Perillic acid (CHEM022529)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:38:40 UTC
Update Date2016-11-09 01:17:31 UTC
Accession NumberCHEM022529
Identification
Common NamePerillic acid
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4-(1-Methylethenyl)-1-cyclohexene-1-carboxylic acidChEBI
4-Isopropenylcyclohex-1-enecarboxylic acidChEBI
4-(1-Methylethenyl)-1-cyclohexene-1-carboxylateGenerator
4-Isopropenylcyclohex-1-enecarboxylateGenerator
PerillateGenerator
4-(2-Propenyl)-1-cyclohexane-1-carboxylic acidHMDB
4-Isopropenylcyclohex-1-ene carboxylic acidHMDB
Chemical FormulaC10H14O2
Average Molecular Mass166.220 g/mol
Monoisotopic Mass166.099 g/mol
CAS Registry Number7694-45-3
IUPAC Name4-(prop-1-en-2-yl)cyclohex-1-ene-1-carboxylic acid
Traditional Nameperillic acid
SMILESCC(=C)C1CCC(=CC1)C(O)=O
InChI IdentifierInChI=1S/C10H14O2/c1-7(2)8-3-5-9(6-4-8)10(11)12/h5,8H,1,3-4,6H2,2H3,(H,11,12)
InChI KeyCDSMSBUVCWHORP-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
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.63 g/LALOGPS
logP2.47ALOGPS
logP2.41ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)4.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity48.2 m³·mol⁻¹ChemAxon
Polarizability18.13 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-05di-5910000000-bd8e6a99a4d3b55c9c03Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-05di-5910000000-bd8e6a99a4d3b55c9c03Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01c3-9400000000-e30b212c252a489b1c8eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9520000000-332aa96c8aa0d2aeaa6eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-024i-3900000000-16e917430a8c841892feSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00ou-9100000000-68409596298e7b6acef3Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-024i-3900000000-16e917430a8c841892feSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0002-9300000000-d7b3cfdc7e8d493dd44cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0002-9400000000-9c643ffb36f6610feaf2Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0002-9400000000-8ccd2f8c0492b0e9ee03Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-0ebacf3cff2e0c00ef11Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00xr-3900000000-7e99a34da9f2f609046dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-9100000000-0d037a2e706cc01ac722Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-64c170dab26143a9232fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xr-0900000000-e177ee19741567205f44Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-4900000000-c2703d191f77cac3113cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014l-4900000000-1573b97140969b3484d3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002f-9400000000-96087ab5a6507e90b024Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002f-9100000000-f029f29fe7fce219e4eeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-349584a3f625d5b5807fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01b9-0900000000-0fa4b2ff935b571f25b9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05r3-9400000000-afb4a1702515ac477382Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0004586
FooDB IDFDB013215
Phenol Explorer IDNot Available
KNApSAcK IDC00010870
BiGG ID2266070
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID1218
ChEBI ID36999
PubChem Compound ID1256
Kegg Compound IDC11924
YMDB IDNot Available
ECMDB IDM2MDB004358
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Semmler, F. W.; Zaar, B. Constituents of Ethereal Oils. Constitution of Perillaldehyde, C10H14O. Berichte der Deutschen Chemischen Gesellschaft (1911), 44 52-7.
2. Semmler, F. W.; Zaar, B. Constituents of Ethereal Oils. Constitution of Perillaldehyde, C10H14O. Berichte der Deutschen Chemischen Gesellschaft (1911), 44 52-7.
3. Ripple GH, Gould MN, Arzoomanian RZ, Alberti D, Feierabend C, Simon K, Binger K, Tutsch KD, Pomplun M, Wahamaki A, Marnocha R, Wilding G, Bailey HH: Phase I clinical and pharmacokinetic study of perillyl alcohol administered four times a day. Clin Cancer Res. 2000 Feb;6(2):390-6.
4. Hudes GR, Szarka CE, Adams A, Ranganathan S, McCauley RA, Weiner LM, Langer CJ, Litwin S, Yeslow G, Halberr T, Qian M, Gallo JM: Phase I pharmacokinetic trial of perillyl alcohol (NSC 641066) in patients with refractory solid malignancies. Clin Cancer Res. 2000 Aug;6(8):3071-80.