コリン

Choline

HCID 305CAS 139741-81-4

基本情報

標準SMILES
C[N+](C)(C)CCO
InChIKey
OEYIOHPDSNJKLS-UHFFFAOYSA-N
分子式
C5H14NO+
平均分子量
104.17 g/mol
単同位体質量
104.10699049

概要

Choline is a choline that is the parent compound of the cholines class, consisting of ethanolamine having three methyl substituents attached to the amino function. It has a role as a neurotransmitter, a nutrient, an allergen, a mouse metabolite, a Saccharomyces cerevisiae metabolite, a plant metabolite, an Escherichia coli metabolite, a human metabolite and a Daphnia magna metabolite.

名称と識別子

優先名称
Choline
IUPAC
2-hydroxyethyl(trimethyl)azanium
現地名
コリン
英語名
CHOLINE
分子式
C5H14NO
分子量
104.17

名称と別名

cholineCholine ionBilineurine62-49-7Choline cation2-Hydroxy-N,N,N-trimethylethanaminiumCholinum(2-Hydroxyethyl)trimethylammoniumEthanaminium, 2-hydroxy-N,N,N-trimethyl-vitamin Jtrimethylethanolamine2-hydroxyethyl(trimethyl)azanium
名称をさらに表示
2-(トリメチルアミニオ)エタノール2-ヒドロキシ-N,N,N-トリメチルエタンアミニウム(2-ヒドロキシエチル)トリメチルアミニウムビリノイリンN-(2-ヒドロキシエチル)トリメチルアミニウム2-ヒドロキシ-N,N,N-トリメチル-1-エタンアミニウムトリメチル-2-ヒドロキシエチルアンモニウム塩N,N,N-トリメチル-2-ヒドロキシエタンアミニウム2-ヒドロキシエチルトリメチルアンモニウム2-ヒドロキシエチルトリメチルアミニウムN,N,N-トリメチル-2-ヒドロキシ-1-エタンアミニウムトリメチル-2-オキシエチルアンモニウム塩ファギンシンカリントリメチル(2-ヒドロキシエチル)アミニウムβヒドロキシエチルトリメチルアンモニウムハイドロオキサイドコリン溶液水酸化2-ヒドロキシエチルトリメチルアンモニウム溶液水酸化2‐ヒドロキシエチルトリメチルアンモニウム溶液コリニウムL-Choline2,4,6-TRIS(4-FLUOROPHENYL)PYRYLIUM TETRAFLUOROBORATESincalincholineionCholine(8CI)CHOLINE, BASE
N-trimethylethanolamine(2-hydroxyethyl)trimethylazaniumN91BDP6H0XN,N,N-trimethylethanol-ammoniumCHEBI:15354DTXSID8043789GabazolamineGaboxetine

データベース識別子

CAS
139741-81-4、5413-08-1、62-49-7
PubChem CID
305
DTXSID
DTXSID8043789
ChEMBL
CHEMBL920
ChEBI
CHEBI:15354
UNII
N91BDP6H0X
EC Number
200-535-1
Nikkaji
J4.822D

物性

構造計算による物性

XLogP
-0.4
極性表面積
20.2 Ų
水素結合供与体数
1
水素結合受容体数
1
回転可能結合数
2
重原子数
7

実験および物理化学的性質

Chemical ClassesBiological Agents -> Vitamins and Derivatives
Drugs · 3 件

Pharmaceuticals -> Brochodilators

Pharmaceuticals

Pharmaceuticals -> Listed in ZINC15

SolubilitySoluble
Dietary IngredientsCholine
Melting Point · 2 件

244-247 °C (as chloride salt)

302 - 303 °C (chloride salt)

Physical Description · 2 件

50% Aqueous solution: Dark brown cloudy liquid; [Sigma-Aldrich MSDS]

Solid

物理化学的性質

融点
232 · 232-233 °C (decomp)
沸点
195.35 °C · 195.35°C (rough estimate)
比重(密度)
1.09 g/mL · 1.09 g/mL at 20 °C
屈折率
20 · n20/D 1.418
貯蔵温度
2 · 2-8°C
溶解性
2 H5)2O, · 易溶(水), 可溶(エタノール), 微溶(アミルアルコール), 不溶((C2H5)2O, CHCl3)

化学的性質

化学的特性Viscous, alkaline liquid. Soluble in water and alcohol. Amounts are expressed in milligrams of choline.

安全と法規制

GHS分類

GHS Classification · 5 件

This chemical does not meet GHS hazard criteria for 1.3% (2 of 149) of reports.

