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Showing metabocard for (+)-Neomenthol (HMDB0035763)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:47:04 UTC
Update Date2023-02-21 17:24:54 UTC
HMDB IDHMDB0035763
Secondary Accession Numbers
  • HMDB35763
Metabolite Identification
Common Name(+)-Neomenthol
Description(+)-Neomenthol 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. Thus, (+)-neomenthol is considered to be an isoprenoid. Based on a literature review a significant number of articles have been published on (+)-Neomenthol.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0035763 ((+)-Neomenthol)

  Mrv1652309042000382D          

 11 11  0  0  0  0            999 V2000
   -0.3466   -0.6121    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0550   -0.1885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0399    0.6382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3163    1.0399    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3025    1.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3907    0.6148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3755   -0.2132    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0826   -0.6370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0826   -1.8378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3617   -1.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3452   -1.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  0  0  0  0
  1 10  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
Download

3D MOL for HMDB0035763 ((+)-Neomenthol)

HMDB0035763
     RDKit          3D
(+)-Neomenthol
 31 31  0  0  0  0  0  0  0  0999 V2000
   -2.6959    1.0766    0.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8501   -0.1406    0.2811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7427   -1.3546    0.1753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7068   -0.2148   -0.7246 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1556   -1.4458   -0.4517 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5744   -1.1321   -0.8662 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1702   -0.2368    0.1966 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3922    0.4935   -0.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1092    0.7522    0.6147 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1873    0.9780   -0.5658 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4644    2.1803   -0.4283 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4838    1.9088    0.7058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7640    0.8232    0.1649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5580    1.3561   -1.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4381   -0.0672    1.3157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6179   -1.8516   -0.8078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5567   -2.0852    0.9825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8241   -1.0559    0.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1460   -0.3105   -1.7363 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1488   -1.5941    0.6530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2318   -2.3325   -0.9915 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1181   -2.1216   -0.8715 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6654   -0.7394   -1.8805 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4417   -0.9051    1.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1568    1.5398   -0.5560 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9196   -0.0095   -1.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0883    0.5728    0.6163 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5881    0.3844    1.4997 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5929    1.7125    0.8684 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8587    1.0863   -1.4661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0870    2.7330    0.2813 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10  4  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  6
  5 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  1
  8 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  6
 11 31  1  0
M  END
Download

3D SDF for HMDB0035763 ((+)-Neomenthol)

  Mrv1652309042000382D          

 11 11  0  0  0  0            999 V2000
   -0.3466   -0.6121    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0550   -0.1885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0399    0.6382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3163    1.0399    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3025    1.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3907    0.6148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3755   -0.2132    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0826   -0.6370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0826   -1.8378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3617   -1.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3452   -1.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  0  0  0  0
  1 10  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035763

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C10H20O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-11H,4-6H2,1-3H3/t8-,9+,10+/m1/s1

> <INCHI_KEY>
NOOLISFMXDJSKH-UTLUCORTSA-N

> <FORMULA>
C10H20O

> <MOLECULAR_WEIGHT>
156.2652

> <EXACT_MASS>
156.151415262

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
19.399617166020654

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexan-1-ol

> <ALOGPS_LOGP>
2.68

> <JCHEM_LOGP>
2.6642731470000007

> <ALOGPS_LOGS>
-2.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.54964736878105

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8087842408951696

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
47.4453

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.58e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+)-neomenthol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0035763 ((+)-Neomenthol)

HMDB0035763
     RDKit          3D
(+)-Neomenthol
 31 31  0  0  0  0  0  0  0  0999 V2000
   -2.6959    1.0766    0.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8501   -0.1406    0.2811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7427   -1.3546    0.1753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7068   -0.2148   -0.7246 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1556   -1.4458   -0.4517 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5744   -1.1321   -0.8662 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1702   -0.2368    0.1966 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3922    0.4935   -0.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1092    0.7522    0.6147 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1873    0.9780   -0.5658 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4644    2.1803   -0.4283 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4838    1.9088    0.7058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7640    0.8232    0.1649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5580    1.3561   -1.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4381   -0.0672    1.3157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6179   -1.8516   -0.8078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5567   -2.0852    0.9825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8241   -1.0559    0.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1460   -0.3105   -1.7363 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1488   -1.5941    0.6530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2318   -2.3325   -0.9915 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1181   -2.1216   -0.8715 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6654   -0.7394   -1.8805 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4417   -0.9051    1.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1568    1.5398   -0.5560 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9196   -0.0095   -1.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0883    0.5728    0.6163 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5881    0.3844    1.4997 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5929    1.7125    0.8684 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8587    1.0863   -1.4661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0870    2.7330    0.2813 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10  4  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  6
  5 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  1
  8 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  6
 11 31  1  0
M  END
Download

PDB for HMDB0035763 ((+)-Neomenthol)

