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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:12:14 UTC

Update Date

2022-03-07 02:54:48 UTC

HMDB ID

HMDB0036139

Secondary Accession Numbers

HMDB0032367
HMDB32367
HMDB36139

Metabolite Identification

Common Name

Menthone 1,2-glyceryl ketal

Description

Menthone 1,2-glyceryl ketal, also known as menthone glycerin acetal or menthyl glycerin acetal, is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids 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. Menthone 1,2-glyceryl ketal is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Menthone 1,2-glyceryl ketal is used as a food additive (EAFUS: Everything Added to Food in the United States). Menthone 1,2-glyceryl ketal is a flavour enhancer for chewing gum and other low moisture foods.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0036139
     RDKit          3D
Menthone 1,2-glyceryl ketal
 40 41  0  0  0  0  0  0  0  0999 V2000
    0.3124    3.7808   -0.2259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1087    2.5603    0.6094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5645    2.3830    0.3960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8198    1.1103   -0.3883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3052   -0.0045    0.4815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8849   -1.3071    0.0168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4232   -2.4823    0.8326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7055   -1.5676   -1.4449 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1799    0.0520    0.5036 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7582    1.4178    0.2927 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6236   -0.5069    1.6980 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6873   -1.3284    1.4133 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0152   -0.9535   -0.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7154   -2.0658   -0.7530 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7961   -1.7094   -2.0973 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7326   -0.7516   -0.5186 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5180    4.5158   -0.2817 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5269    3.4041   -1.2603 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2021    4.2717    0.2040 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0611    2.8930    1.6761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0465    3.2487   -0.1388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0764    2.2426    1.3792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1725    1.1354   -1.3107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8889    0.9711   -0.6350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6850    0.1754    1.5137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9975   -1.2262    0.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2733   -3.2000    1.0203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6337   -3.0744    0.3588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1432   -2.1134    1.8481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7752   -2.1688   -1.6094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7623   -0.6694   -2.0573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5418   -2.2397   -1.7993 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6759    1.4777    0.9509 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1711    1.5608   -0.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5647   -1.1408    2.0791 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4172   -2.4200    1.4206 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6232   -0.0268   -0.0510 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7226   -2.2621   -0.4007 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0683   -2.9760   -0.7069 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4723   -1.0060   -2.2720 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
  5  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 10  2  1  0
 16  9  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
  8 32  1  0
 10 33  1  0
 10 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
M  END

      
  Mrv1652305101818122D          

 16 17  0  0  0  0            999 V2000
10011.183810008.6116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.898510009.0254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10007.528210007.9825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.770110010.1252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.945110010.1252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.532510009.4106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.945210008.6963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.770010008.6962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.182310009.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.667210008.7676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10010.451810009.0224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.451810009.8474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.667210010.1023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10009.177310010.8425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.759510011.5539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.002310010.8486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  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
 11 12  1  0  0  0  0
  7  3  1  0  0  0  0
  9 13  1  0  0  0  0
 12 13  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11  1  1  0  0  0  0
  4  9  1  0  0  0  0
  8  9  1  0  0  0  0
  4 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036139

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)C1CCC(C)CC11OCC(CO)O1

> <INCHI_IDENTIFIER>
InChI=1S/C13H24O3/c1-9(2)12-5-4-10(3)6-13(12)15-8-11(7-14)16-13/h9-12,14H,4-8H2,1-3H3

> <INCHI_KEY>
ZBJCYZPANVLBRK-UHFFFAOYSA-N

> <FORMULA>
C13H24O3

> <MOLECULAR_WEIGHT>
228.3279

> <EXACT_MASS>
228.172544634

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
26.588873767798805

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[9-methyl-6-(propan-2-yl)-1,4-dioxaspiro[4.5]decan-2-yl]methanol

> <ALOGPS_LOGP>
2.00

> <JCHEM_LOGP>
2.6159300283333344

> <ALOGPS_LOGS>
-2.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.596468988842378

