Efficient synthesis of analogs of safflower yellow B, carthamin, and its precursor: two yellow and one red dimeric pigments in safflower petals |
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Authors: | Shingo Sato Takashi Kusakari Tohru Suda Takaharu Kasai Toshihiro Kumazawa Jun-ichi Onodera Heitaro Obara |
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Institution: | Department of Chemistry and Chemical Engineering, Faculty of Engineering, Yamagata University, 4-3-16 Jonan, Yonezawa-shi, Yamagata 992-8510, Japan |
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Abstract: | The synthesis of analogs (8, 12, 14) of two yellow pigments, safflower yellow B and the precursor of carthamin, and carthamin itself, a red pigment, which are produced in safflower (Carthamus tinctrious L.) petals and, which have a common dimeric quinochalcone structure, is reported. The key compound for the synthesis of these analogs, (p-hydroxycinnamoyl)filicinic acid (7) was synthesized in six steps from phloroglucinol in a total yield of 39%, which was reacted with 2,3,4,5,6-penta-O-acetyl-aldehydo-d-glucose, glyoxylic acid, and ethyl orthoformate in the presence of base to afford the corresponding analog, 8, 12, 14, in good yields, respectively. Precursor analog 12 was then converted to carthamin analog 14 by oxidative decarboxylation by treatment with potassium permanganate as well as the natural specimen. |
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Keywords: | Safflower petals Yellow and red pigments Safflower yellow B Carthamin Carthamin precursor Analog (p-Hydroxycinnamoyl)filicinic acid |
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