Auto-Oxidation Products of Astaxanthin

• Published in: Journal of Oleo Science Vol. 61; no. 1; pp. 17 - 21
• Main Authors: Etoh, Hideo, Suhara, Mika, Tokuyama, Sinji, Kato, Hideaki, Nakahigashi, Rie, Maejima, Yasunori, Ishikura, Masaharu, Terada, Yukimasa, Maoka, Takashi
• Format: Journal Article
• Language: English
• Published: Japan Japan Oil Chemists' Society 2012; Japan Science and Technology Agency
• Subjects: apoastaxanthinal; apoastaxanthinone; astaxanthin; auto-oxidation; Chemistry, Physical; Darkness; Oxidation-Reduction; Oxygen; stable molecular energy calculation; Temperature; Time Factors; Xanthophylls - chemistry; Xanthophylls - isolation & purification
• ISSN: 1345-8957; 1347-3352
• DOI: 10.5650/jos.61.17

The auto-oxidation products of astaxanthin were investigated. Astaxanthin was allowed to react with atmospheric oxygen at 55°C in the dark for 35 days. A series of oxidative cleavage products, 7-apoastaxanthinal (1), 9-apoastaxanthinone (2), 11-apoastaxanthinal (3), 13-apoastaxanthinone (4), 15-apoastaxanthinal (5), 14′-apoastaxanthinal (6), 12′-apoastaxanthinal (7), 10′-apoastaxanthinal (8), and 8′-apoastaxanthinal (9), were identified. Among them, 3 and 6 were isolated and characterized for the first time. Cleavage of the double bond in astaxanthin was discussed on the basis of the calculation of the stable molecular energy.