8-Hydroxygeraniol

8-Hydroxygeraniol (also incorrectly called 10-hydroxygeraniol) 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. 8-Hydroxygeraniol is step in the synthesis of the secologanin, a key monoterpene needed for formation of terpene indole alkaloids.

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
KEGG
PubChem CID
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
SMILES
  • 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).
Infobox references

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

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