alpha-Tocopherol (Compound)

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ID237
Namealpha-Tocopherol
SynonymsVitamin E; (+)-alpha-Tocopherol; D-alpha-Tocopherol
StructureThumb
DescriptionThe most important compound with vitamin E activity.
ClassificationCompounds > Diet > Vitamins > Vitamin E (Tocopherol)
CAS number59-02-9
PubChem ID14985
ChEBI ID18145
FooDB IDFDB000565
HMDB IDHMDB01893

Chemical data

MolDBi data

IUPAC Name(2R)-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol
Traditional IUPAC NameVitaE
FormulaC29H50O2
InChIInChI=1S/C29H50O2/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-18-29(8)19-17-26-25(7)27(30)23(5)24(6)28(26)31-29/h20-22,30H,9-19H2,1-8H3/t21-,22-,29-/m1/s1
InChI KeyGVJHHUAWPYXKBD-IEOSBIPESA-N
Molecular weight430.7061
Exact mass430.381080844
SMILESCC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C

ClassyFire Taxonomy

Description belongs to the class of organic compounds known as tocopherols. These are vitamin E derivatives containing a saturated trimethyltridecyl chain attached to the carbon C6 atom of a benzopyran ring system. The differ from tocotrienols that contain an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassQuinone and hydroquinone lipids
Direct ParentTocopherols
Alternative Parents

