ID88
NameLutein
Synonymsall-trans-Lutein
StructureThumb
DescriptionCan coelute with zeaxanthin. This item is only used when "lutein only" is clearly stated, otherwise "Lutein/Zeaxanthin" should be used.
ClassificationCompounds > Diet > Lipids > Carotenoids > Xanthophylls
CAS number127-40-2
PubChem ID5281243
ChEBI ID28838
FooDB IDFDB015471
HMDB IDHMDB03233

Chemical data

MolDBi data

IUPAC Name(1R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1R)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-3,5,5-trimethylcyclohex-3-en-1-ol
Traditional IUPAC Name(1R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1R)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-3,5,5-trimethylcyclohex-3-en-1-ol
FormulaC40H56O2
InChIInChI=1S/C40H56O2/c1-29(17-13-19-31(3)21-23-37-33(5)25-35(41)27-39(37,7)8)15-11-12-16-30(2)18-14-20-32(4)22-24-38-34(6)26-36(42)28-40(38,9)10/h11-25,35-37,41-42H,26-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t35?,36-,37+/m1/s1
InChI KeyKBPHJBAIARWVSC-RTIVXWJOSA-N
Molecular weight568.8714
Exact mass568.428031036
SMILESO[C@@H]1CC(C)=C(\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\[C@H]2C(C)=CC(O)CC2(C)C)C(C)(C)C1

ClassyFire Taxonomy

Description belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTetraterpenoids
Direct ParentXanthophylls
Alternative Parents

Publications with Lutein

TitleFirst authorYear
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 overweight children's fruit and vegetable intake using plasma carotenoidsBurrows2009
Relative validity of fruit and vegetable intake estimated from an FFQ, using carotenoid and flavonoid biomarkers and the method of triadsCarlsen2011
Site-specific concentrations of carotenoids in adipose tissue: relations with dietary and serum carotenoid concentrations in healthy adultsChung2009
Relative validity of a food frequency questionnaire used in the Inter99 studyToft2008
Carotenoid and tocopherol estimates from the NCI diet history questionnaire are valid compared with multiple recalls and serum biomarkersDixon2006
Plasma carotenoids as biomarkers of intake of fruits and vegetables: individual-level correlations in the European Prospective Investigation into Cancer and Nutrition (EPIC)Al-Delaimy2005
Validity and reliability of a new food frequency questionnaire compared to 24 h recalls and biochemical measurements: pilot phase of Golestan cohort study of esophageal cancerMalekshah2006
Assessment of carotenoid status and the relation to glycaemic control in type I diabetics: a follow-up studyGranado-Lorencio2006
Evaluation of three dietary assessment methods and serum biomarkers as measures of fruit and vegetable intake, using the method of triadsAndersen2005
Plasma carotenoid levels in Dutch men and women, and the relation with vegetable and fruit consumptionJansen2004
Serum carotenoids as biomarkers of fruit and vegetable consumption in the New York Women's Health Studyvan Kappel2001
Questionnaire assessment of antioxidants and retinol intakes in Mexican womenRomieu1999
Associations of plasma carotenoid concentrations and dietary intake of specific carotenoids in samples of two prospective cohort studies using a new carotenoid databaseMichaud1998
New carotenoid values for foods improve relationship of food frequency questionnaire intake estimates to plasma valuesRitenbaugh1996
Correlations of vitamin A and E intakes with the plasma concentrations of carotenoids and tocopherols among American men and womenAscherio1992
Intraindividual variability in serum micronutrients: effects on reliability of estimated parametersShvetsov2009
Reliability of selected antioxidants and compounds involved in one-carbon metabolism in two Dutch cohortsLeenders2013
Plasma carotenoids, vitamin C, tocopherols, and retinol and the risk of breast cancer in the European Prospective Investigation into Cancer and Nutrition cohortBakker2016
Plasma carotenoids, vitamin C, retinol and tocopherols levels and pancreatic cancer risk within the European Prospective Investigation into Cancer and Nutrition: a nested case-control study: plasma micronutrients and pancreatic cancer riskJeurnink2015
Plasma and dietary carotenoids and vitamins A, C and E and risk of colon and rectal cancer in the European Prospective Investigation into Cancer and NutritionLeenders2014
Serum carotenoid, tocopherol and retinol concentrations and breast cancer risk in the E3N-EPIC studyMaillard2010
Plasma carotenoids, retinol, and tocopherols and the risk of prostate cancer in the European Prospective Investigation into Cancer and Nutrition studyKey2007
Prediagnostic level of serum retinol in relation to reduced risk of hepatocellular carcinomaYuan2006
Plasma and dietary carotenoid, retinol and tocopherol levels and the risk of gastric adenocarcinomas in the European prospective investigation into cancer and nutritionJenab2006
Antioxidants and basal cell carcinoma of the skin: a nested case-control studyMcNaughton2005
Lower prostate cancer risk in men with elevated plasma lycopene levels: results of a prospective analysisGann1999
Serum micronutrients and upper aerodigestive tract cancerNomura1997
Serum micronutrients and prostate cancer in Japanese Americans in HawaiiNomura1997
Prospective study of serum micronutrients and ovarian cancerHelzlsouer1996
Serum micronutrients and the subsequent risk of oral and pharyngeal cancerZheng1993
Serum micronutrients and the subsequent risk of cervical cancer in a population-based nested case-control studyBatieha1993
Serum carotenoids and alpha-tocopherol and risk of nonmelanoma skin cancerDorgan2004
Plasma carotenoids and retinol and overall and breast cancer risk: a nested case-control studyPouchieu2014
Plasma carotenoids and vitamin C concentrations and risk of urothelial cell carcinoma in the European Prospective Investigation into Cancer and NutritionRos2012
Prediagnostic circulating carotenoid levels and the risk of non-Hodgkin lymphoma: the Multiethnic CohortOllberding2012
Plasma carotenoids, retinol, and tocopherols and postmenopausal breast cancer risk in the Multiethnic Cohort Study: a nested case-control studyEpplein2009
Plasma carotenoids, tocopherols, retinol and breast cancer risk: results from the Shanghai Women Health Study (SWHS)Dorjgochoo2009
Serum lycopene, other carotenoids, and prostate cancer risk: a nested case-control study in the prostate, lung, colorectal, and ovarian cancer screening trialPeters2007
Serum carotenoids and breast cancerToniolo2001
Carotenoids, alpha-tocopherols, and retinol in plasma and breast cancer risk in northern SwedenHulten2001
Prospective study of carotenoids, tocopherols, and retinoid concentrations and the risk of breast cancerSato2002
Prospective study of antioxidant micronutrients in the blood and the risk of developing prostate cancerHuang2003
Circulating Antioxidant Levels and Risk of Prostate Cancer by TMPRSS2:ERGGraff2017

Biomarker data

Measurements of Lutein 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 Lutein 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 Lutein with cancer risk

Cancer associations

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

Exposure data

Measurements of Lutein 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 Lutein 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