Leonurine hydrochloride CAS 24697-74-3
Leonurine hydrochloride Basic information
| Product Name: | Leonurine hydrochloride |
| Synonyms: | Leonurine 4-Guanidino-1-butanol syringate;SCM-198;leonurine hydrochloride;4-Guanidino-1-butanol syringate;4-(diaminomethylideneamino)butyl 4-hydroxy-3,5-dimethoxy-benzoate hydrochloride;Leonurine;LEONURINE HCL;4-Hydroxy-3,5-dimethoxybenzoic acid 4-guanidinobutyl ester |
| CAS: | 24697-74-3 |
| MF: | C14H21N3O5 |
| MW: | 311.33 |
| EINECS: | 683-174-6 |
| Product Categories: | phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;chemical reagent;pharmaceutical intermediate |
| Mol File: | 24697-74-3.mol |
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 |
| 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 | 18780-70-6 867-44-7 24697-74-3 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 | Leonurine (10 mg/kg/d, p.o.) significantly increases the expressions of PPARγ, LXRα, ABCA1 and ABCG1, and decreases both TG and TC levels in serum of mice[1]. Leonurine hydrochloride (50, 100, 200 mg/kg) improves intracellular lipid accumulation via activating AMPK/SREBP1 pathway, enhances biochemical parameters, reduces hepatic lipoperoxide and increases antioxidant levels in mice[2]. Leonurine (20?mg/kg, p.o.) ameliorates osteoarthritis development in mouse DMM model[3]. |
| References | Kubota, Nakajima., Nippon Yakubusugaku Zasshi., 163 (1930) Goto et al., Tetrahedron Lett., 545 (1962) Total synthesis: Kishi et al., Tetrahedron Lett., 637 (1968) |
Leonurine hydrochloride Preparation Products And Raw materials
| Raw materials | 2-Methyl-2-thiopseudourea sulfate-->Syringic acid-->Ethyl chloroformate-->4'-aminobutyl-4-hydroxy-3,5-dimethoxybenzoate-->Benzoic acid, 4-hydroxy-3,5-dimethoxy-, 4-aminobutyl ester |
