Perfluorononanoic acid
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Perfluorononanoic acid
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CAS No:
375-95-1
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Formula:
C9HF17O2
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Chemical Name:
Perfluorononanoic acid
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Synonyms:
Nonanoic acid,2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-heptadecafluoro-;Nonanoic acid,heptadecafluoro-;2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-Heptadecafluorononanoic acid;Perfluoropelargonic acid;Heptadecafluorononanoic acid;Perfluorononanoic acid;C 1800;PFNA
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CAS No:
Description
Perfluorononanoic acid is a white crystalline powder or beige crystals. Perfluorononanoic acid has the ability to react with bases, oxidizing agents, and reducing agents. Upon decomposition, PFNA can form carbon oxides and hydrogen fluoride.
Perfluorononanoic acid is a fluoroalkanoic acid that is nonanoic acid in which all of the hydrogens in the alkyl chain are replaced by fluorines. It has a role as a persistent organic pollutant, a xenobiotic and a surfactant. It derives from a nonanoic acid.
Perfluorononanoic acid Basic Attributes
464.076
464.08
206-801-3
5830Z6S63M
DTXSID8031863
2915900090
Characteristics
37.30000
8.64
white crystalline powder
1.8±0.1 g/cm3
69-71 °C @ Solvent: Carbon tetrachloride
196.4±35.0 °C at 760 mmHg
72.6±25.9 °C
1.289
In water, 6.25X10-2 mg/L at 25 °C (est)
8.3X10-2 mm Hg at 25 deg C (est)
pKa = -0.21
165.06 Ų [M-H]-
Hydroyl radical reaction rate constant = 5.2X10-11 cu cm/molec-sec at 25 °C (est)
Safety Information
III
8
UN3261
3
R22;R34;R52/53
S26-S36
Xi: Irritant;
Stable. Incompatible with strong bases, strong oxidizing agents. Corrosive - causes burns.
P261-P305 + P351 + P338
H315-H319-H335
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.
|Danger|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P260, P261, P263, P264, P270, P271, P280, P281, P301+P312, P304+P312, P304+P340, P305+P351+P338, P308+P313, P310, P312, P314, P330, P405, and P501|H372: Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure]|P260, P264, P270, P314, and P501
Perfluoro-n-nonanoic acid was detected in sewage effluent samples from Norway and the Faeroe Islands and in landfill effluent samples taken from Finland and Norway, concentrations were not reported(1). Perfluoro-n-nonanoic acid was detected in waste water treatment sludge from six plants located across Ontario, Canada, collected in 2002, at <0.0625-0.61 ng/g(2). Perfluoro-n-nonanoic acid concentration was reported in influent, effluent and digested sludge from a waste water treatment plant as 1.1 ng/L, 3.4 ng/L and 9.9 ug/kg, respectively(3). Perfluoro-n-nonanoic acid was not detected (detection limit 1.6 ng/L) in the influent or effluent of the waste water treatment plants along the Glatt Valley Watershed, Switzerland, in Faelianden, Bassersdorf, Niederglatt, Buelach or Glattfelden(4). However, perfluoro-n-nonanoic acid was detected in the influent of Duebendorf at 2.6 to 26 ng/L and in the effluent of Duebendorf and Kloten-Opfikon at <1.6-2.6 and <1.6-5.6 ng/L, respectively, all samples were collected Feb to March 2006(4). Two municipal waste water treatment plants in Taipei had perfluoro-n-nonanoic acid concentrations of 10.6 and 0.4 ng/L in their influent samples and <0.1 and 0.3 ng/L in their effluent samples(5). Perfluoro-n-nonanoic acid was also measured at 10.4 ng/L in the effluent of an industrial waste water treatment plant located in Hsinchu Science Park, Taiwan(5).
