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研究论文

胭脂酮酸的合成新方法

高鑫a, 张晓莹a, 胡志飞a,*, 曹鸿志a,b,c,*   

  1. a中国海洋大学医药学院 海洋药物教育部重点实验室 山东省糖科学与糖药物重点实验室 青岛 266003;
    b中国海洋大学三亚海洋研究院 三亚 572025;
    c青岛海洋科技中心海洋药物与生物制品实验室 青岛 266237
  • 收稿日期:2026-04-06 修回日期:2026-04-22
  • 基金资助:
    国家重点研发计划(No. 2025YFC3409500)、国家自然科学基金(No. 92478131, 22277111, 22577125)、山东省重点研发计划（重大科技创新工程）(No. 2024CXGC010615)和泰山学者特聘专家(No. TSTP20221114)资助项目

A New Method for the Synthesis of Kermesic Acid

Gao xina, Zhang Xiaoyinga, Hu Zhifeia,*, Cao Hongzhia,b,c,*   

  1. aKey Laboratory of Marine Drugs of Ministry of Education, Shandong Key Laboratory of Glycoscience and Glycotherapeutics, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003;
    bSanya Oceanographic Institute, Ocean University of China, Sanya 572025;
    cLaboratory for Marine Drugs and Bioproducts, Qingdao Marine Science and Technology Center, Qingdao 266237
  • Received:2026-04-06 Revised:2026-04-22
  • Contact: *E-mail: zfhu@ouc.edu.cn; hzcao@ouc.edu.cn
  • Supported by:
    National Key Research and Development Program of China (No. 2025YFC3409500), the National Natural Science Foundation of China (No. 92478131, 22277111, and 22577125), the Department of Science and Technology of Shandong Province (No. 2024CXGC010615), the Taishan Scholar Project (No. TSTP20221114).

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胭脂酮酸(kermesic acid)是一种芳香族聚酮化合物,主要从胭脂虫中提取得到,被广泛用作天然红色着色剂。胭脂酮酸在生源途径中经糖基化可得到胭脂红酸,后者在染料、化妆品和食品添加剂等领域均有广泛应用,经济效益显著。因此,胭脂酮酸作为合成胭脂红酸的关键中间体而受到广泛关注。本研究报道了一种化学合成胭脂酮酸的新方法。关键步骤为在二异丙基氨基锂(LDA)作用下,溴代芳烃原位生成苯炔后与苯酞类化合物环化,实现了蒽醌母核的快速构建和主要官能团的便捷引入。后续经氧化态调整及甲基脱除等步骤,以总步数9步,12.5%总产率实现了胭脂酮酸的高效合成,为其功能研究和非动物来源胭脂红酸的合成提供了关键物质基础。

关键词: 胭脂酮酸, 化学合成, 芳炔-苯酞环化反应, 胭脂红酸

Kermesic acid is an aromatic polyketide primarily isolated from cochineal insects, which has been widely employed as a natural red colorant. In the biosynthetic pathway, glycosylation of kermesic acid yields carminic acid, a compound of significant economic value with broad applications in dyes, cosmetics, food additives, and related industries. Accordingly, kermesic acid has attracted extensive attention as a key intermediate for the synthesis of carminic acid. Herein, we report a new chemical method for the synthesis of kermesic acid. The key steps involve the in situ generation of arynes from bromoarenes followed by cyclization with phthalides, under the action of lithium diisopropylamide (LDA), enabling the rapid construction of the anthraquinone core and the convenient introduction of major functional groups. Subsequent manipulations, including oxidation state adjustment and demethylation, enabled the efficient total synthesis of kermesic acid in 9 steps with an overall yield of 12.5%, providing a crucial material foundation for functional studies of kermesic acid and the development of animal-free carminic acid synthesis.

Key words: kermesic acid, chemical synthesis, aryne-phthalide annulation, carminic acid