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绵腹衣酸

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绵腹衣酸
IUPAC名
4-(2,4-Dihydroxy-6-pentylbenzoyl)oxy-2-hydroxy-6-pentylbenzoic acid
识别
CAS号 641-68-9
PubChem 12306720
ChemSpider 31104179
SMILES
 
  • CCCCCC1=C(C(=CC(=C1)O)O)C(=O)OC2=CC(=C(C(=C2)O)C(=O)O)CCCCC
InChI
 
  • 1S/C24H30O7/c1-3-5-7-9-15-11-17(25)13-19(26)22(15)24(30)31-18-12-16(10-8-6-4-2)21(23(28)29)20(27)14-18/h11-14,25-27H,3-10H2,1-2H3,(H,28,29)
InChIKey BEFYPHLCGVCBFF-UHFFFAOYSA-N
ChEBI 144192
性质
化学式 C24H30O7
摩尔质量 430.49 g·mol−1
熔点 122 °C(395 K)
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

绵腹衣酸(英语:Anziaic acid)是在地衣中发现的一种缩酚酸,是橄榄酸的酯二聚体。它在C试验中呈红色反应。[1]

绵腹衣酸通过抑制拓扑异构酶发挥抗菌化合物的作用。[2][3]

绵腹衣酸存在于梅花衣科的一些物种中,包括双歧根属[2]珊瑚枝衣属[4]斑叶属等。[5]

生产

绵腹衣酸可以由人工合成,由橄榄酸通过O-苯酚位置的苄基化,然后与三氟乙酸酐缩合。[1]

性质

绵腹衣酸是无色的,能溶于乙醇、乙醇-水混合物或环己烷-苯混合物。[1]

相关化合物

珠光酸维基数据所列Q83074133dihydroprolichenic acid绵腹衣酸-2'-O-甲醚珠光酸-2-O-甲醚珠光酸-2'-O-甲醚planaic acid是绵腹衣酸的衍生物。[1]

参考资料

  1. ^ 1.0 1.1 1.2 1.3 Elix, J. A. Synthesis of para-olivetol depsides. Australian Journal of Chemistry. 1974, 27 (8): 1767. doi:10.1071/CH9741767. 
  2. ^ 2.0 2.1 Cheng, Bokun; Cao, Shugeng; Vasquez, Victor; Annamalai, Thirunavukkarasu; Tamayo-Castillo, Giselle; Clardy, Jon; Tse-Dinh, Yuk-Ching. Identification of Anziaic Acid, a Lichen Depside from Hypotrachyna sp., as a New Topoisomerase Poison Inhibitor. PLOS ONE. 8 April 2013, 8 (4): e60770. Bibcode:2013PLoSO...860770C. PMC 3620467可免费查阅. PMID 23593306. doi:10.1371/journal.pone.0060770可免费查阅. 
  3. ^ Kekuda, T.R Prashith; Lavanya, D .; Pooja, Rao. Lichens as promising resources of enzyme inhibitors: A review. Journal of Drug Delivery and Therapeutics. March 2019, 9 (2S). doi:10.22270/jddt.v9i2-s.2546 (不活跃 31 January 2024). 
  4. ^ Ramaut, J. L.; Serusiaux, E.; Brouers, M.; Corvisier, M. Lichen Acids of the Stereocaulon ramulosum Group in Central East Africa. The Bryologist. 1978, 81 (3): 415. JSTOR 3242244. doi:10.2307/3242244. 
  5. ^ Mark, Kristiina; Randlane, Tiina; Thor, Göran; Hur, Jae-Seoun; Obermayer, Walter; Saag, Andres. Lichen chemistry is concordant with multilocus gene genealogy in the genus Cetrelia (Parmeliaceae, Ascomycota). Fungal Biology. 2019, 123 (2): 125–139. PMID 30709518. S2CID 73439650. doi:10.1016/j.funbio.2018.11.013.