Stachydrine Chemical Properties

Melting point:

259-260°

alpha 

D20 +37.8° (c = 1 in water)

Stachydrine Usage And Synthesis

Description

This base occurs in the fruit of Capparis torrnentosa, Citrus grandis and in Stachys tubi/era Naudin. It normally crystallizes as the monohydrate which has m.p. 116-8°C. The specific rotation is [α]>_D- 40.25° (c 4.0, H20). It is soluble in EtOH and H20, insoluble in CHC13 and Et20. The free base is unstable in air and decomposes quite rapidly. The hydrochloride yields colourless crystals from EtOH with m.p. 222°C; [α]²⁰_D - 28.1° (c 4.83, H20); aurichloride, m.p. 232°C; platinichloride, decomposing at 200°C; oxalate, colourless needles, m.p. 105- 7°C and the picrate, m.p. 199-2000 C. The structure is that of the methylbetaine of hygric acid.

Uses

Stachydrine is used for various ethnobotany and ethnomedicinal uses. It can also be used to promote healthy neural development in an unborn baby, as well as to determine the differential effects of post-weaning diet and maternal obesity on mouse liver and brain metabolomes.

Definition

ChEBI: An amino-acid betaine that is trans-4-hydroxy-D-proline zwitterion in which both of the hydrogens attached to the nitrogen have been replaced by methyl groups.

References

Schultz, Trier., Z. physiol. Chern., 67, 59 (1910)
Steenbock., J. Bioi. Chern., 35, 1 (1918)
Kuhn, Brydowna., Ber., 70, 1333 (1937)
Henry, King.,J. Chern. Soc., 2866 (1950)
Cornforth, Henry., ibid, 601 (1952)
Paudler, Wagner., Chern. & Ind., 1693 (1963)