beta-Cryptoxanthin (Compound)

Go to Compound classification
ID84
Namebeta-Cryptoxanthin
SynonymsCryptoxanthin; all-trans-beta-Cryptoxanthin
StructureThumb
Description
ClassificationCompounds > Diet > Lipids > Carotenoids > Xanthophylls
CAS number472-70-8
PubChem ID5281235
ChEBI ID10362
FooDB IDFDB012019
HMDB IDHMDB33844

Chemical data

MolDBi data

IUPAC Name(1R)-3,5,5-trimethyl-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohex-1-en-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-3-en-1-ol
Traditional IUPAC Namecryptoxanthin
FormulaC40H56O
InChIInChI=1S/C40H56O/c1-30(18-13-20-32(3)23-25-37-34(5)22-15-27-39(37,7)8)16-11-12-17-31(2)19-14-21-33(4)24-26-38-35(6)28-36(41)29-40(38,9)10/h11-14,16-21,23-26,36,41H,15,22,27-29H2,1-10H3/b12-11+,18-13+,19-14+,25-23+,26-24+,30-16+,31-17+,32-20+,33-21+/t36-/m1/s1
InChI KeyDMASLKHVQRHNES-FKKUPVFPSA-N
Molecular weight552.887
Exact mass552.433116423
SMILESC\C(\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)C[C@@H](O)CC1(C)C

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 beta-Cryptoxanthin

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
Racial differences in correlations between reported dietary intakes of carotenoids and their concentration biomarkersArab2011
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
Validation of overweight children's fruit and vegetable intake using plasma carotenoidsBurrows2009
Carotenoid intakes, assessed by food-frequency questionnaires (FFQs), are associated with serum carotenoid concentrations in the Jackson Heart Study: validation of the Jackson Heart Study Delta NIRI Adult FFQsTalegawkar2008
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
Plasma concentrations of carotenoids and vitamin C are better correlated with dietary intake in normal weight than overweight and obese elderly subjectsVioque2007
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
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
Plasma carotenoid levels in Dutch men and women, and the relation with vegetable and fruit consumptionJansen2004
Assessment of a dietary questionnaire in cancer patients receiving cytotoxic chemotherapyMeyerhardt2005
Reproducibility, validity, and responsiveness to change of a short questionnaire for measuring fruit and vegetable intakeBogers2004
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
Individual carotenoid concentrations in adipose tissue and plasma as biomarkers of dietary intakeEl-Sohemy2002
Application of the method of triads to evaluate the performance of food frequency questionnaires and biomarkers as indicators of long-term dietary intakeKabagambe2001
Serum carotenoids as biomarkers of fruit and vegetable consumption in the New York Women's Health Studyvan Kappel2001
Which plasma antioxidants are most related to fruit and vegetable consumption?Block2001
Validation of three food frequency questionnaires and 24-hour recalls with serum carotenoid levels in a sample of African-American adultsResnicow2000
Plasma carotenoids are biomarkers of long-term high vegetable intake in women with breast cancerMcEligot1999
Carotenoid intakes, assessed by dietary questionnaire, are associated with plasma carotenoid concentrations in an elderly populationTucker1999
Associations of plasma carotenoid concentrations and dietary intake of specific carotenoids in samples of two prospective cohort studies using a new carotenoid databaseMichaud1998
Relative validity and reproducibility of a diet history questionnaire in Spain. III. Biochemical markersGonzalez1997
Plasma carotenoids as biomarkers of vegetable and fruit intakeCampbell1994
Relationship between dietary intake and plasma concentrations of carotenoids in premenopausal women: application of the USDA-NCI carotenoid food-composition databaseYong1994
The correlation between two dietary assessments of carotenoid intake and plasma carotenoid concentrations: application of a carotenoid food-composition databaseForman1993
Validation of a food frequency questionnaire to assess the consumption of carotenoids, fruits and vegetables among adolescents: the method of triadsSlater2010
Validity and systematic error in measuring carotenoid consumption with dietary self-report instrumentsNatarajan2006
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
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
Reliability of plasma carotenoid biomarkers and its relation to study powerAl-Delaimy2008
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
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
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
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
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
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
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
Longitudinal study of serum carotenoid, retinol, and tocopherol concentrations in relation to breast cancer risk among postmenopausal womenKabat2009
Serum carotenoids and alpha-tocopherol and risk of nonmelanoma skin cancerDorgan2004
Prospective study of serum retinol, beta-carotene, beta-cryptoxanthin, and lutein/zeaxanthin and esophageal and gastric cancers in ChinaAbnet2003
Plasma carotenoids and breast cancer risk in the Cancer Prevention Study II Nutrition CohortWang2015
Premenopausal plasma carotenoids, fluorescent oxidation products, and subsequent breast cancer risk in the nurses' health studiesSisti2015
Serum Retinol and Carotenoid Concentrations and Prostate Cancer Risk: Results from the Prostate Cancer Prevention TrialNash2015
Plasma carotenoids and risk of breast cancer over 20 y of follow-upEliassen2015
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
Circulating carotenoids, mammographic density, and subsequent risk of breast cancerTamimi2009
Beta-cryptoxanthin and lung cancer in Shanghai, China--an examination of potential confounding with cigarette smoking using urinary cotinine as a biomarker for true tobacco exposureStram2007
Serum lycopene, other carotenoids, and prostate cancer risk: a nested case-control study in the prostate, lung, colorectal, and ovarian cancer screening trialPeters2007
Dietary and plasma lycopene and the risk of breast cancerSesso2005
Plasma and dietary carotenoids, and the risk of prostate cancer: a nested case-control studyWu2004
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
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
Circulating carotenoids and risk of breast cancer: pooled analysis of eight prospective studiesEliassen2012
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
Circulating Antioxidant Levels and Risk of Prostate Cancer by TMPRSS2:ERGGraff2017

Biomarker data

Measurements of beta-Cryptoxanthin 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 beta-Cryptoxanthin 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 beta-Cryptoxanthin with cancer risk

Cancer associations

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

Exposure data

Measurements of beta-Cryptoxanthin 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 beta-Cryptoxanthin 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