Perfluorooctanesulfonamide (PFOSA) is a synthetic
organofluorine compound
Organofluorine chemistry describes the chemistry of the organofluorines, organic compounds that contain the carbon–fluorine bond. Organofluorine compounds find diverse applications ranging from oil and water repellents to pharmaceuticals, refri ...
. It is a
fluorocarbon
Fluorocarbons are chemical compounds with carbon-fluorine bonds. Compounds that contain many C-F bonds often has distinctive properties, e.g., enhanced stability, volatility, and hydrophobicity. Fluorocarbons and their derivatives are commerci ...
derivative and a
perfluorinated compound
A perfluorinated compound (PFC) or perfluoro compound is an organofluorine compound containing only carbon-fluorines and C−C bonds, as well as potentially heteroatoms. Perfluorinated compounds have properties that result from the presence of flu ...
, having an eight-carbon chain and a terminal
sulfonamide
In organic chemistry, the sulfonamide functional group (also spelled sulphonamide) is an organosulfur group with the structure . It consists of a sulfonyl group () connected to an amine group (). Relatively speaking this group is unreactive. ...
functional group
In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest ...
. PFOSA, a
persistent organic pollutant
Persistent organic pollutants (POPs), sometimes known as "forever chemicals", are organic compounds that are resistant to environmental degradation through chemical, biological, and photolytic processes. They are toxic chemicals that adversely ...
, was an ingredient in
3M's former
Scotchgard
Scotchgard is a 3M brand of products, a stain and durable water repellent applied to fabric, furniture, and carpets to protect them from stains. Scotchgard products typically rely on organofluorine chemicals as the main active ingredient along ...
formulation from 1956 until 2003, and the compound was used to repel grease and water in food packaging along with other consumer applications. It breaks down to form
perfluorooctane sulfonate
Perfluorooctanesulfonic acid (PFOS) (conjugate base perfluorooctanesulfonate) is a chemical compound having an eight-carbon fluorocarbon chain and a sulfonic acid functional group and thus a perfluorosulfonic acid. It is an anthropogenic (man-ma ...
(PFOS).
[ The ]perfluorooctanesulfonyl fluoride
Perfluorooctanesulfonyl fluoride (POSF) is a synthetic perfluorinated compound with a sulfonyl fluoride functional group. It is used to make perfluorooctanesulfonic acid (PFOS) and PFOS-based compounds. These compounds have a variety of industria ...
-based chemistry that was used to make sulfonamides like PFOSA was phased out by 3M in the United States (US) during 2000–2002 but it has grown in China by other producers.
PFOSA can be synthesized from perfluorooctane sulfonyl halides by reaction with liquid ammonia
Ammonia is an inorganic compound of nitrogen and hydrogen with the formula . A stable binary hydride, and the simplest pnictogen hydride, ammonia is a colourless gas with a distinct pungent smell. Biologically, it is a common nitrogenous was ...
azide
In chemistry, azide is a linear, polyatomic anion with the formula and structure . It is the conjugate base of hydrazoic acid . Organic azides are organic compounds with the formula , containing the azide functional group. The dominant applic ...
followed by reduction with Zn and HCl HCL may refer to:
Science and medicine
* Hairy cell leukemia, an uncommon and slowly progressing B cell leukemia
* Harvard Cyclotron Laboratory, from 1961 to 2002, a proton accelerator used for research and development
* Hollow-cathode lamp, a spe ...
. PFOSA is also a metabolic by-product of ''N''-alkylated perfluorooctanesulfonamides.[ For example, ''N''-ethyl perfluorooctanesulfonamidoethanol (''N''-EtFOSE), which was primarily used on paper,
and ''N''-methyl perfluorooctanesulfonamidoethanol (''N''-MeFOSE), which was primarily used on carpets and textiles, both metabolize via ]acetate
An acetate is a salt (chemistry), salt formed by the combination of acetic acid with a base (e.g. Alkali metal, alkaline, Alkaline earth metal, earthy, Transition metal, metallic, nonmetallic or radical Radical (chemistry), base). "Acetate" als ...
s to PFOSA.
In addition, PFOSA is thought to be the biologically active form of the insecticide
Insecticides are substances used to kill insects. They include ovicides and larvicides used against insect eggs and larvae, respectively. Insecticides are used in agriculture, medicine, industry and by consumers. Insecticides are claimed to b ...
Sulfluramid (''N''-ethyl perfluorooctanesulfonamide)uncoupler An uncoupler or uncoupling agent is a molecule that disrupts oxidative phosphorylation in prokaryotes and mitochondria or photophosphorylation in chloroplasts and cyanobacteria by dissociating the reactions of ATP synthesis from the electron transp ...
of oxidative phosphorylation
Oxidative phosphorylation (UK , US ) or electron transport-linked phosphorylation or terminal oxidation is the metabolic pathway in which cells use enzymes to oxidize nutrients, thereby releasing chemical energy in order to produce adenosine tri ...
[
with an IC50 of about 1 ]micromolar
Molar concentration (also called molarity, amount concentration or substance concentration) is a measure of the concentration of a chemical species, in particular of a solute in a solution, in terms of amount of substance per unit volume of sol ...
