Hmdb loader

Showing metabocard for (S)-p-Menth-1-en-4-ol (HMDB0035823)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Show more...Show more...Show more...
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:50:49 UTC
Update Date2023-02-21 17:24:55 UTC
HMDB IDHMDB0035823
Secondary Accession Numbers
  • HMDB35823
Metabolite Identification
Common Name(S)-p-Menth-1-en-4-ol
Description(S)-p-Menth-1-en-4-ol 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. Based on a literature review a significant number of articles have been published on (S)-p-Menth-1-en-4-ol.
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0035823 ((S)-p-Menth-1-en-4-ol)

Carvomenthanol (4-)
  Mrv1652303202019022D          

 11 11  0  0  1  0            999 V2000
    2.1615    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5741    0.5231    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9866    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2885    0.1106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8596    0.1106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2885   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5741   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8596   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8116    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5741    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5741   -1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  9  1  0  0  0  0
  3 10  1  0  0  0  0
  4  6  1  0  0  0  0
  5  8  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7 11  1  0  0  0  0
M  END
Download

3D MOL for HMDB0035823 ((S)-p-Menth-1-en-4-ol)

HMDB0035823
     RDKit          3D
(S)-p-Menth-1-en-4-ol
 29 29  0  0  0  0  0  0  0  0999 V2000
    3.7050   -0.3366   -0.1478 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2101   -0.3216   -0.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5588   -1.2007    0.5783 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0667   -1.2811    0.6596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4612    0.0919    0.3188 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0118    0.9645    1.3009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9507    0.0569    0.4176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5893    1.3922    0.0937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5891   -0.9885   -0.4580 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0532    0.5715   -1.0018 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5399    0.7020   -0.9700 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1165   -1.0617   -0.8569 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0210   -0.6173    0.8821 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0722    0.7008   -0.3162 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1070   -1.9299    1.1660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2681   -2.0557   -0.0555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1947   -1.4961    1.7085 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1920    1.8683    0.9294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2097   -0.1596    1.4820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9553    2.2044    0.5022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7023    1.4607   -1.0079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5821    1.4063    0.5632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9118   -1.2900   -1.2797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5182   -0.5978   -0.9621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9399   -1.8619    0.1398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3696    1.5866   -1.1852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2137   -0.0966   -1.8448 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8575    1.6985   -0.6214 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9441    0.5904   -2.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  1
  5  7  1  0
  7  8  1  0
  7  9  1  0
  5 10  1  0
 10 11  1  0
 11  2  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  4 16  1  0
  4 17  1  0
  6 18  1  0
  7 19  1  0
  8 20  1  0
  8 21  1  0
  8 22  1  0
  9 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
M  END
Download

3D SDF for HMDB0035823 ((S)-p-Menth-1-en-4-ol)

Carvomenthanol (4-)
  Mrv1652303202019022D          

 11 11  0  0  1  0            999 V2000
    2.1615    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5741    0.5231    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9866    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2885    0.1106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8596    0.1106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2885   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5741   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8596   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8116    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5741    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5741   -1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  9  1  0  0  0  0
  3 10  1  0  0  0  0
  4  6  1  0  0  0  0
  5  8  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035823

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)[C@]1(O)CCC(C)=CC1

> <INCHI_IDENTIFIER>
InChI=1S/C10H18O/c1-8(2)10(11)6-4-9(3)5-7-10/h4,8,11H,5-7H2,1-3H3/t10-/m1/s1

> <INCHI_KEY>
WRYLYDPHFGVWKC-SNVBAGLBSA-N

> <FORMULA>
C10H18O

> <MOLECULAR_WEIGHT>
154.253

> <EXACT_MASS>
154.1357652

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
18.704458168600958

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S)-4-methyl-1-(propan-2-yl)cyclohex-3-en-1-ol

> <ALOGPS_LOGP>
2.81

> <JCHEM_LOGP>
2.3302049676666665

> <ALOGPS_LOGS>
-1.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.999288199495165

> <JCHEM_PKA_STRONGEST_BASIC>
-0.6121113415408138

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
48.3079

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.50e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S)-1-isopropyl-4-methylcyclohex-3-en-1-ol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0035823 ((S)-p-Menth-1-en-4-ol)

HMDB0035823
     RDKit          3D
(S)-p-Menth-1-en-4-ol
 29 29  0  0  0  0  0  0  0  0999 V2000
    3.7050   -0.3366   -0.1478 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2101   -0.3216   -0.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5588   -1.2007    0.5783 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0667   -1.2811    0.6596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4612    0.0919    0.3188 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0118    0.9645    1.3009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9507    0.0569    0.4176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5893    1.3922    0.0937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5891   -0.9885   -0.4580 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0532    0.5715   -1.0018 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5399    0.7020   -0.9700 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1165   -1.0617   -0.8569 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0210   -0.6173    0.8821 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0722    0.7008   -0.3162 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1070   -1.9299    1.1660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2681   -2.0557   -0.0555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1947   -1.4961    1.7085 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1920    1.8683    0.9294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2097   -0.1596    1.4820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9553    2.2044    0.5022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7023    1.4607   -1.0079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5821    1.4063    0.5632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9118   -1.2900   -1.2797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5182   -0.5978   -0.9621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9399   -1.8619    0.1398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3696    1.5866   -1.1852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2137   -0.0966   -1.8448 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8575    1.6985   -0.6214 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9441    0.5904   -2.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  1
  5  7  1  0
  7  8  1  0
  7  9  1  0
  5 10  1  0
 10 11  1  0
 11  2  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  4 16  1  0
  4 17  1  0
  6 18  1  0
  7 19  1  0
  8 20  1  0
  8 21  1  0
  8 22  1  0
  9 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
M  END
Download

