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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:28:21 UTC
Update Date2021-10-13 07:03:04 UTC
HMDB IDHMDB0037231
Secondary Accession Numbers
  • HMDB37231
Metabolite Identification
Common NamePerillyl acetate
DescriptionPerillyl acetate belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Based on a literature review a significant number of articles have been published on Perillyl acetate.
Structure
Data?1563862997
Synonyms
ValueSource
Perillyl acetic acidGenerator
(4-Isopropenyl-1-cyclohexen-1-yl)methyl acetateHMDB
1,8-P-Menthadien-7-yl acetateHMDB
1-Cyclohexene-1-methanol, 4-(1-methylethenyl)-, 1-acetateHMDB
1-Cyclohexene-1-methanol, 4-(1-methylethenyl)-, acetateHMDB
4-(1-Methylethenyl)-1-cyclohexene-1-methyl acetateHMDB
4-(1-Methylvinyl)cyclohex-1-ene-1-methyl acetateHMDB
4-Isopropenyl-1-cyclohexene carbinyl acetateHMDB
Cyclohex-1-ene-1-methanol-4-(1-methylethenyl)-acetateHMDB
Dihydrocuminyl acetateHMDB
FEMA 3561HMDB
Menthadien-7-carbinyl acetateHMDB
P-Mentha-1,8-dien-7-ol, acetateHMDB
P-Mentha-1,8-dien-7-yl acetateHMDB
Perilla acetateHMDB
[4-(Prop-1-en-2-yl)cyclohex-1-en-1-yl]methyl acetic acidGenerator
Chemical FormulaC12H18O2
Average Molecular Weight194.2701
Monoisotopic Molecular Weight194.13067982
IUPAC Name[4-(prop-1-en-2-yl)cyclohex-1-en-1-yl]methyl acetate
Traditional Name[4-(prop-1-en-2-yl)cyclohex-1-en-1-yl]methyl acetate
CAS Registry Number15111-96-3
SMILES
CC(=O)OCC1=CCC(CC1)C(C)=C
InChI Identifier
InChI=1S/C12H18O2/c1-9(2)12-6-4-11(5-7-12)8-14-10(3)13/h4,12H,1,5-8H2,2-3H3
InChI KeyWTXBCFKGCNWPLS-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentMenthane monoterpenoids
Alternative Parents
Substituents
  • P-menthane monoterpenoid
  • Monocyclic monoterpenoid
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point218.00 to 223.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0 slightlyThe Good Scents Company Information System
LogP3.610 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.29 g/LALOGPS
logP10(3.63) g/LALOGPS
logP10(2.38) g/LChemAxon
logS10(-2.8) g/LALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity57.41 m³·mol⁻¹ChemAxon
Polarizability22.39 ųChemAxon
Number of Rings1ChemAxon
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]+147.74531661259
DarkChem[M-H]-143.22531661259
DeepCCS[M+H]+141.89630932474
DeepCCS[M-H]-139.25230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Perillyl acetateCC(=O)OCC1=CCC(CC1)C(C)=C1834.7Standard polar33892256
Perillyl acetateCC(=O)OCC1=CCC(CC1)C(C)=C1413.9Standard non polar33892256
Perillyl acetateCC(=O)OCC1=CCC(CC1)C(C)=C1452.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Perillyl acetate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9300000000-442b31e2dc1c386b2c802017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Perillyl acetate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9400000000-93d3eaaf9951a78f27112015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perillyl acetate 10V, Positive-QTOFsplash10-000b-1900000000-b191393adb7d6521ded02016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perillyl acetate 20V, Positive-QTOFsplash10-000i-3900000000-1307c45ae24e114471872016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perillyl acetate 40V, Positive-QTOFsplash10-0gbc-9200000000-a6c963bb131e06865c6d2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perillyl acetate 10V, Negative-QTOFsplash10-0006-3900000000-2bf01d0e16bbcd21ecd92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perillyl acetate 20V, Negative-QTOFsplash10-052f-9800000000-fb08d476359f0347e3382016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perillyl acetate 40V, Negative-QTOFsplash10-052f-9600000000-9c74270b55d346720b802016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perillyl acetate 10V, Negative-QTOFsplash10-0a4i-9000000000-c01bbbf5bed889264ddb2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perillyl acetate 20V, Negative-QTOFsplash10-0a59-9400000000-4c01f51d5d608ecff2252021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perillyl acetate 40V, Negative-QTOFsplash10-0a4i-9000000000-786c8b3bff24576435712021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perillyl acetate 10V, Positive-QTOFsplash10-000b-4900000000-e45fe23e1fc1686118fa2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perillyl acetate 20V, Positive-QTOFsplash10-0006-9300000000-936cfd26bff1f5a7cd0a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perillyl acetate 40V, Positive-QTOFsplash10-0006-9200000000-e7b75605b3853fc700712021-09-25Wishart 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 IDFDB016238
KNApSAcK IDNot Available
Chemspider ID55667
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound61780
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1031171
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.