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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-13 02:18:06 UTC
Update Date2022-03-07 02:49:19 UTC
HMDB IDHMDB0003634
Secondary Accession Numbers
  • HMDB03634
Metabolite Identification
Common NamePerillyl alcohol
DescriptionPerillyl alcohol is a monoterpene isolated from the essential oils of lavendin, peppermint, spearmint, cherries, celery seeds, and several other plants. In animal studies it has been shown to regress pancreatic, mammary, and liver tumors, to exhibit possible application as a chemopreventative agent for colon, skin, and lung cancer, and as a chemotherapeutic agent for neuroblastoma, and prostate and colon cancer.(PMID:9855569 ).
Structure
Data?1582752284
Synonyms
ValueSource
1-Hydroxymethyl-4-isopropenyl-1-cyclohexeneChEBI
1-PerillalcoholChEBI
4-(1-Methylethenyl)-1-cyclohexene-1-methanolChEBI
4-Isopropenyl-1-cyclohexene carbinolChEBI
4-Isopropenylcyclohex-1-en-1-ylmethanolChEBI
Dihydrocuminyl alcoholnChEBI
IsocarveolChEBI
p-Mentha-1,8-dien-7-olChEBI
Perilla alcoholChEBI
PerillolChEBI
(-)-Perillyl alcoholHMDB
(S)-(-)-Perillyl alcoholHMDB
1,8-p-Menthadien-7-olHMDB
4-Isopropenyl-cyclohex-1-ene-1-methanolHMDB
Dihydrocuminic alcoholHMDB
Dihydrocuminyl alcoholHMDB
Hydrocumin alcoholHMDB
Iso-carveolHMDB
Para-mentha-1,8-dien-7-olHMDB
Perill alcoholHMDB
Perillic alcoholHMDB
Cyclohex-1-ene-1-methanol, 4(1-methylethenyl)HMDB
Perilla alcohol, (S)-isomerHMDB
Perilla alcohol, (R)-isomerHMDB
(-)-p-Mentha-1,8-dien-7-olHMDB
(S)-Perillyl alcoholHMDB
Chemical FormulaC10H16O
Average Molecular Weight152.237
Monoisotopic Molecular Weight152.120115135
IUPAC Name[4-(prop-1-en-2-yl)cyclohex-1-en-1-yl]methanol
Traditional Name(-)-perillylalcohol
CAS Registry Number536-59-4
SMILES
CC(=C)C1CCC(CO)=CC1
InChI Identifier
InChI=1S/C10H16O/c1-8(2)10-5-3-9(7-11)4-6-10/h3,10-11H,1,4-7H2,2H3
InChI KeyNDTYTMIUWGWIMO-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
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point244 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP3.17GRIFFIN,S ET AL. (1999)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.9 g/LALOGPS
logP2.5ALOGPS
logP1.94ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)16.86ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity48.26 m³·mol⁻¹ChemAxon
Polarizability18.19 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+134.83131661259
DarkChem[M-H]-131.46831661259
DeepCCS[M+H]+141.45330932474
DeepCCS[M-H]-137.96930932474
DeepCCS[M-2H]-175.17730932474
DeepCCS[M+Na]+150.66230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Perillyl alcoholCC(=C)C1CCC(CO)=CC12006.9Standard polar33892256
Perillyl alcoholCC(=C)C1CCC(CO)=CC11270.3Standard non polar33892256
Perillyl alcoholCC(=C)C1CCC(CO)=CC11288.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Perillyl alcohol,1TMS,isomer #1C=C(C)C1CC=C(CO[Si](C)(C)C)CC11351.4Semi standard non polar33892256
Perillyl alcohol,1TBDMS,isomer #1C=C(C)C1CC=C(CO[Si](C)(C)C(C)(C)C)CC11584.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Perillyl alcohol GC-MS (1 TMS)splash10-0006-9600000000-852faf99c20eb91e98362014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Perillyl alcohol EI-B (Non-derivatized)splash10-00mo-9200000000-6d3cda5b991dc6f0a0982017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Perillyl alcohol EI-B (Non-derivatized)splash10-014l-9300000000-f32f7e87d33288c8045d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Perillyl alcohol GC-MS (Non-derivatized)splash10-0006-9600000000-852faf99c20eb91e98362017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Perillyl alcohol GC-MS (Non-derivatized) - 70eV, Positivesplash10-007x-9400000000-0642824f11b9c7fd315d2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Perillyl alcohol GC-MS (1 TMS) - 70eV, Positivesplash10-05gu-9510000000-9f19c403be332e74c8ad2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Perillyl alcohol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Perillyl