Choline bitartrate

Choline bitartrate is an organic compound with the chemical formula [(CH3)3NCH2CH2OH]+HOOC−CH(OH)−CH(OH)−COO. It is a white crystalline powder with an acid taste. It is hygroscopic when exposed to air. Modern texts refer to the choline salt of the natural form of tartaric acid, that is, the salt called choline dextrobitartrate, choline (2R,3R)-bitartrate or choline L-(+)-bitartrate.

Choline (2R,3R)-bitartrate
Names
IUPAC name
Choline (2R,3R)-bitartrate
Systematic IUPAC name
(2-Hydroxyethyl)trimethylaminium hydrogen (2R,3R)-tartrate
Other names
  • Choline hydrogen L-(+)-tartrate
  • Choline (2R,3R)-tartrate (1:1)
  • (2-Hydroxyethyl)trimethylammonium hydrogen (2R,3R)-tartrate
  • (2-Hydroxyethyl)trimethylammonium L-(+)-bitartrate
  • (2-Hydroxyethyl)trimethylammonium (2R,3R)-bitartrate
  • (2-Hydroxyethyl)trimethylammonium L-(+)-tartrate salt (1:1)
Identifiers
3D model (JSmol)
ECHA InfoCard 100.001.604
UNII
  • : InChI=1S/C5H14NO.C4H6O6/c1-6(2,3)4-5-7;5-1(3(7)8)2(6)4(9)10/h7H,4-5H2,1-3H3;1-2,5-6H,(H,7,8)(H,9,10)/q+1;/p-1/t;1-,2-/m.1/s1
    Key: QWJSAWXRUVVRLH-LREBCSMRSA-M
  • Non-isomeric: C[N+](C)(C)CCO.C(C(C(=O)[O-])O)(C(=O)O)O
  • Isomeric: C[N+](C)(C)CCO.[C@@H]([C@H](C(=O)[O-])O)(C(=O)O)O
Properties
C9H19NO7
Molar mass 253.251 g·mol−1
Appearance White crystalline powder
Odor Odorless or faint trimethylamine-like odor
Melting point 147–153 °C (297–307 °F; 420–426 K)
Solubility Water (slightly), ethanol (slightly), DMSO (slightly), methanol (slightly, when heated); insoluble in diethyl ether, chloroform and benzene
Structure
Tetrahedral molecular geometry at the nitrogen atom
Hazards
Lethal dose or concentration (LD, LC):
200 to 400 grams (as choline, human, estimated)
Related compounds
Other anions
Other cations
N,N-Dimethylethanolamine bitartrate
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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