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9753044642803426

> <JCHEM_POLAR_SURFACE_AREA>
38.69

> <JCHEM_REFRACTIVITY>
62.574100000000016

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.62e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{6-isopropyl-9-methyl-1,4-dioxaspiro[4.5]decan-2-yl}methanol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0036139
     RDKit          3D
Menthone 1,2-glyceryl ketal
 40 41  0  0  0  0  0  0  0  0999 V2000
    0.3124    3.7808   -0.2259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1087    2.5603    0.6094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5645    2.3830    0.3960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8198    1.1103   -0.3883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3052   -0.0045    0.4815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8849   -1.3071    0.0168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4232   -2.4823    0.8326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7055   -1.5676   -1.4449 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1799    0.0520    0.5036 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7582    1.4178    0.2927 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6236   -0.5069    1.6980 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6873   -1.3284    1.4133 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0152   -0.9535   -0.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7154   -2.0658   -0.7530 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7961   -1.7094   -2.0973 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7326   -0.7516   -0.5186 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5180    4.5158   -0.2817 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5269    3.4041   -1.2603 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2021    4.2717    0.2040 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0611    2.8930    1.6761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0465    3.2487   -0.1388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0764    2.2426    1.3792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1725    1.1354   -1.3107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8889    0.9711   -0.6350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6850    0.1754    1.5137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9975   -1.2262    0.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2733   -3.2000    1.0203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6337   -3.0744    0.3588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1432   -2.1134    1.8481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7752   -2.1688   -1.6094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7623   -0.6694   -2.0573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5418   -2.2397   -1.7993 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6759    1.4777    0.9509 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1711    1.5608   -0.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5647   -1.1408    2.0791 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4172   -2.4200    1.4206 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6232   -0.0268   -0.0510 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7226   -2.2621   -0.4007 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0683   -2.9760   -0.7069 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4723   -1.0060   -2.2720 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
  5  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 10  2  1  0
 16  9  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
  8 32  1  0
 10 33  1  0
 10 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
M  END

