8-Hydroxygeraniol

8-Hydroxygeraniol
Names
Preferred IUPAC name
(2E,6E)-2,6-Dimethylocta-2,6-diene-1,8-diol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.209.637 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C10H18O2/c1-9(6-7-11)4-3-5-10(2)8-12/h5-6,11-12H,3-4,7-8H2,1-2H3/b9-6+,10-5+
    Key: PREUOUJFXMCMSJ-TXFIJWAUSA-N
  • InChI=1/C10H18O2/c1-9(6-7-11)4-3-5-10(2)8-12/h5-6,11-12H,3-4,7-8H2,1-2H3/b9-6+,10-5+
    Key: PREUOUJFXMCMSJ-TXFIJWAUBC
  • C/C(=C\CO)/CC/C=C(\C)/CO
Properties
C10H18O2
Molar mass 170.252 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

8-Hydroxygeraniol (also incorrectly called 10-hydroxygeraniol)[1] is a monoterpene synthesized from geraniol by the enzyme geraniol 8-hydroxylase. 8-Hydroxygeraniol is a substrate for 8-hydroxygeraniol dehydrogenase (G80) which synthesizes 8-oxogeranial.[2] 8-Hydroxygeraniol is step in the synthesis of the secologanin, a key monoterpene needed for formation of terpene indole alkaloids.

In the laboratory, 8-hydroxygeraniol can be prepared from geranyl acetate.[3]

  1. ^ Paul M. Dewick (2009). Medicinal Natural Products: A Biosynthetic Approach. doi:10.1002/9780470742761. ISBN 9780470742761.
  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.
  3. ^ Ippoliti, Francesca M.; Barber, Joyann S.; Tang, Yi; Garg, Neil K. (2018). "Synthesis of 8-Hydroxygeraniol". The Journal of Organic Chemistry. 83 (18): 11323–11326. doi:10.1021/acs.joc.8b01544. PMC 6508077. PMID 29969566.