gamma-Tocopherol (Compound)

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ID238
Namegamma-Tocopherol
Synonyms(+)-gamma-Tocopherol; D-gamma-Tocopherol
StructureThumb
Description
ClassificationCompounds > Diet > Vitamins > Vitamin E (Tocopherol)
CAS number54-28-4
PubChem ID92729
ChEBI ID18185
FooDB IDFDB002431
HMDB IDHMDB01492

Chemical data

MolDBi data

IUPAC Name(2R)-2,7,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol
Traditional IUPAC Namegamma-tocopherol
FormulaC28H48O2
InChIInChI=1S/C28H48O2/c1-20(2)11-8-12-21(3)13-9-14-22(4)15-10-17-28(7)18-16-25-19-26(29)23(5)24(6)27(25)30-28/h19-22,29H,8-18H2,1-7H3/t21-,22-,28-/m1/s1
InChI KeyQUEDXNHFTDJVIY-DQCZWYHMSA-N
Molecular weight416.6795
Exact mass416.36543078
SMILES[H][C@@](C)(CCCC(C)C)CCC[C@@]([H])(C)CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2

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 gamma-Tocopherol

TitleFirst authorYear
Reliability and validity of food frequency questionnaire and nutrient biomarkers in elders with and without mild cognitive impairmentBowman2011
Evaluation of an FFQ for assessment of antioxidant intake using plasma biomarkers in an ethnically diverse populationHodge2009
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
Carotenoid and tocopherol estimates from the NCI diet history questionnaire are valid compared with multiple recalls and serum biomarkersDixon2006
Assessment of a dietary questionnaire in cancer patients receiving cytotoxic chemotherapyMeyerhardt2005
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
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
Correlations of vitamin A and E intakes with the plasma concentrations of carotenoids and tocopherols among American men and womenAscherio1992
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
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
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
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 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
Plasma carotenoids, retinol, and tocopherols and risk of breast cancerTamimi2005
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
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
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
Longitudinal study of serum carotenoid, retinol, and tocopherol concentrations in relation to breast cancer risk among postmenopausal womenKabat2009
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
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 vitamins and the subsequent risk of bladder cancerNomura2003
Circulating Antioxidant Levels and Risk of Prostate Cancer by TMPRSS2:ERGGraff2017

Biomarker data

Measurements of gamma-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 gamma-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 gamma-Tocopherol with cancer risk

Cancer associations

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

Exposure data

Measurements of gamma-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 gamma-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