HEADER    PROTEIN                                 10-MAY-18   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAY-18         0                                  
HETATM    1  C   UNK     0    8687.5438682.742   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8688.8778683.514   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8680.7198681.567   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8683.0378685.567   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8681.4978685.567   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8680.7278684.233   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8681.4988682.900   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8683.0378682.900   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8683.8078684.279   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8684.7128683.033   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0    8686.1778683.509   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8686.1778685.049   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0    8684.7128685.524   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0    8683.7988686.906   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8683.0188688.234   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8685.3388686.917   0.000  0.00  0.00           C+0
CONECT    1    2   11                                                       
CONECT    2    1                                                            
CONECT    3    7                                                            
CONECT    4    5    9   14                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    3                                                  
CONECT    8    7    9                                                       
CONECT    9   13   10    4    8                                             
CONECT   10    9   11                                                       
CONECT   11   12   10    1                                                  
CONECT   12   11   13                                                       
CONECT   13    9   12                                                       
CONECT   14    4   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0036139
HETATM    1  C1  UNL     1       0.312   3.781  -0.226  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.109   2.560   0.609  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.564   2.383   0.396  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.820   1.110  -0.388  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.305  -0.004   0.481  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.885  -1.307   0.017  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.423  -2.482   0.833  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.705  -1.568  -1.445  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.180   0.052   0.504  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.758   1.418   0.293  1.00  0.00           C  
HETATM   11  O1  UNL     1       0.624  -0.507   1.698  1.00  0.00           O  
HETATM   12  C11 UNL     1       1.687  -1.328   1.413  1.00  0.00           C  
HETATM   13  C12 UNL     1       2.015  -0.953  -0.015  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.715  -2.066  -0.753  1.00  0.00           C  
HETATM   15  O2  UNL     1       2.796  -1.709  -2.097  1.00  0.00           O  
HETATM   16  O3  UNL     1       0.733  -0.752  -0.519  1.00  0.00           O  
HETATM   17  H1  UNL     1      -0.518   4.516  -0.282  1.00  0.00           H  
HETATM   18  H2  UNL     1       0.527   3.404  -1.260  1.00  0.00           H  
HETATM   19  H3  UNL     1       1.202   4.272   0.204  1.00  0.00           H  
HETATM   20  H4  UNL     1       0.061   2.893   1.676  1.00  0.00           H  
HETATM   21  H5  UNL     1      -2.046   3.249  -0.139  1.00  0.00           H  
HETATM   22  H6  UNL     1      -2.076   2.243   1.379  1.00  0.00           H  
HETATM   23  H7  UNL     1      -1.172   1.135  -1.311  1.00  0.00           H  
HETATM   24  H8  UNL     1      -2.889   0.971  -0.635  1.00  0.00           H  
HETATM   25  H9  UNL     1      -1.685   0.175   1.514  1.00  0.00           H  
HETATM   26  H10 UNL     1      -2.998  -1.226   0.192  1.00  0.00           H  
HETATM   27  H11 UNL     1      -2.273  -3.200   1.020  1.00  0.00           H  
HETATM   28  H12 UNL     1      -0.634  -3.074   0.359  1.00  0.00           H  
HETATM   29  H13 UNL     1      -1.143  -2.113   1.848  1.00  0.00           H  
HETATM   30  H14 UNL     1      -0.775  -2.169  -1.609  1.00  0.00           H  
HETATM   31  H15 UNL     1      -1.762  -0.669  -2.057  1.00  0.00           H  
HETATM   32  H16 UNL     1      -2.542  -2.240  -1.799  1.00  0.00           H  
HETATM   33  H17 UNL     1       1.676   1.478   0.951  1.00  0.00           H  
HETATM   34  H18 UNL     1       1.171   1.561  -0.746  1.00  0.00           H  
HETATM   35  H19 UNL     1       2.565  -1.141   2.079  1.00  0.00           H  
HETATM   36  H20 UNL     1       1.417  -2.420   1.421  1.00  0.00           H  
HETATM   37  H21 UNL     1       2.623  -0.027  -0.051  1.00  0.00           H  
HETATM   38  H22 UNL     1       3.723  -2.262  -0.401  1.00  0.00           H  
HETATM   39  H23 UNL     1       2.068  -2.976  -0.707  1.00  0.00           H  
HETATM   40  H24 UNL     1       3.472  -1.006  -2.272  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3   10   20
CONECT    3    4   21   22
CONECT    4    5   23   24
CONECT    5    6    9   25
CONECT    6    7    8   26
CONECT    7   27   28   29
CONECT    8   30   31   32
CONECT    9   10   11   16
CONECT   10   33   34
CONECT   11   12
CONECT   12   13   35   36
CONECT   13   14   16   37
CONECT   14   15   38   39
CONECT   15   40
END

