Np mrd loader

Showing NP-Card for Perillyl alcohol (NP0001072)

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Record Information
Version2.0
Created at2006-08-13 02:18:06 UTC
Updated at2021-10-07 20:38:51 UTC
NP-MRD IDNP0001072
Secondary Accession NumbersNone
Natural Product 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001072 (Perillyl alcohol)

Perillyl alcohol
  Mrv1652305271900252D          

 11 11  0  0  0  0            999 V2000
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  2  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
M  END
Download

3D MOL for NP0001072 (Perillyl alcohol)

HMDB0003634
     RDKit          3D
Perillyl alcohol
 27 27  0  0  0  0  0  0  0  0999 V2000
   -2.8500   -1.3720   -0.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2746   -0.2303    0.1502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2192    0.9322    0.3675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8125   -0.0665    0.3378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1166   -1.3899    0.1602 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3642   -1.2424    0.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9264   -0.1040   -0.1533 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4073   -0.0140   -0.0674 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7366    1.0452    0.8097 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1950    1.0707   -0.6495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2878    0.9900   -0.5924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3116   -2.2978   -0.4078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9284   -1.4656   -0.3469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6959    1.8843    0.4131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7464    0.7090    1.3244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9494    0.9990   -0.4852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6469    0.2633    1.3876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4070   -1.8134   -0.8148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4172   -2.0880    0.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9402   -2.0644    0.5757 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8666    0.1570   -1.0620 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8656   -0.9257    0.3422 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7093    0.9414    0.9862 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6045    1.9707   -0.1026 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4782    1.2693   -1.7251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6650    1.9735   -0.2178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7653    0.8686   -1.6077 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
 11  4  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  0
  5 18  1  0
  5 19  1  0
  6 20  1  0
  8 21  1  0
  8 22  1  0
  9 23  1  0
 10 24  1  0
 10 25  1  0
 11 26  1  0
 11 27  1  0
M  END
Download

3D SDF for NP0001072 (Perillyl alcohol)

Perillyl alcohol
  Mrv1652305271900252D          

 11 11  0  0  0  0            999 V2000
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  2  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001072

> <DATABASE_NAME>
NP-MRD

> <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

> <FORMULA>
C10H16O

> <MOLECULAR_WEIGHT>
152.237

> <EXACT_MASS>
152.120115135

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
18.186695411456675

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[4-(prop-1-en-2-yl)cyclohex-1-en-1-yl]methanol

> <ALOGPS_LOGP>
2.50

> <JCHEM_LOGP>
1.9390414949999997

> <ALOGPS_LOGS>
-1.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.85657008950134

> <JCHEM_PKA_STRONGEST_BASIC>
-1.986736242852114

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
48.254999999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.90e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(-)-perillylalcohol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0001072 (Perillyl alcohol)

HMDB0003634
     RDKit          3D
Perillyl alcohol
 27 27  0  0  0  0  0  0  0  0999 V2000
   -2.8500   -1.3720   -0.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2746   -0.2303    0.1502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2192    0.9322    0.3675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8125   -0.0665    0.3378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1166   -1.3899    0.1602 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3642   -1.2424    0.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9264   -0.1040   -0.1533 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4073   -0.0140   -0.0674 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7366    1.0452    0.8097 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1950    1.0707   -0.6495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2878    0.9900   -0.5924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3116   -2.2978   -0.4078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9284   -1.4656   -0.3469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6959    1.8843    0.4131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7464    0.7090    1.3244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9494    0.9990   -0.4852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6469    0.2633    1.3876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4070   -1.8134   -0.8148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4172   -2.0880    0.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9402   -2.0644    0.5757 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8666    0.1570   -1.0620 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8656   -0.9257    0.3422 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7093    0.9414    0.9862 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6045    1.9707   -0.1026 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4782    1.2693   -1.7251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6650    1.9735   -0.2178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7653    0.8686   -1.6077 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
 11  4  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  0
  5 18  1  0
  5 19  1  0
  6 20  1  0
  8 21  1  0
  8 22  1  0
  9 23  1  0
 10 24  1  0
 10 25  1  0
 11 26  1  0
 11 27  1  0
M  END
Download

PDB for NP0001072 (Perillyl alcohol)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Perillyl alcohol                                  
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   11                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7   11                                                       
CONECT   11   10    4                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for NP0001072 (Perillyl alcohol)

