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Showing metabocard for p-Menthane-3,8-diol (HMDB0036145)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:12:33 UTC
Update Date2022-03-07 02:54:48 UTC
HMDB IDHMDB0036145
Secondary Accession Numbers
  • HMDB36145
Metabolite Identification
Common Namep-Menthane-3,8-diol
Descriptionp-Menthane-3,8-diol is found in fruits. p-Menthane-3,8-diol is a constituent of the roots of Litsea cubeba (mountain pepper).p-Menthane-3,8-diol, also known as para-menthane-3,8-diol and PMD, is an active ingredient used in insect repellents. It smells similar to menthol and acts as a coolant. PMD is found in the oil within leaves of the Eucalyptus citriodora tree. This tree is native to Australia, but is now cultivated in many warm places around the world. This oil, when refined for use in insect repellents, is known as Oil of Lemon Eucalyptus or, more commonly, Citriodiol. Typically, Citriodiol contains 64% PMD (a mixture of the cis and trans isomers of p-menthane-3,8-diol). Citriodiol has been notified under the European Biocidal Products Directive (BPD) 98/8/EC and is currently proceeding through the registration process with the Heath and Safety Executive in the UK. It is the only natural ingredient that can now be used as an insect repellent
Structure
Data?1563862827
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0036145 (p-Menthane-3,8-diol)

Menthane 3,8-diol (p-)
  Mrv1572001071617222D          

 12 12  0  0  0  0            999 V2000
    0.7145    2.0625    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
    0.0000    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
    0.7145   -1.2375    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
    1.5395   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  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
  2  7  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  5  8  1  0  0  0  0
  6 11  1  0  0  0  0
  8 12  1  0  0  0  0
M  END
Download

3D MOL for HMDB0036145 (p-Menthane-3,8-diol)

HMDB0036145
     RDKit          3D
p-Menthane-3,8-diol
 32 32  0  0  0  0  0  0  0  0999 V2000
    3.6397    0.2537    0.0029 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1841    0.1995   -0.4794 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4815    1.4357   -0.0394 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0203    1.1651    0.3425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4703    0.1052   -0.6117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9637   -0.0481   -0.5964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5059   -0.4319    0.7472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6736    1.1960   -1.0817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2840   -1.0776   -1.4873 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1295   -1.2062   -0.1374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2629   -2.2711   -0.9314 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6048   -1.0732    0.0216 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2232    0.9539   -0.6146 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6926    0.5493    1.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0415   -0.7998   -0.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2628    0.1360   -1.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4109    2.1161   -0.9384 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0080    2.0124    0.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0812    0.7550    1.3922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5492    2.0945    0.3126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1531    0.3710   -1.6252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1798    0.2091    1.5695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3351   -1.5201    0.9423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6288   -0.3316    0.6766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9771    2.0035   -1.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3662    1.5730   -0.3020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3023    0.9979   -1.9853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8565   -1.7623   -1.1016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2982   -1.3759    0.8943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0131   -3.1018   -0.4158 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0868   -1.9123   -0.5394 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9528   -1.2154    1.0844 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  5 10  1  0
 10 11  1  0
 10 12  1  0
 12  2  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  0
  7 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
M  END
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3D SDF for HMDB0036145 (p-Menthane-3,8-diol)

Menthane 3,8-diol (p-)
  Mrv1572001071617222D          

 12 12  0  0  0  0            999 V2000
    0.7145    2.0625    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
    0.0000    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
    0.7145   -1.2375    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
    1.5395   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  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
  2  7  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  5  8  1  0  0  0  0
  6 11  1  0  0  0  0
  8 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036145

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CCC(C(O)C1)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C10H20O2/c1-7-4-5-8(9(11)6-7)10(2,3)12/h7-9,11-12H,4-6H2,1-3H3

> <INCHI_KEY>
LMXFTMYMHGYJEI-UHFFFAOYSA-N

> <FORMULA>
C10H20O2

> <MOLECULAR_WEIGHT>
172.268

> <EXACT_MASS>
172.146329884

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
20.414874481242066

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(2-hydroxypropan-2-yl)-5-methylcyclohexan-1-ol

> <ALOGPS_LOGP>
1.88

> <JCHEM_LOGP>
1.2347151889999997

> <ALOGPS_LOGS>
-1.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.323946312014908

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.614339722218403

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8041647266131493

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
49.18259999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.06e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
p-menthane-3,8-diol

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0036145 (p-Menthane-3,8-diol)