HMDB0036139
     RDKit          3D
Menthone 1,2-glyceryl ketal
 40 41  0  0  0  0  0  0  0  0999 V2000
    0.3124    3.7808   -0.2259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1087    2.5603    0.6094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5645    2.3830    0.3960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8198    1.1103   -0.3883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3052   -0.0045    0.4815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8849   -1.3071    0.0168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4232   -2.4823    0.8326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7055   -1.5676   -1.4449 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1799    0.0520    0.5036 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7582    1.4178    0.2927 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6236   -0.5069    1.6980 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6873   -1.3284    1.4133 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0152   -0.9535   -0.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7154   -2.0658   -0.7530 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7961   -1.7094   -2.0973 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7326   -0.7516   -0.5186 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5180    4.5158   -0.2817 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5269    3.4041   -1.2603 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2021    4.2717    0.2040 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0611    2.8930    1.6761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0465    3.2487   -0.1388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0764    2.2426    1.3792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1725    1.1354   -1.3107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8889    0.9711   -0.6350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6850    0.1754    1.5137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9975   -1.2262    0.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2733   -3.2000    1.0203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6337   -3.0744    0.3588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1432   -2.1134    1.8481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7752   -2.1688   -1.6094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7623   -0.6694   -2.0573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5418   -2.2397   -1.7993 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6759    1.4777    0.9509 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1711    1.5608   -0.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5647   -1.1408    2.0791 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4172   -2.4200    1.4206 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6232   -0.0268   -0.0510 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7226   -2.2621   -0.4007 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0683   -2.9760   -0.7069 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4723   -1.0060   -2.2720 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
  5  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 10  2  1  0
 16  9  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
  8 32  1  0
 10 33  1  0
 10 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Hydroxymethyl-6-isopropyl-9-methyl-1,4-dioxaspiro[4.5]decane	HMDB
6-Isopropyl-9-methyl-1,4-dioxaspiro(4.5)decane-2-methanol	HMDB
9-Methyl-6-(1-methylethyl)-1,4-dioxaspiro[4.5]decane-2-methanol, 9ci	HMDB
FEMA 3807	HMDB
FEMA 3808	HMDB
Frescolat	HMDB
Menthone 1,2-glycerol ketal	HMDB
Frescolat MGA	HMDB
Menthone glycerin acetal	HMDB
Menthyl glycerin acetal	HMDB
Menthone glyceryl acetal	HMDB
Menthone glyceryl ketal	HMDB
MGA	HMDB
L-Menthone 1,2-glycerol ketal	HMDB

Chemical Formula

C₁₃H₂₄O₃

Average Molecular Weight

228.3279

Monoisotopic Molecular Weight

228.172544634

IUPAC Name

[9-methyl-6-(propan-2-yl)-1,4-dioxaspiro[4.5]decan-2-yl]methanol

Traditional Name

{6-isopropyl-9-methyl-1,4-dioxaspiro[4.5]decan-2-yl}methanol

CAS Registry Number

63187-91-7

SMILES

CC(C)C1CCC(C)CC11OCC(CO)O1

InChI Identifier

InChI=1S/C13H24O3/c1-9(2)12-5-4-10(3)6-13(12)15-8-11(7-14)16-13/h9-12,14H,4-8H2,1-3H3

InChI Key

ZBJCYZPANVLBRK-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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Menthane monoterpenoids

Alternative Parents

Substituents

P-menthane monoterpenoid
Ketal
Meta-dioxolane
Oxacycle
Organoheterocyclic compound
Acetal
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Organoleptic effect

Odor

Odorless

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036139)

Source

Endogenous

Endogenous (HMDB: HMDB0036139)

Animal

Animal (HMDB: HMDB0036139)

Exogenous

Food

Food (HMDB: HMDB0036139)

Exogenous (HMDB: HMDB0036139)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036139)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036139)

Lipid metabolism pathway (HMDB: HMDB0036139)

Cellular process

Cell signaling (HMDB: HMDB0036139)

Biochemical process

Lipid transport (HMDB: HMDB0036139)

