Leonurine

Leonurine

Names
IUPAC name 4-(Diaminomethylideneamino)butyl 4-hydroxy-3,5-dimethoxybenzoate
Identifiers
CAS Number	24697-74-3 N
3D model (Jmol)	Interactive image
ChemSpider	141828 Y
ECHA InfoCard	100.208.686
KEGG	C16985 Y
PubChem	161464
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) Y Key: WNGSUWLDMZFYNZ-UHFFFAOYSA-N Y InChI=1/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) Key: WNGSUWLDMZFYNZ-UHFFFAOYAI
SMILES O=C(OCCCC/N=C(\N)N)c1cc(OC)c(O)c(OC)c1
Properties
Chemical formula	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 YN ?)
Infobox references

Leonurine is a pseudoalkaloid 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

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.