| Identification | Back Directory | [Name]
Leonurine hydrochloride | [CAS]
24697-74-3 | [Synonyms]
SCM-198
Leonurin
Leonurine
LEONURINE HCL
Leonurine (SCM-198)
leonurine hydrochloride
4-Guanidinobutyl syringate
4-Guanidino-1-butanol syringate
Leonurine hydrochloride USP/EP/BP
Leonurine Hydrochloride Monohydrate
Syringic acid ζ-guanidinobutyl ester
Leonurine
4-Guanidino-1-butanol syringate
4-Guanidinobutyl 4-hydroxy-3,5-diMethoxybenzoate
Leonurine, 98%, from Leonurus artemisia (Laur.) S. Y. Hu F
4-Hydroxy-3,5-dimethoxybenzoic acid 4-guanidinobutyl ester
4-(diaminomethylideneamino)butyl 4-hydroxy-3,5-dimethoxybenzoate
Benzoic acid, 4-hydroxy-3,5-dimethoxy-, 4-[(aminoiminomethyl)amino]butyl ester
4-(diaminomethylideneamino)butyl 4-hydroxy-3,5-dimethoxy-benzoate hydrochloride
3,5-Dimethoxy-4-hydroxy-benzoic acid (4-guanidino)-1-butyl ester Hydrochloride Monohydrate | [EINECS(EC#)]
683-174-6 | [Molecular Formula]
C14H21N3O5 | [MDL Number]
MFCD09839432 | [MOL File]
24697-74-3.mol | [Molecular Weight]
311.33 |
| Chemical Properties | Back Directory | [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) | [form ]
powder | [pka]
8.26±0.25(Predicted) | [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 |
| Hazard Information | Back Directory | [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. | [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. | [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]
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]. | [storage]
Store at RT | [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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