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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:27:20 UTC
Update Date2019-07-23 06:23:15 UTC
HMDB IDHMDB0037216
Secondary Accession Numbers
  • HMDB37216
Metabolite Identification
Common NameLinalyl phenylacetate
DescriptionLinalyl phenylacetate, also known as fema 3501 or linalyl alpha-toluate, belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. Linalyl phenylacetate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862995
Synonyms
ValueSource
Linalyl phenylacetic acidGenerator
1,5-Dimethyl-1-vinyl-4-hexenyl phenylacetateHMDB
1-Ethenyl-1,5-dimethyl-4-hexenyl benzeneacetateHMDB
3,7-Dimethyl-1,6-octadien-3-yl phenylacetateHMDB
Acetic acid, phenyl-, 1,5-dimethyl-1-vinyl-4-hexenyl esterHMDB
Benzeneacetic acid, 1,5-dimethyl-1-ethenyl-4-hexenyl esterHMDB
Benzeneacetic acid, 1-ethenyl-1,5-dimethyl-4-hexenyl esterHMDB
FEMA 3501HMDB
Linalyl alpha-toluateHMDB
3,7-Dimethylocta-1,6-dien-3-yl 2-phenylacetic acidGenerator
Linalyl phenylacetateMeSH
Chemical FormulaC18H24O2
Average Molecular Weight272.382
Monoisotopic Molecular Weight272.177630012
IUPAC Name3,7-dimethylocta-1,6-dien-3-yl 2-phenylacetate
Traditional Name3,7-dimethylocta-1,6-dien-3-yl 2-phenylacetate
CAS Registry Number7143-69-3
SMILES
CC(C)=CCCC(C)(OC(=O)CC1=CC=CC=C1)C=C
InChI Identifier
InChI=1S/C18H24O2/c1-5-18(4,13-9-10-15(2)3)20-17(19)14-16-11-7-6-8-12-16/h5-8,10-12H,1,9,13-14H2,2-4H3
InChI KeyRROUXOOIXJRTOM-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentAromatic monoterpenoids
Alternative Parents
Substituents
  • Monocyclic monoterpenoid
  • Aromatic monoterpenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0025 g/LALOGPS
logP5.3ALOGPS
logP4.92ChemAxon
logS-5ALOGPS
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity84.08 m³·mol⁻¹ChemAxon
Polarizability31.94 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9200000000-ffe22b4d105ef44b59d0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00xr-3890000000-a1d043cf298f7e9125c9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-8910000000-3e2ddfda9940e5b80e03Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9200000000-1347b2c541458da949bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-2690000000-c998d985360725ec6c8fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uki-2920000000-4d7351a84e2b3f73b553Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00n0-4900000000-ac5c2c3e50587a94f08fSpectrum
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 IDFDB016223
KNApSAcK IDNot Available
Chemspider ID220357
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound251529
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
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.