Grundinformationen
- Standard-SMILES
O=C(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- InChIKey
UZUFPBIDKMEQEQ-UHFFFAOYSA-N- Summenformel
- C8F17COOH
- Durchschnittliche Molmasse
- 464,08 g/mol
- Monoisotopische Masse
- 463,97050901
Überblick
Perfluorononanoic acid (PFNA) and its salts can cause male reproductive toxicity according to an independent committee of scientific and health experts.
Namen und Bezeichner
- Bevorzugter Name
- Perfluorononanoic acid
- IUPAC
- 2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-heptadecafluorononanoic acid
- Lokaler Name
- Perfluornonan-1-sure
- Englischer Name
- Perfluorononanoic acid
- Summenformel
- C9HF17O2
- Molmasse
- 464.08
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
375-95-1- PubChem CID
- 67821
- DTXSID
DTXSID8031863- ChEMBL
CHEMBL426404- ChEBI
CHEBI:38397- UNII
- 5830Z6S63M
- EC Number
- 206-801-3
- Nikkaji
- J213.586H
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 5,6
- Polarare Oberfläche (TPSA)
- 37,3 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 19
- Frei drehbare Bindungen
- 7
- Schwere Atome
- 28
- Formalladung
- 0
- Komplexität
- 615
Experimentelle und physikochemische Eigenschaften
Chemical Classes
Other Classes -> Perfluoroalkyl Acids
Ionic Liquids -> Fluorinated Ionic Liquids
Ionic Liquids
PFAS
PFAS -> Perfluorocarboxylic acids
PFAS
PFAS -> OECD Category
PFAS -> Perfluoroalkyl acids (PFAAs)
PFAS -> PFcarboxylic acids (PFCA)
PFAS -> Other/unspecified
Vapor Pressure
0.08 [mmHg]
-0.18 ± 0.01 [log Psd at 298.15 K (Pa)]
Collision Cross Section
147.0 Ų [M-H-CO2]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: PFAS]
240.71 Ų [2M-H]-
Physikochemische Eigenschaften
- Schmelzpunkt
- 59 · 59-62 °C (lit.)
- Siedepunkt
- 218 °C · 218°C
- Dichte
- 1.7397 · 1.7397 (estimate)
- Flammpunkt
- 218 °C · 218°C
- storage temp.
- Refrigerator
- Löslichkeit
- Acetone (Slightly), DMSO (Slightly), Methanol (Slightly)
- pka
- 0.52 · 0.52±0.10(Predicted)
- Aggregatzustand
- Solid
- Farbe
- Off-White to Beige
- BRN
- 1897287 · 1897287
- Henry's Law Constant
- 4.3 · 4.3×10-2 mol/(m3Pa) at 25℃, Arp et al. (2006)
- Stabilität
- Stable. Incompatible with strong bases, strong oxidizing agents. Corrosive - causes burns.
- InChI
- InChI=1S/C9HF17O2/c10-2(11,1(27)28)3(12,13)4(14,15)5(16,17)6(18,19)7(20,21)8(22,23)9(24,25)26/h(H,27,28)
- InChIKey
- UZUFPBIDKMEQEQ-UHFFFAOYSA-N
- SMILES
- C(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
- CAS Datenbank
- 375 · 375-95-1(CAS DataBase Reference)
- EPA chemische Informationen
- Perfluorononanoic acid (375-95-1)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Danger
H302: Harmful if swallowed [Warning Acute toxicity, oral]
P203, P260, P261, P263, P264, P264+P265, P270, P271, P280, P301+P317, P304+P340, P305+P354+P338, P317, P318, P319, P330, P405, and P501 (click each P-code to see the statement)
Danger
H314 (12.2%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
P260, P261, P264, P264+P265, P271, P280, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P319, P321, P332+P317, P337+P317, P362+P364, P363, P403+P233, P405, and P501 (click each P-code to see the statement)
Gefahrenhinweise
Regulatory Information
Hazard Traits - Bioaccumulation; Carcinogenicity; Developmental Toxicity; Endocrine Toxicity; Environmental Persistence; Hepatotoxicity and Digestive System Toxicity; Immunotoxicity; Reproductive Toxicity
S - indicates a substance that is identified in a final Significant New Use Rule.
Restricted substance: Perfluorononan-1-oic acid
Substance: Perfluorononan-1-oic-acid
Hazards Summary
Causes changes in spleen, inflammation, changes in blood serum composition, androgenic and estrogenic effects, and effects on enzymes in acute oral studies of rats; [RTECS] A skin and strong eye irritant; [Sigma-Aldrich MSDS] Serum PFAS concentrations were not associated with increased cardiometabolic risk measures in this population of firefighters. [PMID 33105404] See Perfluorodecanoic acid. See Perfluorooctane sulfonic acid.
