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Isolation and Identification of Terpene Chlorohydrins Found in Cold-Pressed Orange Oil

Author:
Weiss, Eve R., Pika, Jana, Braddock, Robert J.
Source:
Journal of agricultural and food chemistry 2003 v.51 no.8 pp. 2277-2282
ISSN:
0021-8561
Subject:
adsorption, essential oils, high performance liquid chromatography, nuclear magnetic resonance spectroscopy, silica, stereoisomers, water treatment
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).
Agid:
311924