Leonurine
 | This article needs more medical references for verification or relies too heavily on primary sources. (March 2021) |  |
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| Names | |
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| IUPAC name
4-(Diaminomethylideneamino)butyl 4-hydroxy-3,5-dimethoxybenzoate
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.208.686 
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| KEGG | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C14H21N3O5 | |
| Molar mass | 311.338 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
 (what is   ?)
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| Infobox references | |
Leonurine is a pseudoalkaloid that has been isolated from Leonotis leonurus, Leonotis nepetifolia, Leonotis artemisia, Leonurus cardiaca (Motherwort), Leonurus sibiricus, as well as other plants of family Lamiaceae.[citation needed] Leonurine is easily extracted into water.[1]
Chemical synthesis[]
Leonurine can be synthesized starting from eudesmic acid. Reaction with sulfuric acid produces syringic acid. Protection with ethyl chloroformate followed by reaction with thionyl chloride SOCl2 and then tetrahydrofuran yields 4-carboethoxysyringic acid 4-chloro-1-butyl ester. The chloride is then converted to an amino group via a Gabriel synthesis (with ) followed by (Ing–Manske procedure). The final step is reaction of the amine with salt.
Leonurine synthesis[1]
References[]
- ^ Jump up to: a b "The Leonurine and its preparation". An Hui New Star Pharmaceutical Development Co. 2008. Archived from the original on 2008-05-15. Retrieved 2008-08-28.
Further reading[]
- Cheng KF, Yip CS, Yeung HW, Kong YC (May 1979). "Leonurine, an improved synthesis". Experientia. 35 (5): 571–2. doi:10.1007/BF01960323. PMID 446644. S2CID 22601565.
Categories:
- Alkaloids
- Guanidines
- Benzoate esters
- Phenols
- Phenol ethers