GEOMETRICAL ISOMERIZATION OF CAROTENOIDS IN DICHLOROMETHANE

被引：29

作者：

JEEVARAJAN, AS ^{[1
]}

WEI, CC ^{[1
]}

KISPERT, LD ^{[1
]}

机构：

[1] UNIV ALABAMA, DEPT CHEM, TUSCALOOSA, AL 35487 USA

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 1994年 / 04期

关键词：

D O I：

10.1039/p29940000861

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In a 3 mmol dm(-3) solution of all-trans-canthaxanthin (I) in HPLC grade dichloromethane cis-isomers are formed. Optical absorptions due to cis-isomers in addition to those due to an intermediate are observed in 3 mmol dm(-3) solutions of all-trans-beta-carotene(II) and 8'-apo-beta-caroten-8'-al (III), as a result of 0.1-0.2 mmol dm(-3) acid normally found in HPLC grade dichloromethane. The cis-isomers were separated by HPLC and characterized by optical and NMR spectroscopic techniques. AM1 calculations performed on the ground state and protonated I showed that 9-cis and 13-cis-isomers will be formed by acid induced isomerization in greater yield than other cis and cis,cis-isomers. This was observed experimentally. If an excess amount of hydrochloric acid (similar to 1 mol dm(-3)) is added to the solution of dichloromethane containing the carotenoids. radical cations of the carotenoids are formed.

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页码：861 / 869

页数：9

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