8-Hydroxygeraniol

{{Chembox

| ImageFile = 8-Hydroxygeraniol.svg

| ImageSize = 200px

| PIN = (2E,6E)-2,6-Dimethylocta-2,6-diene-1,8-diol

| OtherNames =

|Section1={{Chembox Identifiers

| CASNo = 26488-97-1

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 6WX29M860A

| PubChem = 5363397

| ChemSpiderID = 4515751

| KEGG = C17621

| ChEBI = 64235

| SMILES = C/C(=C\CO)/CC/C=C(\C)/CO

| 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+

| InChIKey = PREUOUJFXMCMSJ-TXFIJWAUBC

| StdInChI = 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+

| StdInChIKey = PREUOUJFXMCMSJ-TXFIJWAUSA-N

}}

|Section2={{Chembox Properties

| C=10 | H=18 | O=2

| Appearance =

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|Section3={{Chembox Hazards

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8-Hydroxygeraniol (also incorrectly called 10-hydroxygeraniol){{cite book | author = Paul M. Dewick | date = 2009 | title = Medicinal Natural Products: A Biosynthetic Approach | doi = 10.1002/9780470742761| isbn = 9780470742761 }} 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.{{cite journal | doi = 10.1038/ncomms4606| pmid = 24710322| pmc = 3992524| title = The seco-iridoid pathway from Catharanthus roseus| journal = Nature Communications| volume = 5| pages = 3606| year = 2014| last1 = Miettinen| first1 = Karel| last2 = Dong| first2 = Lemeng| last3 = Navrot| first3 = Nicolas| last4 = Schneider| first4 = Thomas| last5 = Burlat| first5 = Vincent| last6 = Pollier| first6 = Jacob| last7 = Woittiez| first7 = Lotte| last8 = Van Der Krol| first8 = Sander| last9 = Lugan| first9 = Raphaël| last10 = Ilc| first10 = Tina| last11 = Verpoorte| first11 = Robert| last12 = Oksman-Caldentey| first12 = Kirsi-Marja| last13 = Martinoia| first13 = Enrico| last14 = Bouwmeester| first14 = Harro| last15 = Goossens| first15 = Alain| last16 = Memelink| first16 = Johan| last17 = Werck-Reichhart| first17 = Danièle| bibcode = }} 8-Hydroxygeraniol is an intermediate 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.{{Cite journal | doi = 10.1021/acs.joc.8b01544 | pmid = 29969566 | title = Synthesis of 8-Hydroxygeraniol | journal = The Journal of Organic Chemistry | volume = 83 | issue = 18 | pages = 11323–11326 | year = 2018 | last1 = Ippoliti | first1 = Francesca M. | last2 = Barber | first2 = Joyann S. | last3 = Tang | first3 = Yi | last4 = Garg | first4 = Neil K. | pmc = 6508077 }}