SEDIMENT: Perfluoro-n-nonanoic acid was not detected (detection limit 0.10 ng/g) in sediment samples from 11 sites in the Daliao River system of northeast China, samples were collected in April 2008(1). Perfluoro-n-nonanoic acid was not detected in 13 sediment samples from the Zhujiang River in Guangzhou and nine sediment samples from the Huangpu River in Shanghai, China, samples were collected March 2009(2). Sediment samples, collected from the Hudson Bay region of northeastern Canada May to Sept 1999 to 2003, had perfluoro-n-nonanoic acid concentrations in 33% of <0.06-0.14 ng/g dry weight(3). Perfluoro-n-nonanoic acid was detected at 0.33-0.55 ng/g dry weight in five sediment samples taken from the Ariake Sea in Jan 2004(4).|SEDIMENT: Perfluoro-n-nonanoic acid was analyzed at different depths in sediment samples from four lakes on Cornwallis Island, Nunavut, Canada(1).[Table#8038]|SEDIMENT: Perfluoro-n-nonanoic acid was detected in a sediment core sample form Tokyo Bay, Japan, sample was taken May 2008(1).[Table#8039]
URBAN/SUBURBAN: Perfluoro-n-nonanoic acid was detected in 3% of atmospheric samples from Barsbuttel, Germany at a maximum concentration of 0.1 pg/cu m, the study was run April 2007 to June 2008(1). Perfluoro-n-nonanoic acid was detected in atmospheric samples from a location in Albany, NY at 0.16-0.31 pg/cu m, samples were taken May to July 2006(2). Perfluoro-n-nonanoic acid was not detected (detection limit 0.02 pg/cu m) in outdoor air samples from six homes in Vancouver, Canada, samples were collected 2007 to 2008(3).|RURAL/REMOTE: Perfluoro-n-nonanoic acid had an average concentration of 0.3 pg/cu m in 8% of 141 atmospheric samples from the Atlantic and Southern Oceans and coastal areas of the Baltic sea, the study was run April 2007 to Jan 2009(1).|INDOOR: Perfluoro-n-nonanoic acid was not detected in 40 indoor air samples from Oslo, Norway households(1). Perfluoro-n-nonanoic acid was detected at <0.02 to 2.166 pg/cu m in indoor air samples from 59 homes in Vancouver, Canada, samples were collected 2007 to 2008(2).
Perfluoro-n-nonanoic acid was detected in paper fiber from three paper mills in Ontario, Canada at 2.0-3.0 ng/g, samples were collected 2002, 2003 and 2008(1). Perfluoro-n-nonanoic acid concentrations on window film in a suburban area was greatest on a sheltered window in the summer followed by a sheltered window in the winter, a lower concentration was found on an unsheltered window in the winter (13 mm precipitation), and the lowest concentration was found on an unsheltered window in the summer (47 mm precipitation)(2). Perfluoro-n-nonanoic acid was detected at <0.06 to 680 ng/g in dust samples from 140 homes in Vancouver, Canada, samples were collected 2007 to 2008(3). Perfluoro-n-nonanoic acid was detected in 41 dust samples from Norwegian households at 3.9 to 92 ng/g(4). Dust samples were collected in 2000 to 2001 from vacuum cleaner bags during the US Environmental Protection Agency's Children's Total Exposure to Persistent Pesticides and Other Persistent Organic Pollutants study, 102 homes and 10 daycare centers in North Carolina and Ohio were sampled, perfluoro-n-nonanoic acid was detected in 42.9% of the samples at a mean concentration of 22.1 ng/g and a maximum of 263 ng/g(5). Perfluoro-n-nonanoic acid was found in indoor dust samples with a mean value of 3.43 ng/g dry weight and a range of 0.66 to 7.32 ng/g dry weight, samples were collected from homes in Nanchang, Shanghai, Beijing and Tianjin, China(6).
Toxicity
/AQUATIC SPECIES/ Perfluorinated surfactants (PFSs) in Asian freshwater fish species were analyzed to investigate tissue distribution, temporal trends, extent of pollution, and level of PFS exposure through food intake. Freshwater fish species, namely carp, snakehead, and catfish, were collected in Japan, Vietnam, India, Malaysia, and Thailand, and 10 PFSs, including perfluorooctanesulfonate (PFOS) and perfluorooctanoate, were analyzed by liquid chromatography-tandem mass spectrometry. PFSs in carp in Tokyo were more concentrated in kidneys (sum of 10 PFSs = 257 +/- 95 ng/g wet weight [ww]) and livers (119 +/- 36 ng/g ww) than in ovaries (43 +/- 2 ng/g ww) and muscles (24 +/- 17 ng/g ww). Concentrations of PFOS and its precursor, perfluorooctane sulfonamide, in livers of carp and in waters in Tokyo showed a dramatic decrease during the last decade, probably because of 3 M's phasing-out of the manufacture of perfluorooctanesulfonyl-fluoride-based products in 2000. In contrast, continuing contamination by long-chain perfluorocarboxylates (PFCAs) with > or =9 fluorinated carbons was seen in multiple media, suggesting that these compounds continue to be emitted. PFS concentrations in freshwater fish species in tropical Asian countries were generally lower than those in developed countries, such as Japan, e.g., for PFOS in muscle, Vietnam < 0.05-0.3 ng/g ww; India < 0.05-0.2 ng/g ww; Malaysia < 0.05-0.2 ng/g ww; Thailand < 0.05 ng/g ww; and Japan (Tokyo) = 5.1-22 ng/g ww. Daily intake of short-chain PFCAs with < or =8 fluorinated carbons from freshwater fish species in Japan was approximately one order of magnitude lower than that from drinking water, whereas daily intake of PFOS and long-chain PFCAs with > or =9 fluorinated carbons from freshwater fish species was comparable with or greater than that from drinking water. Because the risk posed by exposure to these compounds through intake of fish species is a matter of concern, we recommend the continued monitoring of PFS levels in Asian developing countries. /Perfluorinated surfactants/
