8-Oxogeranial

Last updated
8-Oxogeranial
8-Oxogeranial.svg
Names
Preferred IUPAC name
(2E,6E)-2,6-Dimethylocta-2,6-dienedial
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
  • InChI=1S/C10H14O2/c1-9(6-7-11)4-3-5-10(2)8-12/h5-8H,3-4H2,1-2H3/b9-6+,10-5+
    Key: GRHWFPUCRVCMRY-TXFIJWAUSA-N
  • InChI=1/C10H14O2/c1-9(6-7-11)4-3-5-10(2)8-12/h5-8H,3-4H2,1-2H3/b9-6+,10-5+
    Key: GRHWFPUCRVCMRY-TXFIJWAUBP
  • C/C(=C\C=O)/CC/C=C(\C)/C=O
Properties
C10H14O2
Molar mass 166.220 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

8-Oxogeranial is a chemical substance (also incorrectly called 10-oxogeranial), that is a monoterpene. [1] The terpenoid is produced by 8-hydroxygeraniol dehydrogenase which uses 8-hydroxygeraniol as its substrate. 8-Oxogeranial is itself a substrate for iridoid synthase which synthesizes cis-trans-iridodial and cis-trans-nepetalactol. [2]

References

  1. ↑ Dewick, Paul M. (2009-02-06). Medicinal Natural Products: A Biosynthetic Approach (1 ed.). Wiley. doi:10.1002/9780470742761. ISBN   978-0-470-74168-9.
  2. ↑ Miettinen, Karel; Dong, Lemeng; Navrot, Nicolas; Schneider, Thomas; Burlat, Vincent; Pollier, Jacob; Woittiez, Lotte; Van Der Krol, Sander; Lugan, Raphaël; Ilc, Tina; Verpoorte, Robert; Oksman-Caldentey, Kirsi-Marja; Martinoia, Enrico; Bouwmeester, Harro; Goossens, Alain; Memelink, Johan; Werck-Reichhart, Danièle (2014). "The seco-iridoid pathway from Catharanthus roseus". Nature Communications. 5: 3606. doi:10.1038/ncomms4606. PMC   3992524 . PMID   24710322.
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