Role

Biological role

Energy source (HMDB: HMDB0036139)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036139)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	322.00 to 323.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	27.28 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.036 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.76 g/L	ALOGPS
logP	2	ALOGPS
logP	2.62	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	14.6	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.69 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	62.57 m³·mol⁻¹	ChemAxon
Polarizability	26.59 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	151.751	31661259
DarkChem	[M-H]-	150.966	31661259
DeepCCS	[M-2H]-	193.363	30932474
DeepCCS	[M+Na]+	168.744	30932474
AllCCS	[M+H]+	154.3	32859911
AllCCS	[M+H-H2O]+	150.5	32859911
AllCCS	[M+NH4]+	157.8	32859911
AllCCS	[M+Na]+	158.9	32859911
AllCCS	[M-H]-	159.1	32859911
AllCCS	[M+Na-2H]-	159.7	32859911
AllCCS	[M+HCOO]-	160.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
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.	4.31 minutes	32390414
Predicted by Siyang on May 30, 2022	15.3946 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.58 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	25.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2489.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	456.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	177.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	206.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	329.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	723.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	679.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	78.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1185.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	482.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1564.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	408.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	399.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	365.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	453.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	12.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Menthone 1,2-glyceryl ketal	CC(C)C1CCC(C)CC11OCC(CO)O1	2230.6	Standard polar	33892256
Menthone 1,2-glyceryl ketal	CC(C)C1CCC(C)CC11OCC(CO)O1	1589.3	Standard non polar	33892256
Menthone 1,2-glyceryl ketal	CC(C)C1CCC(C)CC11OCC(CO)O1	1669.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Menthone 1,2-glyceryl ketal,1TMS,isomer #1	CC1CCC(C(C)C)C2(C1)OCC(CO[Si](C)(C)C)O2	1692.1	Semi standard non polar	33892256
Menthone 1,2-glyceryl ketal,1TBDMS,isomer #1	CC1CCC(C(C)C)C2(C1)OCC(CO[Si](C)(C)C(C)(C)C)O2	1936.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Menthone 1,2-glyceryl ketal GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9410000000-b382247dd270ed7bd196	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Menthone 1,2-glyceryl ketal GC-MS (1 TMS) - 70eV, Positive	splash10-06yc-9530000000-d3d1d3bd28f704c25a53	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Menthone 1,2-glyceryl ketal GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthone 1,2-glyceryl ketal 10V, Positive-QTOF	splash10-004i-1290000000-2a33c2ffa8194005ed41	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthone 1,2-glyceryl ketal 20V, Positive-QTOF	splash10-004i-9660000000-4dc87a745f4a98040054	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthone 1,2-glyceryl ketal 40V, Positive-QTOF	splash10-0aor-9200000000-a353fa905f01dc6beef6	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthone 1,2-glyceryl ketal 10V, Negative-QTOF	splash10-004i-2090000000-896a1d3ce21e9426591b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthone 1,2-glyceryl ketal 20V, Negative-QTOF	splash10-056s-7590000000-5f419ed783b43a5ae35f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthone 1,2-glyceryl ketal 40V, Negative-QTOF	splash10-0f6x-9700000000-f21e3e951e7f6c37611a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthone 1,2-glyceryl ketal 10V, Negative-QTOF	splash10-004i-0090000000-873da861442811ae04b2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthone 1,2-glyceryl ketal 20V, Negative-QTOF	splash10-0fb9-0790000000-051ca48c22c625175150	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthone 1,2-glyceryl ketal 40V, Negative-QTOF	splash10-0ufs-1910000000-4da8dd1b3f946827b52c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthone 1,2-glyceryl ketal 10V, Positive-QTOF	splash10-004i-0090000000-1e3bb0705c3f525a8fe0	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthone 1,2-glyceryl ketal 20V, Positive-QTOF	splash10-0a4i-9110000000-aa6fefeb9df2fe89aaf2	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Menthone 1,2-glyceryl ketal 40V, Positive-QTOF	splash10-0aou-9200000000-8c4be0723acde91d7cd4	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB014990

KNApSAcK ID

Not Available

Chemspider ID

142428

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162184

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1450851

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
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 ]
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 ]
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 ]
(). EAFUS: Everything Added to Food in the United States.. .
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Menthone 1,2-glyceryl ketal (HMDB0036139)

MOL for HMDB0036139 (Menthone 1,2-glyceryl ketal)

3D MOL for HMDB0036139 (Menthone 1,2-glyceryl ketal)

3D SDF for HMDB0036139 (Menthone 1,2-glyceryl ketal)

3D-SDF for HMDB0036139 (Menthone 1,2-glyceryl ketal)

PDB for HMDB0036139 (Menthone 1,2-glyceryl ketal)

3D PDB for HMDB0036139 (Menthone 1,2-glyceryl ketal)

SMILES for HMDB0036139 (Menthone 1,2-glyceryl ketal)

INCHI for HMDB0036139 (Menthone 1,2-glyceryl ketal)

Structure for HMDB0036139 (Menthone 1,2-glyceryl ketal)

3D Structure for HMDB0036139 (Menthone 1,2-glyceryl ketal)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra