Perfluornonan-1-sure

Perfluorononanoic acid

HCID 67821CAS 375-95-1

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

Perfluorononanoic acid375-95-1heptadecafluorononanoic acidPerfluoro-n-nonanoic acid2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-Heptadecafluorononanoic acidHeptadecafluoropelargonic AcidPerfluorononan-1-oic acidPerfluornonansaeureHeptadecafluornonansaeureHeptadekafluornonansaeureDTXSID80318635830Z6S63M
Weitere Namen anzeigen
PFNAHeptadecperfluorononanoicHic-BWGPERFLUOROPELARGONIC ACIDPerfluorononanoicacid98%
Perfluorononanoic acid (PFNA)CHEBI:38397Nonanoic acid, 2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-heptadecafluoro-RefChem:860227PFNA perfluorononanoic acid21049-39-8 (Na salt)60871-92-3 (Li salt)21049-38-7 (K salt)

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

Experimentelle und physikochemische Eigenschaften

Chemical Classes · 3 Einträge

Other Classes -> Perfluoroalkyl Acids

Ionic Liquids -> Fluorinated Ionic Liquids

Ionic Liquids

PFAS · 6 Einträge

PFAS -> Perfluorocarboxylic acids

PFAS

PFAS -> OECD Category

PFAS -> Perfluoroalkyl acids (PFAAs)

PFAS -> PFcarboxylic acids (PFCA)

PFAS -> Other/unspecified

Endocrine DisruptorsPotential endocrine disrupting compound
Vapor Pressure · 2 Einträge

0.08 [mmHg]

-0.18 ± 0.01 [log Psd at 298.15 K (Pa)]

Physical DescriptionBeige crystalline solid; [Sigma-Aldrich MSDS]
Dissociation ConstantspKa = -0.21

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)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

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 · 4 Einträge

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 · 1 Eintrag

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 · 1 Eintrag

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 · 6 Einträge

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 · 1 Eintrag

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 · 5 Einträge

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 · 3 Einträge

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 · 3 Einträge

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 · 3 Einträge

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]

Average Daily IntakeThe average daily intake of perfluoro-n-nonanoic acid in Canadians in the late 1990s ranged from 0.5 to 1.2 ng/kg of body weight/day, in 2004 the estimated value was 1.1 ng/kg of body weight/day(1).
Ecotoxicity Excerpts · 1 Eintrag

/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/

Regulatorische Informationen

Clean Water Act Requirements · 1 Eintrag

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

Chemie und Industrie

Pharmakologische Informationen

Mechanism of Action · 3 Einträge

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 · 2 Einträge

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.

MeSH Pharmacological ClassificationSubstances or energies, for example heat or light, which when introduced into the air, water, or land threaten life or health of individuals or ECOSYSTEMS.
Absorption, Distribution and Excretion · 3 Einträge

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 · 6 Einträge

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 · 1 Eintrag

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 · 3 Einträge

PFAS -> PFcarboxylic acids (PFCA)

PFAS (per- and polyfluoroalkyl substances) -> OECD Category

PFAS

General Manufacturing InformationNonanoic acid, 2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-heptadecafluoro-: ACTIVE

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.

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Ergänzende Hinweise · 1 Eintrag

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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