Perfluorochemicals like perfluoro-n-nonanoic acid have been widely used since the 1950s in many industrial and consumer products, including protective coatings for fabrics and carpet, paper coatings, insecticide formulations, and surfactants(1). Perfluoro-n-nonanoic acid's production and use may result in its release to the environment through various waste streams(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1.2X10+5(SRC), determined from a structure estimation method(2), indicates that perfluoro-n-nonanoic acid is expected to be immobile in soil(SRC). The pKa of perfluoro-n-nonanoic acid is -0.21(3), indicating that this compound will exist entirely in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization of perfluoro-n-nonanoic acid from moist soil surfaces is not expected to be an important fate process(SRC) based on the pKa(3). Perfluoro-n-nonanoic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 8.3X10-2 mm Hg at 25 °C(SRC), determined from a fragment constant method(5). Organic fluorochemical compounds, such as perfluoro-n-nonanoic acid, are expected to be resistant to biodegradation(6).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1.2X10+5(SRC), determined from a structure estimation method(2), indicates that perfluoro-n-nonanoic acid is expected to adsorb to suspended solids and sediment(SRC). A pKa of -0.21(3) indicates perfluoro-n-nonanoic acid will exist entirely in the anion form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(SRC). According to a classification scheme(4), an estimated BCF of 9100(SRC), from an estimated log Kow of 5.48(5) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is very high(SRC). Perfluoro-n-nonanoic acid is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(7). Organic fluorochemical compounds, such as perfluoro-n-nonanoic acid, are expected to be resistant to biodegradation(8).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), perfluoro-n-nonanoic acid, which has an estimated vapor pressure of 8.3X10-2 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase perfluoro-n-nonanoic acid is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 31 days(SRC), calculated from its rate constant of 5.2X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Perfluoro-n-nonanoic acid does not contain chromophores that absorb at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).
The rate constant for the vapor-phase reaction of perfluoro-n-nonanoic acid with photochemically-produced hydroxyl radicals has been estimated as 5.2X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 31 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Perfluoro-n-nonanoic acid is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). Perfluoro-n-nonanoic acid does not contain chromophores that absorb at wavelengths >290 nm(2) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).
An estimated BCF of 9100 was calculated in fish for perfluoro-n-nonanoic acid(SRC), using an estimated log Kow of 5.48(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is very high(SRC). The log bioaccumulation factors (BAF) for perfluoro-n-nonanoic acid in lake trout from Lake Superior, Lake Huron, Lake Erie and Lake Ontario were 3.7, 3.6, 3.8 and 3.1, respectively, the average log BAF was 3.6(4). The average Log BAF in eel (A anguilla) from 23 locations in The Netherlands was 2.52 with a range of 2.02 to 3.14(5). The steady state biota sediment accumulation factor for perfluoro-n-nonanoic acid in Lumbriculus variegatus was found to be 55(6). Bioaccumulation factors of lake trout in Lake Ontario samples were 5.3, 0.62 and 0.13 based on prey of alewife, smelt and sculpin, respectively, the diet weighted BAF was 2.3 based on all prey(7). Trophic level biomagnification factors were reported as: ringed seal:cod 1.2, beluga:cod 12.9, beluga:herring 5.8, beluga:Artic cisco 2.9, cod:Calanus hyperboreus 0.7, cod:Themisto libellula 0.3(8).
Using a structure estimation method based on molecular connectivity indices(1), the Koc of perfluoro-n-nonanoic acid can be estimated to be 1.2X10+5(SRC). According to a classification scheme(2), this estimated Koc value suggests that perfluoro-n-nonanoic acid is expected to be immobile in soil. The pKa of perfluoro-n-nonanoic acid is -0.21(3), indicating that this compound will exist in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). The log Koc for perfluoro-n-nonanoic acid in three sediments was reported as 2.4(5) and 3.69 in 23 sediments(6).
A pKa of -0.21(1) indicates perfluoro-n-nonanoic acid will exist entirely in the anion form at pH values of 5 to 9 and therefore volatilization from water and moist soil surfaces is not expected to be an important fate process(SRC). Perfluoro-n-nonanoic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 8.3X10-2 mm Hg(SRC), determined from a fragment constant method(2).
