ContaminantDB: Perfluorooctanoic acid

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (11)XML

Record Information

Version

1.0

Creation Date

2014-08-29 04:48:39 UTC

Update Date

2016-10-28 10:04:40 UTC

Accession Number

CHEM002945

Identification

Common Name

Perfluorooctanoic acid

Class

Small Molecule

Description

Perfluorooctanoic 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. .

Contaminant Sources

HPV EPA Chemicals
IARC Carcinogens Group 2B
OECD HPV Chemicals
STOFF IDENT Compounds
Suspected Compounds
Suspected Compounds – Schymanski Project
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Industrial/Workplace Toxin
Metabolite
Organic Compound
Organofluoride
Synthetic Compound

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-Pentadecafluorooctanoic acid	ChEBI
Pentadecafluoro-1-octanoic acid	ChEBI
Pentadecafluoro-N-octanoic acid	ChEBI
Perfluoro-N-octanoic acid	ChEBI
Perfluorocaprylic acid	ChEBI
Perfluoroheptanecarboxylic acid	ChEBI
Perfluorooctylcarboxylic acid	ChEBI
PFOA	ChEBI
2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-Pentadecafluorooctanoate	Generator
Pentadecafluoro-1-octanoate	Generator
Pentadecafluoro-N-octanoate	Generator
Perfluoro-N-octanoate	Generator
Perfluorocaprylate	Generator
Perfluoroheptanecarboxylate	Generator
Perfluorooctylcarboxylate	Generator
Perfluorooctanoate	Generator
PFOA CPD	HMDB
Pentadecafluorooctanoic acid	HMDB
Perfluorinated octanoic acid	HMDB
Perfluorooctanoic acid, monopotassium salt	HMDB
Perfluorooctanoic acid, monosodium salt	HMDB
Perfluorooctanoic acid, anhydride	HMDB
Perfluorooctanoic acid, cobalt (2+) salt	HMDB
Perfluorooctanoic acid, monoammonium salt	HMDB
Perfluorooctanoic acid, monosilver (1+) salt	HMDB
Sodium perfluorooctanoate	HMDB
Ammonium perfluorooctanoate	HMDB
Perfluorooctanoic acid, cesium salt	HMDB
Perfluorooctanoic acid, chromium (3+) salt	HMDB
Perfluorooctanoyl chloride	HMDB
APFO	HMDB
Perfluorooctanoic acid, lithium salt	HMDB

Chemical Formula

C₈HF₁₅O₂

Average Molecular Mass

414.068 g/mol

Monoisotopic Mass

413.974 g/mol

CAS Registry Number

335-67-1

IUPAC Name

pentadecafluorooctanoic acid

Traditional Name

perfluorooctanoic acid

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 Key

SNGREZUHAYWORS-UHFFFAOYSA-N

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Organohalogen compounds

Class

Alkyl halides

Sub Class

Alkyl fluorides

Direct Parent

Perfluoroalkyl 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 Framework

Aliphatic acyclic compounds

External Descriptors

fluoroalkanoic acid (CHEBI:35549 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	40 - 50°C
Boiling Point	189-192°C
Solubility	Soluble

Predicted Properties

Property	Value	Source
Water Solubility	0.021 g/L	ALOGPS
logP	4.29	ALOGPS
logP	5.11	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	41.66 m³·mol⁻¹	ChemAxon
Polarizability	18.53 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kf-0493000000-d38b417b4dd2f5909028	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-014i-3397200000-55d38a84b62977449d81	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-014i-0009000000-d4b554e01a2918700428	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-014i-0219000000-97cdfe7ffa42de297b7d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-014i-0900000000-f052094b4c5ab701e1a5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-014i-0900000000-58850aa2fcf1ba2a2cb7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-03xr-0008900000-c82e739d0fcd8826065d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-014i-0209000000-55a3712c200c9b44fbb1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-014i-0910000000-1d480a0ea33ed137bb39	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-02t9-0900700000-93f45ca6d92a280d400c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-0319200000-ab15643096ea6d0c5820	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-0911100000-a5e29558a7c56b7978e8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-0910000000-286ab096bf19fd043215	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-1900000000-2b23845b192c5dbae4bb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-0900000000-f1f0cd2f1402c9c1dce4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-014i-0609000000-f177a7059eebeea65352	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0000900000-3f60fe94dcf7611a8fd8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0000900000-85b8fc2b2b78bee85da9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udl-9805000000-36e73ccb0d5e24f3c4aa	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03xr-0005900000-9785745e00716d4e24af	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0000900000-b22e7cf9c5b3f0eae032	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-0079100000-efc068700d58f48f3ce9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0000900000-9513d74f71569b693a77	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0000900000-9513d74f71569b693a77	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03xu-0029700000-de86519b701a9cd99edf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0000900000-fcefab210a6952c6d4e5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0000900000-fcefab210a6952c6d4e5	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00ls-8900000000-364c7f569568884a2078	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

2B, possibly carcinogenic to humans. (1)

Uses/Sources

It has been used in the manufacture of such prominent consumer goods as Teflon and Gore-Tex. 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.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Status	Value	Unit	Sample Location	Reference

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0059587

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Perfluorooctanoic_acid

Chemspider ID

9180

ChEBI ID

35549

PubChem Compound ID

9554

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=16020091

2. https://www.ncbi.nlm.nih.gov/pubmed/?term=18467677

Perfluorooctanoic acid (CHEM002945)

Structure for CHEM002945: Perfluorooctanoic acid