alcohol Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-00du-3900000000-a6c07543feea874fe65d2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Perillyl alcohol Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-004u-9000000000-352e042e70150a70fc172012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Perillyl alcohol Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0bvj-9000000000-9a2da0a6d60335f43f462012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Perillyl alcohol EI-B (HITACHI M-80B) , Positive-QTOFsplash10-00mo-9200000000-81544f3016fa24bad81f2012-08-31HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perillyl alcohol 10V, Positive-QTOFsplash10-0udr-1900000000-2f012741782fc72aa3df2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perillyl alcohol 20V, Positive-QTOFsplash10-000i-5900000000-849092ef4eeddd4406872016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perillyl alcohol 40V, Positive-QTOFsplash10-0gc0-9200000000-fd4b15fd9437d4b704092016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perillyl alcohol 10V, Negative-QTOFsplash10-0udi-0900000000-20d0d9f448f90e31136f2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perillyl alcohol 20V, Negative-QTOFsplash10-0uk9-0900000000-a390120b9758e2ca2f5d2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perillyl alcohol 40V, Negative-QTOFsplash10-00di-4900000000-39d18f7a3231672157f52016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perillyl alcohol 10V, Negative-QTOFsplash10-0udi-0900000000-c373c9eea3cebf186f532021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perillyl alcohol 20V, Negative-QTOFsplash10-001i-0900000000-8fa95dbd5fa627e933fa2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perillyl alcohol 40V, Negative-QTOFsplash10-014i-9200000000-7da801ed46abad2dd6282021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perillyl alcohol 10V, Positive-QTOFsplash10-0f84-9800000000-bd8e7097a31172f8ad0e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perillyl alcohol 20V, Positive-QTOFsplash10-0006-9200000000-373d4892dedc5ff6266f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perillyl alcohol 40V, Positive-QTOFsplash10-00mo-9000000000-a6d86d2ceee0f1021fd32021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
Tissue Locations
  • Pancreas
  • Prostate
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.028 (0.023 - 0.032) uMAdult (>18 years old)Female
Perillyl alcohol administration for cancer treatment
details
Associated Disorders and Diseases
Disease References
Perillyl alcohol administration for cancer treatment
  1. Zhang Z, Chen H, Chan KK, Budd T, Ganapathi R: Gas chromatographic-mass spectrometric analysis of perillyl alcohol and metabolites in plasma. J Chromatogr B Biomed Sci Appl. 1999 May 14;728(1):85-95. [PubMed:10379660 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB014923
KNApSAcK IDNot Available
Chemspider ID10362
KEGG Compound IDC02452
BioCyc IDPerillyl-Alcohols
BiGG ID39849
Wikipedia LinkPerillyl alcohol
METLIN ID6969
PubChem Compound10819
PDB IDNot Available
ChEBI ID15420
Food Biomarker OntologyNot Available
VMH IDPERILLYL
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceLi, Qian-he; Zhan, Xiao-xiong; Feng, Zhen-zhen; Li, Xue-hui; Wang, Le-fu. Synthesis of perillyl alcohol via liquid phase rearrangement of 2,10-epoxypinane catalyzed by morpholinium nitrate. Hunan Shifan Daxue Ziran Kexue Xuebao (2006), 29(1), 56-59.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Greenwald P, Milner JA, Anderson DE, McDonald SS: Micronutrients in cancer chemoprevention. Cancer Metastasis Rev. 2002;21(3-4):217-30. [PubMed:12549762 ]
  2. Stayrook KR, McKinzie JH, Burke YD, Burke YA, Crowell PL: Induction of the apoptosis-promoting protein Bak by perillyl alcohol in pancreatic ductal adenocarcinoma relative to untransformed ductal epithelial cells. Carcinogenesis. 1997 Aug;18(8):1655-8. [PubMed:9276644 ]
  3. Belanger JT: Perillyl alcohol: applications in oncology. Altern Med Rev. 1998 Dec;3(6):448-57. [PubMed:9855569 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular weight:
55944.565