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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-10-23 10:11:27 UTC
Update Date2021-09-14 15:43:43 UTC
HMDB IDHMDB0005056
Secondary Accession Numbers
  • HMDB05056
Metabolite Identification
Common NameEnterodiol
DescriptionEnterodiol is one of the most important lignan-type phytoestrogens identified in serum, urine, bile, and seminal fluids of humans and animals. Phytoestrogens are a diverse group of compounds found in many edible plants that have, as their common denominator, a phenolic group that they share with estrogenic steroids. This phenolic group appears to play an important role in determining the estrogenic agonist/antagonistic properties of these compounds. Phytoestrogens have been categorized according to their chemical structures as isoflavones, lignans, and coumestans. Enterodiol is formed by bacteria in the intestinal tract from the plant lignans matairesinol and secoisolariciresinol, which exist in various whole-grain cereals (barley, rye, and wheat), seeds, nuts, legumes, and vegetables (PMID: 12270221 , J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Sep 25;777(1-2):289-309.). Enterodiol is a biomarker for the consumption of soy beans and other soy products.
Structure
Data?1582752343
Synonyms
ValueSource
(-)-EnterodiolHMDB
(2R,3R)-2,3-Bis[(3-hydroxyphenyl)methyl]-1,4-butanediolHMDB
Arbo 9HMDB
[R-(R*,r*)]-2,3-bis[(3-hydroxyphenyl)methyl]-1,4-butanediolHMDB
2,3-Bis(3'-hydroxybenzyl)butane-1,4-diolHMDB
2,3-BHBBDHMDB
2,3-Bis(3-hydroxybenzyl)butane-1,4-diolHMDB
EnterodiolHMDB
Chemical FormulaC18H22O4
Average Molecular Weight302.3649
Monoisotopic Molecular Weight302.151809192
IUPAC Name(2R,3R)-2,3-bis[(3-hydroxyphenyl)methyl]butane-1,4-diol
Traditional Name(-)-enterodiol
CAS Registry Number80226-00-2
SMILES
OC[C@H](CC1=CC(O)=CC=C1)[C@H](CO)CC1=CC(O)=CC=C1
InChI Identifier
InChI=1S/C18H22O4/c19-11-15(7-13-3-1-5-17(21)9-13)16(12-20)8-14-4-2-6-18(22)10-14/h1-6,9-10,15-16,19-22H,7-8,11-12H2/t15-,16-/m0/s1
InChI KeyDWONJCNDULPHLV-HOTGVXAUSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dibenzylbutanediol lignans. These are lignan compounds containing a 2,3-dibenzylbutane-1,4-diol moiety.
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassDibenzylbutane lignans
Sub ClassDibenzylbutanediol lignans
Direct ParentDibenzylbutanediol lignans
Alternative Parents
Substituents
  • Dibenzylbutanediol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
Role
Physical Properties
StateSolid
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 Solubility0.025 g/LALOGPS
logP1.91ALOGPS
logP2.65ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)9.79ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area80.92 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity86.36 m³·mol⁻¹ChemAxon
Polarizability32.76 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]+172.00131661259
DarkChem[M-H]-168.74831661259
DeepCCS[M+H]+167.87530932474
DeepCCS[M-H]-165.51730932474
DeepCCS[M-2H]-199.53730932474
DeepCCS[M+Na]+174.76530932474
AllCCS[M+H]+173.432859911
AllCCS[M+H-H2O]+169.832859911
AllCCS[M+NH4]+176.632859911
AllCCS[M+Na]+177.632859911
AllCCS[M-H]-175.832859911
AllCCS[M+Na-2H]-176.032859911
AllCCS[M+HCOO]-176.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
EnterodiolOC[C@H](CC1=CC(O)=CC=C1)[C@H](CO)CC1=CC(O)=CC=C14406.2Standard polar33892256
EnterodiolOC[C@H](CC1=CC(O)=CC=C1)[C@H](CO)CC1=CC(O)=CC=C13058.2Standard non polar33892256
EnterodiolOC[C@H](CC1=CC(O)=CC=C1)[C@H](CO)CC1=CC(O)=CC=C13066.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Enterodiol,1TMS,isomer #1C[Si](C)(C)OC[C@H](CC1=CC=CC(O)=C1)[C@H](CO)CC1=CC=CC(O)=C12936.4Semi standard non polar33892256
Enterodiol,1TMS,isomer #2C[Si](C)(C)OC1=CC=CC(C[C@@H](CO)[C@H](CO)CC2=CC=CC(O)=C2)=C12862.8Semi standard non polar33892256
Enterodiol,2TMS,isomer #1C[Si](C)(C)OC[C@H](CC1=CC=CC(O[Si](C)(C)C)=C1)[C@H](CO)CC1=CC=CC(O)=C12813.9Semi standard non polar33892256
Enterodiol,2TMS,isomer #2C[Si](C)(C)OC[C@H](CC1=CC=CC(O)=C1)[C@H](CO[Si](C)(C)C)CC1=CC=CC(O)=C12929.4Semi standard non polar33892256
Enterodiol,2TMS,isomer #3C[Si](C)(C)OC[C@H](CC1=CC=CC(O)=C1)[C@H](CO)CC1=CC=CC(O[Si](C)(C)C)=C12822.9Semi standard non polar33892256
Enterodiol,2TMS,isomer #4C[Si](C)(C)OC1=CC=CC(C[C@@H](CO)[C@H](CO)CC2=CC=CC(O[Si](C)(C)C)=C2)=C12796.0Semi standard non polar33892256
Enterodiol,3TMS,isomer #1C[Si](C)(C)OC[C@H](CC1=CC=CC(O)=C1)[C@H](CO[Si](C)(C)C)CC1=CC=CC(O[Si](C)(C)C)=C12808.3Semi standard non polar33892256
Enterodiol,3TMS,isomer #2C[Si](C)(C)OC[C@H](CC1=CC=CC(O[Si](C)(C)C)=C1)[C@H](CO)CC1=CC=CC(O[Si](C)(C)C)=C12770.6Semi standard non polar33892256
Enterodiol,4TMS,isomer #1C[Si](C)(C)OC[C@H](CC1=CC=CC(O[Si](C)(C)C)=C1)[C@H](CO[Si](C)(C)C)CC1=CC=CC(O[Si](C)(C)C)=C12781.4Semi standard non polar33892256
