Enterolactone (Compound)

Go to Compound classification
ID31
NameEnterolactone
Synonyms(-)-Enterolactone
StructureThumb
DescriptionMostly measured after enzymatic hydrolysis.
ClassificationCompounds > Diet > Polyphenols > Phytoestrogens > Lignans
CAS number78473-71-9
PubChem ID10685477
ChEBI ID81555
FooDB IDFDB002488
HMDB IDHMDB06101

Chemical data

MolDBi data

IUPAC Name3,4-bis[(3-hydroxyphenyl)methyl]oxolan-2-one
Traditional IUPAC NameHPMF
FormulaC18H18O4
InChIInChI=1S/C18H18O4/c19-15-5-1-3-12(8-15)7-14-11-22-18(21)17(14)10-13-4-2-6-16(20)9-13/h1-6,8-9,14,17,19-20H,7,10-11H2/t14-,17+/m0/s1
InChI KeyHVDGDHBAMCBBLR-WMLDXEAASA-N
Molecular weight298.3331
Exact mass298.120509064
SMILESOC1=CC=CC(C[C@H]2COC(=O)[C@@H]2CC2=CC(O)=CC=C2)=C1

ClassyFire Taxonomy

Description belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety.
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassFuranoid lignans
Sub ClassTetrahydrofuran lignans
Direct ParentDibenzylbutyrolactone lignans
Alternative Parents

Publications with Enterolactone

TitleFirst authorYear
Relation between plasma enterodiol and enterolactone and dietary intake of lignans in a Dutch Endoscopy-Based PopulationMilder2007
Urine flavonoids and plasma carotenoids in the validation of fruit, vegetable and tea intake during pregnancy in the Norwegian Mother and Child Cohort Study (MoBa)Brantsaeter2007
Validation of a phytoestrogen food frequency questionnaire with urinary concentrations of isoflavones and lignan metabolites in premenopausal womenFrench2007
Correlations of urinary phytoestrogen excretion with lifestyle factors and dietary intakes among middle-aged and elderly Chinese womenWu2012
Urinary flavonoids and phenolic acids as biomarkers of intake for polyphenol-rich foodsMennen2006
A semiquantitative food frequency questionnaire is a valid indicator of the usual intake of phytoestrogens by south Asian women in the UK relative to multiple 24-h dietary recalls and multiple plasma samplesBhakta2005
Phytoestrogen concentrations in serum and spot urine as biomarkers for dietary phytoestrogen intake and their relation to breast cancer risk in European prospective investigation of cancer and nutrition-norfolkGrace2004
Intake of lignans is associated with serum enterolactone concentration in Finnish men and womenKilkkinen2003
Dietary determinants of plasma enterolactoneHorner2002
Urinary isoflavonoid and lignan excretion on a Western diet: relation to soy, vegetable, and fruit intakeLampe1999
Reliability and validity of an assessment of usual phytoestrogen consumption (United States)Horn-Ross2006
Reproducibility of plasma, red blood cell, and urine biomarkers among premenopausal and postmenopausal women from the Nurses' Health StudiesKotsopoulos2010
Short-term variations in enterolactone in serum, 24-hour urine, and spot urine and relationship with enterolactone concentrationsStumpf2003
Temporal variability in urinary concentrations of phthalate metabolites, phytoestrogens and phenols among minority children in the United StatesTeitelbaum2008
Variation in fasting and non-fasting serum enterolactone concentrations in women of the Malmö Diet and Cancer cohortSonestedt2008
Reliability of serum measurements of lignans and isoflavonoid phytoestrogens over a two-year periodZeleniuch-Jacquotte1998
Biomarkers of dietary intake of flavonoids and phenolic acids for studying diet–cancer relationship in humansLinseisen2008
Pilot study of urinary biomarkers of phytoestrogens, phthalates, and phenols in girlsWolff2007
Plasma enterolactone and risk of prostate cancer in middle-aged Swedish menWallstrom2018
Plasma phytoestrogens concentration and risk of colorectal cancer in two different Asian populationsKo2018
Longitudinal biobanks-based study on the joint effects of infections, nutrition and hormones on risk of prostate cancerLumme2016
Plasma enterolactone and breast cancer risk in the Nurses' Health Study IIXie2013
Isoflavones from phytoestrogens and gastric cancer risk: a nested case-control study within the Korean Multicenter Cancer CohortKo2010
Plasma phyto-oestrogens and prostate cancer in the European Prospective Investigation into Cancer and NutritionTravis2009
The protective association of high plasma enterolactone with breast cancer is reasonably robust in women with polymorphisms in the estrogen receptor alpha and beta genesSonestedt2009
Urinary phytoestrogen excretion and prostate cancer risk: a nested case-control study in the Multiethnic CohortPark2009
Urinary phytoestrogen excretion and postmenopausal breast cancer risk: the multiethnic cohort studyGoodman2009
Breast cancer risk in relation to urinary and serum biomarkers of phytoestrogen exposure in the European Prospective into Cancer-Norfolk cohort studyWard2008
Lack of prospective associations between plasma and urinary phytoestrogens and risk of prostate or colorectal cancer in the European Prospective into Cancer-Norfolk studyWard2008
Enterolactone is differently associated with estrogen receptor beta-negative and -positive breast cancer in a Swedish nested case-control studySonestedt2008
Plasma enterolignan concentrations and colorectal cancer risk in a nested case-control studyKuijsten2008
Plasma phytoestrogens and subsequent breast cancer riskVerheus2007
Circulating enterolactone and risk of endometrial cancerZeleniuch-Jacquotte2006
Phytoestrogen exposure, polymorphisms in COMT, CYP19, ESR1, and SHBG genes, and their associations with prostate cancer riskLow2006
Circulating enterolactone and risk of breast cancer: a prospective study in New YorkZeleniuch-Jacquotte2004
Prospective study of plasma enterolactone and prostate cancer risk (Sweden)Stattin2004
Plasma enterolactone and breast cancer incidence by estrogen receptor statusOlsen2004
Serum enterolactone concentration is not associated with breast cancer risk in a nested case-control studyKilkkinen2004
Serum enterolactone concentration is not associated with prostate cancer risk in a nested case-control studyKilkkinen2003
Circulating enterolactone and prostate cancer risk: a Nordic nested case-control studyStattin2002
An incident case-referent study on plasma enterolactone and breast cancer riskHulten2002
Serum enterolactone and risk of breast cancer: a case-control study in eastern FinlandPietinen2001
Urinary phytoestrogens and postmenopausal breast cancer riskden Tonkelaar2001
Serum enterolactone levels and the risk of breast cancer in women with palpable cystsBoccardo2004
Plasma enterolactone and incidence of endometrial cancer in a case-cohort study of Danish womenAarestrup2013
Plasma enterolactone and risk of colon and rectal cancer in a case-cohort study of Danish men and womenJohnsen2010

