Leonurine

Base Information

• Chemical Name: Leonurine
• CAS No.: 24697-74-3
• Molecular Formula: C14H21N3O5
• Molecular Weight: 311.338
• Hs Code.: 29399990
• European Community (EC) Number: 683-174-6
• UNII: 09Q5W34QDA
• DSSTox Substance ID: DTXSID70179434
• Nikkaji Number: J19.938I
• Wikipedia: Leonurine
• Wikidata: Q410290
• Metabolomics Workbench ID: 123269
• ChEMBL ID: CHEMBL1290284
• Mol file: 24697-74-3.mol

Synonyms:4-guanidino-n-butyl syringate;leonurine;SCM-198;SCM198

Chemical Property of Leonurine

Chemical Property:

• Appearance/Colour: brown powder
• Melting Point: 191-193oC
• Boiling Point: 531.6 °C at 760 mmHg
• PKA: 8.26±0.25(Predicted)
• Flash Point: 275.3 °C
• PSA: 126.89000
• Density: 1.29 g/cm³
• LogP: 2.02040
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble2mg/mL, clear (warmed)
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 311.14812078
• Heavy Atom Count: 22
• Complexity: 360

Purity/Quality:

99% ^*data from raw suppliers

Leonurine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=CC(=C1O)OC)C(=O)OCCCCN=C(N)N
• 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.

Technology Process of Leonurine

There total 14 articles about Leonurine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

4-(2,3-bis(tert-butoxycarbonyl)guanidino)butyl 4-hydroxy-3,5-dimethoxybenzoate → Leonurine (24697-74-3,7097-09-8)

Guidance literature:

With zinc dibromide; In dichloromethane; at 20 ℃;

DOI:10.1016/j.ejmech.2020.112469

Reference yield: 65.0%

Leonuramin (18780-70-6) + S-Methylisothiourea sulfate (867-44-7,147895-43-0) → Leonurine (24697-74-3,7097-09-8)

Guidance literature:

In water; N,N-dimethyl-formamide; at 120 ℃; for 6h;

DOI:10.1016/j.cclet.2017.03.041

Reference yield: 65.0%

S-methylisothiourea hemisulphate (147895-43-0) + Leonuramin (18780-70-6) → Leonurine (24697-74-3,7097-09-8)

Guidance literature:

In water; N,N-dimethyl-formamide; at 120 ℃; for 6h;

upstream raw materials:

Leonuramin

N,N'-bis-Boc-S-methyl-isothiourea

4-ethoxycarbonyloxy-3,5-dimethoxy-benzoyl chloride

S-methylisothiourea hemisulphate

Downstream raw materials:

leonurine-O-glucuronide

Refernces

• 1、 Liu, Junkai,Luo, Shanshan,Ma, Fenfen,Xu, Shengtao,Zhu, Yi Zhun. "Design and synthesis of novel SCM-198 analogs as cardioprotective agents: Structure-activity relationship studies and biological evaluations". . . Retrieved 2020/06/03.
• 2、 -. "Synthetic method for leonurine". . . Retrieved 2017/07/21.