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Cholin

Choline

HCID 305
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Grundinformationen

CAS
139741-81-4
Standard-SMILES
C[N+](C)(C)CCO
InChIKey
OEYIOHPDSNJKLS-UHFFFAOYSA-N
Summenformel
C5H14NO+
Durchschnittliche Molmasse
104,17 g/mol
Monoisotopische Masse
104,10699049

Überblick

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.

Namen und Bezeichner

Bevorzugter Name
Choline
IUPAC
2-hydroxyethyl(trimethyl)azanium
Lokaler Name
Cholin
Englischer Name
CHOLINE
Summenformel
C5H14NO
Molmasse
104.17

Namen und Synonyme

cholineCholine ionBilineurine62-49-7Choline cation2-Hydroxy-N,N,N-trimethylethanaminiumCholinum(2-Hydroxyethyl)trimethylammoniumEthanaminium, 2-hydroxy-N,N,N-trimethyl-vitamin Jtrimethylethanolamine2-hydroxyethyl(trimethyl)azanium
Weitere Namen anzeigen
L-Choline2,4,6-TRIS(4-FLUOROPHENYL)PYRYLIUM TETRAFLUOROBORATESincalincholineionCholine(8CI)CHOLINE, BASE
N-trimethylethanolamine(2-hydroxyethyl)trimethylazaniumN91BDP6H0XN,N,N-trimethylethanol-ammoniumCHEBI:15354DTXSID8043789GabazolamineGaboxetine

Datenbank-Bezeichner

CAS
139741-81-4、5413-08-1、62-49-7
PubChem CID
305
DTXSID
DTXSID8043789
ChEMBL
CHEMBL920

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
-0,4
Polarare Oberfläche (TPSA)
20,2 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
1
Frei drehbare Bindungen
2
Schwere Atome
7
Formalladung
1
Komplexität
46,5

Experimentelle und physikochemische Eigenschaften

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

Pharmaceuticals -> Brochodilators

Pharmaceuticals

Pharmaceuticals -> Listed in ZINC15

SolubilitySoluble
Dietary IngredientsCholine
Melting Point · 2 Einträge

244-247 °C (as chloride salt)

302 - 303 °C (chloride salt)

Physical Description · 2 Einträge

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

Solid

Collision Cross Section · 6 Einträge

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)]

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 5 Einträge

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.

Gefahrenhinweise

Regulatory Information · 4 Einträge

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%)

Toxikologische Informationen

Chemie und Industrie

Pharmakologische Informationen

Pharmacodynamics · 1 Eintrag

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 Eintrag

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 Einträge

Zugehörige Reaktionen

33
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 219505
HRID 219505als Eduktuspto-grants-2012_06
Reaktionsgleichung von HRID 235795
HRID 235795als Produktuspto-grants-1987_02
Reaktionsgleichung von HRID 235796
HRID 235796als Eduktuspto-grants-1987_02
Reaktionsgleichung von HRID 436720
HRID 436720als Produktuspto-grants-1977_06
Reaktionsgleichung von HRID 483076
HRID 483076als Eduktuspto-grants-1986_03
Reaktionsgleichung von HRID 522490
HRID 522490als Eduktuspto-grants-2016_05
Reaktionsgleichung von HRID 544638
HRID 544638als Katalysatoruspto-grants-1984_05
Reaktionsgleichung von HRID 677242
HRID 677242als Produktals EduktTraining data from https://doi.org/10.1039/C8SC04228D (3/10)
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ChEBI
CHEBI:15354
UNII
N91BDP6H0X
EC Number
200-535-1
Nikkaji
J4.822D

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

117 Ų [M]+ [CCS Type: TW; Method: calibrated with polyalanine]

117.4 Ų [M+H]+

Physikochemische Eigenschaften

Schmelzpunkt
232 · 232-233 °C (decomp)
Siedepunkt
195.35 °C · 195.35°C (rough estimate)
Dichte
1.09 g/mL · 1.09 g/mL at 20 °C
Brechungsindex
20 · n20/D 1.418
storage temp.
2 · 2-8°C
Löslichkeit
2 H5)2O, · Easily soluble (water), soluble (ethanol), slightly soluble (amyl alcohol), insoluble ((C2H5)2O, CHCl3)
pka
13.9 · 13.9(at 25℃)
CAS Datenbank
62 · 62-49-7(CAS DataBase Reference)
EPA chemische Informationen
Choline (62-49-7)
Adverse Effects
Dermatotoxin - Skin burns.

Sicherheitsdaten

F
8-9-23
wgk
1
tsca
TSCA listed
ridadr
UN 3286 3/PG 2
risk_code
34
hazard_code
C
safety_code
26-36/37/39-45
hazard_class
8
packing_group
II

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
Metabolite PathwaysCystathionine Beta-Synthase Deficiency

Verwendung und Herstellung

Uses · 2 Einträge

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

Anwendungen

VerwendenCholine 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.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

EthylenoxidAmmoniumchloridFormaldehyd

Nachgelagerte Produkte

2-Bromethyltrimethylammoniumbromid[R-(Z,Z)]-(7-Oleoyl-4-oxido-10-oxo-3,5,9-trioxa-4-phosphaheptacos-18-enyl)trimethylammonium-4-oxidEthanaminium, 2-(acetyloxy)-N,N,N-trimethyl-, hydroxide (1:1)(2-Iodethyl)trimethylammoniumiodid

Ergänzende Hinweise

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