PDB for HMDB0035823 ((S)-p-Menth-1-en-4-ol)

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Carvomenthanol (4-)                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  O   UNK     0       4.035   2.310   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.805   0.976   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.575   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.139   0.206   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.471   0.206   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.139  -1.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.805  -2.104   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.471  -1.334   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.115   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.805   3.644   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.805  -3.644   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2    9   10                                                  
CONECT    4    2    6                                                       
CONECT    5    2    8                                                       
CONECT    6    4    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    5    7                                                       
CONECT    9    3                                                            
CONECT   10    3                                                            
CONECT   11    7                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
Download

3D PDB for HMDB0035823 ((S)-p-Menth-1-en-4-ol)

COMPND    HMDB0035823
HETATM    1  C1  UNL     1       3.705  -0.337  -0.148  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.210  -0.322  -0.144  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.559  -1.201   0.578  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.067  -1.281   0.660  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.461   0.092   0.319  1.00  0.00           C  
HETATM    6  O1  UNL     1       0.012   0.965   1.301  1.00  0.00           O  
HETATM    7  C6  UNL     1      -1.951   0.057   0.418  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.589   1.392   0.094  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.589  -0.989  -0.458  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.053   0.571  -1.002  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.540   0.702  -0.970  1.00  0.00           C  
HETATM   12  H1  UNL     1       4.116  -1.062  -0.857  1.00  0.00           H  
HETATM   13  H2  UNL     1       4.021  -0.617   0.882  1.00  0.00           H  
HETATM   14  H3  UNL     1       4.072   0.701  -0.316  1.00  0.00           H  
HETATM   15  H4  UNL     1       2.107  -1.930   1.166  1.00  0.00           H  
HETATM   16  H5  UNL     1      -0.268  -2.056  -0.056  1.00  0.00           H  
HETATM   17  H6  UNL     1      -0.195  -1.496   1.708  1.00  0.00           H  
HETATM   18  H7  UNL     1       0.192   1.868   0.929  1.00  0.00           H  
HETATM   19  H8  UNL     1      -2.210  -0.160   1.482  1.00  0.00           H  
HETATM   20  H9  UNL     1      -1.955   2.204   0.502  1.00  0.00           H  
HETATM   21  H10 UNL     1      -2.702   1.461  -1.008  1.00  0.00           H  
HETATM   22  H11 UNL     1      -3.582   1.406   0.563  1.00  0.00           H  
HETATM   23  H12 UNL     1      -1.912  -1.290  -1.280  1.00  0.00           H  
HETATM   24  H13 UNL     1      -3.518  -0.598  -0.962  1.00  0.00           H  
HETATM   25  H14 UNL     1      -2.940  -1.862   0.140  1.00  0.00           H  
HETATM   26  H15 UNL     1      -0.370   1.587  -1.185  1.00  0.00           H  
HETATM   27  H16 UNL     1      -0.214  -0.097  -1.845  1.00  0.00           H  
HETATM   28  H17 UNL     1       1.857   1.698  -0.621  1.00  0.00           H  
HETATM   29  H18 UNL     1       1.944   0.590  -2.018  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    3   11
CONECT    3    4   15
CONECT    4    5   16   17
CONECT    5    6    7   10
CONECT    6   18
CONECT    7    8    9   19
CONECT    8   20   21   22
CONECT    9   23   24   25
CONECT   10   11   26   27
CONECT   11   28   29
END
Download

SMILES for HMDB0035823 ((S)-p-Menth-1-en-4-ol)

CC(C)[C@]1(O)CCC(C)=CC1
Download

INCHI for HMDB0035823 ((S)-p-Menth-1-en-4-ol)

InChI=1S/C10H18O/c1-8(2)10(11)6-4-9(3)5-7-10/h4,8,11H,5-7H2,1-3H3/t10-/m1/s1
Download
View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
(+)-Terpinen-4-olHMDB
(S)-(+)-P-Menth-1-en-4-olHMDB
(S)-1-Isopropyl-4-methyl-3-cyclohexen-1-olHMDB
S-4-CarvomenthenolHMDB
S-OriganolHMDB
Chemical FormulaC10H18O
Average Molecular Weight154.253
Monoisotopic Molecular Weight154.1357652
IUPAC Name(1S)-4-methyl-1-(propan-2-yl)cyclohex-3-en-1-ol
Traditional Name(1S)-1-isopropyl-4-methylcyclohex-3-en-1-ol
CAS Registry Number2438-10-0
SMILES
CC(C)[C@]1(O)CCC(C)=CC1
InChI Identifier
InChI=1S/C10H18O/c1-8(2)10(11)6-4-9(3)5-7-10/h4,8,11H,5-7H2,1-3H3/t10-/m1/s1
InChI KeyWRYLYDPHFGVWKC-SNVBAGLBSA-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
  • Tertiary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Biological roleIndustrial application
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point211.00 to 213.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility386.6 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.538 (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 IDFDB014586
KNApSAcK IDC00010928
Chemspider ID2006320
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound2724161
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1618181
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.