Publications with alpha-Tocopherol

TitleFirst authorYear
Effect of cooking loss in the assessment of vitamin intake for epidemiological data in JapanKobayashi2011
Reliability and validity of food frequency questionnaire and nutrient biomarkers in elders with and without mild cognitive impairmentBowman2011
Biochemical validation of food frequency questionnaire-estimated carotenoid, a-Tocopherol, and folate intakes among African Americans and non-Hispanic Whites in the Southern Community Cohort StudySignorello2010
Evaluation of an FFQ for assessment of antioxidant intake using plasma biomarkers in an ethnically diverse populationHodge2009
Validation of an antioxidant nutrient questionnaire in Whites and African AmericansSatia2009
Carotenoid, tocopherol, and fatty acid biomarkers and dietary intake estimated by using a brief self-administered diet history questionnaire for older Japanese children and adolescentsOkuda2009
Relationships between different types of fruit and vegetable consumption and serum concentrations of antioxidant vitaminsDauchet2008
Evaluating associations between Mediterranean diet adherence indexes and biomarkers of diet and diseaseBach-Faig2006
Carotenoid and tocopherol estimates from the NCI diet history questionnaire are valid compared with multiple recalls and serum biomarkersDixon2006
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
Validation of a food-frequency questionnaire assessment of carotenoid and vitamin E intake using weighed food records and plasma biomarkers: the method of triads modelMcNaughton2005
Assessment of a dietary questionnaire in cancer patients receiving cytotoxic chemotherapyMeyerhardt2005
Dietary evaluation and attenuation of relative risk: multiple comparisons between blood and urinary biomarkers, food frequency, and 24-hour recall questionnaires: the DEARR studyShai2005
Reasonable estimates of serum vitamin E, vitamin C, and beta-cryptoxanthin are obtained with a food frequency questionnaire in older black and white adultsTangney2004
Frequent intake of tropical fruits that are rich in beta-cryptoxanthin is associated with higher plasma beta-cryptoxanthin concentrations in Costa Rican adolescentsIrwig2002
Application of the method of triads to evaluate the performance of food frequency questionnaires and biomarkers as indicators of long-term dietary intakeKabagambe2001
Which plasma antioxidants are most related to fruit and vegetable consumption?Block2001
Comparing biological measurements of vitamin C, folate, alpha-tocopherol and carotene with 24-hour dietary recall information in nonhispanic blacks and whitesKnutsen2001
Dietary assessment in Whitehall II: comparison of 7 d diet diary and food-frequency questionnaire and validity against biomarkersBrunner2001
Population-based study of alpha- and gamma-tocopherol in plasma and adipose tissue as biomarkers of intake in Costa Rican adultsEl-Sohemy2001
Questionnaire assessment of antioxidants and retinol intakes in Mexican womenRomieu1999
Validation of a food frequency questionnaire for use in a Scottish population: correlation of antioxidant vitamin intakes with biochemical measuresBodner1998
Evaluation of a food frequency questionnaire with weighed records, fatty acids, and alpha-tocopherol in adipose tissue and serumAndersen1999
Indexes of food and nutrient intakes as predictors of serum concentrations of nutrients: the problem of inadequate discriminant validity. The Polyp Prevention Trial Study GroupMarshall1997
Relationships between dietary intakes and fasting plasma concentrations of fat-soluble vitamins in humansBooth1997
Relative validity and reproducibility of a diet history questionnaire in Spain. III. Biochemical markersGonzalez1997
The Dutch EPIC food frequency questionnaire. II. Relative validity and reproducibility for nutrientsOcke1997
Biochemical validation of a self-administered semi-quantitative food-frequency questionnairePorrini1995
Plasma carotenoids as biomarkers of vegetable and fruit intakeCampbell1994
The accuracy of parental reports of their children's intake of fruits and vegetables: validation of a food frequency questionnaire with serum levels of carotenoids and vitamins C, A, and EByers1993
Comparison of micronutrient intake measured by a dietary questionnaire and biochemical indicators of micronutrient statusJacques1993
Correlations of vitamin A and E intakes with the plasma concentrations of carotenoids and tocopherols among American men and womenAscherio1992
Antioxidant vitamin intakes assessed using a food-frequency questionnaire: correlation with biochemical status in smokers and non-smokersBolton-Smith1991
Validation of a dietary questionnaire with plasma carotenoid and alpha-tocopherol levelsWillett1983
Intraindividual variability in serum micronutrients: effects on reliability of estimated parametersShvetsov2009
Intraindividual variability of plasma antioxidants, markers of oxidative stress, C-reactive protein, cotinine, and other biomarkersBlock2006
Reproducibility of plasma, red blood cell, and urine biomarkers among premenopausal and postmenopausal women from the Nurses' Health StudiesKotsopoulos2010
Reliability of selected antioxidants and compounds involved in one-carbon metabolism in two Dutch cohortsLeenders2013
Metabolomics in nutritional epidemiology: identifying metabolites associated with diet and quantifying their potential to uncover diet-disease relations in populationsGuertin2014
Comparing metabolite profiles of habitual diet in serum and urinePlaydon2016
Plasma carotenoids, vitamin C, tocopherols, and retinol and the risk of breast cancer in the European Prospective Investigation into Cancer and Nutrition cohortBakker2016
Association of serum alpha-tocopherol, beta-carotene, and retinol with liver cancer incidence and chronic liver disease mortalityLai2014
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
Serum beta-carotene in relation to risk of prostate cancer: the Kuopio Ischaemic Heart Disease Risk Factor studyKarppi2012
Serum alpha-tocopherol and gamma-tocopherol concentrations and prostate cancer risk in the PLCO Screening Trial: a nested case-control studyWeinstein2012