Enterodiol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H](CC1=CC=CC(O)=C1)[C@H](CO)CC1=CC=CC(O)=C13181.2Semi standard non polar33892256
Enterodiol,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=CC(C[C@@H](CO)[C@H](CO)CC2=CC=CC(O)=C2)=C13110.4Semi standard non polar33892256
Enterodiol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H](CC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1)[C@H](CO)CC1=CC=CC(O)=C13286.6Semi standard non polar33892256
Enterodiol,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC[C@H](CC1=CC=CC(O)=C1)[C@H](CO[Si](C)(C)C(C)(C)C)CC1=CC=CC(O)=C13411.6Semi standard non polar33892256
Enterodiol,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC[C@H](CC1=CC=CC(O)=C1)[C@H](CO)CC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C13290.2Semi standard non polar33892256
Enterodiol,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC=CC(C[C@@H](CO)[C@H](CO)CC2=CC=CC(O[Si](C)(C)C(C)(C)C)=C2)=C13284.2Semi standard non polar33892256
Enterodiol,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H](CC1=CC=CC(O)=C1)[C@H](CO[Si](C)(C)C(C)(C)C)CC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C13445.6Semi standard non polar33892256
Enterodiol,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC[C@H](CC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1)[C@H](CO)CC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C13444.8Semi standard non polar33892256
Enterodiol,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H](CC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1)[C@H](CO[Si](C)(C)C(C)(C)C)CC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C13625.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Enterodiol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-2950000000-4ed8a5eb8bfaabb7a2632017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Enterodiol GC-MS (4 TMS) - 70eV, Positivesplash10-004i-6520390000-6840ee48e5d508b92d942017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Enterodiol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Enterodiol 30V, Positive-QTOFsplash10-0a4i-0900000000-6fd5b1caf0b11ab3dd172021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Enterodiol 10V, Positive-QTOFsplash10-014i-0290000000-b01fb4b064e58a38e1702021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Enterodiol 50V, Positive-QTOFsplash10-0a4i-3900000000-4ed09c20e4a4fb3f38752021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Enterodiol 10V, Positive-QTOFsplash10-0aor-0940000000-786ff272cb009339906f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Enterodiol 10V, Positive-QTOFsplash10-0aor-0940000000-a340102680583cfc68f02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Enterodiol 50V, Positive-QTOFsplash10-0pb9-3900000000-aa3626a0e9a6776858b72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Enterodiol 10V, Positive-QTOFsplash10-0aor-0940000000-41e4cc9deb7aa9c799c02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Enterodiol 10V, Positive-QTOFsplash10-014i-0290000000-179116fcc815df1446fe2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Enterodiol 6V, Positive-QTOFsplash10-014i-0290000000-fd222de6f034fee01c312021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Enterodiol 50V, Positive-QTOFsplash10-0ar3-2900000000-ee35613960c900d06fb42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Enterodiol 6V, Positive-QTOFsplash10-014i-0290000000-2de3385ce84eba140c882021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Enterodiol 30V, Positive-QTOFsplash10-0a4i-0900000000-9fba8f3772864b12ddbb2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Enterodiol 10V, Positive-QTOFsplash10-014i-0290000000-ebad5296a50b0dcf053a2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enterodiol 10V, Positive-QTOFsplash10-0udr-0398000000-f09da6eee4bc76ff516a2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enterodiol 20V, Positive-QTOFsplash10-0frj-0971000000-bce5b39682ed3570612f2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enterodiol 40V, Positive-QTOFsplash10-05r9-0960000000-6920c1866fa29475fabc2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enterodiol 10V, Negative-QTOFsplash10-0udi-0039000000-c4358f7b97aab38a1ecf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enterodiol 20V, Negative-QTOFsplash10-0udi-0096000000-fbf3e7cc759ef05d54252016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enterodiol 40V, Negative-QTOFsplash10-0fdo-1690000000-046c3b836806f630a4ed2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enterodiol 10V, Positive-QTOFsplash10-0udi-0859000000-8fb5cc787a664fd76c342021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enterodiol 20V, Positive-QTOFsplash10-0690-1950000000-7ae3b12589c277c0e3772021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enterodiol 40V, Positive-QTOFsplash10-0a4l-2940000000-bfd4fbb4059ae278438f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enterodiol 