1-Methylcyclopropene
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Names | |||
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Preferred IUPAC name
1-Methylcycloprop-1-ene | |||
Identifiers | |||
3D model (
JSmol ) |
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Abbreviations | 1-MCP | ||
ChEBI | |||
ChemSpider | |||
ECHA InfoCard
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100.130.871 | ||
PubChem CID
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UNII | |||
CompTox Dashboard (EPA)
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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 their standard state (at 25 °C [77 °F], 100 kPa).
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1-Methylcyclopropene (1-MCP) is a
Synthesis
1-Methylcyclopropene is synthesized by the reaction of methallyl chloride and phenyllithium, which functions as a base:
The phenyllithium should be free of lithium halides. The corresponding reaction of allyl chloride and phenyllithium main affords cyclopropylbenzene.[3]
Isomers
Methylcyclopropene can refer to either of two
Mechanism of action
Commercial use
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 the
Under the brand name SmartFresh, 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 a
See also
- Ethylene as a plant hormone
- Methylenecyclopropane, an isomer
References
- ^ Daly James and Kourelis Bob, January 25, 2000. Synthesis methods, complexes and delivery methods for the safe and convenient storage, transport and application of compounds for inhibiting the ethylene response in plants. US Patent 6,017,849.
- .
- .
- ^ Chem->Sink 3-methylcyclopropene
- PMID 16882977.
- PMID 16492477.
- .
- S2CID 260252729.
- U.S. Environmental Protection Agency
- ^ Jim Daly; Anne Schluter (2001). "EthylBloc — An Industry Perspective" (PDF). Perishables Handling Quarterly (108): 5. Archived from the original (PDF) on 2010-06-13. Retrieved 2008-02-05.
- ^ What is EthylBloc technology? Archived 2008-01-30 at the Wayback Machine, at agrofresh.com
- ^ EthylBloc Ethylene Inhibitor Archived 2009-01-22 at the Wayback Machine, at floralife.com
- ^ SmartFresh Quality System Archived 2008-02-11 at the Wayback Machine at agrofresh.com
- ^ Europeans buying year-old apples Archived 2007-03-14 at the Wayback Machine, by Leah Vyse, December 13, 2005.
- ^ Syngenta-Agrofresh Alliance: New crop protection technology takes aim at row crops Archived 2008-06-26 at the Wayback Machine, Farm Industry News, Jan 18, 2008