GROUND WATER: Perfluoro-n-nonanoic acid was detected in one of 19 well water samples at 25.7 ng/L, samples were taken around Decatur, AL, from area farms that have a history of being treated with fluorochemical industry impacted biosolids(1). Perfluoro-n-nonanoic acid was detected in groundwater samples from the Highland Creek watershed, Canada, taken Feb to March 2010 at 0.071 to 0.54 ng/L(2). Perfluoro-n-nonanoic acid was detected in 15 ground water samples taken in the city of Tokyo, Japan, Sept to Nov 2006; concentrations were 0.1 to 94 ng/L(3).|DRINKING WATER: Drinking water samples from seven waste water treatment plants throughout the US tested positive in four for perfluoro-n-nonanoic acid at 1.0-9.7 ng/L(1). Perfluoro-n-nonanoic acid was not detected (detection limit 10 ng/L) in the finish water from four wastewater treatment plants in New York State, but was detected in two others at 4 to 376 ng/L(2). Perfluoro-n-nonanoic acid was not detected (detection limit 0.22 ng/L) in drinking water samples collected in three homes that receive water from different water works in Oslo, Norway, samples were collected between Oct 2008 and Jan 2009(3). Perfluoro-n-nonanoic acid was detected in 79% of 43 tap water samples taken from homes, schools, offices, restaurants, commercial centers, hotels and an airport in 2006 and 2008 from 10 cities in China(4).|SURFACE WATER: Surface water samples taken from US streams in the Great Lakes basin tested positive for perfluoro-n-nonanoic acid in 38% of 8 samples taken 1994 to 2000 at concentrations of 0.00003 to 0.0004 ug/L(1). Perfluoro-n-nonanoic acid was detected in creek and river samples collected throughout Canada at concentrations of <125 to 3000 pg/L(2). Perfluoro-n-nonanoic acid was detected in nine of 32 surface water samples at 12.4 to 286 ng/L, samples were taken around Decatur, AL, from area ponds and streams near farms that have a history of being treated with fluorochemical industry impacted biosolids(3). Perfluoro-n-nonanoic acid was detected in surface water samples from the Highland Creek watershed, Canada, collected Feb to March 2010 at 0.80 to 2.4 ng/L(4). Out of 100 samples taken from 80 sites in the Cape Fear River Basin, North Carolina, the 11 samples with the highest total perfluorinated organic compound concentrations had perfluoro-n-nonanoic acid concentrations of 2.24-194 ng/L, samples were collected in the spring of 2006(5).|SURFACE WATER: Lake water samples from four lakes on Cornwallis Island, Nunavut, Canada were tested for perfluoro-n-nonanoic acid(1).[Table#8040]|For more Environmental Water Concentrations (Complete) data for Perfluoro-n-nonanoic acid (8 total), please visit the HSDB record page.
Seven types of seafood were purchased from local markets in Zhoushan and Guangzhou, China in 2004, perfluoro-n-nonanoic acid was only detected in sand swimming crab and swimming crab at 0.28 and 0.61 ng/g wet weight, respectively(1). Perfluoro-n-nonanoic acid was sampled in food, tea and milk purchased in grocery stores in Oslo, Norway between Oct 2008 and Jan 2009, concentrations were (pg/g fresh weight): cheese (16), bread (9.5), strawberry jam (3.7), pork meat (5.5), beef (15), chicken meat (6.8), salmon (10), cod (5.9) and cod liver (14)(2). All other products (lettuce, carrot, potato, margarine, milk, egg, fish sticks, canned mackerel) were listed at less than detection limit (detection limits varied)(2). In Nov 2009, food products of 15 food categories were randomly purchased in several Dutch retail stores, perfluoro-n-nonanoic acid was detected as follows (pg/g product); fatty fish (5), lean fish (77), crustaceans (58), butter (2), cheese (7), milk (<1), eggs (6), pork (2), beef (4), chicken/poultry (1), bakery products (1), vegetables/fruit (1), flour (15), vegetable oil (<0.1), industrial oil (<0.3)(3). Concentrations of perfluoro-n-nonanoic acid in food products sampled for the 2004 Canadian Total Diet Study were 3.75 and 1.72 ng/g wet weight in cold cuts and cookies, <0.75, <0.79, <1.43, <0.74, <0.74 and <0.78 ng/g wet weight in processed cheese, peppers, canned lunch meats, pizza, cheese and beef frozen dinner, respectively(4). Perfluoro-n-nonanoic acid was detected in one of three popcorn packaging paper before and after cooking at 2.1 and 2.5 ng/sq cm, respectively(5).|Concentration of perfluoro-n-nonanoic acid in aquatic traditional Inuit foods collected between 1997 and 1999 in Nunavut, Canada(1).[Table#8035]|Concentration of perfluoro-n-nonanoic acid in terrestrial traditional Inuit foods collected between 1997 and 1999 in Nunavut, Canada(1).[Table#8036]