Biomarker data

Measurements of Enterolactone in biospecimens

Concentration values

IDParent IDDepthSubject groupPopulationCountryCohortBiomarker Time definitionBiospecimenAnalytical methodBiomarkerBiomarker detailMeasurement sizeDetected (nb)Detected (%)Detected only?Arithmethic meanArithmethic SDGeometric meanGeometric SDMinMin (detected)Percentile_05Percentile_10Percentile_25MedianPercentile_75Percentile_90Percentile_95MaxInterquartile rangeMean 95% CI lowerMean 95% CI upperGMean 95% CI lowerGMean 95% CI upperUnitConverted arithmetic meanConverted geometric meanConverted medianConverted unitAdjustment typeAdjusted onRegressed onExpressed asPublication

Reproducibility values

IDExcretion IDSubject groupPopulationCountryCohortBiomarker Time definitionBiospecimenAnalytical methodBiomarkerBiomarker detailArithmetic meanGeometric meanMedianUnitAdjusted onReproducibility sizeICCICC 95% CI lowerICC 95% CI upperCV% WSCV% BSVAR WSVAR BSPublication

Associations of Enterolactone with exposures

Correlation values

IDIntake IDExcretion IDSubject groupPopulationCountryCohortIntake Time definitionIntake Assessment methodIntakeIntake detailSupplement intakes included?Intake Arithmetic meanIntake Geometric meanIntake MedianIntake UnitIntake Adjusted onBiomarker Time definitionBiospecimenAnalytical methodBiomarkerBiomarker detailBiomarker Arithmetic meanBiomarker Geometric meanBiomarker MedianBiomarker UnitBiomarker Adjusted onCorrelation sizeCorrelation typeCorrelation valueCorrelation 95% CI lowerCorrelation 95% CI upperCorrelation p-valueSignificant?Measurement adjustmentDeattenuated?CovariatesPublication

Metabolomic associations

IDIntake IDExcretion IDSubject groupPopulationCountryCohortNo. of subjectsIntake Assessment methodIntakeIntervention doseBiospecimenAnalytical methodBiomarkerStructural identificationFeature selectionArea under curveSensitivitySpecificityPLS-DA VIPBeta coefficientBeta coefficient p-valueANOVA p-valuePublication

Associations of Enterolactone with cancer risk

Cancer associations

IDExcretion IDSubject groupPopulationCountryCohortNo. of subjectsNo. of casesNo. of controlsBiospecimenAnalytical methodBiomarkerBiomarker detailCancerStudy designPublication

Exposure data

Measurements of Enterolactone exposures in populations

Intake values

IDParent IDDepthSubject groupPopulationCountryCohortIntake Time definitionIntake assessment toolIntake food coverageIntake time coverageIntake Assessment methodIntakeIntake detailFood descriptionSupplement intakes included?Measurement sizeDetected (nb)Detected (%)Detected only?Arithmethic meanArithmethic SDGeometric meanGeometric SDMinMin (detected)Percentile_05Percentile_10Percentile_25MedianPercentile_75Percentile_90Percentile_95MaxInterquartile rangeMean 95% CI lowerMean 95% CI upperGMean 95% CI lowerGMean 95% CI upperUnitConverted arithmetic meanConverted geometric meanConverted medianConverted unitAdjustment typeAdjusted onRegressed onExpressed asPublication

Associations of Enterolactone exposures with biomarkers

Correlation values

IDIntake IDExcretion IDSubject groupPopulationCountryCohortIntake Time definitionIntake Assessment methodIntakeIntake detailSupplement intakes included?Intake Arithmetic meanIntake Geometric meanIntake MedianIntake UnitIntake Adjusted onBiomarker Time definitionBiospecimenAnalytical methodBiomarkerBiomarker detailBiomarker Arithmetic meanBiomarker Geometric meanBiomarker MedianBiomarker UnitBiomarker Adjusted onCorrelation sizeCorrelation typeCorrelation valueCorrelation 95% CI lowerCorrelation 95% CI upperCorrelation p-valueSignificant?Measurement adjustmentDeattenuated?CovariatesPublication