 | |||
| |||
| Names | |||
|---|---|---|---|
| Preferred IUPAC name 1-Methylcycloprop-1-ene | |||
| Identifiers | |||
3D model (JSmol) | |||
| Abbreviations | 1-MCP | ||
| ChEBI | |||
| ChemSpider |
| ||
| ECHA InfoCard | 100.130.871 | ||
| UNII | |||
| |||
| |||
| Properties | |||
| C4H6 | |||
| Molar mass | 54.092 g·mol−1 | ||
| Boiling point | 12 °C (54 °F; 285 K)(approx)[1] | ||
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |||
1-Methylcyclopropene (1-MCP) is acyclopropene derivative used as a syntheticplant growth regulator. It is structurally related to the natural plant hormoneethylene and it is used commercially to slow down the ripening of fruit and to help maintain the freshness ofcut flowers.[2]
1-Methylcyclopropene is synthesized by the reaction of methallyl chloride andphenyllithium, which functions as a base:
The phenyllithium should be free of lithium halides. The corresponding reaction ofallyl chloride and phenyllithium main affords cyclopropylbenzene.[3]
Methylcyclopropene can refer to either of twoisomers,1-methylcyclopropene covered in this article, or3-methylcyclopropene[4] which is not covered in this article. 2-methylcyclopropene would be an incorrect name for 1-methylcyclopropene. Also note:methylcyclopropane is yet a differentchemical compound, which is acycloalkane with the formula C4H8.
Ethylene is a gas acting at trace levels (typically between a few tenths and a few thousandsppm in the gas atmosphere) throughout the life of a plant by stimulating or regulating various processes such as theripening ofclimacteric fruit, the opening of flowers (dehiscence process), and the shedding of leaves (abscission process).[5][6] Themechanism of action of 1-MCP involves its tightly binding to theethylene receptor in plants, thereby blocking the effects of ethylene (competitive inhibitor).[7][8]
1-MCP is used commercially to maintain the freshness of ornamental plants and flowers and preventing the ripening of fruits. It is used in enclosed sites, such as coolers, truck trailers, greenhouses, storage facilities, and shipping containers.[9]
Under the brand name EthylBloc, 1-MCP was approved in 1999 by theU.S. Environmental Protection Agency for use on ornamental crops.[10] For cut flowers, potted flowers, and bedding, nursery and foliage plants, 1-MCP prevents or delays wilting, leaf yellowing, opening, and death.[11][12]
Under the brand nameSmartFresh, 1-MCP is used in the agriculture industry by growers, packers, and shippers to prevent or delay the natural ripening process. The use of 1-MCP in agricultural products including apples, kiwifruit, tomatoes, bananas, plums, persimmons, avocados, and melons has been approved and accepted for use in more than 34 countries including the European Union and the United States.[13] Although benefiting from fresher produce and lower cost, the consumer however may be purchasing fruit that is older than expected.[14]
1-MCP is also being developed as acrop protection technique. By spraying 1-MCP on growing field crops during times of stress, the crops may be protected from moderate heat and drought conditions.[15]