Perfluoro-n-nonanoic acid was not detected (detection limit 2.1 pg/g) in milk samples purchased at grocery stores in Oslo, Norway between Oct 2008 and Jan 2009(1). In Nov 2009, milk samples randomly purchased in several Dutch retail stores did not contain perfluoro-n-nonanoic acid (detection limit <1 pg/g)(2). Perfluoro-n-nonanoic acid was not detected (detection limit 2.20 pg/mL) in 21 infant formula samples purchased from retail stores in Washington, DC and Boston, MA in 2007, or in 12 dairy milk samples purchased from retail stores and local farms in Albany, NY in 2008(3).|In 12 sets of maternal serum, cord serum and milk samples from mothers that gave birth at the National Hospital in Torshavn, Faroe Islands, perfluoro-n-nonanoic acid was not detected in transitional milk samples taken 3-5 days after delivery(1).|Perfluoro-n-nonanoic acid concentrations in breast milk samples from seven Asian Countries, samples, collected 1999 to 2005, primarily from women living in major cities(1).[Table#8037]
Occupational exposure to perfluoro-n-nonanoic acid may occur through inhalation and dermal contact with this compound at workplaces where perfluoro-n-nonanoic acid is produced or used. Monitoring data indicate that the general population may be exposed to perfluoro-n-nonanoic acid via inhalation of ambient air, ingestion of food and drinking water, and dermal contact with products containing perfluoro-n-nonanoic acid. (SRC)
Perfluoro-n-nonanoic acid was detected in all serum samples from the US population (1562 participants) as studied in the National Health and Nutrition Examination Survey (NHANES) conducted 1999 thru 2000, with a mean concentration of 0.5 ng/mL and concentration range of 0.5-0.7 ng/mL(1). In the NHANES survey conducted 2003 thru 2004 perfluoro-n-nonanoic acid was detected at a mean concentration of 1.0 ng/mL and concentration range of 0.8-1.1 ng/mL in 100% of the 2094 serum samples analyzed(2). Perfluoro-n-nonanoic acid was detected in 20 pooled blood samples (at least 10 individual donors per sample) at concentrations of 0.34 to 1.8 ug/L, samples were obtained from donors across the Midwestern US in 2004, 2005 and 2008(3). Pooled serum samples from participants of NHANES 2001 to 2002, based on age and demographics had perfluoro-n-nonanoic acid concentrations of 0.7-15.2 and 0.6-1.4 ng/mL in 3-5 and 6-11 year olds, respectively(4). The concentration of perfluoro-n-nonanoic acid in the serum of 20 Atlanta, GA residents was 1.3 to 4.4 ng/mL, samples were collected July 2003(6). Perfluoro-n-nonanoic acid was not detected (detection limit 1.0 ng/mL) in two human milk samples, collection information was not provided(6).|Perfluoro-n-nonanoic acid levels in New York State infants using Newborn Screening Programs dried blood spots analysis(1).[Table#8026]|Perfluoro-n-nonanoic acid concentration was <0.050 ng/mL (1977), increased to 1.7 ng/mL (1986), and then stabilized at 0.55 to 1.2 ng/mL (1988-2006) in 24 pooled serum samples from men, age 40 to 50 years, representing 1977 to 2006(1). Perfluoro-n-nonanoic acid was found in 40 pooled serum samples collected from 3802 Australian residents collected Nov 2002 to April 2003 at 0.4 to 2.0 ng/mL(2). Perfluoro-n-nonanoic acid was detected in 61 of 66 human blood samples collected from 11 counties in Sweden during the period of 1997 to 2000, concentrations were <0.1-1.9 ng/mL(3). From March to Sept 2008, 138 human blood samples were taken from donors from seven cities in Liaoning province, China, perfluoro-n-nonanoic acid was detected as follows - city (ng/mL): Fuxin (0.24-2.2), Jinzhou (<0.013-1.8), Shenyang (<0.013-1.75), Anshan (0.16-1.02), Yingkou (0.17-2.88), Dalian (0.16-1.44) and Huludao (0.16-1.58)(4). In 12 sets of maternal serum, cord serum and milk samples from mothers that gave birth at the National Hospital in Torshavn, Faroe Islands, the average concentrations of perfluoro-n-nonanoic acid were 0.76 and 0.37 ng/mL in maternal and cord serum, it was not detected in transitional milk samples taken 3-5 days after delivery(5). From 2006 to 2008, 233 human blood samples were taken from donors from the capital cities of 12 provinces or districts of China, perfluoro-n-nonanoic acid was detected as follows - city (ng/mL): Harbin (0.522), Hohhot (0.429), Lanzhou (0.545), Taiyuan (0.221), Shijiazhuang (0.852), Qingdao (0.657), Ningbo (0.984), Changsha (0.295), Chengdu (0.430), Chongqing (0.564), Kumming (3.39) and Guizhou (2.29)(6). Perfluoro-n-nonanoic acid was detected in 100% of 84 pools of human blood serum taken from 2420 Queensland, Australia donors in 2006 to 2007, concentrations reported were 0.1-1.4 ng/mL(7). Human blood samples from volunteer donors from five Chinese cities (Shenyang, Beijing, Gulyang, Jintan, Nanjing) collected in 2004 had perfluoro-n-nonanoic acid concentrations of 0.0630 to 1.34 ng/mL(8).|Concentration of perfluoro-n-nonanoic acid in adult (age 19-62) human blood, 15 samples from each category, taken from citizens of Gdansk, Poland and nearby villages. Blood donations were all collected July 2003(1).[Table#8027]|For more Body Burden (Complete) data for Perfluoro-n-nonanoic acid (9 total), please visit the HSDB record page.
