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Choline

HCID 305
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
139741-81-4
Standard SMILES
C[N+](C)(C)CCO
InChIKey
OEYIOHPDSNJKLS-UHFFFAOYSA-N
Molecular formula
C5H14NO+
Average molar mass
104.17 g/mol
Monoisotopic mass
104.10699049

Overview

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.

Names & identifiers

Preferred name
Choline
IUPAC
2-hydroxyethyl(trimethyl)azanium
English name
CHOLINE
Molecular formula
C5H14NO
Molecular weight
104.17

Names & synonyms

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

Database identifiers

CAS
139741-81-4、5413-08-1、62-49-7
PubChem CID
305
DTXSID
DTXSID8043789
ChEMBL
CHEMBL920
ChEBI
CHEBI:15354
UNII
N91BDP6H0X

Properties

Computed structural propertiesFilling in

XLogP
-0.4
Topological polar surface area
20.2 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
1
Rotatable bonds
2
Heavy atoms
7
Formal charge
1
Complexity
46.5

Experimental & physicochemical properties

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

Pharmaceuticals -> Brochodilators

Pharmaceuticals

Pharmaceuticals -> Listed in ZINC15

SolubilitySoluble
Dietary IngredientsCholine
Melting Point · 2 items

244-247 °C (as chloride salt)

302 - 303 °C (chloride salt)

Physical Description · 2 items

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

Solid

Collision Cross Section · 6 items

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]

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 5 items

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.

Hazard information

Regulatory Information · 4 items

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%)

Toxicology

Adverse Effects

Chemistry & industry

Pharmacology

Pharmacodynamics · 1 item

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 item

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 items

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.

Related reactions

33 records
New reaction record
HRID 219505 reaction equation
HRID 219505As reactantuspto-grants-2012_06
HRID 235795 reaction equation
HRID 235795As productuspto-grants-1987_02
HRID 235796 reaction equation
HRID 235796As reactantuspto-grants-1987_02
HRID 436720 reaction equation
HRID 436720As productuspto-grants-1977_06
HRID 483076 reaction equation
HRID 483076As reactantuspto-grants-1986_03
HRID 522490 reaction equation
HRID 522490As reactantuspto-grants-2016_05
HRID 544638 reaction equation
HRID 544638As catalystuspto-grants-1984_05
HRID 677242 reaction equation
HRID 677242As productAs reactantTraining data from https://doi.org/10.1039/C8SC04228D (3/10)
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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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EC Number
200-535-1
Nikkaji
J4.822D

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

117.4 Ų [M+H]+

Physicochemical properties

Melting point
232 · 232-233 °C (decomp)
Boiling point
195.35 °C · 195.35°C (rough estimate)
Density
1.09 g/mL · 1.09 g/mL at 20 °C
refractive index
20 · n20/D 1.418
storage temp.
2 · 2-8°C
solubility
2 H5)2O, · Easily soluble (water), soluble (ethanol), slightly soluble (amyl alcohol), insoluble ((C2H5)2O, CHCl3)
pka
13.9 · 13.9(at 25℃)
CAS DataBase Reference
62 · 62-49-7(CAS DataBase Reference)
FDA 21 CFR
101.9 · 101.9; 107.10; 310.545
EWG's Food Scores
1 · 1-3
NCI Dictionary of Cancer Terms
choline
FDA UNII
91 BDP6H0X · N91BDP6H0X
EPA Substance Registry System
Choline (62-49-7)
Symbol(GHS)
2 · GHS02,GHS08,GHS05
Signal word
Danger
Hazard statements
370 · H370-H225-H314-H360
Precautionary statements
260 · P260-P264-P280-P301+P330+P331-P303+P361+P353-P363-P304+P340-P310-P321-P305+P351+P338-P405-P501-P260-P264-P270-P307+P311-P321-P405-P501-P210-P233-P240-P241-P242-P243-P280-P303+P361+P353-P370+P378-P403+P235-P501
Hazard Codes
C
Risk Statements
34 · 34
Safety Statements
26 · 26-36/37/39-45
RIDADR
3286 · UN 3286 3/PG 2
WGK Germany
1 · 1
F
8 · 8-9-23
TSCA
TSCA listed
HazardClass
8 · 8
PackingGroup
II
REACH Registrations
Active
Dermatotoxin - Skin burns.

Safety data

F
8-9-23
wgk
1
tsca
TSCA listed
ridadr
UN 3286 3/PG 2
risk_code
34
Signal word
Danger
Symbol(GHS)
GHS02,GHS08,GHS05
hazard_code
C
safety_code
26-36/37/39-45
hazard_class
8
packing_group
II
Hazard statements
H370-H225-H314-H360
REACH Registrations
Active
Precautionary statements
P260-P264-P280-P301+P330+P331-P303+P361+P353-P363-P304+P340-P310-P321-P305+P351+P338-P405-P501-P260-P264-P270-P307+P311-P321-P405-P501-P210-P233-P240-P241-P242-P243-P280-P303+P361+P353-P370+P378-P403+P235-P501

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

Uses & manufacturing

Uses · 2 items

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

Applications

UsesCholine 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.

Upstream & downstream products

Upstream raw materials

ETHYLENE OXIDEAmmonium chlorideFormaldehyde

Downstream products

(2-Bromoethyl)trimethylammonium bromide1,2-DIOLEOYL-SN-GLYCERO-3-PHOSPHOCHOLINEEthanaminium, 2-(acetyloxy)-N,N,N-trimethyl-, hydroxide (1:1)(2-iodoethyl)trimethylammonium iodide

Additional notes

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