Synthesis of 1-(2,2-Dimethylpropyl)-Cyclopropene (1-DCP) as an Ethylene Antagonist.

Abstract

Ethylene is a gaseous hydrocarbon molecule known as a plant hormone that promotes fruit ripening and senescence. Efficiently controlling ethylene is a central key to maintaining the quality of agricultural products. The current study uncovered a synthetic method for 1-(2,2-dimethylpropyl)-cyclopropene (1-DCP) as a cyclopropene derivative to inhibit ethylene action in fruit ripening and senescence. We synthesized 1-DCP using α-diisobutylene through a two-step process, including allylic chlorination by hypochlorite and HCl, followed by α-elimination of the allylic chloride using a strong base, lithium diethylamide. GC-MS and NMR analyses demonstrated that 1-DCP was synthesized efficiently with 35% yield and 95% purity. When treated as an aqueous emulsion on plants, including persimmon and banana fruits, 1 mM 1-DCP showed effective inhibition of ethylene action by delaying the flesh softening and peel degreening, which are representative phenomena of fruit ripening and senescence induced by ethylene. Our data demonstrated that 1-DCP could be synthesized and used as a sprayable ethylene antagonist for pre- or post-harvest growth regulation in plants and fruits.