ-6-メチル-3-ピリジニル)メチル3-クロロメチル-4-ヒドロキシメチル-6-メチルピリジン-5-オール1,3-ジヒドロ-6-メチルフロ[3,4-c]ピリジン-7-オール
補足説明 · 2 件

定義本品は、ピリドキシン(*)の塩酸塩であり、次の化学式で表される。参照表示名称：ピリドキシン

定義ChEBI: 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.