10259. 1-Methylcyclopropene

Nomenclature

CAS number: 3100-04-7
1-MCP; EthylBloc (AgroFresh); Invinsa (AgroFresh); SmartFresh (AgroFresh).
C4H6; mol wt 54.09.
C 88.82%, H 11.18%.

Description and references

Ethylene inhibiting plant growth regulator. Prepn from 2-methylallyl chloride and NaNH2: F. Fisher, D. E. Applequist, J. Org. Chem. 30, 2089 (1965) DOI; from 2-methylallyl chloride and phenyllithium: R. M. Magid et al., ibid. 36, 1320 (1971) DOI; and proposed mode of action: E. C. Sisler, M. Serek, Physiol. Plant. 100, 577 (1997) DOI. Microwave structural studies: M. K. Kemp, W. H. Flygare, J. Am. Chem. Soc. 89, 3925 (1967) DOI; eidem, ibid. 91, 3163 (1969) DOI. Kinetics of encapsulation into α-cyclodextrin: T. L. Neoh et al., J. Agric. Food Chem. 55, 11020 (2007) DOI PubMed. Review of mechanism of action: B. M. Binder, A. B. Bleecker, Acta Hortic. 628, 177-187 (2003); of agricultural applications: S. M. Blankenship, J. M. Dole, Postharvest Biol. Technol. 28, 1-25 (2003) DOI; of use on fruits and vegetables: C. B. Watkins, Biotechnol. Adv. 24, 389-409 (2006) DOI PubMed.

Chemical structure

Properties

Gas at standard temperature and pressure, bp ≤10°. In some commercial powder formulations, 1-MCP is enclosed in a cyclodextrin cage that releases 1-MCP when mixed with water. LC50 in rats by inhalation: >2.5 mg/l (Blankenship, Dole).

Use

Blocks the ripening and aging effects of ethylene in harvested fruits and vegetables, cut and potted flowers, and foliage plants.