Carotenoid Sulfates. 4. Syntheses and Properties of Carotenoid Sulfates.

Publisher Website
Google Scholar
Abstract
Carotenoid sulfates have been prepared from 14 selected carotenols for spectroscopic characterization, studies of their stability in solution and their water solubility. Carotenoids containing sec non-allylic hydroxy groups provided sulfates stable in methanol solution, exemplified by zeaxanthin mono- and disulfate, alloxanthin mono- and disulfate, fucoxanthin monosulfate, peridinin monosulfate, capsorubin mono- and disulfate and astaxanthin mono- and disulfate. Acid catalyzed methanolysis of zeaxanthin disulfate gave zeaxanthin with complete retention of configuration. Enzymatic hydrolysis of alloxanthin monosulfate is reported. Less stable sulfates were obtained from sec vic diol type-, phenolic and tert-carotenols; caloxanthin, nostoxanthin, 3-hydroxyisorenieratene, 3,3''-dihydrosyisorenieratene, rhodovibrin, di-OH-lycopene and OH-chlorobactene. Acid catalyzed methanolysis of the tert carotenoids proceeded via carbocations, judged by the solvolysis products characterized. Characteristic spectroscopic properties of carotenoid sulfates are pointed out. Water solubilities were studied.

This publication has 11 references indexed in Scilit: