Leonurine hydrochloride Chemical Properties

Melting point:

238 °C

Boiling point:

496.7±55.0 °C(Predicted)

Density 

1.29±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

solubility 

DMSO: soluble2mg/mL, clear (warmed)

pka

8.26±0.25(Predicted)

form 

powder

color 

white to beige

Stability:

Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month.

InChI

InChI=1S/C14H21N3O5/c1-20-10-7-9(8-11(21-2)12(10)18)13(19)22-6-4-3-5-17-14(15)16/h7-8,18H,3-6H2,1-2H3,(H4,15,16,17)

InChIKey

WNGSUWLDMZFYNZ-UHFFFAOYSA-N

SMILES

C(OCCCCNC(N)=N)(=O)C1=CC(OC)=C(O)C(OC)=C1

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-24/25

WGK Germany 

3

HS Code 

29399990

Leonurine hydrochloride Usage And Synthesis

Description

An amorphous alkaloid, leonurine has been obtained from the leaves of Leonurus sibiricus L. and is characterized as the crystalline hydrochloride hydra te, m.p. 19l-4°C. Hydrolysis yields syringic acid and Q-hydroxybutylguanidine. The total synthesis of the alkaloid has been achieved, confirming the above structure.

Chemical Properties

White crystalline powder, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from motherwort.

Uses

Leonurine is a pseudoalkaloid that has been isolated from Leonotis leonurus. A natural product with antioxidant, anti-inflammatory and cardioprotective properties for the treatment of wild variety of conditions including stroke, cerebral thrombosis and cardiovascular diseases.

Uses

Leonurine Hydrochloride is an alkaloid plant extract used in the treatment of uterine disorders. Used in the modification of uterine contractions in rats.

Definition

ChEBI: Leonurine is a trihydroxybenzoic acid.

Synthesis

GENERAL STEPS: To a stirred solution of 4-amino-butyl 4-hydroxy-3,5-dimethoxybenzoate (5.6 g, 20 mmol) in N,N-dimethylformamide (DMF, 15 mL) was slowly added S-methylisothiourea sulfate (15% aqueous solution, 23.1 g, 25 mmol). The reaction mixture was heated to 120 °C and kept at reflux with continuous stirring for 6 hours. The progress of the reaction was monitored by high performance liquid chromatography (HPLC) and the heating was stopped after confirming the complete consumption of raw materials. The solvent was evaporated under reduced pressure and the residue was dissolved in an appropriate amount of water. Sodium bicarbonate (NaHCO3, 2.31 g, 27.5 mmol) was added to the aqueous solution in batches, and a large amount of solid precipitated during stirring. The solid product was collected by filtration and washed with an appropriate amount of water, and dried to give 4-guanidinobutyl 4-hydroxy-3,5-dimethoxybenzoate (Leonurine, 4.0 g, 65% yield) as a white solid. The structure of the product was confirmed by nuclear magnetic resonance hydrogen spectroscopy (1H NMR, 400 MHz, with trifluoroacetic acid as solvent): δ 7.38 (s, 2H), 4.42 (t, 2H, J=6.2 Hz), 3.91 (s, 6H), 3.30 (t, 2H, J=6.7 Hz), 1.89 (dt, 2H, J=13.3,6.5 Hz), 1.83- 1.71 (m, 2H).

in vivo

References

Kubota, Nakajima., Nippon Yakubusugaku Zasshi., 163 (1930)
Goto et al., Tetrahedron Lett., 545 (1962)
Total synthesis:
Kishi et al., Tetrahedron Lett., 637 (1968)

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