Drug Information
Using nuclear magnetic resonance (NMR) spectroscopy, we investigated the importance of carbon chain length with regard to the hepatic effects associated with perfluoro-n-carboxylic acids. Male F-344 rats were administered a single intraperitoneal dose of either perfluoro-n-heptanoic acid (C7-PFA), perfluoro-n-nonanoic acid (C9-PFA), or perfluoro-n-undecanoic acid (C11-PFA). Data from previous studies involving perfluoro-n-octanoic acid (C8-PFA) and perfluoro-n-decanoic acid (C10-PFA) are included for comparison. Food consumption/body weight was monitored daily for all groups. C9- and C11-PFA treatment yields a prolonged hypophagic response while C7-PFA shows a more acute response. Fluorine-19 NMR spectra of urine and bile samples show no evidence of fluorometabolites and suggest that the distribution of perfluorocarbons into urine or bile is dependent upon carbon chain length. The aqueous solubility of C7-PFA appears to facilitate rapid urinary excretion, similar to that observed for C8-PFA. The relative hydrophobicity of C9- and C11-PFA appears to favor biliary enterohepatic recirculation, yielding a more protracted toxicity, similar to C10-PFA. Phosphorus-31 NMR studies of liver in vivo and liver extracts show that perfluorocarbons of > or = C9 carbons produce a significant increase in liver phosphocholine concentration. These data are discussed with regard to the impact of these chemicals on hepatic phospholipid metabolism. Hepatic peroxisomal fatty acyl CoA-oxidase activity (FAO) was measured to determine if C7-, C9-, and C11-PFA are peroxisome proliferators. Data indicate that the induction of peroxisomal enzyme activity by perfluorocarbons requires a chain length greater than seven carbons. In general, these results demonstrate the significance of carbon chain length in the hepatotoxic response and provide clues toward understanding the processes involved in the biological activities associated with exposure to these compounds.|Perfluorononanoic acid (PFNA) is a fluorinated organic chemical found at low levels in the environment, but is detectable in humans and wildlife. The present study compared the pharmacokinetic properties of PFNA in two laboratory rodent species. ... CD-1 mice were given a single oral dose of PFNA of 1 or 10mg/kg, and 4 males and 4 females were killed at /1, 2, 3, 4, 7, 16, 21, 28, 35, 42 and 50 days after treatment/; trunk blood, liver and kidney were collected. Serum and tissue concentrations of PFNA were determined by LC-MS/MS. ... In the mouse, the rates of PFNA serum elimination are non-linear with exposure dose and are slightly faster in females than males, with terminal estimated serum half-life of 25.8-68.4 days and 34.3-68.9 days, respectively. PFNA is also stored preferentially in the mouse liver but not in the kidneys. Hepatic uptake appears to be more efficient and storage capacity greater in male mice than in females. These data suggest that (1) PFNA is more persistent in the mouse than in the rat; (2) there is a major sex difference in the serum elimination of PFNA in the rat, but much less so in the mouse; and (3) there is a significantly higher hepatic accumulation of PFNA in male mice than in females.|Perfluorononanoic acid (PFNA) is a fluorinated organic chemical found at low levels in the environment, but is detectable in humans and wildlife. The present study compared the pharmacokinetic properties of PFNA in two laboratory rodent species. Male and female Sprague-Dawley rats were given a single dose of PFNA by oral gavage at 1, 3, or 10mg/kg, and blood was collected from the tail vein at 1, 2, 3, 4, 7, 16, 21, 28, 35, 42 and 50 days after treatment. In addition, livers and kidneys were collected for PFNA analysis at the terminal time point. ... Serum and tissue concentrations of PFNA were determined by LC-MS/MS. Serum elimination of PFNA is by and large linear with exposure doses in the rat; however, like PFOA, a major sex difference in the rate of elimination is observed, with an estimated half-life of 30.6 days for males and 1.4 days for females. PFNA is stored preferentially in the liver but not in the kidneys. ... These data suggest that (1) PFNA is more persistent in the mouse than in the rat; (2) there is a major sex difference in the serum elimination of PFNA in the rat, but much less so in the mouse; and (3) there is a significantly higher hepatic accumulation of PFNA in male mice than in females.
