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Identification
YMDB IDYMDB01728
NameLinalool acetate
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionLinalyl acetate, also known as bergamiol or bergamot mint oil, belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Linalyl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa). Linalyl acetate is a potentially toxic compound.
Structure
Thumb
Synonyms
  • 1,5-Dimethyl-1-vinyl-4-hexenyl acetate
  • 1,6-Octadien-3-ol, 3, 7-dimethyl-, acetate
  • 3,7-Dimethyl-1,6-octadien-3-ol acetate
  • 3,7-Dimethyl-1,6-octadien-3-yl acetate
  • ACETATE ION
  • Acetic acid linalool ester
  • acetic acid, ion(1-)
  • Azetat
  • Bergamiol
  • Bergamol
  • Bergamot mint oil
  • Ethanoat
  • ethanoate
  • Licareol acetate
  • Linalol acetate
  • Linalool acetate
  • Linalyl acetate
  • Lynalyl acetate
  • MeCO2 anion
  • Phanteine
  • Linalyl acetic acid
  • (+)-1,5-Dimethyl-1-vinylhex-4-enyl acetate
  • (-)-S-Linalyl acetate
  • (1)-1,5-Dimethyl-1-vinylhex-4-enyl acetate
  • (R)-Linalyl acetate
  • 1,5-Dimethyl-1-vinylhex-4-en-1-yl acetate
  • 1,6-Octadien-3-ol, 3,7-dimethyl-, 3-acetate
  • 1,6-Octadien-3-ol, 3,7-dimethyl-, acetate
  • 3,7-Dimethyl-1,6-ctadien-3-ol acetate
  • 3,7-Dimethyl-3-acetate(3R)-1,6-octadien-3-ol
  • 3,7-Dimethyl-acetate(3R)-1,6-octadien-3-ol
  • Aetic acid linalool ester
  • Dehydrolinalool, acetate
  • Ex bois de rose (synthetic)
  • FEMA 2636
  • Linalyl acetate synthetic
  • Linalyl acetate, (+-)-isomer
  • Linalyl acetate, (R)-isomer
  • Linalyl acetate, (S)-isomer
  • 3,7-Dimethylocta-1,6-dien-3-yl acetic acid
CAS number115-95-7
WeightAverage: 196.286
Monoisotopic: 196.146329884
InChI KeyUWKAYLJWKGQEPM-UHFFFAOYSA-N
InChIInChI=1S/C12H20O2/c1-6-12(5,14-11(4)13)9-7-8-10(2)3/h6,8H,1,7,9H2,2-5H3
IUPAC Name3,7-dimethylocta-1,6-dien-3-yl acetate
Traditional IUPAC Namelinalyl acetate
Chemical FormulaC12H20O2
SMILESCC(C)=CCCC(C)(OC(C)=O)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
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point< 25 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogP3.93 [GRIFFIN,S ET AL. (1999)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.061 g/LALOGPS
logP4.03ALOGPS
logP3.09ChemAxon
logS-3.5ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity59.36 m³·mol⁻¹ChemAxon
Polarizability23.21 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
BergamotFDB019133
CitrusFDB019133
FruitFDB019133
GreenFDB019133
LavenderFDB019133
SweetFDB019133
WoodyFDB019133
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)splash10-006x-9100000000-a199bdb794a1711d64d6JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9200000000-2efbf1c4700ba9b34ab7JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-b497b7871d82184bce3aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-c5a2a32609163f1d8a4dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-006x-9100000000-a199bdb794a1711d64d6JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9200000000-2efbf1c4700ba9b34ab7JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-b497b7871d82184bce3aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-c5a2a32609163f1d8a4dJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00ko-9400000000-d9b638a0936492863bcaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-1900000000-0f6c80cf638628060579JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05n0-7900000000-c24d96c54b634a5ce01eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9100000000-edecc6807b28c4e59a9dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1900000000-e20da33a45dcd63c6105JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfs-3900000000-f698e30236a468ad6ab9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0553-9800000000-80dff10f3d6586f64ec2JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0006-9100000000-712e3c9398c0bf42fe1aJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Loscos, N., Hernandez-Orte, P., Cacho, J., Ferreira, V. (2007). "Release and formation of varietal aroma compounds during alcoholic fermentation from nonfloral grape odorless flavor precursors fractions." J Agric Food Chem 55:6674-6684.17616208
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID78333
HMDB IDHMDB0039522
Pubchem Compound ID8294
Kegg IDC09863
ChemSpider ID13850082
FOODB IDFDB019133
Wikipedia IDLinalyl acetate
BioCyc IDNot Available