Clean Water Act Requirements
Monitoring requirements for unregulated contaminants. This section specifies the monitoring and quality control requirements that must be followed if you own or operate a public water system (PWS) that is subject to the Unregulated Contaminant Monitoring Regulation (UCMR), as specified in paragraphs (a)(1) and (2) of this section. Perfluorononanoic acid (PFNA) is included on this list.
Hazard Classes and Categories
Skin Corr. 1C (12.2%)
Carcinogenicity - category 2
Reproductive toxicity - Category 1B, Additional category: Effects on or via lactation
Specific target organ toxicity - Repeated exposure - Category 1 (genetic organs (women))
Reproductive toxicity - Category 1B, Additional category for effects on or via lactation
Carc. 2
Sicherheit und Schutzausrüstung
Disposal Methods
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.
Toxikologische Informationen
Body Burden
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#8014]
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#8015]
For more Body Burden (Complete) data for Perfluoro-n-nonanoic acid (9 total), please visit the HSDB record page.
Environmental Fate
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).
Food Survey Values
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#8023]
Concentration of perfluoro-n-nonanoic acid in terrestrial traditional Inuit foods collected between 1997 and 1999 in Nunavut, Canada(1).[Table#8024]
Milk Concentrations
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#8025]
Ecotoxicity Excerpts
/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/
Animal Concentrations
The mean concentration of perfluoro-n-nonanoic acid in herring gull eggs collected in 2007 from 15 colonies in the Laurentian Great Lakes (Granite, Big Sister, Gull, Channel-Shelter, Double, Chantry, Fighting, Middle, Snake and Strachan Islands, Agawa Rocks, Port Colborne, Niagara River, Hamilton and Toronto Harbor) was 0.64-9.6 ng/g wet weight(1). Archived liver samples for northern sea otters (Enhydra lutris kenyoni) from south-central Alaska had perfluoro-n-nonanoic acid concentrations of 1.3, <0.9, 8.0, 3.4, 2.8, 2.1, 1.9, 2.3, 6.0, 5.6, 5.9, <2.0, 3.9, 4.3 and 9.4 ng/g wet weight in 1992, 1993, 1994, 1996, 1997, 1998, 1999, 2000, 2001, 2002, 2003, 2004, 2005, 2006 and 2007, respectively(2). An average concentration of 2.1 ng/g wet weight (range <1-16 ng/g wet weight) of perfluoro-n-nonanoic acid was found in 80 female sea otters from the California coast samples from 1992 to 2002(3). Perfluoro-n-nonanoic acid was detected at 0.07-3.0 ng/g wet weight in little brown bats (Myotis lucifugus) that had signs of white nose syndrome, collected from caves in eastern New York State from Feb to March 2008(4). Perfluoro-n-nonanoic acid was detected in serum samples from 58 of 73 loggerhead turtles at <100-4420 pg/mL and in all six Kemp's ridley sea turtles at 258-6500 pg/mL, turtles were caught off the US southeastern coast(5). Eider duck and white winged scoter liver samples, collected from the Hudson Bay region of northeastern Canada, May to Sept 1999 to 2003, contain perfluoro-n-nonanoic acid at <0.02-1.1 and 0.24-27.3 ng/g wet weight, respectively(6). Perfluoro-n-nonanoic acid was detected in 26 of 27 beluga whale liver samples at <0.502-5.67 ng/g, collected from Cook Inlet, AK from 1992 to 2006 and in 38 of 41 beluga whale liver samples at <0.180-5.46 ng/g, collected from Chukchi Sea, AK from 1989 to 2000(7).
Reported perfluoro-n-nonanoic acid concentrations in beluga whales collected from the Hudson Bay region of northeastern Canada, May to Sept 1999 to 2003(1).[Table#8005]
Perfluoro-n-nonanoic acid concentrations in plasma of free-range bottlenose dolphins from the Gulf of Mexico and the Atlantic Ocean were studied June to Sept 2003(1).[Table#8006]
Perfluoro-n-nonanoic acid was detected in all the marine mammal (grey seal, minke whale, pilot whale) samples taken from Sweden, Denmark, Iceland and the Faeroe Islands(1). Perfluoro-n-nonanoic acid was detected in thick-billed murres collected 1975 (5 samples), 1993 (10 samples) and 2004 (10 samples) at 0.02-0.16, 0.01-0.24 and 0.07-0.60 ng/g wet weight, respectively, and in northern fulmars collected 1975 (9 samples), 1987 (8 samples), 1993 (10 samples) and 2003 (9 samples) at concentrations of <0.19, 0.02-0.97, 0.03-0.44 and 0.01-0.09 ng/g wet weight, respectively, all waterfowl were from Prince Leopold Island, Nunavut, Canada(2). Perfluoro-n-nonanoic acid was not detected (detection limit 7.6 ng/g dry weight) in liver samples of Tucuxi dolphins (Sotalia guianensis), samples were taken from 23 dolphins from Guanabara Bay and six were collected off the coast of Rio de Janeiro state, Brazil at other locations(3). Blood samples from 16 eider duck (Sommateria mollisima), collected from the Gulf of Gdansk in Feb 2003, contained perfluoro-n-nonanoic acid at 300-900 