10V, Negative-QTOFsplash10-0udi-0039000000-7d394202ae81237c33a92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enterodiol 20V, Negative-QTOFsplash10-0udi-0393000000-63ea158a62162e087ae02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enterodiol 40V, Negative-QTOFsplash10-0r13-0890000000-72542e20683700bfc0c22021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0014 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.000992 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.0015 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.00152 uMAdult (>18 years old)FemaleNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.01 (0.0 -0.3) umol/mmol creatinineChildren (1-13 years old)BothNormal details
UrineDetected and Quantified0.0733 +/-0.04 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.0533 +/- 0.0266 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.032 +/- 0.072 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.013 +/- 0.019 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.065 +/- 0.039 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.013 +/- 0.019 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0065 +/- 0.019 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.00 +/- 0.0065 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0065 +/- 0.0065 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0247 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.0501 +/- 0.100 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 1009 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 1009 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 1009 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 1009 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 1009 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 1009 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 1009 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 1009 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 1009 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 1009 details
UrineDetected and Quantified0.0140 (0.0120-0.0163) umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal
    • National Health a...
details
UrineDetected and Quantified0.0176 (0.0140-0.0222) umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal
    • National Health a...
details
UrineDetected and Quantified0.0373 +/- 0.0560 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.0240 +/- 0.0240 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.447 +/- 1.00667 umol/mmol creatinineAdult (>18 years old)Female
Normal
details
UrineDetected and Quantified0.0108 umol/mmol creatinineChildren (1 - 13 years old)BothNormal details
UrineDetected and Quantified0.0800 +/- 0.100 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0833 +/- 0.229 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.133 +/- 0.220 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0211 umol/mmol creatinineChildren (1 - 13 years old)FemaleNormal details
UrineDetected and Quantified0.0258 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.0339 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.05 +/- 0.12 umol/mmol creatinineAdult (>18 years old)FemaleBreast cancer details
Associated Disorders and Diseases
Disease References
Perillyl alcohol administration for cancer treatment
  1. Grace PB, Mistry NS, Carter MH, Leathem AJ, Teale P: High throughput quantification of phytoestrogens in human urine and serum using liquid chromatography/tandem mass spectrometry (LC-MS/MS). J Chromatogr B Analyt Technol Biomed Life Sci. 2007 Jun 15;853(1-2):138-46. Epub 2007 Mar 18. [PubMed:17403619 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021828
KNApSAcK IDC00000702
Chemspider ID102992
KEGG Compound IDC18166
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEnterodiol
METLIN IDNot Available
PubChem Compound115089
PDB IDNot Available
ChEBI ID544560
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000467
Good Scents IDNot Available
References
Synthesis ReferenceMahalanabis, K. K.; Mumtax, M.; Snieckuz, V. Dimetalated tertiary succinamides. Synthesis of several classes of lignans including the mammalian urinary lignans enterolactone and enterodiol. Tetrahedron Letters (1982), 23(39), 3975-8.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Wang LQ: Mammalian phytoestrogens: enterodiol and enterolactone. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Sep 25;777(1-2):289-309. [PubMed:12270221 ]
  2. Koistinen VM (2019). Effects of Food Processing and Gut Microbial Metabolism on Whole Grain Phytochemicals: A Metabolomics Approach. In Publications of the University of Eastern Finland. Dissertations in Health Sciences., no 510 (pp. 26-58). University of Eastern Finland. [ISBN:978-952-61-3088-0 ]