ChemicalBook > CAS DataBase List > Leonurine hydrochloride

Leonurine hydrochloride

Product Name: Leonurine hydrochloride
CAS No.: 24697-74-3
Chemical Name: Leonurine hydrochloride
Synonyms: Leonurine;Leonurin;SCM-198;LEONURINE HCL;Leonurine (7CI);Leonurine (SCM-198);leonurine hydrochloride;Leonurine, 10 mM in DMSO;4-Guanidinobutyl syringate;4-Guanidino-1-butanol syringate
CBNumber: CB1547245
Molecular Formula: C14H21N3O5
Formula Weight: 311.33
MOL File: 24697-74-3.mol

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Leonurine hydrochloride Property

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

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Safety

Hazard Codes: Xi
Risk Statements: 36/37/38
Safety Statements: 26-24/25
WGK Germany: 3
HS Code: 29399990

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: SML0670
Product name: Leonurine
Purity: ≥98% (HPLC)
Packaging: 5mg
Price: $119.7
Updated: 2025/07/31

Sigma-Aldrich

Product number: SML0670
Product name: Leonurine
Purity: ≥98% (HPLC)
Packaging: 25mg
Price: $347.2
Updated: 2025/07/31

Cayman Chemical

Product number: 26850
Product name: Leonurine
Packaging: 10mg
Price: $49
Updated: 2024/03/01

Cayman Chemical

Product number: 26850
Product name: Leonurine
Packaging: 250mg
Price: $830
Updated: 2024/03/01

Cayman Chemical

Product number: 26850
Product name: Leonurine
Packaging: 50mg
Price: $216
Updated: 2024/03/01

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Leonurine hydrochloride Chemical Properties,Usage,Production

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

Preparation Products

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View Lastest Price from Leonurine hydrochloride manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD

Product: Leonurine hydrochloride 24697-74-3
Price: US $0.00/KG
Min. Order: 1KG
Purity: 98%min
Supply Ability: 30tons/month
Release date: 2023-01-11

Changsha Staherb Natural Ingredients Co., Ltd.

Product: Leonurine hydrochloride 24697-74-3
Price: US $0.00/KG
Min. Order: 1KG
Purity: ≥98% HPLC&GC
Supply Ability: 1000KG
Release date: 2022-09-30

HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD

Product: Leonurine hydrochloride 24697-74-3
Price: US $100.00-75.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 5000Ton
Release date: 2024-08-13

24697-74-3, Leonurine hydrochlorideRelated Search:

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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

Syringic acid ζ-guanidinobutyl ester

3,5-Dimethoxy-4-hydroxy-benzoic acid (4-guanidino)-1-butyl ester Hydrochloride Monohydrate

4-Guanidinobutyl syringate

4-Guanidinobutyl 4-hydroxy-3,5-diMethoxybenzoate

Leonurine, 98%, from Leonurus artemisia (Laur.) S. Y. Hu F

Leonurine Hydrochloride Monohydrate

Benzoic acid, 4-hydroxy-3,5-dimethoxy-, 4-[(aminoiminomethyl)amino]butyl ester

Leonurin

4-(diaminomethylideneamino)butyl 4-hydroxy-3,5-dimethoxybenzoate

Leonurine (SCM-198)

Leonurine hydrochloride USP/EP/BP

Leonurine (7CI)

Leonurine, 10 mM in DMSO

24697-74-3

4697-74-3

C14H21O5N3HClH2O

C14H22ClN3O5

C14H21O5N3

C14H24ClN3O6

phytochemical

reference standards from Chinese medicinal herbs (TCM).

standardized herbal extract

chemical reagent

pharmaceutical intermediate