[ (≈500 ]nanogram
To help compare different orders of magnitude, the following lists describe various mass levels between 10−59 kg and 1052 kg. The least massive thing listed here is a graviton, and the most massive thing is the observable universe ...
s per milliliter
The litre (international spelling) or liter (American English spelling) (SI symbols L and l, other symbol used: ℓ) is a metric unit of volume. It is equal to 1 cubic decimetre (dm3), 1000 cubic centimetres (cm3) or 0.001 cubic metre (m3). ...
or parts per billion
In science and engineering, the parts-per notation is a set of pseudo-units to describe small values of miscellaneous dimensionless quantities, e.g. mole fraction or mass fraction. Since these fractions are quantity-per-quantity measures, they ...
). PFOSA was the most toxic perfluorinated compound in a study with PC12 cells.biomonitoring
In analytical chemistry, biomonitoring is the measurement of the body burden of toxic chemical compounds, elements, or their metabolites, in biological substances. Often, these measurements are done in blood and urine. Biomonitoring is performed ...
studies have found the highest level of PFOSA in the liver
The liver is a major Organ (anatomy), organ only found in vertebrates which performs many essential biological functions such as detoxification of the organism, and the Protein biosynthesis, synthesis of proteins and biochemicals necessary for ...
of common dolphin
The common dolphin (''Delphinus delphis'') is the most abundant cetacean in the world, with a global population of about six million. Despite this fact and its vernacular name, the common dolphin is not thought of as the archetypal dolphin, with ...
(Mediterranean Sea
The Mediterranean Sea is a sea connected to the Atlantic Ocean, surrounded by the Mediterranean Basin and almost completely enclosed by land: on the north by Western and Southern Europe and Anatolia, on the south by North Africa, and on the ea ...
, Italy) with a concentration of 878 parts per billion
In science and engineering, the parts-per notation is a set of pseudo-units to describe small values of miscellaneous dimensionless quantities, e.g. mole fraction or mass fraction. Since these fractions are quantity-per-quantity measures, they ...
; the liver of mink
Mink are dark-colored, semiaquatic, carnivorous mammals of the genera ''Neogale'' and '' Mustela'' and part of the family Mustelidae, which also includes weasels, otters, and ferrets. There are two extant species referred to as "mink": the A ...
from Illinois
Illinois ( ) is a U.S. state, state in the Midwestern United States, Midwestern United States. Its largest metropolitan areas include the Chicago metropolitan area, and the Metro East section, of Greater St. Louis. Other smaller metropolita ...
, US, contained 590 parts per billion.[Supporting Information]
(PDF). In fish, the highest levels detected were in the liver of Norway Pike
Pike, Pikes or The Pike may refer to:
Fish
* Blue pike or blue walleye, an extinct color morph of the yellow walleye ''Sander vitreus''
* Ctenoluciidae, the "pike characins", some species of which are commonly known as pikes
* ''Esox'', genus of ...
(91 parts per billion) and homogenate
Homogeneity and heterogeneity are concepts often used in the sciences and statistics relating to the uniformity of a substance or organism. A material or image that is homogeneous is uniform in composition or character (i.e. color, shape, s ...
s of slimy sculpin
The slimy sculpin (''Cottus cognatus'') is a freshwater species of fish belonging to the family Cottidae, which is the largest sculpin family. They usually inhabit cold rocky streams or lakes across North America, ranging from the Great Lakes, so ...
(150 parts per billion) from Lake Ontario
Lake Ontario is one of the five Great Lakes of North America. It is bounded on the north, west, and southwest by the Canadian province of Ontario, and on the south and east by the U.S. state of New York. The Canada–United States border sp ...
.[ Differences in biotransformation across species could explain some of its presence.][ In humans, PFOSA has been detected in sub- to low-parts per billion levels;][ for example, in 1999–2000 US serum samples, the 95th ]percentile
In statistics, a ''k''-th percentile (percentile score or centile) is a score ''below which'' a given percentage ''k'' of scores in its frequency distribution falls (exclusive definition) or a score ''at or below which'' a given percentage falls ...
(or value where only 5% of the population was higher) was 1.4 parts per billion while in 2003–2004 the 95th percentile fell to 0.2 parts per billion.[Supplemental Material]
(PDF). However, whole-blood concentrations are about five times higher than those in blood plasma or serum.
See also
*Fluorosurfactant
Per- and polyfluoroalkyl substances (PFASs) are synthetic organofluorine chemical compounds that have multiple fluorine atoms attached to an alkyl chain. An early definition, from 2011, required that they contain at least one perfluoroalkyl mo ...
*Ionophore
In chemistry, an ionophore () is a chemical species that reversibly binds ions. Many ionophores are lipid-soluble entities that transport ions across the cell membrane. Ionophores catalyze ion transport across hydrophobic membranes, such as liq ...
References
{{reflist, 2
External links
Perfluorinated Alkylated Substances (PFAS) in the European Nordic Environment
Perfluorinated compounds
Sulfonamides