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Showing metabocard for Butyl butyrate (HMDB0039620)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-12 01:07:30 UTC
Update Date2023-02-21 17:27:02 UTC
HMDB IDHMDB0039620
Secondary Accession Numbers
  • HMDB39620
Metabolite Identification
Common NameButyl butyrate
DescriptionButyl butyrate, or butyl butanoate, is an organic compound that is an ester formed by the condensation of butyric acid and n-butanol. It is a clear, colorless liquid that is insoluble in water, but miscible with ethanol and diethyl ether. Its refractive index is 1.406 at 20 °C. Butyl butyrate is found in alcoholic beverages. Butyl butyrate is present in many fruits, e.g. banana, cherry, melon, plum, also present in gruyere de comte cheese, cider, soybean etc. Butyl butyrate is used in fruit flavour compositions Butyl butyrate is an organic compound which is an ester formed by the condensation of butyric acid and butanol. It is a clear, colorless liquid that is insoluble in water, but miscible with ethanol and diethyl ether.
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0039620 (Butyl butyrate)

  Mrv1652305271900042D          

 10  9  0  0  0  0            999 V2000
   -2.3645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3513   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6368   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9224   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2211   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4934   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  8  2  0  0  0  0
 10  7  1  0  0  0  0
 10  8  1  0  0  0  0
M  END
Download

3D MOL for HMDB0039620 (Butyl butyrate)

HMDB0039620
     RDKit          3D
Butyl butyrate
 26 25  0  0  0  0  0  0  0  0999 V2000
    4.1121    0.6841   -0.1553 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1544   -0.4367   -0.4640 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8139   -0.2312    0.2450 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9332   -1.4030   -0.1296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3389   -1.3503    0.4518 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2657   -0.3439    0.2683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9493    0.6122   -0.4843 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6087   -0.3651    0.9304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3759    0.8715    0.5254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5167    0.8337   -0.9825 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9930    1.4802   -0.9220 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1743    0.3390   -0.2117 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9685    1.1281    0.8314 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9927   -0.5454   -1.5572 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6169   -1.3766   -0.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3583    0.7052   -0.1394 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0220   -0.2006    1.3311 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4365   -2.3199    0.2952 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9354   -1.5477   -1.2187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5296   -0.3845    2.0208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1063   -1.3013    0.6053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7547    1.7433    0.8446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3609    0.8838    1.0337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2979   -0.1725   -1.3970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5516    1.0869   -1.2983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8550    1.6107   -1.4040 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  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  4 18  1  0
  4 19  1  0
  8 20  1  0
  8 21  1  0
  9 22  1  0
  9 23  1  0
 10 24  1  0
 10 25  1  0
 10 26  1  0
M  END
Download

3D SDF for HMDB0039620 (Butyl butyrate)

  Mrv1652305271900042D          

 10  9  0  0  0  0            999 V2000
   -2.3645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3513   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6368   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9224   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2211   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4934   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  8  2  0  0  0  0
 10  7  1  0  0  0  0
 10  8  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0039620

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCOC(=O)CCC

> <INCHI_IDENTIFIER>
InChI=1S/C8H16O2/c1-3-5-7-10-8(9)6-4-2/h3-7H2,1-2H3

> <INCHI_KEY>
XUPYJHCZDLZNFP-UHFFFAOYSA-N

> <FORMULA>
C8H16O2

> <MOLECULAR_WEIGHT>
144.2114

> <EXACT_MASS>
144.115029756

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
17.34434242152357

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
butyl butanoate

> <ALOGPS_LOGP>
2.82

> <JCHEM_LOGP>
2.391551868333333

> <ALOGPS_LOGS>
-2.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.032619365198107

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
40.514300000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.36e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
butyl butyrate

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0039620 (Butyl butyrate)

HMDB0039620
     RDKit          3D
Butyl butyrate
 26 25  0  0  0  0  0  0  0  0999 V2000
    4.1121    0.6841   -0.1553 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1544   -0.4367   -0.4640 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8139   -0.2312    0.2450 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9332   -1.4030   -0.1296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3389   -1.3503    0.4518 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2657   -0.3439    0.2683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9493    0.6122   -0.4843 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6087   -0.3651    0.9304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3759    0.8715    0.5254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5167    0.8337   -0.9825 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9930    1.4802   -0.9220 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1743    0.3390   -0.2117 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9685    1.1281    0.8314 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9927   -0.5454   -1.5572 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6169   -1.3766   -0.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3583    0.7052   -0.1394 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0220   -0.2006    1.3311 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4365   -2.3199    0.2952 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9354   -1.5477   -1.2187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5296   -0.3845    2.0208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1063   -1.3013    0.6053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7547    1.7433    0.8446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3609    0.8838    1.0337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2979   -0.1725   -1.3970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5516    1.0869   -1.2983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8550    1.6107   -1.4040 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  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  4 18  1  0
  4 19  1  0
  8 20  1  0
  8 21  1  0
  9 22  1  0
  9 23  1  0
 10 24  1  0
 10 25  1  0
 10 26  1  0
M  END
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PDB for HMDB0039620 (Butyl butyrate)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      -4.414  -1.897   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.256  -1.897   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.080  -2.667   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.922  -2.667   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.746  -1.897   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.588  -1.897   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.413  -2.667   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.255  -2.667   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.255  -4.207   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.921  -1.897   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5   10                                                       
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    7    8                                                       
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
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3D PDB for HMDB0039620 (Butyl butyrate)

