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Identification
YMDB IDYMDB01656
NameCitral
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionGeranial, also known as alpha-citral or neral, belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Thus, geranial is considered to be an isoprenoid lipid molecule. Geranial is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Geranial is a potentially toxic compound.
Structure
Thumb
Synonyms
  • (2E)-3,7-Dimethyl-2,6-octadienal
  • 2, 6-Octadienal, 3,7-dimethyl-
  • 2,6-Octadienal, 3,7-dimethyl-
  • 3,7-Dimethyl-1,2, 6-octadienal
  • 3,7-Dimethyl-1,2,6-octadienal
  • 3,7-Dimethyl-2,6-octadienal
  • cis-Citral
  • cis,trans-Citral
  • Citral (cis and trans)
  • Citral acis-3,7-dimethyl-2,6-octadienal
  • Geranial
  • Lemarome n
  • Neral
  • trans-Citral
  • Z-3,7-Dimethyl-2,6-octadiene-1-al
  • (e)-Citral
  • (e)-Geranial
  • alpha-Citral
  • Citral a
  • Lemonal
  • a-Citral
  • Α-citral
  • (e)-3,7-Dimethyl-2,6-octadienal
  • (e)-3,7-Dimethylocta-2,6-dienal
  • 3,7-Dimethyl-(2E)-2,6-octadienal
  • 3,7-Dimethyl-(e)-2,6-octadienal
  • 3,7-Dimethyl-trans-2,6-octadienal
  • alpha -Citral
  • beta-Geranial
  • Citral-a
  • Genanial
  • Geranal
  • trans-3,7-Dimethyl-2,6-octadienal
  • (Z)-Citral
  • Citral
  • (2E)-3,7-Dimethyl-2,6-octadien-1-al
  • Geranaldehyde
  • beta-Neral
  • trans-3,7-Dimethyl-2,6-octadien-1-al
  • trans-Geranial
  • β-Geranial
  • β-Neral
  • 3,7-Dimethyl-2,6-octadien-1-al
CAS number5392-40-5
WeightAverage: 152.2334
Monoisotopic: 152.120115134
InChI KeyWTEVQBCEXWBHNA-JXMROGBWSA-N
InChIInChI=1S/C10H16O/c1-9(2)5-4-6-10(3)7-8-11/h5,7-8H,4,6H2,1-3H3/b10-7+
IUPAC Name(2E)-3,7-dimethylocta-2,6-dienal
Traditional IUPAC Nameα-citral
Chemical FormulaC10H16O
SMILESCC(C)=CCC\C(C)=C\C=O
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
  • Medium-chain aldehyde
  • Enal
  • Alpha,beta-unsaturated aldehyde
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateLiquid
Charge0
Melting point<-10 °C
Experimental Properties
PropertyValueReference
Water Solubility1.34 mg/mL at 37 oC [YALKOWSKY,SH & HE,Y (2003)]PhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.4 g/LALOGPS
logP3.37ALOGPS
logP2.66ChemAxon
logS-2.6ALOGPS
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity50.12 m³·mol⁻¹ChemAxon
Polarizability18.6 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic Properties
Flavour/OdourSource
BitterFDB013721
LemonFDB013721
SharpFDB013721
SweetFDB013721
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 - EI-B (Non-derivatized)splash10-014l-9000000000-ccb0a3f327b5d2362bb9JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-9100000000-131249cb1d7fb343fe10JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-9100000000-dcdfd8342f2d4ce5a439JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-9100000000-3c1a8e898f563c833b2cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kf-9000000000-90723459c49195367705JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014l-9000000000-ccb0a3f327b5d2362bb9JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-9100000000-131249cb1d7fb343fe10JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-9100000000-dcdfd8342f2d4ce5a439JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-9100000000-3c1a8e898f563c833b2cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kf-9000000000-90723459c49195367705JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014l-9000000000-ccb0a3f327b5d2362bb9JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-9100000000-131249cb1d7fb343fe10JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-9100000000-dcdfd8342f2d4ce5a439JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-9100000000-3c1a8e898f563c833b2cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kf-9000000000-90723459c49195367705JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014l-9000000000-ccb0a3f327b5d2362bb9JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-9100000000-131249cb1d7fb343fe10JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-9100000000-dcdfd8342f2d4ce5a439JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-9100000000-3c1a8e898f563c833b2cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kf-9000000000-90723459c49195367705JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0159-9300000000-625c688e32f3edaf287cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1900000000-84bd30b4e03200f6db52JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-1010-8900000000-8aa62bcc7a1bcaa41a1eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9000000000-79a3e6745a117da8309bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-21d238fd55ee29af690fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1900000000-b84583833bad67467cf0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9700000000-a5e231c57e7f56a65d6dJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-014l-9100000000-92c761fd6ee64c67e40eJSpectraViewer | MoNA
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID16980
HMDB IDHMDB0035078
Pubchem Compound ID8843
Kegg IDC01499
ChemSpider ID553578
FOODB IDFDB013721
Wikipedia IDCitral
BioCyc IDNot Available