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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 01:00:33 UTC
Update Date2023-02-21 17:26:59 UTC
HMDB IDHMDB0039522
Secondary Accession Numbers
  • HMDB39522
Metabolite Identification
Common NameLinalyl acetate
DescriptionLinalyl acetate, also known as 3,7-dimethylocta-1,6-dien-3-yl acetate, is a monoterpenoid that is the acetate ester of linalool. It forms a principal component of the essential oils from bergamot and lavender. It is an acetate ester and a monoterpenoid that derives from linalool. Linalyl acetate is isolated from numerous plants and essential oils, e.g. clary sage, lavender, lemon etc., and it is used as a flavouring ingredient. Synthetic linalyl acetate is sometimes used as an adulterant in essential oils to make them more marketable.
Structure
Data?1677000419
Synonyms
ValueSource
Linalyl acetic acidGenerator
(+)-1,5-Dimethyl-1-vinylhex-4-enyl acetateHMDB
(-)-S-Linalyl acetateHMDB
(1)-1,5-Dimethyl-1-vinylhex-4-enyl acetateHMDB
(R)-Linalyl acetateHMDB
1,5-Dimethyl-1-vinyl-4-hexenyl acetateHMDB
1,5-Dimethyl-1-vinylhex-4-en-1-yl acetateHMDB
1,6-Octadien-3-ol, 3, 7-dimethyl-, acetateHMDB
1,6-Octadien-3-ol, 3,7-dimethyl-, 3-acetateHMDB
1,6-Octadien-3-ol, 3,7-dimethyl-, acetateHMDB
3,7-Dimethyl-1,6-ctadien-3-ol acetateHMDB
3,7-Dimethyl-1,6-octadien-3-ol acetateHMDB
3,7-Dimethyl-1,6-octadien-3-yl acetateHMDB
3,7-Dimethyl-3-acetate(3R)-1,6-octadien-3-olHMDB
3,7-Dimethyl-acetate(3R)-1,6-octadien-3-olHMDB
Acetic acid linalool esterHMDB
Aetic acid linalool esterHMDB
BergamiolHMDB
BergamolHMDB
Bergamot mint oilHMDB
Dehydrolinalool, acetateHMDB
Ex bois de rose (synthetic)HMDB
FEMA 2636HMDB
Licareol acetateHMDB
Linalol acetateHMDB
Linalool acetateHMDB
Linalyl acetate syntheticHMDB
Lynalyl acetateHMDB
PhanteineHMDB
Linalyl acetate, (+-)-isomerMeSH, HMDB
Linalyl acetate, (R)-isomerMeSH, HMDB
Linalyl acetate, (S)-isomerMeSH, HMDB
3,7-Dimethylocta-1,6-dien-3-yl acetic acidGenerator
Linalyl acetateMeSH
Chemical FormulaC12H20O2
Average Molecular Weight196.286
Monoisotopic Molecular Weight196.146329884
IUPAC Name3,7-dimethylocta-1,6-dien-3-yl acetate
Traditional Namelinalyl acetate
CAS Registry Number115-95-7
SMILES
CC(C)=CCCC(C)(OC(C)=O)C=C
InChI Identifier
InChI=1S/C12H20O2/c1-6-12(5,14-11(4)13)9-7-8-10(2)3/h6,8H,1,7,9H2,2-5H3
InChI KeyUWKAYLJWKGQEPM-UHFFFAOYSA-N
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
Ontology
Physiological effect
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling Point220.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility20.12 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.93Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+146.41331661259
DarkChem[M-H]-144.90331661259
DeepCCS[M+H]+144.41330932474
DeepCCS[M-H]-141.75230932474
DeepCCS[M-2H]-177.99130932474
DeepCCS[M+Na]+153.52930932474
AllCCS[M+H]+148.032859911
AllCCS[M+H-H2O]+144.332859911
AllCCS[M+NH4]+151.532859911
AllCCS[M+Na]+152.632859911
AllCCS[M-H]-147.832859911
AllCCS[M+Na-2H]-149.132859911
AllCCS[M+HCOO]-150.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Linalyl acetateCC(C)=CCCC(C)(OC(C)=O)C=C1615.4Standard polar33892256
Linalyl acetateCC(C)=CCCC(C)(OC(C)=O)C=C1267.5Standard non polar33892256
Linalyl acetateCC(C)=CCCC(C)(OC(C)=O)C=C1284.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Linalyl acetate EI-B (Non-derivatized)splash10-006x-9100000000-a199bdb794a1711d64d62017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Linalyl acetate EI-B (Non-derivatized)splash10-0006-9200000000-2efbf1c4700ba9b34ab72017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Linalyl acetate EI-B (Non-derivatized)splash10-0006-9100000000-b497b7871d82184bce3a2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Linalyl acetate EI-B (Non-derivatized)splash10-0006-9100000000-c5a2a32609163f1d8a4d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Linalyl acetate EI-B (Non-derivatized)splash10-006x-9100000000-a199bdb794a1711d64d62018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Linalyl acetate EI-B (Non-derivatized)splash10-0006-9200000000-2efbf1c4700ba9b34ab72018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Linalyl acetate EI-B (Non-derivatized)splash10-0006-9100000000-b497b7871d82184bce3a2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Linalyl acetate EI-B (Non-derivatized)splash10-0006-9100000000-c5a2a32609163f1d8a4d2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Linalyl acetate GC-MS (Non-derivatized) - 70eV, Positivesplash10-00ko-9400000000-d9b638a0936492863bca2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Linalyl acetate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9100000000-712e3c9398c0bf42fe1a2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linalyl acetate 10V, Positive-QTOFsplash10-0002-1900000000-0f6c80cf6386280605792016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linalyl acetate 20V, Positive-QTOFsplash10-05n0-7900000000-c24d96c54b634a5ce01e2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linalyl acetate 40V, Positive-QTOFsplash10-014i-9100000000-edecc6807b28c4e59a9d2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linalyl acetate 10V, Negative-QTOFsplash10-0002-1900000000-e20da33a45dcd63c61052016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linalyl acetate 20V, Negative-QTOFsplash10-0zfs-3900000000-f698e30236a468ad6ab92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linalyl acetate 40V, Negative-QTOFsplash10-0553-9800000000-80dff10f3d6586f64ec22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linalyl acetate 10V, Negative-QTOFsplash10-0a4i-9400000000-fe0af33cbf0db86bab7b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linalyl acetate 20V, Negative-QTOFsplash10-0a4i-9200000000-f337ba0b5012d00f9c122021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linalyl acetate 40V, Negative-QTOFsplash10-0a4i-9000000000-f855cab3bee89dd8f2672021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linalyl acetate 10V, Positive-QTOFsplash10-001i-9300000000-db6bdfd0a5edf9f3864c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linalyl acetate 20V, Positive-QTOFsplash10-053r-9200000000-7cd15204eb37717e97262021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linalyl acetate 40V, Positive-QTOFsplash10-004i-9000000000-91362b0817199d37003e2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB019133
KNApSAcK IDC00003048
Chemspider ID13850082
KEGG Compound IDC09863
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLinalyl acetate
METLIN IDNot Available
PubChem Compound8294
PDB IDNot Available
ChEBI ID78333
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1007892
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.