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Details

Stereochemistry ACHIRAL
Molecular Formula C8HF17O3S
Molecular Weight 500.13
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PERFLUOROOCTANESULFONIC ACID

SMILES

OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F

InChI

InChIKey=YFSUTJLHUFNCNZ-UHFFFAOYSA-N
InChI=1S/C8HF17O3S/c9-1(10,3(13,14)5(17,18)7(21,22)23)2(11,12)4(15,16)6(19,20)8(24,25)29(26,27)28/h(H,26,27,28)

HIDE SMILES / InChI

Molecular Formula C8HF17O3S
Molecular Weight 500.13
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Perfluorooctane sulfonic acid (PFOS) is a global pollutant and an environmental toxicant, widely used as a fabric protector, serving as a stain repellant in drapery, carpets, and clothing. While its use in Europe, Canada, and the U.S. has been banned due to its human toxicity, it continues to be used in China and other developing countries as a global pollutant. However, epidemiologic evidence does not support a causal association between PFOS exposure and cancer risk in humans. However, in utero exposure to PFOS adversely affect the fetal synthesis and secretion of reproductive hormones (e.g., testosterone, estradiol, and inhibin B) in humans. Since the half-life of PFOS is relatively long, at 5.4-yr, even low-dose exposure to PFOS can accumulate in the body over an extended period of time. The mechanisms of PFOA -induced hepatic dysfunction are not completely understood but was shown, that PFOS induces their effects via targeting hepatocyte nuclear factor 4-alpha (HNF4α) and thus altered its conformation. In addition, some recent experiments in vitro revealed, that PFOS-induced male reproductive dysfunction can possibly be managed through an intervention on Akt1/2 expression.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P41235|||Q6B4V6
Gene ID: 3172.0
Gene Symbol: HNF4A
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Preliminary screening of perfluorooctane sulfonate (PFOS) and other fluorochemicals in fish, birds and marine mammals from Greenland and the Faroe Islands.
2005-07
Anaerobic biodegradability and methanogenic toxicity of key constituents in copper chemical mechanical planarization effluents of the semiconductor industry.
2005-06
Perfluorinated compounds in aquatic organisms at various trophic levels in a Great Lakes food chain.
2005-05
Historical comparison of perfluorooctanesulfonate, perfluorooctanoate, and other fluorochemicals in human blood.
2005-05
Effects of PFOS and PFOA on L-type Ca2+ currents in guinea-pig ventricular myocytes.
2005-04-08
Perflouroalkyl contaminants in liver tissue from East Greenland polar bears (Ursus maritimus).
2005-04
Perfluorinated organic compounds in human blood serum and seminal plasma: a study of urban and rural tea worker populations in Sri Lanka.
2005-04
Microcosm evaluation of the toxicity and risk to aquatic macrophytes from perfluorooctane sulfonic acid.
2005-04
Synthesis of environmentally relevant fluorinated surfactants--a review.
2005-03
Development and characterization of a solvent extraction-gas chromatographic/mass spectrometric method for the analysis of perfluorooctanesulfonamide compounds in solid matrices.
2005-02-25
Development of a solid-phase extraction-HPLC/single quadrupole MS method for quantification of perfluorochemicals in whole blood.
2005-02-01
Temporal trends of PFOS and PFOA in guillemot eggs from the Baltic Sea, 1968--2003.
2005-01-01
[Effects of perfluorooctane sulfonate on spermiogenesis function of male rats].
2005-01
Fluorinated organic compounds in an eastern Arctic marine food web.
2004-12-15
Canada moves to eliminate PFOS stain repellents.
2004-12-01
Analysis of perfluorinated acids at parts-per-quadrillion levels in seawater using liquid chromatography-tandem mass spectrometry.
2004-11-01
Partial life-cycle toxicity and bioconcentration modeling of perfluorooctanesulfonate in the northern leopard frog (Rana pipiens).
2004-11
Mitochondrial permeability transition as the critical target of N-acetyl perfluorooctane sulfonamide toxicity in vitro.