HMDB0036145
     RDKit          3D
p-Menthane-3,8-diol
 32 32  0  0  0  0  0  0  0  0999 V2000
    3.6397    0.2537    0.0029 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1841    0.1995   -0.4794 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4815    1.4357   -0.0394 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0203    1.1651    0.3425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4703    0.1052   -0.6117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9637   -0.0481   -0.5964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5059   -0.4319    0.7472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6736    1.1960   -1.0817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2840   -1.0776   -1.4873 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1295   -1.2062   -0.1374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2629   -2.2711   -0.9314 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6048   -1.0732    0.0216 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2232    0.9539   -0.6146 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6926    0.5493    1.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0415   -0.7998   -0.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2628    0.1360   -1.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4109    2.1161   -0.9384 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0080    2.0124    0.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0812    0.7550    1.3922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5492    2.0945    0.3126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1531    0.3710   -1.6252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1798    0.2091    1.5695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3351   -1.5201    0.9423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6288   -0.3316    0.6766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9771    2.0035   -1.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3662    1.5730   -0.3020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3023    0.9979   -1.9853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8565   -1.7623   -1.1016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2982   -1.3759    0.8943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0131   -3.1018   -0.4158 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0868   -1.9123   -0.5394 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9528   -1.2154    1.0844 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  5 10  1  0
 10 11  1  0
 10 12  1  0
 12  2  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  0
  7 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
M  END
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PDB for HMDB0036145 (p-Menthane-3,8-diol)

HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Menthane 3,8-diol (p-)                            
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   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  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.874  -2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -0.206  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    2                                                       
CONECT    8    9   10    5   12                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    6                                                            
CONECT   12    8                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
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3D PDB for HMDB0036145 (p-Menthane-3,8-diol)

COMPND    HMDB0036145
HETATM    1  C1  UNL     1       3.640   0.254   0.003  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.184   0.200  -0.479  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.481   1.436  -0.039  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.020   1.165   0.342  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.470   0.105  -0.612  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.964  -0.048  -0.596  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.506  -0.432   0.747  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.674   1.196  -1.082  1.00  0.00           C  
HETATM    9  O1  UNL     1      -2.284  -1.078  -1.487  1.00  0.00           O  
HETATM   10  C9  UNL     1       0.130  -1.206  -0.137  1.00  0.00           C  
HETATM   11  O2  UNL     1      -0.263  -2.271  -0.931  1.00  0.00           O  
HETATM   12  C10 UNL     1       1.605  -1.073   0.022  1.00  0.00           C  
HETATM   13  H1  UNL     1       4.223   0.954  -0.615  1.00  0.00           H  
HETATM   14  H2  UNL     1       3.693   0.549   1.069  1.00  0.00           H  
HETATM   15  H3  UNL     1       4.041  -0.800  -0.060  1.00  0.00           H  
HETATM   16  H4  UNL     1       2.263   0.136  -1.602  1.00  0.00           H  
HETATM   17  H5  UNL     1       1.411   2.116  -0.938  1.00  0.00           H  
HETATM   18  H6  UNL     1       2.008   2.012   0.728  1.00  0.00           H  
HETATM   19  H7  UNL     1       0.081   0.755   1.392  1.00  0.00           H  
HETATM   20  H8  UNL     1      -0.549   2.095   0.313  1.00  0.00           H  
HETATM   21  H9  UNL     1      -0.153   0.371  -1.625  1.00  0.00           H  
HETATM   22  H10 UNL     1      -2.180   0.209   1.570  1.00  0.00           H  
HETATM   23  H11 UNL     1      -2.335  -1.520   0.942  1.00  0.00           H  
HETATM   24  H12 UNL     1      -3.629  -0.332   0.677  1.00  0.00           H  
HETATM   25  H13 UNL     1      -1.977   2.004  -1.372  1.00  0.00           H  
HETATM   26  H14 UNL     1      -3.366   1.573  -0.302  1.00  0.00           H  
HETATM   27  H15 UNL     1      -3.302   0.998  -1.985  1.00  0.00           H  
HETATM   28  H16 UNL     1      -2.856  -1.762  -1.102  1.00  0.00           H  
HETATM   29  H17 UNL     1      -0.298  -1.376   0.894  1.00  0.00           H  
HETATM   30  H18 UNL     1      -0.013  -3.102  -0.416  1.00  0.00           H  
HETATM   31  H19 UNL     1       2.087  -1.912  -0.539  1.00  0.00           H  
HETATM   32  H20 UNL     1       1.953  -1.215   1.084  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3   12   16
CONECT    3    4   17   18
CONECT    4    5   19   20
CONECT    5    6   10   21
CONECT    6    7    8    9
CONECT    7   22   23   24
CONECT    8   25   26   27
CONECT    9   28
CONECT   10   11   12   29
CONECT   11   30
CONECT   12   31   32
END
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SMILES for HMDB0036145 (p-Menthane-3,8-diol)

CC1CCC(C(O)C1)C(C)(C)O
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INCHI for HMDB0036145 (p-Menthane-3,8-diol)

