Juvabione

Juvabione
Names
Preferred IUPAC name
Methyl (4R)-4-[(2R)-6-methyl-4-oxoheptan-2-yl]cyclohex-1-ene-1-carboxylate
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/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 ☒N
    Key: IIWNDLDEVPJIBT-OLZOCXBDSA-N ☒N
  • 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
    Key: IIWNDLDEVPJIBT-OLZOCXBDBI
  • O=C(C[C@@H](C)[C@]1([H])CCC(C(OC)=O)=CC1)CC(C)C
  • C[C@H](CC(=O)CC(C)C)[C@@H]1CCC(=CC1)C(=O)OC
Properties
C16H26O3
Molar mass 266.381 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Juvabione, historically known as the paper factor, is the methyl ester of todomatuic acid. Both are sesquiterpenes (C15) found in the wood of true firs of the genus Abies.[1][2][3][4][5][6][7] They occur naturally as part of a mixture of sesquiterpenes based upon the bisabolane scaffold. Sesquiterpenes of this family are known as insect juvenile hormone analogues (IJHA) because of their ability to mimic juvenile activity in order to stifle insect reproduction and growth.[3] These compounds play important roles in conifers as the second line of defense against insect induced trauma and fungal pathogens.[3][4]

  1. ^ Manville, J. F.; Kriz, C. D. (1977). "Juvabione and its analogues. IV. Isolation, identification, and occurrence of juvabione, juvabiol, epijuvabiol from the whole wood of Abies lasiocarpa". Can. J. Chem. 55: 2547–2553. doi:10.1139/v77-351.
  2. ^ Manville, J. F. (1975). "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. 53: 1579–1585. doi:10.1139/v75-223.
  3. ^ a b c Bohlmann, J.; Crock, J.; Jetter, R.; Croteau, R. (1998). "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. 95 (12): 6756–6761. Bibcode:1998PNAS...95.6756B. doi:10.1073/pnas.95.12.6756. PMC 22624. PMID 9618485.
  4. ^ a b Phillips, M. A; Bohlmann, J.; Gershenzon, J. (2006). "Molecular regulation of induced terpenoid biosynthesis in conifers". Phytochemistry Reviews. 55 (5): 179–189. doi:10.1007/s11101-006-0001-6. S2CID 25713264.
  5. ^ Bohlmann, J.; Meyer-Gauen, G.; Croteau, R. (1998). "Plant terpenoid synthases: Molecular biology and phylogenetic analysis". Proc. Natl. Acad. Sci. USA. 95 (8): 4126–4133. Bibcode:1998PNAS...95.4126B. doi:10.1073/pnas.95.8.4126. PMC 22453. PMID 9539701.
  6. ^ Steele, C. L.; Crock, J.; Bohlmann, J.; Croteau, R. (1998). "Sesquiterpene Synthases from Grand Fir (Abies grandis)". J. Biol. Chem. 273 (4): 2078–2089. doi:10.1074/jbc.273.4.2078. PMID 9442047.
  7. ^ Higuchi, T. (1985). Biosynthesis and biodegradation of wood components. Academic Press. pp. 380–429.