1-Methylcyclopropene (1-MCP) is a cyclopropene derivative used as a synthetic plant growth regulator. It is structurally related to the natural plant hormone ethylene and it is used commercially to slow down the ripening of fruit and to help maintain the freshness of cut flowers.[2]
The phenyllithium should be free of lithium halides. The corresponding reaction of allyl chloride and phenyllithium main affords cyclopropylbenzene.[3]
Isomersedit
Methylcyclopropene can refer to either of two isomers, 1-methylcyclopropene covered in this article, or 3-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 different chemical compound, which is a cycloalkane with the formula C4H8.
Mechanism of actionedit
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).[5][6] 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).[7][8]
Commercial useedit
Two same-aged Abate Fetel 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.[9]
Under the brand name EthylBloc, 1-MCP was approved in 1999 by the U.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 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 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.[15]
^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.
^Blankenship, Sylvia M; Dole, John M (April 2003). "1-Methylcyclopropene: a review". Postharvest Biology and Technology. 28 (1): 1–25. doi:10.1016/S0925-5214(02)00246-6.
^Clarke, T. C.; Duncan, C. D.; Magid, R. M. (1971). "An Efficient and Convenient Synthesis of 1-Methylcyclopropene". J. Org. Chem. 36 (9): 1320–1321. doi:10.1021/jo00808a041.
^Chow B, McCourt P (2006). "Plant hormone receptors: perception is everything". Genes Dev. 20 (15): 1998–2008. doi:10.1101/gad.1432806. PMID 16882977.
^De Paepe A, Van der Straeten D (2005). "Ethylene biosynthesis and signaling: an overview". Vitam Horm. Vitamins & Hormones. 72: 399–430. doi:10.1016/S0083-6729(05)72011-2. ISBN978-0-12-709872-2. PMID 16492477.
^Serek, M.; Tamari, G.; Sisler, E.C.; Borochov, A. (1995). "Inhibition of ethylene-induced cellular senescence symptoms by 1-methylcyclopropene, a new inhibitor of ethylene action". Physiol. Plant. 94 (2): 229–232. doi:10.1111/j.1399-3054.1995.tb05305.x.
^Sisler E.C., Serek M. (2003). "Compounds interacting with the ethylene receptor in plants". Plant Biol. 5 (5): 473–80. Bibcode:2003PlBio...5..473S. doi:10.1055/s-2003-44782. S2CID 260252729.
^Jim Daly; Anne Schluter (2001). (PDF). Perishables Handling Quarterly (108): 5. Archived from the original (PDF) on 2010-06-13. Retrieved 2008-02-05.
^What is EthylBloc technology? 2008-01-30 at the Wayback Machine, at agrofresh.com
^EthylBloc Ethylene Inhibitor 2009-01-22 at the Wayback Machine, at floralife.com
^SmartFresh Quality System 2008-02-11 at the Wayback Machine at agrofresh.com
^Europeans buying year-old apples 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 2008-06-26 at the Wayback Machine, Farm Industry News, Jan 18, 2008
Wikimedia Commons has media related to 1-Methylcyclopropene.
April 10, 2024
methylcyclopropene, cyclopropene, derivative, used, synthetic, plant, growth, regulator, structurally, related, natural, plant, hormone, ethylene, used, commercially, slow, down, ripening, fruit, help, maintain, freshness, flowers, ball, stick, cyclopropene, w. 1 Methylcyclopropene 1 MCP is a cyclopropene derivative used as a synthetic plant growth regulator It is structurally related to the natural plant hormone ethylene and it is used commercially to slow down the ripening of fruit and to help maintain the freshness of cut flowers 2 1 Methylcyclopropene Ball and stick of cyclopropene van der Waals model of cyclopropeneNamesPreferred IUPAC name 1 Methylcycloprop 1 eneIdentifiersCAS Number 3100 04 7 Y3D model JSmol Interactive imageAbbreviations 1 MCPChEBI CHEBI 132592 YChemSpider 133162 YECHA InfoCard 100 130 871PubChem CID 151080UNII J6UJO23JGU YCompTox Dashboard EPA DTXSID2035643InChI InChI 1S C4H6 c1 4 2 3 4 h2H 3H2 1H3 YKey SHDPRTQPPWIEJG UHFFFAOYSA N YInChI 1 C4H6 c1 4 2 3 4 h2H 3H2 1H3Key SHDPRTQPPWIEJG UHFFFAOYAJSMILES C 1 C C C 1PropertiesChemical formula C 4H 6Molar mass 54 092 g mol 1Boiling 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 Infobox references Contents 1 Synthesis 2 Isomers 3 Mechanism of action 4 Commercial use 5 See also 6 ReferencesSynthesis edit1 Methylcyclopropene is synthesized by the reaction of methallyl chloride and phenyllithium which functions as a base Methallyl chloride nbsp Phenyl lithium nbsp base LiCl PhH nbsp 1 Methyl cyclopropene nbsp The phenyllithium should be free of lithium halides The corresponding reaction of allyl chloride and phenyllithium main affords cyclopropylbenzene 3 Isomers editMethylcyclopropene can refer to either of two isomers 1 methylcyclopropene covered in this article or 3 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 different chemical compound which is a cycloalkane with the formula C4H8 Mechanism of action editEthylene 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 5 6 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 7 8 Commercial use edit nbsp Two same aged Abate Fetel pears unlike the left one the right one was treated with 1 MCP after the harvest1 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 U 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 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 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 15 See also editEthylene as a plant hormone Methylenecyclopropane an isomerReferences edit 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 Blankenship Sylvia M Dole John M April 2003 1 Methylcyclopropene a review Postharvest Biology and Technology 28 1 1 25 doi 10 1016 S0925 5214 02 00246 6 Clarke T C Duncan C D Magid R M 1971 An Efficient and Convenient Synthesis of 1 Methylcyclopropene J Org Chem 36 9 1320 1321 doi 10 1021 jo00808a041 Chem gt Sink 3 methylcyclopropene Chow B McCourt P 2006 Plant hormone receptors perception is everything Genes Dev 20 15 1998 2008 doi 10 1101 gad 1432806 PMID 16882977 De Paepe A Van der Straeten D 2005 Ethylene biosynthesis and signaling an overview Vitam Horm Vitamins amp Hormones 72 399 430 doi 10 1016 S0083 6729 05 72011 2 ISBN 978 0 12 709872 2 PMID 16492477 Serek M Tamari G Sisler E C Borochov A 1995 Inhibition of ethylene induced cellular senescence symptoms by 1 methylcyclopropene a new inhibitor of ethylene action Physiol Plant 94 2 229 232 doi 10 1111 j 1399 3054 1995 tb05305 x Sisler E C Serek M 2003 Compounds interacting with the ethylene receptor in plants Plant Biol 5 5 473 80 Bibcode 2003PlBio 5 473S doi 10 1055 s 2003 44782 S2CID 260252729 1 Methylcyclopropene Fact Sheet 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 nbsp Wikimedia Commons has media related to 1 Methylcyclopropene Retrieved from https en wikipedia org w index php title 1 Methylcyclopropene amp oldid 1194878784, wikipedia, wiki, book, books, library,
