ID135
NameRetinol
SynonymsVitamin A; Retinol; Preformed vitamin A
StructureThumb
Description
ClassificationCompounds > Diet > Vitamins > Vitamin A (Retinol)
CAS number68-26-8
PubChem ID445354
ChEBI ID17336
FooDB IDFDB013828
HMDB IDHMDB00305

Chemical data

MolDBi data

IUPAC Name(2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol
Traditional IUPAC Name13-cis retinol
FormulaC20H30O
InChIInChI=1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3/b9-6+,12-11+,16-8+,17-13+
InChI KeyFPIPGXGPPPQFEQ-OVSJKPMPSA-N
Molecular weight286.4516
Exact mass286.229665582
SMILESC\C(=C/CO)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C

ClassyFire Taxonomy

Description belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassRetinoids
Direct ParentRetinoids
Alternative Parents

Publications with Retinol

TitleFirst authorYear
Validity and reproducibility of a food frequency questionnaire for assessment of fruit and vegetable intake in Iranian adultsMohammadifard2011
Effect of cooking loss in the assessment of vitamin intake for epidemiological data in JapanKobayashi2011
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
Evaluating associations between Mediterranean diet adherence indexes and biomarkers of diet and diseaseBach-Faig2006
Validity of protein, retinol, folic acid and n–3 fatty acid intakes estimated from the food-frequency questionnaire used in the Danish National Birth CohortMikkelsen2006
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
Reasonable estimates of serum vitamin E, vitamin C, and beta-cryptoxanthin are obtained with a food frequency questionnaire in older black and white adultsTangney2004
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
Relationships between dietary intakes and fasting plasma concentrations of fat-soluble vitamins in humansBooth1997
The Dutch EPIC food frequency questionnaire. II. Relative validity and reproducibility for nutrientsOcke1997
Reproducibility and relative validity of an extensive semi-quantitative food frequency questionnaire using dietary records and biochemical markers among Greek schoolteachersKatsouyanni1997
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
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
Vitamin E and smoking and the risk of lung cancerKnekt1993
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 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
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
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
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
Fruits, vegetables, and antioxidants and risk of gastric cancer among male smokersNouraie2005
Dietary and serum alpha-tocopherol, beta-carotene and retinol, and risk for colorectal cancer in male smokersMalila2002
Prospective study of serum retinol, beta-carotene, beta-cryptoxanthin, and lutein/zeaxanthin and esophageal and gastric cancers in ChinaAbnet2003
Serum retinol and risk of prostate cancerMondul2011
Dietary carotenoids, serum beta-carotene, and retinol and risk of lung cancer in the alpha-tocopherol, beta-carotene cohort studyHolick2002
Serum Retinol and Carotenoid Concentrations and Prostate Cancer Risk: Results from the Prostate Cancer Prevention TrialNash2015
Plasma carotenoids and retinol and overall and breast cancer risk: a nested case-control studyPouchieu2014
Prediagnostic circulating carotenoid levels and the risk of non-Hodgkin lymphoma: the Multiethnic CohortOllberding2012
Serum retinol and prostate cancer risk: a nested case-control study in the prostate, lung, colorectal, and ovarian cancer screening trialSchenk2009
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 carotenoids and breast cancerToniolo2001
Vegetable consumption, serum retinol level, and risk of hepatocellular carcinomaYu1995
Vitamin D, season, and risk of prostate cancer: a nested case-control study within Norwegian health studiesMeyer2013
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
Gastric dysplasia and gastric cancer: Helicobacter pylori, serum vitamin C, and other risk factorsYou2000
Serum retinol and retinol-binding protein levels do not predict subsequent lung cancerFriedman1986
Serum lycopene and the risk of cancer: the Kuopio Ischaemic Heart Disease Risk Factor (KIHD) studyKarppi2009
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
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
Gastric cancer among the Japanese in HawaiiNomura1995
Circulating Antioxidant Levels and Risk of Prostate Cancer by TMPRSS2:ERGGraff2017

Biomarker data

Measurements of Retinol 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 Retinol 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 Retinol with cancer risk

Cancer associations

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

Exposure data

Measurements of Retinol 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 Retinol 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