Quaternary ammonium derivatives of natural terpenoids. Synthesis and properties

In this review, we summarized and analyzed the literature data (from 1963 to March, 2014) on the synthesis and properties of quaternary ammonium derivatives of citronellal, menthol, camphor, lambertian acid, dehydroabietic acid, levopimaric acid, isosteviol, steviol, betulinic acid, dihydrobetulinic...

Full description

Saved in:
Bibliographic Details
Published in:Russian chemical bulletin 2014-09, Vol.63 (9), p.1884-1900
Main Authors: Kataev, V. E., Strobykina, I. Yu, Zakharova, L. Ya
Format: Article
Language:English
Subjects:
Acids
Aqueous solutions
Camphor
Chemical synthesis
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Citronellal
Derivatives
Inorganic Chemistry
Ionic liquids
Ions
Lipids
Liposomes
Menthol
Organic Chemistry
Properties (attributes)
Reviews
Steroids
Terpenes
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:In this review, we summarized and analyzed the literature data (from 1963 to March, 2014) on the synthesis and properties of quaternary ammonium derivatives of citronellal, menthol, camphor, lambertian acid, dehydroabietic acid, levopimaric acid, isosteviol, steviol, betulinic acid, dihydrobetulinic acid, platanic acid, oleanolic acid, ursolic acid, and polyprenols. Functionalization of terpenoids with ammnoium groups offers them new properties, such as cholinotropic, antiviral, and antimicrobial activities, or transforms them into chiral ionic liquids having a practical potential for application as chiral phasetransfer catalysts. The synthesis of ammonium derivatives of terpenoids possessing properties of cationic lipids or dimeric bis-quaternary ammonium surfactants was proved to have a promising outlook. A specific attention was paid to the method developed for transformation of any hydrophobic terpenoid or steroid into an amphiphilic water-soluble compound self-organized in the aqueous medium into vesicles (liposomes) forming cell-penetrating complexes with DNA.
ISSN:1066-5285
1573-9171
DOI:10.1007/s11172-014-0680-x