515-24-2

Basic information

• Product Name: Stachydrine
• Synonyms: Stachydrine;turicine;cis-4-hydroxy-D-proline betaine
• CAS NO: 515-24-2
• Molecular Formula: C₇H₁₃NO₃
• Molecular Weight: 159.18302
• Mol File: 515-24-2.mol
• Article Data: 3

Chemical Properties

• Melting Point: 259-260°
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• CAS DataBase Reference: Stachydrine(CAS DataBase Reference)
• NIST Chemistry Reference: Stachydrine(515-24-2)
• EPA Substance Registry System: Stachydrine(515-24-2)

Safety Data

• Hazardous Substances Data: 515-24-2(Hazardous Substances Data)

Usage

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]20D - 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.

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betaine that is trans-4-hydroxy-D-proline zwitterion in which both of the hydrogens attached to the nitrogen have been replaced by methyl groups.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

InChI:InChI=1/C7H13NO3/c1-8(2)4-5(9)3-6(8)7(10)11/h5-6,9H,3-4H2,1-2H3/t5-,6-/m1/s1

Upstream product

• 51-35-4 4-hydroxyproline 
• 74-88-4 methyl iodide 

Relevant articles and documents

Characterization of amino acid-derived betaines by electrospray ionization tandem mass spectrometry

Betaines belong to the naturally occurring osmoprotectants or compatible solutes present in a variety of plants, animals and microorganisms. In recent years, metabolomic techniques have been emerging as a fundamental tool for biologists because the constellation of these molecules and their relative proportions provide with information about the actual biochemical condition of a biological system. Therefore, identification and characterization of biologically important betaines are crucial, especially for metabolomic studies. Most of the natural betaines are derived from amino acids and related homologues. Although, theoretically, all the amino acids can be converted to corresponding betaines by simple methylation of the amine group, only a few of the amino acid-derived betaines were fully characterized in the literature. Here, we report a combined electrospray ionization tandem and high-resolution mass spectrometry study of all the betaines derived from amino acids, including the isomeric betaines. The decomposition pathway of protonated, sodiated and potassiated molecule ions that enable unambiguous characterization of the betaines including the isomeric betaines and overlapping ionic species of different betaines is distinctive. Copyright

ISOLATION, STRUCTURE DETERMINATION, SYNTHESIS AND BIOACTIVITY OF DAMIPIPECOLIN AND DAMITURICIN

Two new bromopyrrole alkaloids, compounds (1) and (2), have been isolated from the Mediterranean sponge Axinella damicυrnis, and their structure established through spectroscopic methods. Compounds (1) and (2 )display a modulating effect of the serotonin