Isolation and identification of terpene chlorohydrins found in cold-pressed orange oil.
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).
Weiss
Eve R
ER
Citrus Research and Education Center, University of Florida, 700 Experiment Station Road, Lake Alfred, Florida 33850, USA.
Pika
Jana
J
Braddock
Robert J
RJ
D002728:Chlorohydrins / Q000032:analysis* / Q000138:chemical synthesis / Q000302:isolation & purification; D002849:Chromatography, Gas; D002851:Chromatography, High Pressure Liquid; D002957:Citrus / Q000737:chemistry*; D003080:Cold Temperature; D053138:Cyclohexenes; D006997:Hypochlorous Acid / Q000737:chemistry; D000077222:Limonene; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D009822:Oils, Volatile / Q000737:chemistry; D010938:Plant Oils / Q000737:chemistry*; D013729:Terpenes / Q000032:analysis* / Q000737:chemistry
D002728:Chlorohydrins; D053138:Cyclohexenes; D009822:Oils, Volatile; D010938:Plant Oils; D013729:Terpenes; D006997:Hypochlorous Acid; D000077222:Limonene