Turicine

Title: Turicine
CAS Registry Number: 515-24-2
CAS Name: (2R-cis)-2-Carboxy-4-hydroxy-1,1-dimethylpyrrolidinium inner salt
Additional Names: d-N,N-dimethyl-4-hydroxypyrrolidine-2-carboxylic acid betaine; d-4-hydroxyproline betaine; d-4-hydroxystachydrine; allohydroxy-D-proline betaine
Molecular Formula: C7H13NO3
Molecular Weight: 159.18
Percent Composition: C 52.82%, H 8.23%, N 8.80%, O 30.15%
Literature References: Isolated from Stachys (betonica) officinalis L., Trev., and Stachys sylvatica L., Wald-Ziest, Labiatae: Küng, Trier, Z. Physiol. Chem. 85, 209 (1913); Guggenheim, Die biogenen Amine (S. Karger, New York, 1951) p 247. Stereoisomeric with betonicine. Prepd by the reaction of allohydroxy-D-proline with methyl iodide and silver oxide: Patchett, Witkop, J. Am. Chem. Soc. 79, 185 (1957).
Properties: Crystals from water, ethanol and ethyl acetate, mp 259-260°. [a]D20 +37.8° (c = 1 in water).
Melting point: mp 259-260°
Optical Rotation: [a]D20 +37.8° (c = 1 in water)
Derivative Type: Monohydrate
Properties: Efflorescent prisms from water. Sweet taste. Less sol in water than betonicine; slightly sol in alcohol. Neutral to litmus.
Derivative Type: Hydrochloride
Molecular Formula: C7H13NO3.HCl
Molecular Weight: 195.64
Percent Composition: C 42.97%, H 7.21%, N 7.16%, O 24.53%, Cl 18.12%
Properties: Needles from abs alcohol, dec 222°. [a]D24 +25° (c = 7).
Optical Rotation: [a]D24 +25° (c = 7)
Derivative Type: Aurichloride
Molecular Formula: C7H13NO3.HAuCl4
Molecular Weight: 498.97
Percent Composition: C 16.85%, H 2.83%, N 2.81%, O 9.62%, Au 39.47%, Cl 28.42%
Properties: Scaly clusters from water, mp 232°.
Melting point: mp 232°
Derivative Type: Platinichloride monohydrate
Molecular Formula: (C7H13NO3)2.H2PtCl6.H2O
Molecular Weight: 746.19
Percent Composition: C 22.53%, H 4.05%, N 3.75%, O 15.01%, Pt 26.14%, Cl 28.51%
Properties: Dec 223°.
Derivative Type: L-Turicine
Additional Names: Allohydroxy-L-proline betaine
Properties: Crystals, mp 252-254°. [a]D20 -39.0° (c = 1 in water). Ref: Friess et al., J. Am. Chem. Soc. 79, 459 (1957).
Melting point: mp 252-254°
Optical Rotation: [a]D20 -39.0° (c = 1 in water)
Status: This monograph has been retired and is no longer subject to revision or update.
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