Arachidonic acid (AA; cis-20:4n-6) (Compound)

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ID224
NameArachidonic acid (AA; cis-20:4n-6)
Synonymsall-cis-5,8,11,14-Eicosatetraenoic acid; Arachidonate
StructureThumb
Description
ClassificationCompounds > Diet > Lipids > Fatty acids > PUFA
CAS number506-32-1
PubChem ID444899
ChEBI ID15843
FooDB IDFDB011872
HMDB IDHMDB01043

Chemical data

MolDBi data

IUPAC Name(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid
Traditional IUPAC Namearachidonic acid
FormulaC20H32O2
InChIInChI=1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-15-
InChI KeyYZXBAPSDXZZRGB-DOFZRALJSA-N
Molecular weight304.4669
Exact mass304.240230268
SMILESCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O

ClassyFire Taxonomy

Description belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents

Publications with Arachidonic acid (AA; cis-20:4n-6)

TitleFirst authorYear
Is marine mammal fat or fish intake most strongly associated with omega-3 blood levels among the Nunavik Inuit?Lucas2010
Reliability and validity of food frequency questionnaire and nutrient biomarkers in elders with and without mild cognitive impairmentBowman2011
Linoleic acid is associated with lower long-chain n–6 and n–3 fatty acids in red blood cell lipids of Canadian pregnant womenFriesen2010
Comparison between plasma and erythrocyte fatty acid content as biomarkers of fatty acid intake in US womenSun2007
Plasma n-6 and n-3 polyunsaturated fatty acids as biomarkers of their dietary intakes: a cross-sectional study within a cohort of middle-aged French men and womenAstorg2008
Validation of a FFQ to estimate the intake of PUFA using plasma phospholipid fatty acids and weighed foods recordsMcNaughton2007
Plasma phospholipid fatty acid composition as a biomarker of habitual dietary fat intake in an ethnically diverse cohortHodge2007
Fatty acid composition of habitual omnivore and vegetarian dietsMann2006
Home use of margarine is an important determinant of plasma trans fatty acid status: a biomarker studySkeaff2006
Fasting whole blood as a biomarker of essential fatty acid intake in epidemiologic studies: comparison with adipose tissue and plasmaBaylin2005
Plasma concentrations of (n-3) highly unsaturated fatty acids are good biomarkers of relative dietary fatty acid intakes: a cross-sectional studyKuriki2003
Adipose tissue biomarkers of fatty acid intakeBaylin2002
Erythrocyte cell membrane phospholipid levels compared against reported dietary intakes of polyunsaturated fatty acids in pregnant Mexican womenParra2002
Dietary conjugated linoleic acid (CLA) intake assessment and possible biomarkers of CLA intake in young womenFremann2002
Very-long-chain omega-3 fatty acids as markers for habitual fish intake in a population consuming mainly lean fish: the EPIC cohort of GipuzkoaAmiano2001
Site-specific differences in the fatty acid composition of abdominal adipose tissue in an obese population from a Mediterranean area: relation with dietary fatty acids, plasma lipid profile, serum insulin, and central obesityGaraulet2001
Single measurement of serum phospholipid fatty acid as a biomarker of specific fatty acid intake in middle-aged Japanese menKobayashi2001
Pentadecanoic acid in serum as a marker for intake of milk fat: relations between intake of milk fat and metabolic risk factorsSmedman1999
The relation between dietary intake and adipose tissue composition of selected fatty acids in US womenGarland1998
Serum phospholipid fatty acid composition and habitual intake of marine foods registered by a semi-quantitative food frequency questionnaireHjartaker1997
Omega-3 fatty acids in adipose tissue of obese patients with non-insulin-dependent diabetes mellitus reflect long-term dietary intake of eicosapentaenoic and docosahexaenoic acidPopp-Snijders1995
Adipose tissue fatty acids as biomarkers of dietary exposure in Danish men and womenTjonneland1993
Human plasma fatty acid variations and how they are related to dietary intakeLopes1991
Fatty acid composition of subcutaneous adipose tissue and diet in postmenopausal US womenLondon1991
Evaluation of a food frequency questionnaire with weighed records, fatty acids, and alpha-tocopherol in adipose tissue and serumAndersen1999
Reliability of fatty acid composition in human serum phospholipidsZeleniuch-Jacquotte2000
Characterizing Blood Metabolomics Profiles Associated with Self-Reported Food Intakes in Female TwinsPallister2016
Plasma phospholipid fatty acids and prostate cancer risk in the SELECT trialBrasky2013
A prospective evaluation of plasma phospholipid fatty acids and breast cancer risk in the EPIC studyChajes2017
Effect Modification by Time Since Blood Draw on the Association Between Circulating Fatty Acids and Prostate Cancer RiskYang2016
Prospective associations between plasma saturated, monounsaturated and polyunsaturated fatty acids and overall and breast cancer risk - modulation by antioxidants: a nested case-control studyPouchieu2014
Association between serum trans-monounsaturated fatty acids and breast cancer risk in the E3N-EPIC StudyChajes2008
Serum fatty acids and breast cancer incidenceRissanen2003
Serum fatty acids and risk of breast cancer in a nested case-control study of the New York University Women's Health StudySaadatian-Elahi2002
Erythrocyte membrane fatty acids and subsequent breast cancer: a prospective Italian studyPala2001
Fatty-acid composition in serum phospholipids and risk of breast cancer: an incident case-control study in SwedenChajes1999
Plasma phospholipids fatty acids, dietary fatty acids, and breast cancer riskBassett2016
Plasma phospholipid fatty acids, dietary fatty acids and prostate cancer riskBassett2013
Dietary and biomarker estimates of fatty acids and risk of colorectal cancerHodge2015
Plasma fatty acids and risk of colon and rectal cancers in the Singapore Chinese Health StudyButler2017
Blood levels of long-chain polyunsaturated fatty acids, aspirin, and the risk of colorectal cancerHall2007
Serum levels of polyunsaturated fatty acids and risk of colorectal cancer: a prospective studyKojima2005

Biomarker data

Measurements of Arachidonic acid (AA; cis-20:4n-6) 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 Arachidonic acid (AA; cis-20:4n-6) 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 Arachidonic acid (AA; cis-20:4n-6) with cancer risk

Cancer associations

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

Exposure data

Measurements of Arachidonic acid (AA; cis-20:4n-6) 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 Arachidonic acid (AA; cis-20:4n-6) 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