Choline

Not to be confused with chlorine.

Choline
Choline cation skeletal formula
Ball-and-stick model
Names
IUPAC name
2-Hydroxyethyl(trimethyl)azanium[1]
Preferred IUPAC name
2-Hydroxy-N,N,N-trimethylethan-1-aminium
Other names
  • Bilineurine
  • (2-Hydroxyethyl)trimethylammonium
  • 2-Hydroxy-N,N,N-trimethylethanaminium
Identifiers
3D model (JSmol)
1736748
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.487 Edit this at Wikidata
EC Number
  • 200-535-1
324597
KEGG
UNII
  • InChI=1S/C5H14NO/c1-6(2,3)4-5-7/h7H,4-5H2,1-3H3/q+1 checkY
    Key: OEYIOHPDSNJKLS-UHFFFAOYSA-N checkY
  • C[N+](C)(C)CCO
Properties
[(CH3)3NCH2CH2OH]+
Molar mass 104.173 g·mol−1
Appearance Viscous colorless deliquescent liquid (choline hydroxide)[2]
Very soluble (choline hydroxide)[2]
Solubility soluble in ethanol,[2] insoluble in diethylether and chloroform[3] (choline hydroxide)
Structure
Tetrahedral at the nitrogen atom
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Corrosive
GHS labelling:
GHS05: Corrosive
Danger
H314
P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth (blue): no hazard codeFlammability (red): no hazard codeInstability (yellow): no hazard codeSpecial hazard COR: Corrosive; strong acid or base. E.g. sulfuric acid, potassium hydroxide
COR
Lethal dose or concentration (LD, LC):
3–6 g/kg (rat, oral)[2]
Safety data sheet (SDS) 4
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Choline is a cation with the chemical formula [(CH3)3NCH2CH2OH]+.[1][4][5] Choline forms various salts, such as choline chloride and choline bitartrate. It is an essential nutrient for humans and many other animals, and is a structural part of phospholipids and cell membranes.[4][5]

Choline is used to synthesize acetylcholine, a neurotransmitter involved in muscle control and numerous functions of the nervous system.[4][5] Choline is involved in early development of the brain, gene expression, cell membrane signaling, and brain metabolism.[5]

Although humans synthesize choline in the liver, the amount produced naturally is insufficient to meet cellular functions, requiring that some choline be obtained from foods or dietary supplements.[5] Foods rich in choline include meats, poultry, eggs, and other animal-based products, cruciferous vegetables, beans, nuts, and whole grains.[5] Choline is present in breast milk and is commonly added as an ingredient to baby foods.[5]

  1. ^ a b "Choline". PubChem, National Library of Medicine, US National Institutes of Health. 26 October 2024. Retrieved 31 October 2024.
  2. ^ a b c d Cite error: The named reference Kirk 2000 was invoked but never defined (see the help page).
  3. ^ Cite error: The named reference ze was invoked but never defined (see the help page).
  4. ^ a b c "Choline". Micronutrient Information Center, Linus Pauling Institute, Oregon State University, Corvallis. July 2023. Retrieved 31 October 2024.
  5. ^ a b c d e f g "Choline". Office of Dietary Supplements, US National Institutes of Health. 2 June 2022. Retrieved 31 October 2024.