Association between alpha-tocopherol, gamma-tocopherol, selenium, and subsequent prostate cancerHelzlsouer2000
Vitamin E and smoking and the risk of lung cancerKnekt1993
Prediagnostic serum tocopherol levels and the risk of non-hodgkin lymphoma: the multiethnic cohortMorimoto2013
Serum carotenoid, tocopherol and retinol concentrations and breast cancer risk in the E3N-EPIC studyMaillard2010
Association of selenium, tocopherols, carotenoids, retinol, and 15-isoprostane F(2t) in serum or urine with prostate cancer risk: the multiethnic cohortGill2009
Plasma carotenoids, retinol, and tocopherols and postmenopausal breast cancer risk in the Multiethnic Cohort Study: a nested case-control studyEpplein2009
Association of plasma micronutrient levels and urinary isoprostane with risk of lung cancer: the multiethnic cohort studyEpplein2009
Plasma carotenoids, tocopherols, retinol and breast cancer risk: results from the Shanghai Women Health Study (SWHS)Dorjgochoo2009
Plasma levels of carotenoids, retinol and tocopherol and the risk of gastric cancer in Japan: a nested case-control studyPersson2008
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
Serum alpha-tocopherol and gamma-tocopherol in relation to prostate cancer risk in a prospective studyWeinstein2005
Serum carotenoids, retinol, and tocopherols, and colorectal cancer risk in a Japanese cohort: effect modification by sex for carotenoidsWakai2005
Plasma carotenoids, retinol, and tocopherols and risk of breast cancerTamimi2005
Antioxidants and basal cell carcinoma of the skin: a nested case-control studyMcNaughton2005
Prediagnostic levels of serum micronutrients in relation to risk of gastric cancer in Shanghai, ChinaYuan2004
Lower prostate cancer risk in men with elevated plasma lycopene levels: results of a prospective analysisGann1999
Is low selenium status a risk factor for lung cancer?Knekt1998
Relationships of serum carotenoids, retinol, alpha-tocopherol, and selenium with breast cancer risk: results from a prospective study in Columbia, Missouri (United States)Dorgan1998
Serum micronutrients and upper aerodigestive tract cancerNomura1997
Serum micronutrients and prostate cancer in Japanese Americans in HawaiiNomura1997
Risk of squamous cell carcinoma of the skin in relation to plasma selenium, alpha-tocopherol, beta-carotene, and retinol: a nested case-control studyKaragas1997
Prospective study of serum micronutrients and ovarian cancerHelzlsouer1996
Serological precursors of cancer: malignant melanoma, basal and squamous cell skin cancer, and prediagnostic levels of retinol, beta- carotene, lycopene, alpha-tocopherol, and seleniumBreslow1995
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
Prospective study of serum vitamin E levels and esophageal and gastric cancersTaylor2003
Repeated measurements of serum carotenoid, retinol and tocopherol levels in relation to colorectal cancer risk in the Women's Health InitiativeKabat2012
Serum antioxidants and skin cancer risk: an 8-year community-based follow-up studyvan der Pols2009
Vitamin E intake, alpha-tocopherol status, and pancreatic cancer in a cohort of male smokersStolzenberg-Solomon2009
Longitudinal study of serum carotenoid, retinol, and tocopherol concentrations in relation to breast cancer risk among postmenopausal womenKabat2009
Serum and dietary vitamin E in relation to prostate cancer riskWeinstein2007
Fruits, vegetables, and antioxidants and risk of gastric cancer among male smokersNouraie2005
Serum carotenoids and alpha-tocopherol and risk of nonmelanoma skin cancerDorgan2004
Dietary and serum alpha-tocopherol, beta-carotene and retinol, and risk for colorectal cancer in male smokersMalila2002
Serum alpha-tocopherol and subsequent risk of lung cancer among male smokersWoodson1999
The association between baseline vitamin E, selenium, and prostate cancer in the alpha-tocopherol, beta-carotene cancer prevention studyHartman1998
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
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
The risk of developing lung cancer associated with antioxidants in the blood: ascorbic acid, carotenoids, alpha-tocopherol, selenium, and total peroxyl radical absorbing capacityComstock1997
Prospective study of antioxidant micronutrients in the blood and the risk of developing prostate cancerHuang2003
Gastric dysplasia and gastric cancer: Helicobacter pylori, serum vitamin C, and other risk factorsYou2000
Serum lycopene and the risk of cancer: the Kuopio Ischaemic Heart Disease Risk Factor (KIHD) studyKarppi2009
Serum vitamin E, serum selenium and the risk of gastrointestinal cancerKnekt1988
Plasma retinol, beta-carotene and vitamin E levels in relation to the future risk of breast cancerWald1984
Prediagnostic levels of serum beta-cryptoxanthin and retinol predict smoking-related lung cancer risk in Shanghai, ChinaYuan2001
Metabolomic screening of pre-diagnostic serum samples identifies association between alpha- and gamma-tocopherols and glioblastoma riskBjorkblom2016
Serum carotenoids and other antioxidative substances associated with urothelial cancer risk in a nested case-control study in Japanese menOzasa2005
Serum vitamins and the subsequent risk of bladder cancerNomura2003
Serum alpha-tocopherol concentration in relation to subsequent colorectal cancer: pooled data from five cohortsLongnecker1992
Gastric cancer among the Japanese in HawaiiNomura1995
Circulating Antioxidant Levels and Risk of Prostate Cancer by TMPRSS2:ERGGraff2017
Prediagnostic serum levels of carotenoids and vitamin E as related to subsequent cancer in Washington County, MarylandComstock1991
A prospective study of serum metabolites and glioma riskHuang2017

Biomarker data

Measurements of alpha-Tocopherol 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 alpha-Tocopherol 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 alpha-Tocopherol with cancer risk

Cancer associations

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

Exposure data

Measurements of alpha-Tocopherol 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 alpha-Tocopherol 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