pg/mL(4). The concentration of perfluoro-n-nonanoic acid in melon headed whales stranded along the Japanese coast was <1.1 ng/g wet weigh in 1982, 5.2-15.5 ng/g wet weight in 2001/2002 and 9.5-20.5 ng/g wet weight in 2006(5). Perfluoro-n-nonanoic acid was not detected in 10 guillemot egg samples collected from Vestmannaeyjar, Iceland, Sandoy Faroe, Islands, Sklinna and Hjelmsoy, Norway but was detected in five of 10 egg samples collected from Stora Karlso, Sweden at <32 to 120 ng/g wet weight, samples were collected in 2005(6). Dolphin samples from Paraiba do Sul River, Brazil had perfluoro-n-nonanoic acid concentrations of <0.49-1.70, <1.46-1.60 and <1.76 ng/g wet weight in liver, muscle and kidney tissue, respectively(7). Liver samples from 29 polar bear captured in eastern Greenland contained a mean concentration of 236 ng/g wet weight of perfluoro-n-nonanoic acid(8). The mean concentration of perfluoro-n-nonanoic acid was 12.2 to 540 ng/g wet weight in liver tissue from polar bears collected at seven locations in the North American and European Arctic(9). Harbor porpoises from the Black Sea coast, collected 1997 and 1998, contained perfluoro-n-nonanoic acid at 1.4-7.2 ng/g wet weight(10). Perfluoro-n-nonanoic acid was detected in the egg yolks of 17 little ringed plover at 6.4-106.7 ng/g wet weight, seven parrot bill at 5.7-97.3 and 20 little egret at 3.9-68.6 ng/g wet weight, samples were collected around Lake Shihwa, Korea in May 2006(11).
For more Animal Concentrations (Complete) data for Perfluoro-n-nonanoic acid (11 total), please visit the HSDB record page.
Ongoing Test Status
The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical.[Available from, as of June 21, 2012: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=375-95-1]
Effluent Concentrations
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).
Soil Adsorption/Mobility
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).
Atmospheric Concentrations
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).
Human Toxicity Excerpts
/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.
Regulatorische Informationen
Clean Water Act Requirements
Monitoring requirements for unregulated contaminants. This section specifies the monitoring and quality control requirements that must be followed if you own or operate a public water system (PWS) that is subject to the Unregulated Contaminant Monitoring Regulation (UCMR), as specified in paragraphs (a)(1) and (2) of this section. Perfluorononanoic acid (PFNA) is included on this list.
Sicherheitsdaten
- wgk
- 3
- tsca
- TSCA listed
- ridadr
- UN3261
- hs_code
- 29159000
- risk_code
- 36/37/38
- hazard_code
- Xi
- hazard_note
- Corrosive
- safety_code
- 26-36
- hazard_class
- 8
- packing_group
- III
- Speicherklasse
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Giftige Stoffe Daten
- 375-95-1(Hazardous Substances Data)
- Hazard Classifications
- Acute Tox. 4 InhalationAcute Tox. 4 OralCarc. 2Lact.Repr. 1BSTOT RE 1
Chemie und Industrie
Pharmakologische Informationen
Mechanism of Action
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.
Biological Half-Life
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.
Absorption, Distribution and Excretion
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.
Verwendung und Herstellung
Uses
Used as a surfactant; [HSDB] Used mainly as a processing aid in the manufacture of fluoropolymers; Also as a lubricating oil additive, surfactant for fire extinguishers, cleaning agent, textile finishing agent, polishing surfactant, and in liquid crystal display panels; [ExPub: ECHA - Proposal for Harmonised Classification and Labelling]
Textiles (Printing, Dyeing, or Finishing) [Category: Industry]
Long-chain perfluoroalkanecarboxylic acids and their salts are surface-active chemicals (surfactants), which greatly reduce the surface tension (surface energy) of water, aqueous solutions, and organic liquids even at low concentrations. These acids (C6- C12) and derivatives are used as wetting, dispersing, emulsifying, and foaming agents. /Long-chain perfluoroalkanecarboxylic acids/
non-polymer PFAS -> Textile and upholstery -> Textile and upholstery
• Detected in ski wax [Ref: Plassmann2013]
Perfluorononanoic acid, or PFNA, is a synthetic perfluorinated carboxylic acid and fluorosurfactant that is also an environmental contaminant found in people and wildlife along with PFOS and PFOA.
Methods of 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/
Use Classification
PFAS -> PFcarboxylic acids (PFCA)
PFAS (per- and polyfluoroalkyl substances) -> OECD Category
PFAS
Anwendungen
VerwendenPerfluorinated 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.
Anbieter50 Anbieter
Ergänzende Hinweise
DefinitionChEBI: 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 is functionally related to a nonanoic acid.
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