2004-11
Perfluoroalkyl contaminants in a food web from Lake Ontario.
2004-10-15
Determination of perfluorooctane sulfonate, perfluorooctanoate and perfluorooctane sulfonylamide in human plasma by column-switching liquid chromatography-electrospray mass spectrometry coupled with solid-phase extraction.
2004-10-15
Perfluorooctanesulfonate and related fluorochemicals in human blood from several countries.
2004-09-01
Determination of perfluorooctane sulfonate and perfluorooctanoic acid in human plasma by large volume injection capillary column switching liquid chromatography coupled to electrospray ionization mass spectrometry.
2004-09
Toxicity of perfluorooctane sulfonic acid and perfluorooctanoic acid to Chironomus tentans.
2004-09
Detection of perfluorooctane surfactants in Great Lakes water.
2004-08-01
Perfluorinated compounds in coastal waters of Hong Kong, South China, and Korea.
2004-08-01
Analysis of episodes of care in a perfluorooctanesulfonyl fluoride production facility.
2004-08
Perfluorooctane sulfonate (PFOS) and related perfluorinated compounds in human maternal and cord blood samples: assessment of PFOS exposure in a susceptible population during pregnancy.
2004-08
The developmental toxicity of perfluoroalkyl acids and their derivatives.
2004-07-15
Automated solid-phase extraction and measurement of perfluorinated organic acids and amides in human serum and milk.
2004-07-01
[Status of perfluorochemicals in adult serum and umbilical blood in Shenyang].
2004-07
Contaminant exposure and reproductive success of ospreys (Pandion haliaetus) nesting in Chesapeake Bay regions of concern.
2004-07
trans-activation of PPARalpha and induction of PPARalpha target genes by perfluorooctane-based chemicals.
2004-07
A pilot study on the determination of perfluorooctanesulfonate and other perfluorinated compounds in blood of Canadians.
2004-06
Biochemical effect evaluation of perfluorooctane sulfonic acid-contaminated wood mice (Apodemus sylvaticus).
2004-05
Effects of perfluorooctane sulfonate and perfluorooctanoic acid on the zooplanktonic community.
2004-05
A highly efficient microwave-assisted suzuki coupling reaction of aryl perfluorooctylsulfonates with boronic acids.
2004-04-29
Indoor and outdoor air concentrations and phase partitioning of perfluoroalkyl sulfonamides and polybrominated diphenyl ethers.
2004-03-01
Perfluorinated sources outside and inside.
2004-03-01
The influence of time, sex and geographic factors on levels of perfluorooctane sulfonate and perfluorooctanoate in human serum over the last 25 years.
2004-03
Serum concentrations of perfluorooctanesulfonate and other fluorochemicals in an elderly population from Seattle, Washington.
2004-03
Biotransformation of N-ethyl perfluorooctanesulfonamide by rainbow trout (Onchorhynchus mykiss) liver microsomes.
2004-02-01
Attenuated total reflectance FTIR detection and quantification of low concentrations of aqueous polyatomic anions.
2004-02-01
Predicting the biodegradation products of perfluorinated chemicals using CATABOL.
2004-02
Aqueous microemulsions of a fluorinated surfactant and oil studied by PFG-NMR: transformation from threadlike to spherical micelles.
2004-01-20
Identification of long-chain perfluorinated acids in biota from the Canadian Arctic.
2004-01-15
Perfluorooctanoate and perfluorooctane sulfonate concentrations in surface water in Japan.
2004-01
Perfluorooctane sulfonate--a quite mobile anionic anthropogenic surfactant, ubiquitously found in the environment.
2004
Perfluorinated chemicals infiltrate ocean waters: link between exposure levels and stable isotope ratios in marine mammals.
2003-12-15
Determination of fluorinated surfactants and their metabolites in sewage sludge samples by liquid chromatography with mass spectrometry and tandem mass spectrometry after pressurised liquid extraction and separation on fluorine-modified reversed-phase sorbents.
2003-12-05
Prenatal window of susceptibility to perfluorooctane sulfonate-induced neonatal mortality in the Sprague-Dawley rat.
2003-12
Patents

