Record Information
Version1.0
Creation date2015-10-09 22:28:45 UTC
Update date2017-01-19 02:36:13 UTC
FoodComEx IDPC000134
FoodDB RecordFDB000710
Chemical Information
NameCholine
DescriptionCholine, also known as bilineurine, is an organic compound containing a N, N, N-trimethylethanolammonium cation. Choline is an extremely weak basic (essentially neutral) compound (based on its pKa). Choline is a basic constituent of lecithin that is found in many plants and animal organs. It is important as a precursor of acetylcholine, as a methyl donor in various metabolic processes, and in lipid metabolism. In plants, the first step in de novo biosynthesis of choline involves the decarboxylation of serine into ethanolamine, which is catalyzed by a serine decarboxylase. The synthesis of choline from ethanolamine involves three consecutive N-methylation steps catalyzed by a methyl transferase. In terms of human health, choline is now considered to be an essential vitamin. While humans can synthesize small amounts (by converting phosphatidylethanolamine to phosphatidylcholine), it must be consumed in the diet to maintain health. Required levels are between 425 mg/day (female) and 550 mg/day (male). Milk, eggs, liver, and peanuts are especially rich in choline. Most choline is found in phospholipids, namely phosphatidylcholine or lecithin. Choline can be oxidized to form betaine, which is a methyl source for many reactions (i.e. conversion of homocysteine into methionine). Lack of sufficient amounts of choline in the diet can lead to fatty liver disease and general liver damage. This arises from the lack of VLDL , which is necessary to transport fats away from the liver. Choline deficiency also leads to elevated serum levels of alanine amino transferase and is associated with increased incidence of liver cancer.
CAS Number62-49-7
Structure
Thumb
Synonyms
SynonymSource
(2-Hydroxyethyl)trimethyl ammoniumbiospider
(2-Hydroxyethyl)trimethylammoniumHMDB
(beta-Hydroxyethyl)trimethylammoniumbiospider
2-Hydroxy-N,N,N-trimethyl-ethanaminiumHMDB
2-Hydroxy-N,N,N-trimethylethanaminiumHMDB
2-Hydroxy-N,N,N-trimethylethanaminium(1+), 9CIdb_source
2-Hydroxyethyl-trimethylazaniumbiospider
Amanitin?db_source
Arachinedb_source
Araquinedb_source
Bilineurinedb_source
Choline (8CI)biospider
Choline cationHMDB
Choline ionbiospider
CholinumHMDB
Ethanaminium, 2-hydroxy-N,N,N-trimethyl- (9CI)biospider
HormoclineHMDB
N-TrimethylethanolamineChEBI
N,N,N-Trimethylethanol-ammoniumbiospider
N,N,N-TrimethylethanolammoniumHMDB
NeocolinaHMDB
Sincalindb_source
Sinkalindb_source
TrimethylethanolamineChEBI
Chemical FormulaC5H14NO
IUPAC name(2-hydroxyethyl)trimethylazanium
InChI IdentifierInChI=1S/C5H14NO/c1-6(2,3)4-5-7/h7H,4-5H2,1-3H3/q+1
InChI KeyOEYIOHPDSNJKLS-UHFFFAOYSA-N
Isomeric SMILESC[N+](C)(C)CCO
Average Molecular Weight104.1708
Monoisotopic Molecular Weight104.107539075
Chemical Taxonomy
ClassificationNot classified
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting Point302-303 oC (Chloride salt)
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 300 mg
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
Not Available