1-Methylcyclopropene

1-Methylcyclopropene is synthesized by the reaction of methallyl chloride and phenyllithium, which functions as a base:

{{Biochem reaction subunit/top}}

{{Biochem reaction subunit|compound=Methallyl chloride|image=MethallylCl.png|class=skin-invert-image}}

{{Biochem reaction subunit|compound=Phenyl lithium|image=Phenyllithium.svg|class=skin-invert-image|title_lower=(base)}}

{{Biochem reaction subunit|direction=forward|for_prod=LiCl + PhH|container_style=min-width:80px}}

{{Biochem reaction subunit|compound=1-Methyl{{shy}}cyclopropene|link=1-Methylcyclopropene|image=Methylcyclopropene.png|class=skin-invert-image}}

{{Biochem reaction subunit/end}}

The phenyllithium should be free of lithium halides. The corresponding reaction of allyl chloride and phenyllithium main affords cyclopropylbenzene.{{cite journal |author= Clarke, T. C. |author2= Duncan, C. D. |author3= Magid, R. M. |title= An Efficient and Convenient Synthesis of 1-Methylcyclopropene |journal= J. Org. Chem. |year= 1971 |volume= 36 |issue= 9 |pages= 1320–1321 |doi= 10.1021/jo00808a041}}

Methylcyclopropene can refer to either of two isomers, 1-methylcyclopropene covered in this article, or 3-methylcyclopropene[http://www.chemsink.com/compound/638076/ Chem->Sink 3-methylcyclopropene] which is not covered in this article. 2-methylcyclopropene would be an incorrect name for 1-methylcyclopropene. Also note: methylcyclopropane is yet a different chemical compound, which is a cycloalkane with the formula C₄H₈.

Ethylene is a gas acting at trace levels (typically between a few tenths and a few thousands ppm in the gas atmosphere) throughout the life of a plant by stimulating or regulating various processes such as the ripening of climacteric fruit, the opening of flowers (dehiscence process), and the shedding of leaves (abscission process).{{cite journal |vauthors=Chow B, McCourt P | title = Plant hormone receptors: perception is everything. | journal = Genes Dev | volume = 20 | issue = 15 | pages = 1998–2008 | year = 2006 | pmid = 16882977 | doi = 10.1101/gad.1432806| doi-access = free }}{{cite journal |vauthors=De Paepe A, Van der Straeten D | title = Ethylene biosynthesis and signaling: an overview | journal = Vitam Horm | volume = 72 | pages = 399–430 | year = 2005 | pmid = 16492477 | doi = 10.1016/S0083-6729(05)72011-2 | series = Vitamins & Hormones | isbn = 978-0-12-709872-2}} The mechanism of action of 1-MCP involves its tightly binding to the ethylene receptor in plants, thereby blocking the effects of ethylene (competitive inhibitor).{{cite journal|author1=Serek, M. |author2=Tamari, G. |author3=Sisler, E.C. |author4=Borochov, A. |year=1995 |title=Inhibition of ethylene-induced cellular senescence symptoms by 1-methylcyclopropene, a new inhibitor of ethylene action |journal=Physiol. Plant. |volume=94 |pages=229–232 |doi=10.1111/j.1399-3054.1995.tb05305.x| issue=2}}{{cite journal |author=Sisler E.C., Serek M. |year=2003 |title=Compounds interacting with the ethylene receptor in plants |journal=Plant Biol |volume=5 |pages=473–80 |doi=10.1055/s-2003-44782 |issue=5|bibcode=2003PlBio...5..473S |s2cid=260252729 }}

File:Fruit Abate Fetel 1mcp.jpg pears: unlike the left one, the right one was treated with 1-MCP after the harvest]]

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.[https://web.archive.org/web/20030202061457/http://www.epa.gov/pesticides/biopesticides/ingredients/factsheets/factsheet_224459.htm 1-Methylcyclopropene Fact Sheet], U.S. Environmental Protection Agency

Under the brand name EthylBloc, 1-MCP was approved in {{YEAR|1999}} by the U.S. Environmental Protection Agency for use on ornamental crops.{{cite journal |url=http://postharvest.ucdavis.edu/datastorefiles/234-95.pdf |title=EthylBloc — An Industry Perspective |author=Jim Daly |author2=Anne Schluter |year=2001 |issue=108 |journal=Perishables Handling Quarterly |pages=5 |access-date=2008-02-05 |archive-url=https://web.archive.org/web/20100613073125/http://postharvest.ucdavis.edu/datastorefiles/234-95.pdf |archive-date=2010-06-13 |url-status=dead }} For cut flowers, potted flowers, and bedding, nursery and foliage plants, 1-MCP prevents or delays wilting, leaf yellowing, opening, and death.[http://www.agrofresh.com/ethylbloc.html What is EthylBloc technology?] {{Webarchive|url=https://web.archive.org/web/20080130063240/http://www.agrofresh.com/ethylbloc.html |date=2008-01-30 }}, at agrofresh.com[http://www.floralife.com/industry_professionals/our_products/ethylbloc.asp EthylBloc Ethylene Inhibitor] {{Webarchive|url=https://web.archive.org/web/20090122070758/http://floralife.com/industry_professionals/our_products/ethylbloc.asp |date=2009-01-22 }}, at floralife.com

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.[http://www.agrofresh.com/smartfresh.html SmartFresh Quality System] {{Webarchive|url=https://web.archive.org/web/20080211234805/http://www.agrofresh.com/smartfresh.html |date=2008-02-11 }} at agrofresh.com Although benefiting from fresher produce and lower cost, the consumer however may be purchasing fruit that is older than expected.[http://www.foodanddrinkeurope.com/news/ng.asp?id=64546-sainsbury-s-apples-smartfresh Europeans buying year-old apples] {{Webarchive|url=https://web.archive.org/web/20070314085812/http://www.foodanddrinkeurope.com/news/ng.asp?id=64546-sainsbury-s-apples-smartfresh |date=2007-03-14 }}, by Leah Vyse, December 13, 2005.

1-MCP is also being developed as a crop 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.[http://farmindustrynews.com/crop-protection/0118-syngenta-agrofresh-alliance/ Syngenta-Agrofresh Alliance: New crop protection technology takes aim at row crops] {{Webarchive|url=https://web.archive.org/web/20080626191315/http://farmindustrynews.com/crop-protection/0118-syngenta-agrofresh-alliance/ |date=2008-06-26 }}, Farm Industry News, Jan 18, 2008

• Ethylene as a plant hormone
• Methylenecyclopropane, an isomer

{{Reflist}}

{{Commons category|1-Methylcyclopropene}}

{{Hydrocarbons}}

{{DEFAULTSORT:Methylcyclopropene, 1-}}

Category:Cyclopropenes

Category:Plant growth regulators