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Showing metabocard for alpha-Phellandrene (HMDB0035850)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 20:52:24 UTC
Update Date2022-03-07 02:54:40 UTC
HMDB IDHMDB0035850
Secondary Accession Numbers
  • HMDB35850
Metabolite Identification
Common Namealpha-Phellandrene
Descriptionalpha-Phellandrene, also known as α-phellandren or dihydro-p-cymene, 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 alpha-Phellandrene.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0035850 (alpha-Phellandrene)

Phellandrene-alpha
  Mrv1572001071617092D          
  Marvin  05270811492D          
 10 10  0  0  1  0            999 V2000
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    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    0.8250    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
    0.0023   -1.6505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7110   -2.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7191   -2.0586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0023    1.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  4  1  0  0  0  0
  1  5  1  0  0  0  0
  4  5  2  0  0  0  0
  5 10  1  0  0  0  0
  6  2  1  0  0  0  0
  6  3  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
M  END
Download

3D MOL for HMDB0035850 (alpha-Phellandrene)

HMDB0035850
     RDKit          3D
alpha-Phellandrene
 26 26  0  0  0  0  0  0  0  0999 V2000
    3.7179    0.4324   -0.2067 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2523    0.1109   -0.2465 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7345   -0.4658    0.8014 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3318   -0.8378    0.9100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5216   -0.5215   -0.2474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6592    0.3659    0.2807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5886    0.7414   -0.8414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4107   -0.4462    1.2832 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1602    0.1264   -1.3746 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4384    0.4299   -1.4014 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8579    1.3657    0.3765 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2154   -0.4054    0.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0770    0.5108   -1.2504 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4295   -0.6850    1.6734 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2637   -1.9690    1.0560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0752   -0.3901    1.8766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0395   -1.4609   -0.6002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2198    1.2947    0.6930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0246   -0.2059   -1.2680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4561    1.2663   -0.3795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0897    1.3528   -1.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5191   -0.3194    1.1518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2233   -1.5306    1.2152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1620   -0.0558    2.2981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4222    0.3892   -2.2805 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9328    0.9068   -2.2344 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  0
  6  7  1  0
  6  8  1  0
  5  9  1  0
  9 10  2  0
 10  2  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  5 17  1  0
  6 18  1  0
  7 19  1  0
  7 20  1  0
  7 21  1  0
  8 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
M  END
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3D SDF for HMDB0035850 (alpha-Phellandrene)

Phellandrene-alpha
  Mrv1572001071617092D          
  Marvin  05270811492D          
 10 10  0  0  1  0            999 V2000
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    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    0.8250    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
    0.0023   -1.6505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7110   -2.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7191   -2.0586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0023    1.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  4  1  0  0  0  0
  1  5  1  0  0  0  0
  4  5  2  0  0  0  0
  5 10  1  0  0  0  0
  6  2  1  0  0  0  0
  6  3  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035850

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)C1CC=C(C)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4-6,8,10H,7H2,1-3H3

> <INCHI_KEY>
OGLDWXZKYODSOB-UHFFFAOYSA-N

> <FORMULA>
C10H16

> <MOLECULAR_WEIGHT>
136.238

> <EXACT_MASS>
136.125200515

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
17.14339757127084

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methyl-5-(propan-2-yl)cyclohexa-1,3-diene

> <ALOGPS_LOGP>
4.29

> <JCHEM_LOGP>
3.2055368060000005

> <ALOGPS_LOGS>
-3.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
47.8194

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.33e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+-)-α phellandrene

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0035850 (alpha-Phellandrene)

HMDB0035850
     RDKit          3D
alpha-Phellandrene
 26 26  0  0  0  0  0  0  0  0999 V2000
    3.7179    0.4324   -0.2067 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2523    0.1109   -0.2465 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7345   -0.4658    0.8014 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3318   -0.8378    0.9100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5216   -0.5215   -0.2474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6592    0.3659    0.2807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5886    0.7414   -0.8414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4107   -0.4462    1.2832 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1602    0.1264   -1.3746 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4384    0.4299   -1.4014 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8579    1.3657    0.3765 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2154   -0.4054    0.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0770    0.5108   -1.2504 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4295   -0.6850    1.6734 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2637   -1.9690    1.0560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0752   -0.3901    1.8766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0395   -1.4609   -0.6002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2198    1.2947    0.6930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0246   -0.2059   -1.2680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4561    1.2663   -0.3795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0897    1.3528   -1.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5191   -0.3194    1.1518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2233   -1.5306    1.2152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1620   -0.0558    2.2981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4222    0.3892   -2.2805 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9328    0.9068   -2.2344 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  0
  6  7  1  0
  6  8  1  0
  5  9  1  0
  9 10  2  0
 10  2  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  5 17  1  0
  6 18  1  0
  7 19  1  0
  7 20  1  0
  7 21  1  0
  8 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
M  END
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PDB for HMDB0035850 (alpha-Phellandrene)

HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Phellandrene-alpha                                
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.004  -3.081   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.327  -3.849   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.342  -3.843   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.004   3.077   0.000  0.00  0.00           C+0
CONECT    1    2    5                                                       
CONECT    2    1    6                                                       
CONECT    3    4    6                                                       
CONECT    4    3    5                                                       
CONECT    5    1    4   10                                                  
CONECT    6    2    3    7                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    5                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
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3D PDB for HMDB0035850 (alpha-Phellandrene)

COMPND    HMDB0035850
HETATM    1  C1  UNL     1       3.718   0.432  -0.207  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.252   0.111  -0.246  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.735  -0.466   0.801  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.332  -0.838   0.910  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.522  -0.522  -0.247  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.659   0.366   0.281  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.589   0.741  -0.841  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.411  -0.446   1.283  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.160   0.126  -1.375  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.438   0.430  -1.401  1.00  0.00           C  
HETATM   11  H1  UNL     1       3.858   1.366   0.377  1.00  0.00           H  
HETATM   12  H2  UNL     1       4.215  -0.405   0.323  1.00  0.00           H  
HETATM   13  H3  UNL     1       4.077   0.511  -1.250  1.00  0.00           H  
HETATM   14  H4  UNL     1       2.429  -0.685   1.673  1.00  0.00           H  
HETATM   15  H5  UNL     1       0.264  -1.969   1.056  1.00  0.00           H  
HETATM   16  H6  UNL     1      -0.075  -0.390   1.877  1.00  0.00           H  
HETATM   17  H7  UNL     1      -1.039  -1.461  -0.600  1.00  0.00           H  
HETATM   18  H8  UNL     1      -1.220   1.295   0.693  1.00  0.00           H  
HETATM   19  H9  UNL     1      -3.025  -0.206  -1.268  1.00  0.00           H  
HETATM   20  H10 UNL     1      -3.456   1.266  -0.380  1.00  0.00           H  
HETATM   21  H11 UNL     1      -2.090   1.353  -1.608  1.00  0.00           H  
HETATM   22  H12 UNL     1      -3.519  -0.319   1.152  1.00  0.00           H  
HETATM   23  H13 UNL     1      -2.223  -1.531   1.215  1.00  0.00           H  
HETATM   24  H14 UNL     1      -2.162  -0.056   2.298  1.00  0.00           H  
HETATM   25  H15 UNL     1      -0.422   0.389  -2.281  1.00  0.00           H  
HETATM   26  H16 UNL     1       1.933   0.907  -2.234  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3    3   10
CONECT    3    4   14
CONECT    4    5   15   16
CONECT    5    6    9   17
CONECT    6    7    8   18
CONECT    7   19   20   21
CONECT    8   22   23   24
CONECT    9   10   10   25
CONECT   10   26
END
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SMILES for HMDB0035850 (alpha-Phellandrene)

CC(C)C1CC=C(C)C=C1
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INCHI for HMDB0035850 (alpha-Phellandrene)

InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4-6,8,10H,7H2,1-3H3
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View in JSmolView Stereo Labels
Synonyms
Chemical FormulaC10H16
Average Molecular Weight136.238
Monoisotopic Molecular Weight136.125200515
IUPAC Name2-methyl-5-(propan-2-yl)cyclohexa-1,3-diene
Traditional Name(+-)-α phellandrene
CAS Registry Number99-83-2
SMILES
CC(C)C1CC=C(C)C=C1
InChI Identifier
InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4-6,8,10H,7H2,1-3H3
InChI KeyOGLDWXZKYODSOB-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
  • Branched unsaturated hydrocarbon
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationSource
ProcessNot Available
Role
Industrial applicationBiological role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point249.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point463.70 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility5000 mg/L @ 25 °C (exp)The Good Scents Company Information System
LogP-0.830 (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 Locations
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
Abnormal Concentrations
Associated Disorders and Diseases
Disease References
Ulcerative colitis
  1. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
  2. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
  3. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Diarrhoea predominant irritable bowel syndrome
  1. Ahmed I, Greenwood R, Costello Bde L, Ratcliffe NM, Probert CS: An investigation of fecal volatile organic metabolites in irritable bowel syndrome. PLoS One. 2013;8(3):e58204. doi: 10.1371/journal.pone.0058204. Epub 2013 Mar 13. [PubMed:23516449 ]
Crohn's disease
  1. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
  2. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB003865
KNApSAcK IDC00003051
Chemspider ID7180
KEGG Compound IDNot Available
BioCyc IDCPD-12226
BiGG IDNot Available
Wikipedia LinkPhellandrene
METLIN IDNot Available
PubChem Compound7460
PDB IDNot Available
ChEBI ID50035
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1167241
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.