gamma-Linolenic acid (GLA; cis-18:3n-6) (Compound)

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ID433
Namegamma-Linolenic acid (GLA; cis-18:3n-6)
Synonymsall-cis-6,9,12-Octadecatrienoic acid
StructureThumb
Description
ClassificationCompounds > Diet > Lipids > Fatty acids > PUFA
CAS number506-26-3
PubChem ID5280933
ChEBI ID28661
FooDB IDFDB002943
HMDB IDHMDB03073

Chemical data

MolDBi data

IUPAC Name(6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid
Traditional IUPAC Namegamma linolenic acid
FormulaC18H30O2
InChIInChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10,12-13H,2-5,8,11,14-17H2,1H3,(H,19,20)/b7-6-,10-9-,13-12-
InChI KeyVZCCETWTMQHEPK-QNEBEIHSSA-N
Molecular weight278.4296
Exact mass278.224580204
SMILESCCCCC\C=C/C\C=C/C\C=C/CCCCC(O)=O

ClassyFire Taxonomy

Description belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassLineolic acids and derivatives
Direct ParentLineolic acids and derivatives
Alternative ParentsNot Available

Publications with gamma-Linolenic acid (GLA; cis-18:3n-6)

TitleFirst authorYear
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
Fasting whole blood as a biomarker of essential fatty acid intake in epidemiologic studies: comparison with adipose tissue and plasmaBaylin2005
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
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
Pentadecanoic acid in serum as a marker for intake of milk fat: relations between intake of milk fat and metabolic risk factorsSmedman1999
Adipose tissue fatty acids as biomarkers of dietary exposure in Danish men and womenTjonneland1993
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
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
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
Serum levels of polyunsaturated fatty acids and risk of colorectal cancer: a prospective studyKojima2005

Biomarker data

Measurements of gamma-Linolenic acid (GLA; cis-18:3n-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 gamma-Linolenic acid (GLA; cis-18:3n-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 gamma-Linolenic acid (GLA; cis-18:3n-6) with cancer risk

Cancer associations

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

Exposure data

Measurements of gamma-Linolenic acid (GLA; cis-18:3n-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 gamma-Linolenic acid (GLA; cis-18:3n-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