You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2006-08-13 02:18:06 UTC
Update Date2016-02-11 01:06:24 UTC
HMDB IDHMDB03634
Secondary Accession NumbersNone
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
Thumb
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
Chemical FormulaC10H16O
Average Molecular Weight152.2334
Monoisotopic Molecular Weight152.120115134
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 KeyInChIKey=NDTYTMIUWGWIMO-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Menthane monoterpenoid
  • Monocyclic monoterpenoid
  • Cyclic alcohol
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Drug
  • Plant
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point244 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP3.17GRIFFIN,S ET AL. (1999)
Predicted Properties
PropertyValueSource
Water Solubility1.9 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity48.25 m3·mol-1ChemAxon
Polarizability18.19 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0006-9600000000-852faf99c20eb91e9836View in MoNA
GC-MSGC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00du-3900000000-a6c07543feea874fe65dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004u-9000000000-352e042e70150a70fc17View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0bvj-9000000000-9a2da0a6d60335f43f46View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-00mo-9200000000-81544f3016fa24bad81fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue Location
  • Pancreas
  • Prostate
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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. [10379660 ]
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB014923
KNApSAcK IDNot Available
Chemspider ID10362
KEGG Compound IDC02452
BioCyc IDCPD-261
BiGG ID39849
Wikipedia LinkNot Available
NuGOwiki LinkHMDB03634
Metagene LinkHMDB03634
METLIN ID6969
PubChem Compound10819
PDB IDNot Available
ChEBI ID15420
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. [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. [9276644 ]
  3. Belanger JT: Perillyl alcohol: applications in oncology. Altern Med Rev. 1998 Dec;3(6):448-57. [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