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羽扇豆異黃酮

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Luteone
IUPAC名
2′,4′,5,7-Tetrahydroxy-6-(3-methylbut-2-en-1-yl)isoflavone
系統名
3-(2,4-Dihydroxyphenyl)-5,7-dihydroxy-6-(3-methylbut-2-en-1-yl)-4H-1-benzopyran-4-one
識別
CAS號 41743-56-0  checkY
PubChem 5281797
ChemSpider 4445109
SMILES
 
  • CC(=CCC1=C(C=C2C(=C1O)C(=O)C(=CO2)C3=C(C=C(C=C3)O)O)O)C
InChI
 
  • 1S/C20H18O6/c1-10(2)3-5-13-16(23)8-17-18(19(13)24)20(25)14(9-26-17)12-6-4-11(21)7-15(12)22/h3-4,6-9,21-24H,5H2,1-2H3
InChIKey MMPVAPMCVABQPS-UHFFFAOYSA-N
3DMet B03983
ChEBI 27917
KEGG C10498
性質
化學式 C20H18O6
摩爾質量 354.35 g·mol−1
外觀 淺黃色柱狀晶體[1]
熔點 223—225 °C(496—498 K)[1]
若非註明,所有數據均出自標準狀態(25 ℃,100 kPa)下。

羽扇豆異黃酮是一種異黃酮類有機化合物,化學式為C20H18O6。它存在於毒豆[2]狹葉羽扇豆[3]中。它可人工合成得到。[4]

吡啶存在下,它在110 °C和乙酸酐反應,可以得到羽扇豆異黃酮-2',4',5,7-四乙酸酯。[1]

參考文獻

[編輯]
  1. ^ 1.0 1.1 1.2 Masao Tsukayama, Hironari Wada, Yasuhiko Kawamura, Kazuyo Yamashita, Masaki Nishiuchi. Regioselective Synthesis of 6-Alkyl- and 6-Prenylpolyhydroxyisoflavones and 6-Alkylcoumaronochromone Derivatives. Chemical & Pharmaceutical Bulletin (2004), 52(11), 1285-1289. doi:10.1248/cpb.52.1285.
  2. ^ Sato H.; Tahara S.; Ingham J. L.; Dziedzic S. Z. Isoflavones from pods of Laburnum anagyroides. Phytochemistry. 1995, 39 (3): 673–676. doi:10.1016/0031-9422(95)00029-7. 
  3. ^ Xiaomeng Liang; Jan H. Christensen; Thomas D. Bucheli; Nikoline Juul Nielsen. Source-Supported Suspect Screening (4S) of Phytotoxins in Terrestrial and Aquatic Environments: A Field Study of Lupinus angustifolius L. (Blue Lupin). Environ. Sci. Technol. 2023, 57, 6, 2333–2340. doi:10.1021/acs.est.2c05387.
  4. ^ Tsukayama M.; Wada H.; Kishida M.; Nishiuchi M.; Kawamura Y. Regioselective Synthesis of Prenylisoflavones. Syntheses of Luteone and Luteone Hydrate. Chem Lett. 2000, 29 (12): 1362–1363. doi:10.1246/cl.2000.1362.