Leonurine

Leonurine
Names
IUPAC name
4-(Diaminomethylideneamino)butyl 4-hydroxy-3,5-dimethoxybenzoate
Identifiers
24697-74-3 N
ChemSpider 141828 YesY
Jmol interactive 3D Image
KEGG C16985 YesY
PubChem 161464
Properties
C14H21N3O5
Molar mass 311.34 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Leonurine is an alkaloid that has been isolated from Leonotis leonurus (Lion's tail), Leonotis nepetifolia, Leonotis artemisia, Leonurus cardiaca (Motherwort), Leonurus sibiricus, as well as other plants of family Lamiaceae. 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 potassium pthalimide) followed by hydrazinolysis (Ing–Manske procedure). The final step is reaction of the amine with S-methylisothiourea hemisulfate salt.[2]

Leonurine synthesis[1]

References

  1. 1 2 "The Leonurine and its preparation". An Hui New Star Pharmaceutical Development Co. 2008. Retrieved 2008-08-28.
  2. ↑ "S-Methylisothiourea sulfate structure.". ChemSpider (RSC). 2014. Retrieved 2014-07-09.

Further reading

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