Danger

H225 (70.5%): Highly Flammable liquid and vapor [Danger Flammable liquids]

P203, P210, P233, P240, P241, P242, P243, P260, P264, P264+P265, P270, P280, P301+P330+P331, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P308+P316, P316, P317, P318, P321, P363, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 149 reports by companies from 5 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: Ethanaminium, 2-hydroxy-N,N,N-trimethyl-

Regulation (EC) No 178/2002 (amended)

Status: Active Update: 25-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/25288

Ethanaminium, 2-hydroxy-N,N,N-trimethyl-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Other Safety InformationIMAP assessments - Ethanaminium, 2-hydroxy-N,N,N-trimethyl-: Environment tier I assessment
Hazards Summary50% Aqueous solution: Causes burns; Inhalation may cause corrosive injuries to upper respiratory tract and lungs; [Sigma-Aldrich MSDS]
Hazard Classes and CategoriesFlam. Liq. 2 (70.5%)

毒性情報

Adverse EffectsDermatotoxin - Skin burns.

安全データ

F
8-9-23
wgk
1
tsca
TSCA listed
ridadr
UN 3286 3/PG 2
risk_code
34
安衛法
有機溶剤中毒予防規則:第2種有機溶剤,57,57-2

化学と産業

薬理情報

Pharmacodynamics · 1 件

This compound is needed for good nerve conduction throughout the CNS (central nervous system) as it is a precursor to acetylcholine (ACh). Choline is also needed for gallbladder regulation, liver function and lecithin (a key lipid) formation. Choline also aids in fat and cholesterol metabolism and prevents excessive fat build up in the liver. Choline has been used to mitigate the effects of Parkinsonism and tardive dyskinesia. Choline deficiencies may result in excessive build-up of fat in the liver, high blood pressure, gastric ulcers, kidney and liver dysfunction and stunted growth.

Mechanism of Action · 1 件

Choline is a major part of the polar head group of phosphatidylcholine. Phosphatidylcholine's role in the maintenance of cell membrane integrity is vital to all of the basic biological processes: information flow, intracellular communication and bioenergetics. Inadequate choline intake would negatively affect all these processes. Choline is also a major part of another membrane phospholipid, sphingomyelin, also important for the maintenance of cell structure and function. It is noteworthy and not surprising that choline deficiency in cell culture causes apoptosis or programmed cell death. This appears to be due to abnormalities in cell membrane phosphatidylcholine content and an increase in ceramide, a precursor, as well as a metabolite, of sphingomyelin. Ceramide accumulation, which is caused by choline deficiency, appears to activate Caspase, a type of enzyme that mediates apoptosis. Betaine or trimethylglycine is derived from choline via an oxidation reaction. Betaine is one of the factors that maintains low levels of homocysteine by resynthesizing L-methionine from homocysteine. Elevated homocysteine levels are a significant risk factor for atherosclerosis, as well as other cardiovascular and neurological disorders. Acetylcholine is one of the major neurotransmitters and requires choline for its synthesis. Adequate acetylcholine levels in the brain are believed to be protective against certain types of dementia, including Alzheimer's disease.

Metabolism/MetabolitesCholine has known human metabolites that include Trimethylazanium and acetaldehyde.
MeSH Pharmacological Classification · 2 件

Endogenous factors or drugs that increase the transport and metabolism of LIPIDS including the synthesis of LIPOPROTEINS by the LIVER and their uptake by extrahepatic tissues.

Drugs used to specifically facilitate learning or memory, particularly to prevent the cognitive deficits associated with dementias. These drugs act by a variety of mechanisms.

Tissue LocationsBasal Ganglia
Cellular LocationsCytoplasm

用途と製造

Uses · 2 件

An essential nutrient in plants and animals for biosynthesis of cell membrane components (phospholipids); Found in eggs, meats, peanuts, and wheat germ; Used as a nutrient, dietary supplement, and ionic liquid solvent; [Merck Index]

Use (kg; approx.) in Germany (2009): >750

General Manufacturing InformationEthanaminium, 2-hydroxy-N,N,N-trimethyl-: ACTIVE
応用分野 · 2 件

解説C5H14NO(104.17).(CH3)3N+-CH2-CH2-OH.A. Streckerにより,ブタの胆汁から水酸化物塩として単離された.OH基の遊離形,またはホスファチジルコリン(レシチン),またはアセチルコリンの形で動物,植物組織や酵母に含まれる.動物組織では,おもに脳,胆汁,肝臓,卵黄などに,植物組織では,おもに種子に含まれる.2-クロロエタノールまたはエチレンオキシドとトリメチルアミンから合成される.通常は粘ちゅうな悪臭のあるシロップである.水,メタノール,エタノールに可溶,エーテル,石油エーテル,ベンゼン,トルエン,四塩化炭素,アセトン,クロロホルムに難溶.ビタミン B2 複合体の一つとして抗脂肝因子としてはたらく.脂肪代謝異常による脂肪肝,肝硬変,アテローム性動脈硬化,心臓疾患に用いられる.[CAS 62-49-7]森北出版「化学辞典(第2版)

使用Choline is a substance grouped as a member of the vitamin b complex, although not a vitamin by definition. it is water soluble and is important in nerve function and fat metabolism. it occurs in egg yolk, beef liver, and grains.

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補足説明

定義ChEBI: A choline that is the parent compound of the cholines class, consisting of ethanolamine having three methyl substituents attached to the amino function.

関連反応

33 件

関連ノート

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