CD-1 mice were given a single oral dose of perfluorononanoic acid (PFNA) of 1 or 10mg/kg, and 4 males and 4 females were killed at /1, 2, 3, 4, 7, 16, 21, 28, 35, 42 and 50 days after treatment./ ... In the mouse, the rates of PFNA serum elimination are non-linear with exposure dose and are slightly faster in females than males, with terminal estimated serum half-life of 25.8-68.4 days and 34.3-68.9 days,|Male and female Sprague-Dawley rats were given a single dose of perfluorononanoic acid (PFNA) by oral gavage at 1, 3, or 10mg/kg, and blood was collected from the tail vein at 1, 2, 3, 4, 7, 16, 21, 28, 35, 42 and 50 days after treatment. ... Serum elimination of PFNA is by and large linear with exposure doses in the rat ... with an estimated half-life of 30.6 days for males and 1.4 days for females.
The potency of the induction of peroxisomal beta-oxidation was compared between perfluorinated fatty acids (PFCAs) with different carbon chain lengths in the liver of male and female rats. In male rats, perfluoroheptanoic acid (PFHA) has little effect, although perfluorooctanoic acid (PFOA), perfluorononanoic acid (PFNA) and perfluorodecanoic acid (PFDA) potentially induced the activity. By contrast, PFHA and PFOA did not induce the activity of peroxisomal beta-oxidation in the liver of female rats while PFNA and PFDA effectively induced the activity. The induction of the activity by these PFCAs was in a dose-dependent manner, and there is a highly significant correlation between the induction and hepatic concentrations of PFCAs in the liver regardless of their carbon chain lengths. These results strongly suggest that the difference in their chemical structure is not the cause of the difference in the potency of the induction. Hepatic concentrations of PFOA and PFNA was markedly higher in male compared with female rats. Castration of male rats reduced the concentration of PFNA in the liver and treatment with testosterone entirely restored the reduction. In contrast to the results obtained from the in vivo experiments, the activity of peroxisomal beta-oxidation was induced by PFDA and PFOA to the same extent in cultured hepatocytes prepared from both male and female rats. These results, taken together, indicate that difference in accumulation between PFCAs in the liver was responsible for the different potency of the induction of peroxisomal beta-oxidation between PFCAs with different carbon chain lengths and between sexes.|Perfluorononanoate (PFNA), a perfluorinated alkyl acid containing nine carbon chains, has been detected in abiotic and biotic matrices worldwide. Although a few studies have reported toxic effects of PFNA, little information of the mechanism has been offered. In this study, the effects of PFNA exposure on thymus and the related mechanisms were investigated. Male rats were orally dosed with 0, 1, 3, or 5 mg PFNA/kg/day for 14 days. A significant decrease of body weight and thymus weight were observed in the rats receiving 3 or 5 mg PFNA/kg/day. Histopathological examination revealed dose-dependent increases in thymocyte apoptosis. Rats receiving 3 or 5 mg PFNA/kg/day exhibited increased interleukin (IL)-1 and decreased IL-2 concentrations in sera, whereas elevated IL-4 and cortisol levels only occurred in the highest dose group. Quantitative real-time PCR indicated that expression of peroxisome proliferator-activated receptor alpha (PPAR-alpha) was increased in the thymi of all dosed rats, and a similar trend occurred for PPAR-gamma in the two highest dose groups. The mRNA levels of c-Jun NH(2)-terminal kinase (JNK), nuclear factor-kappa B, p65 subunit, and inhibitory protein IkappaBalpha were unchanged; however, increased and decreased mRNA levels of p38 kinase were found in rats exposed to 3 or 5 mg PFNA/kg/day, respectively. Decreased Bcl-2 mRNA levels were observed in rats receiving 5 mg PFNA/kg/day. A significant increase in protein levels of phospho-JNK was found in all PFNA-treated rats. Phospho-p38 was significantly enhanced in 1 and 3 mg PFNA/kg/day groups, whereas phospho-IkappaBalpha remained consistent in all rats studied. Together, these data suggested that apart from the activation of PPARs, PFNA exposure in rats lead to the alteration of serum cytokines, which subsequently activated mitogen-activated protein kinase signaling pathways and potentially modulated the immune system. Additionally, increased serum cortisol and decreased expression of Bcl-2 in thymus likely contributed to the PFNA-induced thymocyte apoptosis.|... This study explored the possible involvement of apoptotic signaling pathways in a nine-carbon-chain length PFAA-perfluorononanoic acid (PFNA)-induced splenocyte apoptosis. After a 14-day exposure to PFNA, rat spleens showed dose-dependent levels of apoptosis. The production of pro-inflammatory and anti-inflammatory cytokines was significantly increased and decreased, respectively. However, protein levels of tumor necrosis factor receptor 1 (TNFR1), fas-associated protein with death domain (FADD), caspase 8 and caspase 3, which are involved in inflammation-related and caspase-dependent apoptosis, were discordant. Peroxisome proliferator-activated receptors alpha (PPARalpha) and PPARgamma genes expression was up-regulated in rats treated with 3 or 5 mg/kg/day of PFNA, and the level of hydrogen peroxide (H2O2) increased concurrently in rats treated with the highest dose. Moreover, superoxide dismutase (SOD) activity and Bcl-2 protein levels were dramatically decreased in spleens after treatment with 3 and 5 mg/kg/day of PFNA. However, protein levels of Bax were unchanged. Apoptosis-inducing factor (AIF), an initiator of caspase-independent apoptosis, was significantly increased in all PFNA-dosed rats. Thus, oxidative stress and the activation of a caspase-independent apoptotic signaling pathway contributed to PFNA-induced apoptosis in rat splenocytes.
