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Partial Synthesis and Characterization of Capsokarpoxanthins and 3,6-Epoxcapsanthins

✍ Scribed by József Deli; Péter Molnár; Zoltán Matus; Gyula Tóth; Andrea Steck; Hanspeter Pfander


Publisher
John Wiley and Sons
Year
1998
Tongue
German
Weight
815 KB
Volume
81
Category
Article
ISSN
0018-019X

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✦ Synopsis


The acid-catalyzed hydrolysis of (3S,5R,6S,3'SS'R)-5,6-epoxycapsanthin (5) led to (3S,5R,6R,3'S,5'R)-( ) and (3S,5R,6S,3'S,SR)-capsokarpoxanthin (8). In addition, (3S,5R,SR,3'S,5'R)-( ), (3S,5R,8S,3'S,5'R)capsochrome (lo), and (3S,5R,6R,3'S,SR)-3.6-epoxycdpsanthin (1 1) were obtained. The acid-catalyzed hydrolysis of (3S,5S,6R,3'S,SR)-5,6-epoxycapsanthin (6) afforded (3S,SS,6R,3'S,SR)-capsokarpoxanthin (12), (3S,SS,8S,3'S,5'R)-( ) and (3S,5S,SR,3'S,5'S)-capsochrome (14) as well as (3SS,6R.3'S,SR)-3,6-epoxyepicapsdnthin (15). Compounds 5-15 were isolated in crystalline form and characterized by their UVjVIS, CD. 'H-and I3C-NMR, and mass spectra.


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Partial Synthesis and Characterization o
✍ Péter Molnár; József Deli; Zoltán Matus; Gyula Tóth; Andrea Steck; Hanspeter Pfa 📂 Article 📅 1997 🏛 John Wiley and Sons 🌐 German ⚖ 469 KB

## Abstract β‐Cryptoxanthin (1) was acetylated and then epoxidized with monoperoxyphthalic acid. After hydrolysis, repeated chromatography, and crystallization, (3__S__,5__R__,6__S__)‐5,6‐epoxy‐β‐cryptoxanthin (3), (3__S__,5__S__,6__R__)‐5,6‐epoxy‐β‐cryptoxanthin (4), (3__R__,5′__R__,6′__R__)‐5′,6′