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保幼酮

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保幼酮
IUPAC名
Methyl (4R)-4-[(2R)-6-methyl-4-oxoheptan-2-yl]cyclohex-1-ene-1-carboxylate
识别
CAS号 17904-27-7  checkY
PubChem 442381
ChemSpider 390830
SMILES
 
  • O=C(C[C@@H](C)[C@]1([H])CCC(C(OC)=O)=CC1)CC(C)C
InChI
 
  • 1/C16H26O3/c1-11(2)9-15(17)10-12(3)13-5-7-14(8-6-13)16(18)19-4/h7,11-13H,5-6,8-10H2,1-4H3/t12-,13+/m1/s1
InChIKey IIWNDLDEVPJIBT-OLZOCXBDBI
性质
化学式 C16H26O3
摩尔质量 266.38 g·mol−1
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

保幼酮(英语:Juvabione)是一种有机化合物,化学式C16H26O3,能视为倍半萜椴松酸甲酯,属于昆虫保幼激素的相似物,由植物合成抵御昆虫。[1][2][3][4][5][6][7]

保幼酮、椴松酸保幼激素III

参考文献

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  1. ^ Manville, J. F.; Kriz, C. D. Juvabione and its analogues. IV. Isolation, identification, and occurrence of juvabione, juvabiol, epijuvabiol from the whole wood of Abies lasiocarpa. Can. J. Chem. 1977, 55: 2547–2553. doi:10.1139/v77-351可免费查阅. 
  2. ^ Manville, J. F. Juvabione and its analogues. Juvabione and delta4'-dehydrojuvabione isolated from the whole wood of Abies balsamea, have the R>R stereoconfigurations, not R,S. Can. J. Chem. 1975, 53: 1579–1585. doi:10.1139/v75-223可免费查阅. 
  3. ^ Bohlmann, J.; Crock, J.; Jetter, R.; Croteau, R. Terpenoid-based defenses in conifers: cDNA cloning, characterization, and functional expression of wound-inducible (E)-alpha-bisabolene synthase from grand fir (Abies grandis). Proc. Natl. Acad. Sci. USA. 1998, 95 (12): 6756–6761. Bibcode:1998PNAS...95.6756B. PMC 22624可免费查阅. PMID 9618485. doi:10.1073/pnas.95.12.6756可免费查阅. 
  4. ^ Phillips, M. A; Bohlmann, J.; Gershenzon, J. Molecular regulation of induced terpenoid biosynthesis in conifers. Phytochemistry Reviews. 2006, 55 (5): 179–189. S2CID 25713264. doi:10.1007/s11101-006-0001-6. 
  5. ^ Bohlmann, J.; Meyer-Gauen, G.; Croteau, R. Plant terpenoid synthases: Molecular biology and phylogenetic analysis. Proc. Natl. Acad. Sci. USA. 1998, 95 (8): 4126–4133. Bibcode:1998PNAS...95.4126B. PMC 22453可免费查阅. PMID 9539701. doi:10.1073/pnas.95.8.4126可免费查阅. 
  6. ^ Steele, C. L.; Crock, J.; Bohlmann, J.; Croteau, R. Sesquiterpene Synthases from Grand Fir (Abies grandis). J. Biol. Chem. 1998, 273 (4): 2078–2089. PMID 9442047. doi:10.1074/jbc.273.4.2078可免费查阅. 
  7. ^ Higuchi, T. Biosynthesis and biodegradation of wood components. Academic Press. 1985: 380–429.