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
名称をさらに表示
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
- 形式電荷
- 1
- 複雑度
- 46.5
実験および物理化学的性質
Drugs
Pharmaceuticals -> Brochodilators
Pharmaceuticals
Pharmaceuticals -> Listed in ZINC15
Melting Point
244-247 °C (as chloride salt)
302 - 303 °C (chloride salt)
Physical Description
50% Aqueous solution: Dark brown cloudy liquid; [Sigma-Aldrich MSDS]
Solid
Collision Cross Section
117.7 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID9047467]
117.6 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
117.8 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
119 Ų [M]+ [CCS Type: DT; Method: stepped-field]
117 Ų [M]+ [CCS Type: TW; Method: calibrated with polyalanine]
117.4 Ų [M+H]+
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)
- 酸解離定数(Pka)
- 13.9 · 13.9(at 25℃)
- CAS データベース
- 62 · 62-49-7(CAS DataBase Reference)
- EPAの化学物質情報
- Choline (62-49-7)
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
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
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.
毒性情報
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
- 消防法
- 危-4-1-S-II
- hazard_code
- C
- safety_code
- 26-36/37/39-45
- hazard_class
- 8
- packing_group
- II
化学と産業
薬理情報
Pharmacodynamics
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
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.
MeSH Pharmacological Classification
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.
用途と製造
Uses
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
応用分野
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.
上流・下流製品情報
上流原料
下流製品
サプライヤー46 社
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
関連ノート
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