/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/
/EPIDEMIOLOGY STUDIES/ /The investigators/ analyzed 458 plasma samples of New York State (NYS) employees and National Guard personnel assigned to work in the vicinity of the WTC between September 11 and December 23, 2001, to assess exposure to perfluorochemicals released in dust and smoke. The plasma samples collected from NYS WTC responders were grouped based on estimated levels of exposure to dust and smoke, as follows: more dust exposure (MDE), less dust exposure (LDE), more smoke exposure (MSE), and less smoke exposure (LSE). Furthermore, samples were grouped, based on self-reported symptoms at the time of sampling, as symptomatic and asymptomatic. Eight perfluorochemicals were measured in 458 plasma samples. PFOS, PFOA, perfluorohexanesulfonate (PFHxS), and perfluorononanoic acid (PFNA), were consistently detected in almost all samples. ... Concentrations of PFNA were significantly higher in the MSE group than in the LSE group. ... A significant negative correlation existed between plasma lipid content and concentrations of certain perfluorochemicals. ...|/BIOMONITORING/ /Reaserchers/ studied occurrence and levels of PFCs in human milk in relation to maternal serum together with the temporal trend in milk levels between 1996 and 2004 in Sweden. Matched, individual human milk and serum samples from 12 primiparous women in Sweden were analyzed together with composite milk samples (25-90 women/year) from 1996 to 2004. Eight PFCs were detected in the serum samples, and five of them were also above the detection limits in the milk samples. Perfluorooctanesulfonate (PFOS) and perfluorohexanesulfonate (PFHxS) were detected in all milk samples at mean concentrations of 0.201 ng/mL and 0.085 ng/mL, respectively. Perfluorooctanesulfonamide (PFOSA), perfluorooctanoic acid (PFOA), and perfluorononanoic acid (PFNA) were detected less frequently. The total PFC concentration in maternal serum was 32 ng/mL, and the corresponding milk concentration was 0.34 ng/mL. The PFOS milk level was on average 1% of the corresponding serum level. There was a strong association between increasing serum concentration and increasing milk concentration for PFOS (r(2) = 0.7) and PFHxS (r(2) = 0.8). PFOS and PFHxS levels in composite milk samples were relatively unchanged between 1996 and 2004, with a total variation of 20 and 32% coefficient of variation, respectively. The calculated total amount of PFCs transferred by lactation to a breast-fed infant in this study was approximately 200 ng/day. Lactation is a considerable source of exposure for infants, and reference concentrations for hazard assessments are needed.
C9-PFA
Perfluorononanoic acid Use and Manufacturing
Long-chain perfluorocarboxylic acids are prepared by the Simons electrochemical fluorination of the corresponding acyl halide ... The acids are obtained by hydrolysis of the perfluoroacyl fluoride, followed by distillation. Some carbon-carbon bond scission occurs to form lower homologous acids along with inert fluorocarbons and cyclic ethers. The acid yield decreases with increasing chain length. /Long-chain perfluorocarboxylic acids/
Perfluorinated compounds (PFCs) are persistent in environments due to the high energy of C-F bond routes. PFNA may interfere in a toxic fashion on the immune system, liver, development, and endocrine systems.
Nonanoic acid, 2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-heptadecafluoro-: ACTIVE|S - indicates a substance that is identified in a final Significant New Use Rule.
PFAS (per- and polyfluoroalkyl substances) -> OECD Category|PFAS
Computed Properties
Molecular Weight:464.08
XLogP3:5.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:19
Rotatable Bond Count:7
Exact Mass:463.9705080
Monoisotopic Mass:463.9705080
Topological Polar Surface Area:37.3
Heavy Atom Count:28
Complexity:615
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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