COMPND    HMDB0003634
HETATM    1  C1  UNL     1      -2.850  -1.372  -0.214  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.275  -0.230   0.150  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.219   0.932   0.368  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.812  -0.067   0.338  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.117  -1.390   0.160  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.364  -1.242   0.225  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.926  -0.104  -0.153  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.407  -0.014  -0.067  1.00  0.00           C  
HETATM    9  O1  UNL     1       3.737   1.045   0.810  1.00  0.00           O  
HETATM   10  C9  UNL     1       1.195   1.071  -0.650  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.288   0.990  -0.592  1.00  0.00           C  
HETATM   12  H1  UNL     1      -2.312  -2.298  -0.408  1.00  0.00           H  
HETATM   13  H2  UNL     1      -3.928  -1.466  -0.347  1.00  0.00           H  
HETATM   14  H3  UNL     1      -2.696   1.884   0.413  1.00  0.00           H  
HETATM   15  H4  UNL     1      -3.746   0.709   1.324  1.00  0.00           H  
HETATM   16  H5  UNL     1      -3.949   0.999  -0.485  1.00  0.00           H  
HETATM   17  H6  UNL     1      -0.647   0.263   1.388  1.00  0.00           H  
HETATM   18  H7  UNL     1      -0.407  -1.813  -0.815  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.417  -2.088   0.961  1.00  0.00           H  
HETATM   20  H9  UNL     1       1.940  -2.064   0.576  1.00  0.00           H  
HETATM   21  H10 UNL     1       3.867   0.157  -1.062  1.00  0.00           H  
HETATM   22  H11 UNL     1       3.866  -0.926   0.342  1.00  0.00           H  
HETATM   23  H12 UNL     1       4.709   0.941   0.986  1.00  0.00           H  
HETATM   24  H13 UNL     1       1.605   1.971  -0.103  1.00  0.00           H  
HETATM   25  H14 UNL     1       1.478   1.269  -1.725  1.00  0.00           H  
HETATM   26  H15 UNL     1      -0.665   1.973  -0.218  1.00  0.00           H  
HETATM   27  H16 UNL     1      -0.765   0.869  -1.608  1.00  0.00           H  
CONECT    1    2    2   12   13
CONECT    2    3    4
CONECT    3   14   15   16
CONECT    4    5   11   17
CONECT    5    6   18   19
CONECT    6    7    7   20
CONECT    7    8   10
CONECT    8    9   21   22
CONECT    9   23
CONECT   10   11   24   25
CONECT   11   26   27
END
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SMILES for NP0001072 (Perillyl alcohol)

CC(=C)C1CCC(CO)=CC1
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INCHI for NP0001072 (Perillyl alcohol)

InChI=1S/C10H16O/c1-8(2)10-5-3-9(7-11)4-6-10/h3,10-11H,1,4-7H2,2H3
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View in JSmol
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 Mass152.2370 Da
Monoisotopic Mass152.12012 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Bunium persicumLOTUS Database
Canella winteranaLOTUS Database
Carum carviFooDB
Cedronella canariensisLOTUS Database
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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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point244 °CNot Available
Boiling Point119.00 to 121.00 °C. @ 11.00 mm HgThe Good Scents Company Information System
Water Solubility471 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.17Griffin, S., Wyllie, S. G., & Markham, J. (1999). Determination of octanol-water partition coefficient for terpenoids using reversed-phase high-performance liquid chromatography. Journal of Chromatography A, 864(2), 221-228.
Predicted 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
HMDB IDHMDB0003634
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014923
KNApSAcK IDC00053669
Chemspider ID10362
KEGG Compound IDC02452
BioCyc IDPerillyl-Alcohols
BiGG ID39849
Wikipedia LinkPerillyl alcohol
METLIN ID6969
PubChem Compound10819
PDB IDNot Available
ChEBI ID15420
Good Scents IDrw1031131
References
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 ]
  4. 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. doi: 10.1016/s0378-4347(99)00065-1. [PubMed:10379660 ]
  5. Clark SS, Perman SM, Sahin MB, Jenkins GJ, Elegbede JA: Antileukemia activity of perillyl alcohol (POH): uncoupling apoptosis from G0/G1 arrest suggests that the primary effect of POH on Bcr/Abl-transformed cells is to induce growth arrest. Leukemia. 2002 Feb;16(2):213-22. doi: 10.1038/sj.leu.2402369. [PubMed:11840288 ]