InChI=1S/C10H20O2/c1-7-4-5-8(9(11)6-7)10(2,3)12/h7-9,11-12H,4-6H2,1-3H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
2-(1-Hydroxy-1-methylethyl)-5-methylcyclohexanolChEBI
(1Alpha,3beta,4beta)-P-Menthane-3,8-diolHMDB
2-(2-Hydroxy-2-propyl)-5-methyl-cyclohexanolHMDB
2-(2-Hydroxypropan-2-yl)-5-methylcyclohexan-1-olHMDB
2-Hydroxy-a,a,4-trimethylcyclohexanemethanol, 9ciHMDB
2-Hydroxy-alpha,alpha,4-trimethyl-cyclohexanemethanolHMDB
2-Hydroxy-alpha,alpha,4-trimethylcyclohexanemethanolHMDB, MeSH
cis-1,3,trans-1,4-P-Menthane-3,8-diolHMDB
CubebaolHMDB
Isopulegol hydrateHMDB
MenthoglycolHMDB
2-(2'-Hydroxypropan-2'-yl)-5-methylcyclohexanolMeSH
Para-menthane-3,8-diolMeSH
TerpinMeSH
Terpin, titanium (+4) saltMeSH
GeranodyleMeSH
p-Menthane-1,8-diolMeSH
Terpin, monohydrate(cis)-isomerMeSH
Terpin hydrateMeSH
Chemical FormulaC10H20O2
Average Molecular Weight172.268
Monoisotopic Molecular Weight172.146329884
IUPAC Name2-(2-hydroxypropan-2-yl)-5-methylcyclohexan-1-ol
Traditional Namep-menthane-3,8-diol
CAS Registry Number42822-86-6
SMILES
CC1CCC(C(O)C1)C(C)(C)O
InChI Identifier
InChI=1S/C10H20O2/c1-7-4-5-8(9(11)6-7)10(2,3)12/h7-9,11-12H,4-6H2,1-3H3
InChI KeyLMXFTMYMHGYJEI-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
  • Cyclohexanol
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point267.58 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility670.7 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.374 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility10.6 g/LALOGPS
logP1.88ALOGPS
logP1.23ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)14.61ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity49.18 m³·mol⁻¹ChemAxon
Polarizability20.41 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+141.46331661259
DarkChem[M-H]-134.56231661259
DeepCCS[M+H]+143.38530932474
DeepCCS[M-H]-140.69630932474
DeepCCS[M-2H]-176.82130932474
DeepCCS[M+Na]+152.3630932474
AllCCS[M+H]+139.632859911
AllCCS[M+H-H2O]+135.532859911
AllCCS[M+NH4]+143.532859911
AllCCS[M+Na]+144.732859911
AllCCS[M-H]-143.532859911
AllCCS[M+Na-2H]-144.932859911
AllCCS[M+HCOO]-146.632859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. 3.35 minutes32390414
Predicted by Siyang on May 30, 202210.7555 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.52 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid33.3 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1748.8 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid278.9 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid137.9 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid166.4 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid111.0 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid505.0 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid542.5 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)72.6 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid820.1 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid346.0 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1043.4 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid288.8 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid316.8 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate319.7 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA338.9 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water37.2 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
p-Menthane-3,8-diolCC1CCC(C(O)C1)C(C)(C)O2273.0Standard polar33892256
p-Menthane-3,8-diolCC1CCC(C(O)C1)C(C)(C)O1280.2Standard non polar33892256
p-Menthane-3,8-diolCC1CCC(C(O)C1)C(C)(C)O1361.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
p-Menthane-3,8-diol,1TMS,isomer #1CC1CCC(C(C)(C)O)C(O[Si](C)(C)C)C11439.4Semi standard non polar33892256
p-Menthane-3,8-diol,1TMS,isomer #2CC1CCC(C(C)(C)O[Si](C)(C)C)C(O)C11461.9Semi standard non polar33892256
p-Menthane-3,8-diol,2TMS,isomer #1CC1CCC(C(C)(C)O[Si](C)(C)C)C(O[Si](C)(C)C)C11487.6Semi standard non polar33892256
p-Menthane-3,8-diol,1TBDMS,isomer #1CC1CCC(C(C)(C)O)C(O[Si](C)(C)C(C)(C)C)C11658.9Semi standard non polar33892256
p-Menthane-3,8-diol,1TBDMS,isomer #2CC1CCC(C(C)(C)O[Si](C)(C)C(C)(C)C)C(O)C11706.4Semi standard non polar33892256
p-Menthane-3,8-diol,2TBDMS,isomer #1CC1CCC(C(C)(C)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C11928.1Semi standard non polar33892256
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB014996
KNApSAcK IDC00000147
Chemspider ID484204
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkP-Menthane-3,8-diol
METLIN IDNot Available
PubChem Compound556998
PDB IDNot Available
ChEBI ID48250
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1375461
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.