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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:49:25 UTC
Update Date2022-03-07 02:53:20 UTC
HMDB IDHMDB0032368
Secondary Accession Numbers
  • HMDB32368
Metabolite Identification
Common NameMenthyl pyrrolidone carboxylate
DescriptionMenthyl pyrrolidone carboxylate, also known as 1-menthyl-b-D-glucoside, belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. Based on a literature review a small amount of articles have been published on Menthyl pyrrolidone carboxylate.
Structure
Data?1563862254
Synonyms
ValueSource
(-)-Menthyl O-beta-glucopyranosideChEBI
(-)-Menthyl O-beta-D-glucosideChEBI
(-)-Menthyl O-b-glucopyranosideGenerator
(-)-Menthyl O-β-glucopyranosideGenerator
(-)-Menthyl O-b-D-glucosideGenerator
(-)-Menthyl O-β-D-glucosideGenerator
Menthyl pyrrolidone carboxylic acidGenerator
(-)-Menthyl b-D-glucosideHMDB
(-)-Menthyl β-D-glucosideHMDB
1-Menthyl-b-D-glucosideHMDB
1-Menthyl-β-D-glucosideHMDB
Chemical FormulaC16H30O6
Average Molecular Weight318.4058
Monoisotopic Molecular Weight318.204238692
IUPAC Name(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl]oxy}oxane-3,4,5-triol
Traditional Name(-)-menthyl β-D-glucoside
CAS Registry Number52528-10-6
SMILES
CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
InChI Identifier
InChI=1S/C16H30O6/c1-8(2)10-5-4-9(3)6-11(10)21-16-15(20)14(19)13(18)12(7-17)22-16/h8-20H,4-7H2,1-3H3/t9-,10+,11-,12-,13-,14+,15-,16-/m1/s1
InChI KeyGZSDZJZIZBGBON-NZZARTGWSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene glycosides
Direct ParentTerpene glycosides
Alternative Parents
Substituents
  • Terpene glycoside
  • Glycosyl compound
  • O-glycosyl compound
  • Monocyclic monoterpenoid
  • Monoterpenoid
  • P-menthane monoterpenoid
  • Oxane
  • Monosaccharide
  • Secondary alcohol
  • Polyol
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Primary alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility12.2 g/LALOGPS
logP0.47ALOGPS
logP0.89ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)12.21ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area99.38 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity79.86 m³·mol⁻¹ChemAxon
Polarizability34.44 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+174.51131661259
DarkChem[M-H]-169.49631661259
DeepCCS[M+H]+174.99630932474
DeepCCS[M-H]-172.630932474
DeepCCS[M-2H]-205.97530932474
DeepCCS[M+Na]+180.90830932474
AllCCS[M+H]+179.332859911
AllCCS[M+H-H2O]+176.332859911
AllCCS[M+NH4]+182.032859911
AllCCS[M+Na]+182.832859911
AllCCS[M-H]-177.232859911
AllCCS[M+Na-2H]-177.732859911
AllCCS[M+HCOO]-178.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Menthyl pyrrolidone carboxylateCC(C)[C@@H]1CC[C@@H](C)C[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O3171.1Standard polar33892256
Menthyl pyrrolidone carboxylateCC(C)[C@@H]1CC[C@@H](C)C[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O2368.4Standard non polar33892256
Menthyl pyrrolidone carboxylateCC(C)[C@@H]1CC[C@@H](C)C[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O2460.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Menthyl pyrrolidone carboxylate,1TMS,isomer #1CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]1O2284.0Semi standard non polar33892256
Menthyl pyrrolidone carboxylate,1TMS,isomer #2CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O2266.4Semi standard non polar33892256
Menthyl pyrrolidone carboxylate,1TMS,isomer #3CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O2274.3Semi standard non polar33892256
Menthyl pyrrolidone carboxylate,1TMS,isomer #4CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C2262.7Semi standard non polar33892256
Menthyl pyrrolidone carboxylate,2TMS,isomer #1CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O2317.7Semi standard non polar33892256
Menthyl pyrrolidone carboxylate,2TMS,isomer #2CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O2341.4Semi standard non polar33892256
Menthyl pyrrolidone carboxylate,2TMS,isomer #3CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C2306.2Semi standard non polar33892256
Menthyl pyrrolidone carboxylate,2TMS,isomer #4CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O2315.9Semi standard non polar33892256
Menthyl pyrrolidone carboxylate,2TMS,isomer #5CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C2319.5Semi standard non polar33892256
Menthyl pyrrolidone carboxylate,2TMS,isomer #6CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C2313.7Semi standard non polar33892256
Menthyl pyrrolidone carboxylate,3TMS,isomer #1CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O2339.0Semi standard non polar33892256
Menthyl pyrrolidone carboxylate,3TMS,isomer #2CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C2354.8Semi standard non polar33892256
Menthyl pyrrolidone carboxylate,3TMS,isomer #3CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C2332.6Semi standard non polar33892256
Menthyl pyrrolidone carboxylate,3TMS,isomer #4CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C2320.5Semi standard non polar33892256
