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Chromatographische Trennung und Identifizierung diastereomerer Carotinoide mit grossem räumlichem Abstand der chiralen Zentren
Author(s) -
Vecchi Max,
Englert Gerhard,
Mayer Hans
Publication year - 1982
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19820650338
Subject(s) - diastereomer , chemistry , diol , chromatography , chromatographic separation , stereochemistry , high performance liquid chromatography , organic chemistry
Chroma to graphic Separation and Identification of Diastereomeric Carotinoids with Distant Chiral Centers The high‐performance liquid chromatographic separation of diastereomeric C 40 ‐carotinoids is described possessing chiral centers which are separated by 18 C‐atoms (nonaene system). The method is applied to the separation of the two diastereomers of 6,6′‐dihydrorhodoxanthin 1a and 1b (ε,ε‐carotene‐3,3′‐dione) and the six diastereomers of tunaxanlhin (ε,ε‐carotene‐3,3′‐diol; 2a–2f ). Conditions for the separation of lutein [(3 R , 3′ R , 6′ R )‐β,ε‐carotene‐3.3′‐diol, 3a ], 3′‐epi‐lutein [(3 R ,3′ S ,6′ R )‐β, ε‐carotene‐3,3′‐diol, 3b ] and its 13′‐ cis ‐ ( 3c ) and 13‐ cis ‐stereo‐isomers( 3d ) are also reported. Identification of the different chromatographic fractions was possible by use of authentic synthetic samples or by 1 H‐NMR. spectroscopy.