Sample Use Guides

toxicity in rats: Dietary 100 ppm perfluorooctane sulfonate (PFOS) fed to male mice and rats for 4 weeks caused hepatic steatosis through an unknown mechanism
Route of Administration: Oral
PFOS (perfluorooctanesulfonic acid) perturbs TJ- and basal ES-protein localization in Sertoli cells. Sertoli cells isolated from 20-day-old rat testes were cultured in vitro for 3 days to form a cell epithelium with an established functional TJ-barrier, which mimicked the Sertoli cell BTB in vivo. This in vitro-based system has been widely used by investigators to study BTB dynamics, and many of the findings were subsequently confirmed by studies in vivo. Thereafter, these cells were treated with PFOS at 10, 20 or 50 µM for 24 hr. It was noted that PFOS perturbed the Sertoli cell TJ-permeability barrier function dose-dependently with PFOS at 50 µM was more effectively to perturb the TJ function than at 20 µM. The range of PFOS concentration at 20–50 µM (i.e., at 10–25 µg/ml) used in the study herein was shown not to be cytotoxic as recently reported from our laboratory, and no cytotoxicity was found at concentration up to 100 µM. The acceptable daily intake (ADI) of PFOS is 150 ng/kg/day. But since PFOS has a human elimination half-life of 5.4-year, a considerable level of PFOS could build up in humans in particular among industrial workers such as those who utilize PFOS for manufacturing of stain resistant carpets and fabrics.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:51:51 GMT 2025
Edited
by admin
on Mon Mar 31 18:51:51 GMT 2025
Record UNII
9H2MAI21CL
Record Status Validated (UNII)
Record Version
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Name Type Language
PERFLUOROOCTANE SULFONIC ACID
HSDB  
Preferred Name English
PERFLUOROOCTANESULFONIC ACID
Systematic Name English
PERFLUOROOCTYLSULFONIC ACID
Systematic Name English
PERFLUOROOCTANE SULFONIC ACID [HSDB]
Common Name English
PERFLUORO-N-OCTANESULFONIC ACID
Common Name English
1-OCTANESULFONIC ACID, 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8- HEPTADECAFLUORO-
Systematic Name English
PFOS
Common Name English
PERFLUOROOCTANE SULFONATE
Systematic Name English
HEPTADECAFLUOROOCTANE-1-SULPHONIC ACID
Systematic Name English
n-perfluorooctane sulfonic acid
Common Name English
Code System Code Type Description
PUBCHEM
74483
Created by admin on Mon Mar 31 18:51:51 GMT 2025 , Edited by admin on Mon Mar 31 18:51:51 GMT 2025
PRIMARY
EPA CompTox
DTXSID3031864
Created by admin on Mon Mar 31 18:51:51 GMT 2025 , Edited by admin on Mon Mar 31 18:51:51 GMT 2025
PRIMARY
ECHA (EC/EINECS)
217-179-8
Created by admin on Mon Mar 31 18:51:51 GMT 2025 , Edited by admin on Mon Mar 31 18:51:51 GMT 2025
PRIMARY
FDA UNII
9H2MAI21CL
Created by admin on Mon Mar 31 18:51:51 GMT 2025 , Edited by admin on Mon Mar 31 18:51:51 GMT 2025
PRIMARY
MESH
C076994
Created by admin on Mon Mar 31 18:51:51 GMT 2025 , Edited by admin on Mon Mar 31 18:51:51 GMT 2025
PRIMARY
CAS
1763-23-1
Created by admin on Mon Mar 31 18:51:51 GMT 2025 , Edited by admin on Mon Mar 31 18:51:51 GMT 2025
PRIMARY
WIKIPEDIA
Perfluorooctane sulfonic acid
Created by admin on Mon Mar 31 18:51:51 GMT 2025 , Edited by admin on Mon Mar 31 18:51:51 GMT 2025
PRIMARY
SMS_ID
300000053521
Created by admin on Mon Mar 31 18:51:51 GMT 2025 , Edited by admin on Mon Mar 31 18:51:51 GMT 2025
PRIMARY
HSDB
7099
Created by admin on Mon Mar 31 18:51:51 GMT 2025 , Edited by admin on Mon Mar 31 18:51:51 GMT 2025
PRIMARY
CHEBI
39421
Created by admin on Mon Mar 31 18:51:51 GMT 2025 , Edited by admin on Mon Mar 31 18:51:51 GMT 2025
PRIMARY
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