Menthyl pyrrolidone carboxylate,4TMS,isomer #1CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C2325.3Semi standard non polar33892256
Menthyl pyrrolidone carboxylate,1TBDMS,isomer #1CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]1O2505.6Semi standard non polar33892256
Menthyl pyrrolidone carboxylate,1TBDMS,isomer #2CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O2505.1Semi standard non polar33892256
Menthyl pyrrolidone carboxylate,1TBDMS,isomer #3CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O2497.4Semi standard non polar33892256
Menthyl pyrrolidone carboxylate,1TBDMS,isomer #4CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C2498.8Semi standard non polar33892256
Menthyl pyrrolidone carboxylate,2TBDMS,isomer #1CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O2772.6Semi standard non polar33892256
Menthyl pyrrolidone carboxylate,2TBDMS,isomer #2CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O2771.0Semi standard non polar33892256
Menthyl pyrrolidone carboxylate,2TBDMS,isomer #3CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C2780.2Semi standard non polar33892256
Menthyl pyrrolidone carboxylate,2TBDMS,isomer #4CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O2756.2Semi standard non polar33892256
Menthyl pyrrolidone carboxylate,2TBDMS,isomer #5CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C2759.4Semi standard non polar33892256
Menthyl pyrrolidone carboxylate,2TBDMS,isomer #6CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C2759.8Semi standard non polar33892256
Menthyl pyrrolidone carboxylate,3TBDMS,isomer #1CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O3011.5Semi standard non polar33892256
Menthyl pyrrolidone carboxylate,3TBDMS,isomer #2CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C3023.3Semi standard non polar33892256
Menthyl pyrrolidone carboxylate,3TBDMS,isomer #3CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C3016.1Semi standard non polar33892256
Menthyl pyrrolidone carboxylate,3TBDMS,isomer #4CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C2998.7Semi standard non polar33892256
Menthyl pyrrolidone carboxylate,4TBDMS,isomer #1CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C3234.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Menthyl pyrrolidone carboxylate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0k9i-9452000000-42588a0886876e47aa342017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Menthyl pyrrolidone carboxylate GC-MS (4 TMS) - 70eV, Positivesplash10-0006-3200190000-cfcaef8b68862ed10a742017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Menthyl pyrrolidone carboxylate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Menthyl pyrrolidone carboxylate 10V, Positive-QTOFsplash10-0ap0-0904000000-5987737bc24c24d02b912016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Menthyl pyrrolidone carboxylate 20V, Positive-QTOFsplash10-0a4r-2900000000-98832b544c236461ab7b2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Menthyl pyrrolidone carboxylate 40V, Positive-QTOFsplash10-0a4r-9800000000-f8510defb41929ee73cc2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Menthyl pyrrolidone carboxylate 10V, Negative-QTOFsplash10-066r-1916000000-a378c1511bac4d5b07a12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Menthyl pyrrolidone carboxylate 20V, Negative-QTOFsplash10-0a4i-1910000000-2399f4fa758e520d32ed2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Menthyl pyrrolidone carboxylate 40V, Negative-QTOFsplash10-0a4r-3900000000-645e98d305305d5993252016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Menthyl pyrrolidone carboxylate 10V, Positive-QTOFsplash10-014i-2904000000-54f8af8655aa2de8ed162021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Menthyl pyrrolidone carboxylate 20V, Positive-QTOFsplash10-000t-9301000000-7bb143c4dbd965c6464a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Menthyl pyrrolidone carboxylate 40V, Positive-QTOFsplash10-0002-9420000000-9b565aa778157c0d33832021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Menthyl pyrrolidone carboxylate 10V, Negative-QTOFsplash10-014i-0009000000-d77dc8a8103d351ee52a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Menthyl pyrrolidone carboxylate 20V, Negative-QTOFsplash10-0aor-4916000000-136c5db92fabfe126e602021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Menthyl pyrrolidone carboxylate 40V, Negative-QTOFsplash10-0k9i-2900000000-496b2b88c3e880eeffbe2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • 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 IDFDB006135
KNApSAcK IDNot Available
Chemspider ID4573550
KEGG Compound IDC03962
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5459767
PDB IDNot Available
ChEBI ID15411
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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. (). EAFUS: Everything Added to Food in the United States.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.