You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2012-10-25 14:44:47 UTC
Update Date2018-05-19 23:28:42 UTC
HMDB IDHMDB0059587
Secondary Accession Numbers
  • HMDB59587
Metabolite Identification
Common NamePerfluorooctanoic acid
DescriptionPerfluorooctanoic acid (PFOA), also known as C8 and perfluorooctanoate, is a synthetic, stable perfluorinated carboxylic acid and fluorosurfactant. One industrial application is as a surfactant in the emulsion polymerization of fluoropolymers. It has been used in the manufacture of such prominent consumer goods as Teflon and Gore-Tex. PFOA has been manufactured since the 1940s in industrial quantities. It is also formed by the degradation of precursors such as some fluorotelomers. PFOA persists indefinitely in the environment. It is a toxicant and carcinogen in animals. PFOA has been detected in the blood of more than 98% of the general US population in the low and sub-parts per billion range, and levels are higher in chemical plant employees and surrounding subpopulations. Exposure has been associated with increased cholesterol and uric acid levels, and recently higher serum levels of PFOA were found to be associated with increased risk of chronic kidney disease in the general United States population, consistent with earlier animal studies. "This association was independent of confounders such as age, sex, race/ethnicity, body mass index, diabetes, hypertension, and serum cholesterol level." (Wikipedia).
Structure
Thumb
Synonyms
ValueSource
2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-Pentadecafluorooctanoic acidChEBI
pentadecafluoro-1-Octanoic acidChEBI
pentadecafluoro-N-Octanoic acidChEBI
perfluoro-N-Octanoic acidChEBI
Perfluorocaprylic acidChEBI
Perfluoroheptanecarboxylic acidChEBI
Perfluorooctylcarboxylic acidChEBI
PFOAChEBI
2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-PentadecafluorooctanoateGenerator
PerfluorooctanoateGenerator
pentadecafluoro-1-OctanoateGenerator
pentadecafluoro-N-OctanoateGenerator
perfluoro-N-OctanoateGenerator
PerfluorocaprylateGenerator
PerfluoroheptanecarboxylateGenerator
PerfluorooctylcarboxylateGenerator
PFOA CPDMeSH
Pentadecafluorooctanoic acidMeSH
Perfluorinated octanoic acidMeSH
Perfluorooctanoic acid, monopotassium saltMeSH
Perfluorooctanoic acid, monosodium saltMeSH
Perfluorooctanoic acid, anhydrideMeSH
Perfluorooctanoic acid, cobalt (2+) saltMeSH
Perfluorooctanoic acid, monoammonium saltMeSH
Perfluorooctanoic acid, monosilver (1+) saltMeSH
Sodium perfluorooctanoateMeSH
Ammonium perfluorooctanoateMeSH
Perfluorooctanoic acid, cesium saltMeSH
Perfluorooctanoic acid, chromium (3+) saltMeSH
Perfluorooctanoyl chlorideMeSH
APFOMeSH
Perfluorooctanoic acid, lithium saltMeSH
Chemical FormulaC8HF15O2
Average Molecular Weight414.0684
Monoisotopic Molecular Weight413.973702351
IUPAC Namepentadecafluorooctanoic acid
Traditional Nameperfluorooctanoic acid
CAS Registry Number335-67-1
SMILES
[H]OC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F
InChI Identifier
InChI=1S/C8HF15O2/c9-2(10,1(24)25)3(11,12)4(13,14)5(15,16)6(17,18)7(19,20)8(21,22)23/h(H,24,25)
InChI KeySNGREZUHAYWORS-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as perfluoroalkyl carboxylic acid and derivatives. These are organic compounds containing an alkyl chain attached to the C-alpha of a carboxylic acid group (or a derivative thereof), where all hydrogens of the alkyl chain are replaced by fluorine atoms.
KingdomOrganic compounds
Super ClassOrganohalogen compounds
ClassAlkyl halides
Sub ClassAlkyl fluorides
Direct ParentPerfluoroalkyl carboxylic acid and derivatives
Alternative Parents
Substituents
  • Perfluoroalkyl carboxylic acid or derivatives
  • Medium-chain fatty acid
  • Halogenated fatty acid
  • Fatty acyl
  • Fatty acid
  • Alpha-halocarboxylic acid
  • Alpha-halocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Organofluoride
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point40 – 50 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0Not Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.021 g/LALOGPS
logP4.29ALOGPS
logP5.11ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)-4.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity41.66 m³·mol⁻¹ChemAxon
Polarizability18.53 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kf-0493000000-d38b417b4dd2f5909028View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-014i-3397200000-55d38a84b62977449d81View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-014i-0009000000-d4b554e01a2918700428View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-014i-0219000000-97cdfe7ffa42de297b7dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-014i-0900000000-f052094b4c5ab701e1a5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-014i-0900000000-58850aa2fcf1ba2a2cb7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-03xr-0008900000-c82e739d0fcd8826065dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-014i-0209000000-55a3712c200c9b44fbb1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-014i-0910000000-1d480a0ea33ed137bb39View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-02t9-0900700000-93f45ca6d92a280d400cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0319200000-ab15643096ea6d0c5820View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0911100000-a5e29558a7c56b7978e8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0910000000-286ab096bf19fd043215View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-1900000000-2b23845b192c5dbae4bbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-f1f0cd2f1402c9c1dce4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-014i-0609000000-f177a7059eebeea65352View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000900000-3f60fe94dcf7611a8fd8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000900000-85b8fc2b2b78bee85da9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udl-9805000000-36e73ccb0d5e24f3c4aaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03xr-0005900000-9785745e00716d4e24afView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0000900000-b22e7cf9c5b3f0eae032View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0079100000-efc068700d58f48f3ce9View in MoNA
MSMass Spectrum (Electron Ionization)splash10-00ls-8900000000-364c7f569568884a2078View in MoNA
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00753 (0.00686-0.00828) uMAdult (>18 years old)Not SpecifiedNormal
    • National Health a...
details
BloodDetected and Quantified0.00698(0.00657-0.00742) uMAdult (>18 years old)BothNormal
    • Report on Human B...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID9180
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPerfluorooctanoic_acid
METLIN IDNot Available
PubChem Compound9554
PDB IDNot Available
ChEBI ID35549
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available