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Human Metabolome Database Version 3.5

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Showing metabocard for Perillyl alcohol (HMDB03634)

Record Information
Version 3.5
Creation Date 2006-08-12 20:18:06 -0600
Update Date 2013-02-08 17:12:41 -0700
HMDB ID HMDB03634
Secondary Accession Numbers None
Metabolite Identification
Common Name Perillyl alcohol
Description Perillyl 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 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (-)-Perillyl alcohol
  2. (S)-(-)-Perillyl alcohol
  3. 1,8-p-Menthadien-7-ol
  4. 4-Isopropenyl-1-cyclohexene carbinol
  5. 4-Isopropenyl-cyclohex-1-ene-1-methanol
  6. 4-Isopropenylcyclohex-1-en-1-ylmethanol
  7. Dihydrocuminic alcohol
  8. Dihydrocuminyl alcohol
  9. Hydrocumin alcohol
  10. Iso-carveol
  11. Isocarveol
  12. p-Mentha-1,8-dien-7-ol
  13. Para-mentha-1,8-dien-7-ol
  14. Perill alcohol
  15. Perilla alcohol
  16. Perillic alcohol
  17. Perillol
Chemical Formula C10H16O
Average Molecular Weight 152.2334
Monoisotopic Molecular Weight 152.120115134
IUPAC Name [4-(prop-1-en-2-yl)cyclohex-1-en-1-yl]methanol
Traditional IUPAC Name perillyl alcohol
CAS Registry Number 536-59-4
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 Key NDTYTMIUWGWIMO-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Prenol Lipids
Sub Class Monoterpenes
Other Descriptors
  • Aliphatic Homomonocyclic Compounds
  • Monoterpenes
Substituents
  • Cyclic Alcohol
  • Cyclohexene
  • Primary Alcohol
Direct Parent Monocyclic Monoterpenes
Ontology
Status Detected and Quantified
Origin
  • Plant
  • Drug
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
State Solid
Experimental Properties
Property Value Reference
Melting Point 244 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP 3.17 GRIFFIN,S ET AL. (1999)
Predicted Properties
Property Value Source
Water Solubility 1.9 g/L ALOGPS
LogP 2.50 ALOGPS
LogP 1.94 ChemAxon
LogS -1.90 ALOGPS
pKa (strongest acidic) 16.86 ChemAxon
pKa (strongest basic) -2 ChemAxon
Hydrogen Acceptor Count 1 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 20.23 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 48.25 ChemAxon
Polarizability 18.19 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum EI-B (HITACHI M-80B)
MS/MS Spectrum GC-MS
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue Location
  • Pancreas
  • Prostate
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
0.028 (0.023 - 0.032) uM Adult (>18 years old) Female Perillyl alcohol administration for cancer treatment AJCC Stage I–IIIa breast cancer after oral...
Associated Disorders and Diseases
Disease References
Perillyl alcohol administration for cancer treatment
  • 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 Link_out
    Associated OMIM IDs None
    DrugBank ID Not Available
    Phenol Explorer Compound ID Not Available
    Phenol Explorer Metabolite ID Not Available
    FoodDB ID FDB014923
    KNApSAcK ID Not Available
    Chemspider ID 10362 Link_out
    KEGG Compound ID C02452 Link_out
    BioCyc ID CPD-261 Link_out
    BiGG ID 39849 Link_out
    Wikipedia Link Not Available
    NuGOwiki Link HMDB03634 Link_out
    Metagene Link HMDB03634 Link_out
    METLIN ID 6969 Link_out
    PubChem Compound 10819 Link_out
    PDB ID Not Available
    ChEBI ID 15420 Link_out
    References
    Synthesis Reference Li, 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 Link_out
    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 Link_out
    Enzymes
    Name: Cytochrome P450 2C9
    Reactions:
    • (R)-limonene + NADPH + H+ + O2 = (+)-trans-carveol + NADP+ + H2O [RN:R06119]
    Gene Name: CYP2C9
    Uniprot ID: P11712 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Cytochrome P450 2C19
    Reactions:
    • (R)-limonene + NADPH + H+ + O2 = (+)-trans-carveol + NADP+ + H2O [RN:R06119]
    Gene Name: CYP2C19
    Uniprot ID: P33261 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA