3,7-Dimethyl-6-octen-1-ol (YMDB01372)

Identification
YMDB IDYMDB01372
Name3,7-Dimethyl-6-octen-1-ol
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionCitronellol, also known as beta-citronellol or cephrol, belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Citronellol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • (R)-(+)-Citronellol
  • 2,3-Dihydrogeraniol
  • 2,6-Dimethyl-2-octen-8-ol
  • 3, 7-Dimethyl-6-octen-1-ol
  • 3,7-Dimethyl-6-octen-1-ol
  • 6-Octen-1-ol, 3,7-dimethyl-
  • beta-Citronellol
  • Cephrol
  • Citronellol
  • Elenol
  • R-(+)-3,7-Dimethyl-6-octen-1-ol
  • R-(+)-beta-Citronellol
  • RHODINOL
  • Rodinol
  • b-Citronellol
  • Β-citronellol
  • Citronellol, (S)-isomer
  • Citronellol, (R)-isomer
  • Citronellol, (+-)-isomer
  • Citronellol, titanium (+4) salt
CAS number106-22-9
WeightAverage: 156.2652
Monoisotopic: 156.151415262
InChI KeyQMVPMAAFGQKVCJ-UHFFFAOYSA-N
InChIInChI=1S/C10H20O/c1-9(2)5-4-6-10(3)7-8-11/h5,10-11H,4,6-8H2,1-3H3
IUPAC Name3,7-dimethyloct-6-en-1-ol
Traditional IUPAC Namecitronellol, (+-)-
Chemical FormulaC10H20O
SMILESCC(CCO)CCC=C(C)C
Chemical Taxonomy
Description belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentAcyclic monoterpenoids
Alternative Parents
Substituents
  • Acyclic monoterpenoid
  • Fatty alcohol
  • Fatty acyl
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point< 25 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogP3.91 [GRIFFIN,S ET AL. (1999)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.85 g/LALOGPS
logP3.48ALOGPS
logP2.75ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)17.11ChemAxon
pKa (Strongest Basic)-1.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity50.49 m³·mol⁻¹ChemAxon
Polarizability20.05 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
Organoleptic Properties
Flavour/OdourSource
CitrusFDB014490
FloralFDB014490
GeraniumFDB014490
LeatherFDB014490
RoseFDB014490
Rose budFDB014490
WaxyFDB014490
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-02go-9400000000-68f35447a1addaa3c7e9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-1900000000-9f559c6b6bae07c69978JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-8900000000-f8c3d1ff7e6f87d6e43dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-066u-9100000000-8ae7fa4f01b76f1eed16JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-82f8313ff8eb7c68242bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-0900000000-de94d5335c77bdb5afcfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6u-9800000000-b04acf4b20ad46274796JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Tsakiris, A., Koutinas, A. A., Psarianos, C., Kourkoutas, Y., Bekatorou, A. (2010). "A new process for wine production by penetration of yeast in uncrushed frozen grapes." Appl Biochem Biotechnol 162:1109-1121.20151225
  • Kogan, G. L., Filipp, D., Arman, I. P., Leibovich, B. A., Beliaeva, E. S. (1991). "[Cloning of segments of the Drosophila melanogaster genome using artificial chromosomes of the yeast Saccharomyces cerevisiae]." Genetika 27:1316-1323.1761208
  • Gramatica, P., Manitto, P., Ranzi, B. M., Delbianco, A., & Francavilla, M. (1982) Stereospecific reduction of geraniol to (R)-(+)-citronellol by Saccharomyces cerevisiae. Experientia, 38, 775–776
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID50462
HMDB IDHMDB0171174
Pubchem Compound ID7793
Kegg IDC09849
ChemSpider ID13850135
FOODB IDFDB014490
WikipediaCitronellol
BioCyc IDNot Available