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0      -0.647  -1.143   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.969  -0.352   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.941   1.191   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.590   1.941   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.565   3.477   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.729   1.148   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.701  -0.398   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.021  -1.189   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.021  -3.431   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.675  -2.683   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.644  -3.477   0.000  0.00  0.00           C+0
CONECT    1    2    7   10                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    1    6    8                                                  
CONECT    8    7                                                            
CONECT    9   10                                                            
CONECT   10    1    9   11                                                  
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for HMDB0035763 ((+)-Neomenthol)

COMPND    HMDB0035763
HETATM    1  C1  UNL     1      -2.696   1.077   0.002  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.850  -0.141   0.281  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.743  -1.355   0.175  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.707  -0.215  -0.725  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.156  -1.446  -0.452  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.574  -1.132  -0.866  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.170  -0.237   0.197  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.392   0.493  -0.260  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.109   0.752   0.615  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.187   0.978  -0.566  1.00  0.00           C  
HETATM   11  O1  UNL     1      -0.464   2.180  -0.428  1.00  0.00           O  
HETATM   12  H1  UNL     1      -2.484   1.909   0.706  1.00  0.00           H  
HETATM   13  H2  UNL     1      -3.764   0.823   0.165  1.00  0.00           H  
HETATM   14  H3  UNL     1      -2.558   1.356  -1.054  1.00  0.00           H  
HETATM   15  H4  UNL     1      -1.438  -0.067   1.316  1.00  0.00           H  
HETATM   16  H5  UNL     1      -2.618  -1.852  -0.808  1.00  0.00           H  
HETATM   17  H6  UNL     1      -2.557  -2.085   0.983  1.00  0.00           H  
HETATM   18  H7  UNL     1      -3.824  -1.056   0.289  1.00  0.00           H  
HETATM   19  H8  UNL     1      -1.146  -0.310  -1.736  1.00  0.00           H  
HETATM   20  H9  UNL     1       0.149  -1.594   0.653  1.00  0.00           H  
HETATM   21  H10 UNL     1      -0.232  -2.332  -0.991  1.00  0.00           H  
HETATM   22  H11 UNL     1       2.118  -2.122  -0.871  1.00  0.00           H  
HETATM   23  H12 UNL     1       1.665  -0.739  -1.881  1.00  0.00           H  
HETATM   24  H13 UNL     1       2.442  -0.905   1.052  1.00  0.00           H  
HETATM   25  H14 UNL     1       3.157   1.540  -0.556  1.00  0.00           H  
HETATM   26  H15 UNL     1       3.920  -0.009  -1.094  1.00  0.00           H  
HETATM   27  H16 UNL     1       4.088   0.573   0.616  1.00  0.00           H  
HETATM   28  H17 UNL     1       0.588   0.384   1.500  1.00  0.00           H  
HETATM   29  H18 UNL     1       1.593   1.712   0.868  1.00  0.00           H  
HETATM   30  H19 UNL     1       0.859   1.086  -1.466  1.00  0.00           H  
HETATM   31  H20 UNL     1      -0.087   2.733   0.281  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    4   15
CONECT    3   16   17   18
CONECT    4    5   10   19
CONECT    5    6   20   21
CONECT    6    7   22   23
CONECT    7    8    9   24
CONECT    8   25   26   27
CONECT    9   10   28   29
CONECT   10   11   30
CONECT   11   31
END
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SMILES for HMDB0035763 ((+)-Neomenthol)

CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O
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INCHI for HMDB0035763 ((+)-Neomenthol)

InChI=1S/C10H20O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-11H,4-6H2,1-3H3/t8-,9+,10+/m1/s1
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Synonyms
ValueSource
(1S,2S,5R)-(+)-NeomentholHMDB
(1S,2S,5R)-2-Isopropyl-5-methylcyclohexanolHMDB
(1S,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexan-1-olHMDB
(1S,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexanolHMDB
D-NeomentholHMDB
FEMA 2666HMDB
Chemical FormulaC10H20O
Average Molecular Weight156.2652
Monoisotopic Molecular Weight156.151415262
IUPAC Name(1S,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexan-1-ol
Traditional Name(+)-neomenthol
CAS Registry Number2216-52-6
SMILES
CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O
InChI Identifier
InChI=1S/C10H20O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-11H,4-6H2,1-3H3/t8-,9+,10+/m1/s1
InChI KeyNOOLISFMXDJSKH-UTLUCORTSA-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
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Biological roleIndustrial application
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-22 °CNot Available
Boiling Point95.00 °C. @ 12.00 mm HgThe Good Scents Company Information System
Water Solubility434.5 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.216 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • 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 IDFDB014500
KNApSAcK IDC00053546
Chemspider ID388397
KEGG Compound IDC00553
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound439263
PDB IDNot Available
ChEBI ID15402
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1060561
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.