COMPND    HMDB0039620
HETATM    1  C1  UNL     1       4.112   0.684  -0.155  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.154  -0.437  -0.464  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.814  -0.231   0.245  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.933  -1.403  -0.130  1.00  0.00           C  
HETATM    5  O1  UNL     1      -0.339  -1.350   0.452  1.00  0.00           O  
HETATM    6  C5  UNL     1      -1.266  -0.344   0.268  1.00  0.00           C  
HETATM    7  O2  UNL     1      -0.949   0.612  -0.484  1.00  0.00           O  
HETATM    8  C6  UNL     1      -2.609  -0.365   0.930  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.376   0.871   0.525  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.517   0.834  -0.983  1.00  0.00           C  
HETATM   11  H1  UNL     1       3.993   1.480  -0.922  1.00  0.00           H  
HETATM   12  H2  UNL     1       5.174   0.339  -0.212  1.00  0.00           H  
HETATM   13  H3  UNL     1       3.969   1.128   0.831  1.00  0.00           H  
HETATM   14  H4  UNL     1       2.993  -0.545  -1.557  1.00  0.00           H  
HETATM   15  H5  UNL     1       3.617  -1.377  -0.107  1.00  0.00           H  
HETATM   16  H6  UNL     1       1.358   0.705  -0.139  1.00  0.00           H  
HETATM   17  H7  UNL     1       2.022  -0.201   1.331  1.00  0.00           H  
HETATM   18  H8  UNL     1       1.436  -2.320   0.295  1.00  0.00           H  
HETATM   19  H9  UNL     1       0.935  -1.548  -1.219  1.00  0.00           H  
HETATM   20  H10 UNL     1      -2.530  -0.385   2.021  1.00  0.00           H  
HETATM   21  H11 UNL     1      -3.106  -1.301   0.605  1.00  0.00           H  
HETATM   22  H12 UNL     1      -2.755   1.743   0.845  1.00  0.00           H  
HETATM   23  H13 UNL     1      -4.361   0.884   1.034  1.00  0.00           H  
HETATM   24  H14 UNL     1      -3.298  -0.172  -1.397  1.00  0.00           H  
HETATM   25  H15 UNL     1      -4.552   1.087  -1.298  1.00  0.00           H  
HETATM   26  H16 UNL     1      -2.855   1.611  -1.404  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3   14   15
CONECT    3    4   16   17
CONECT    4    5   18   19
CONECT    5    6
CONECT    6    7    7    8
CONECT    8    9   20   21
CONECT    9   10   22   23
CONECT   10   24   25   26
END
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SMILES for HMDB0039620 (Butyl butyrate)

CCCCOC(=O)CCC
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INCHI for HMDB0039620 (Butyl butyrate)

InChI=1S/C8H16O2/c1-3-5-7-10-8(9)6-4-2/h3-7H2,1-2H3
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View in JSmolView Stereo Labels
Synonyms
Chemical FormulaC8H16O2
Average Molecular Weight144.2114
Monoisotopic Molecular Weight144.115029756
IUPAC Namebutyl butanoate
Traditional Namebutyl butyrate
CAS Registry Number109-21-7
SMILES
CCCCOC(=O)CCC
InChI Identifier
InChI=1S/C8H16O2/c1-3-5-7-10-8(9)6-4-2/h3-7H2,1-2H3
InChI KeyXUPYJHCZDLZNFP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentFatty acid esters
Alternative Parents
Substituents
  • Fatty acid ester
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic 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-91.5 °CNot Available
Boiling Point166.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0.5 mg/mL at 20 °CNot Available
LogP2.823 (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
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
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 ]
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 ]
Autism
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Pervasive developmental disorder not otherwise specified
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB019248
KNApSAcK IDC00035546
Chemspider ID7694
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkButyl_butyrate
METLIN IDNot Available
PubChem Compound7983
PDB IDNot Available
ChEBI ID87429
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1014091
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.