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  • Title: Isolation and identification of terpene chlorohydrins found in cold-pressed orange oil.
    Author: Weiss ER, Pika J, Braddock RJ.
    Journal: J Agric Food Chem; 2003 Apr 09; 51(8):2277-82. PubMed ID: 12670170.
    Abstract:
    Three terpene chlorohydrins found in cold-pressed orange oil were concentrated by silica adsorption chromatography and purified by preparative HPLC. Formation of these chlorohydrins was determined to be the result of a reaction of d-limonene, the major component of cold-pressed oil, with hypochlorous acid, found in chlorinated treatment water used in the oil recovery process. NMR analyses indicated that the major chlorohydrin present was the diequatorially substituted (1R,2R,4R)-2-chloro-8-p-menthen-1-ol (1). The other two compounds were the diaxial trans stereoisomer, (1S,2S,4R)-2-chloro-8-p-menthen-1-ol (2), and the dichlorohydrin, (1R,2R,4R)-2,9-dichloro-8-p-menthen-1-ol (3).
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