(2-trans,6-trans)-Farnesol (YMDB00404)

Identification
YMDB IDYMDB00404
Name(2-trans,6-trans)-Farnesol
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionFarnesol, also known as (2E,6E)-farnesol or trans-farnesol, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Thus, farnesol is considered to be an isoprenoid. Based on a literature review a significant number of articles have been published on Farnesol.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • (2-trans,6-trans)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol
  • (2E,6E)-3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol
  • (2E,6E)-Farnesol
  • (E,E)-Farnesol
  • (E)-farnesol
  • 2-cis,6-trans-Farnesol
  • 2-trans,6-trans-Farnesol
  • 2,6-Di-trans-Farnesol
  • 3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol
  • All-trans-Farnesol
  • Farnesol
  • Farnesol (2E,6E)
  • Farnesol, (E,E)-
  • Farnesyl alcohol
  • Nikkosome
  • trans-Farnesol
  • trans,trans-alpha-Farnesol
  • trans,trans-Farnesol
  • Ditrans,polycis-polyprenol
  • trans,trans-a-Farnesol
  • trans,trans-Α-farnesol
  • FCI 119a
  • (E)-beta-Farnesol
  • (E)-β-Farnesol
  • (E,E)-3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol
  • (E,E)-Farnesyl alcohol
  • (t,t)-Farnesol
  • 2,6-trans,trans-Farnesol
  • 3,7,11-Trimethyldodeca-2-trans,6-trans,10-trien-1-ol
  • all-E-Farnesol
  • trans-1-Hydroxy-3,7,11-trimethyl-2,6,10-dodecatriene
  • trans-2,trans-6-Farnesol
  • 3,7,11-Trimethyl-2,6,10-dodecen-1-ol
CAS number106-28-5
WeightAverage: 222.3663
Monoisotopic: 222.198365454
InChI KeyCRDAMVZIKSXKFV-YFVJMOTDSA-N
InChIInChI=1S/C15H26O/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-16/h7,9,11,16H,5-6,8,10,12H2,1-4H3/b14-9+,15-11+
IUPAC Name(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol
Traditional IUPAC Name(E)-farnesol
Chemical FormulaC15H26O
SMILESCC(C)=CCC\C(C)=C\CC\C(C)=C\CO
Chemical Taxonomy
Description belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Farsesane sesquiterpenoid
  • Sesquiterpenoid
  • 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
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.059 g/LALOGPS
logP4.84ALOGPS
logP4.16ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)16.33ChemAxon
pKa (Strongest Basic)-2.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity74.98 m³·mol⁻¹ChemAxon
Polarizability28.7 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-000x-9800000000-0366097ae9a2af6bafceJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-001l-9800000000-eec57a93bb5862e554f1JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-000x-8900000000-9c20df8f2d1959c137d7JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000x-9800000000-0366097ae9a2af6bafceJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001l-9800000000-eec57a93bb5862e554f1JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000x-8900000000-9c20df8f2d1959c137d7JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4u-9830000000-5e08d59a4cc2e87c9984JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05xr-9860000000-2eeca721058a47519afdJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-003u-0790000000-578343425424f42c9d58JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-1590000000-88a1356fe7cab3171954JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0avi-7930000000-81c18181dbd66735216aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gi0-9400000000-e44ecbea8a96f84abd43JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0390000000-9beef594142e0da5de92JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-1980000000-3b9708ac6185abaf6d96JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05bf-4910000000-a8db2089f5647c8532adJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-ab61d8a2af41e6ed2e49JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0690000000-8a43271c10743cad1e3eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00l2-4900000000-7dcaa3b1e66cfbe960c9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05gi-5930000000-9f54facb49232e1c6a46JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05o0-9600000000-55d109ed92e3da30c7eaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00l6-9100000000-bcc664ee21d185da076eJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-014l-9200000000-8e5fae6943a545e4bc0bJSpectraViewer | MoNA
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:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Synthesis Reference:Imai, Kunio; Marumo, Shingo. Stereochemistry of C-1 hydrogen exchange during 2,3-double bond trans-cis isomerization of farnesol by Helminthosporium sativum. Tetrahedron Letters (1974), (49/50), 4401-4.
External Links:
ResourceLink
CHEBI ID16619
HMDB IDHMDB04305
Pubchem Compound ID445070
Kegg IDC01126
ChemSpider ID24841982
FOODB IDFDB014891
WikipediaFarnesol
BioCyc ID2-TRANS6-TRANS-FARNESOL

Enzymes

Protein Details
1. Repressible alkaline phosphatase
General function:
Involved in catalytic activity
Specific function:
A phosphate monoester + H(2)O = an alcohol + phosphate
Gene Name:
PHO8
Uniprot ID:
P11491
Molecular weight:
63003.60156
Reactions
A phosphate monoester + H(2)O → an alcohol + phosphate.
(2E,6E)-farnesyl diphosphate + H(2)O → (2E,6E)-farnesol + diphosphate.
beta-D-fructose 2,6-bisphosphate + H2O → beta-D-fructofuranose 2-phosphate + phosphate