12-09952. Turicine [Archived]

Nomenclature

CAS number: 515-24-2
(2R-cis)-2-Carboxy-4-hydroxy-1,1-dimethylpyrrolidinium inner salt; d-N,N-dimethyl-4-hydroxypyrrolidine-2-carboxylic acid betaine; d-4-hydroxyproline betaine; d-4-hydroxystachydrine; allohydroxy-d-proline betaine.
C7H13NO3; mol wt 159.18.
C 52.82%, H 8.23%, N 8.80%, O 30.15%.

Description and 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).

Chemical structure

Properties

Crystals from water, ethanol and ethyl acetate, mp 259-260°. [α]D20 +37.8° (c = 1 in water).

Derivative

Monohydrate.

Properties

Efflorescent prisms from water. Sweet taste. Less sol in water than betonicine; slightly sol in alcohol. Neutral to litmus.

Derivative

Hydrochloride.
C7H13NO3.HCl; mol wt 195.64.
C 42.97%, H 7.21%, N 7.16%, O 24.53%, Cl 18.12%.

Properties

Needles from abs alcohol, dec 222°. [α]D24 +25° (c = 7).

Derivative

Aurichloride.
C7H13NO3.HAuCl4; mol wt 498.97.
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°.

Derivative

Platinichloride monohydrate.
(C7H13NO3)2.H2PtCl6.H2O; mol wt 746.19.
C 22.53%, H 4.05%, N 3.75%, O 15.01%, Pt 26.14%, Cl 28.51%.

Properties

Dec 223°.

Derivative

l-Turicine.

Nomenclature

Allohydroxy-l-proline betaine.

Properties

Crystals, mp 252-254°. [α]D20 39.0° (c = 1 in water). Ref: Friess et al., J. Am. Chem. Soc. 79, 459 (1957).

Status

This monograph has been retired and is no longer subject to revision or update.