Choline

Choline
Names
	IUPAC name 2-Hydroxyethyl(trimethyl)azanium
	Preferred IUPAC name 2-Hydroxy-N,N,N-trimethylethan-1-aminium
	Other names Bilineurine; (2-Hydroxyethyl)trimethylammonium; 2-Hydroxy-N,N,N-trimethylethanaminium;
Identifiers
CAS Number	62-49-7 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1736748
ChEBI	CHEBI:15354 ;
ChEMBL	ChEMBL920 ;
ChemSpider	299 ;
DrugBank	DB00122 ;
ECHA InfoCard	100.000.487
EC Number	200-535-1;
Gmelin Reference	324597
IUPHAR/BPS	4551;
KEGG	C00114 ;
PubChem CID	305;
UNII	N91BDP6H0X ;
CompTox Dashboard (EPA)	DTXSID8043789 ;
	InChI InChI=1S/C5H14NO/c1-6(2,3)4-5-7/h7H,4-5H2,1-3H3/q+1 Key: OEYIOHPDSNJKLS-UHFFFAOYSA-N ;
	SMILES C[N+](C)(C)CCO;
Properties
Chemical formula	[(CH3)3NCH2CH2OH]+
Molar mass	104.173 g·mol−1
Appearance	Viscous colorless deliquescent liquid (choline hydroxide)
Solubility in water	Very soluble (choline hydroxide)
Solubility	soluble in ethanol, insoluble in diethylether and chloroform (choline hydroxide)
Structure
Coordination geometry	Tetrahedral at the nitrogen atom
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Corrosive
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H314
Precautionary statements	P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P405, P501
NFPA 704 (fire diamond)	COR
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	3–6 g/kg (rat, oral)
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). verify (what is ?) Infobox references

Choline (/ˈkoʊliːn/ KOH-leen)^[4] is an essential nutrient for humans and many other animals, which was formerly classified as a B vitamin (vitamin B₄).^[5]^[6] It is a structural part of phospholipids and a methyl donor in metabolic one-carbon chemistry. The compound is related to trimethylglycine in the latter respect. It is a cation with the chemical formula [(CH₃)₃NCH₂CH₂OH]⁺. Choline forms various salts, for example choline chloride and choline bitartrate.

^ "Choline".
^ ^a ^b ^c ^d Cite error: The named reference :2 was invoked but never defined (see the help page).
^ Cite error: The named reference ze was invoked but never defined (see the help page).
^ "Choline". Lexico Dictionaries. Archived from the original on 24 October 2019. Retrieved 9 November 2019.
^ "Choline". Micronutrient Information Center, Linus Pauling Institute, Oregon State University. February 2015. Retrieved 11 November 2019.
^ Choline. The Metabolomics Innovation Centre, University of Alberta, Edmonton, Canada. 17 August 2016. Retrieved 13 September 2016. {{cite encyclopedia}}: |website= ignored (help)

[pubchem-1] "Choline".

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[4] "Choline". Lexico Dictionaries. Archived from the original on 24 October 2019. Retrieved 9 November 2019.

[lpi-5] "Choline". Micronutrient Information Center, Linus Pauling Institute, Oregon State University. February 2015. Retrieved 11 November 2019.

[Choline_HMDB-6] Choline. The Metabolomics Innovation Centre, University of Alberta, Edmonton, Canada. 17 August 2016. Retrieved 13 September 2016. {{cite encyclopedia}}: |website= ignored (help)

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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
CAS Number	62-49-7^Y
3D model (JSmol)	Interactive image
Beilstein Reference	1736748
ChEBI	CHEBI:15354^Y
ChEMBL	ChEMBL920^Y
ChemSpider	299^Y
DrugBank	DB00122^Y
ECHA InfoCard	100.000.487
EC Number	200-535-1
Gmelin Reference	324597
IUPHAR/BPS	4551
KEGG	C00114^Y
PubChem CID	305
UNII	N91BDP6H0X^Y
CompTox Dashboard (EPA)	DTXSID8043789
InChI InChI=1S/C5H14NO/c1-6(2,3)4-5-7/h7H,4-5H2,1-3H3/q+1^Y Key: OEYIOHPDSNJKLS-UHFFFAOYSA-N^Y
SMILES C[N+](C)(C)CCO
Properties
Chemical formula	[(CH₃)₃NCH₂CH₂OH]⁺
Molar mass	104.173 g·mol⁻¹
Appearance	Viscous colorless deliquescent liquid (choline hydroxide)^[2]
Solubility in water	Very soluble (choline hydroxide)^[2]
Solubility	soluble in ethanol,^[2] insoluble in diethylether and chloroform^[3] (choline hydroxide)
Structure
Coordination geometry	Tetrahedral at the nitrogen atom
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Corrosive
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H314
Precautionary statements	P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P405, P501
NFPA 704 (fire diamond)	COR
Lethal dose or concentration (LD, LC):
LD₅₀ (median dose)	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). Y verify (what is ^YN ?) Infobox references

Choline

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