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Home > Encyclopedia > Perfluoroheptanoic acid

Perfluoroheptanoic acid

Perfluoroheptanoic acid structure

Perfluoroheptanoic acid 

structure
  • CAS No:

    375-85-9

  • Formula:

    C7HF13O2

  • Chemical Name:

    Perfluoroheptanoic acid

  • Synonyms:

    Heptanoic acid,2,2,3,3,4,4,5,5,6,6,7,7,7-tridecafluoro-;Heptanoic acid,tridecafluoro-;2,2,3,3,4,4,5,5,6,6,7,7,7-Tridecafluoroheptanoic acid;Perfluoroenanthic acid;Perfluoroheptanoic acid;Tridecafluoroheptanoic acid;Perfluoro-n-heptanoic acid;PFHpA

  • Categories:

    Organic Chemistry  >  Carboxylic Acids and Derivatives

Description

Perfluoroheptanoic acid is a white solid under ambient conditions, but it has a relatively low melting point (Huang, et al., 1987). In comparison, the C6 homologue, PFHxA, and other short-chain perfluorocarboxylic acids are volatile liquids (NICNAS, 2015a). The C8 homologue is also a solid under ambient conditions, although it has a relatively low sublimation temperature of 40°C (Kaiser, et al., 2010). Based on the properties of this long-chain homologue, solid PFHpA may sublime under ambient c


Perfluoroheptanoic acid is a fluoroalkanoic acid that is perfluorinated heptanoic acid. It has a role as a xenobiotic and an environmental contaminant. It derives from a perfluoroheptane and a heptanoic acid.

Perfluoroheptanoic acid Basic Attributes

364.06

364.06

1808210

206-798-9

DTXSID1037303

Beige crystalline solid|Low melting solid

2915900090

Characteristics

37.3

4.3

Clear colorless to pale yellow Liquid After Melting

1.7±0.1 g/cm3

31-36 °C @ Solvent: Carbon tetrachloride

177 °C

>230 °F

1.289

Insoluble in water.

Keep container tightly closed in a dry and well-ventilated place.

0.133 mm Hg at 25 deg C

Henry's Law constant = 0.017 atm-cu m/mole at 25 °C (est)

pKa = -2.29 (est)

147.61 Ų [M-H]-

Hydroxyl radical reaction rate constant = 5.2X10-13 cu cm/molecule-sec at 25 °C (est)

Safety Information

8

UN 3261 8/PG 2

3

22-34

26-36/37/39-45

C

Corrosive

Stable. Incompatible with strong bases.

P280-P305 + P351 + P338-P310

H302-H314

SRP: 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 air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.|Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber; Contaminated packaging: Dispose of as unused product.

Incompatible materials: Strong oxidizing agents

|Danger|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P260, P261, P264, P270, P271, P280, P281, P301+P312, P304+P340, P305+P351+P338, P308+P313, P310, P311, P314, P321, P330, P403+P233, P405, and P501|P260, P264, P270, P280, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P330, P363, P405, and P501

Eye/face protection: Face shield and safety glasses. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).|Skin protection: Handle with gloves.|Body Protection: Complete suit protecting against chemicals. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.|Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face particle respirator type N100 (US) or type P3 (EN 143) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.|Advice for firefighters: Wear self contained breathing apparatus for fire fighting if necessary.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust; Environmental precautions: Do not let product enter drains; Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.

Precautions for safe handling: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed. Normal measures for preventive fire protection.|Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.|Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.|SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.

Perfluoroheptanoic acid was detected in 14 urban (Albany, NY) surface water runoff samples at <0.25-6.44 ng/L; samples were collected Jan to March 2007(1). Perfluoroheptanoic acid was detected in influent and effluent samples collected from 10 wastewater treatment facilities located throughout the US at not detected to 25 and not detected to 23 ng/L, respectively(2). Perfluoroheptanoic acid was detected in untreated wastewater, wastewater effluent and surface runoff samples from Tokyo Bay(3). Samples of effluent from three sewage treatment plants located in the Tsurumi River region of Japan contained 5.5-7.2 ng/L of perfluoroheptanoic acid; samples were collected Jan to March 2006(4). Samples of effluent from 13 sewage treatment plants located in the Hayabuchi River region of Japan contained 3.3-19.1 ng/L of perfluoroheptanoic acid; samples were collected Jan 9, 2007(5). Perfluoroheptanoic acid was detected in 94% of effluent samples collected from 90 European wastewater treatment plants at 1-2962 ng/L (average 82.9 ng/L, median 5.1 ng/L); samples were collected 2010(6). Perfluoroheptanoic acid was detected in samples from urban canals, drainage canals, influent and effluent samples from wastewater treatment plants in Shenyang, China at 2.56-4.90, 1.28-146, 3.14-17.9 and 1.60-24.2 ng/L, respectively; samples were collected July to Sept 2009(7). Influent and effluent samples from two municipal wastewater treatment plants contained 0.8-1.9 and <0.1 ng/L perfluoroheptanoic acid, respectively; the effluent from an industrial wastewater treatment plant contained 14.5 ng/L perfluoroheptanoic acid; all plants are located in Taipei, Taiwan(8).|Perfluoroheptanoic acid concentrations in the influent or effluent samples from waste water treatment plants along the Glatt Valley Watershed, Switzerland were reported; all samples were collected Feb to March 2006(1).[Table#8301]

SEDIMENT: Perfluoroheptanoic acid was detected in sediment samples collected in 2003, 2006 and 2009 from Etobicoke Creek (Toronto, Canada) at <0.05-0.1, <0.05-0.6 and <0.1 ng/g dry weight, respectively(1). Sediment samples from Resolute, Char and Amituk lakes on Cornwallis Island, Nunavut, Canada contained perfluoroheptanoic acid at <0.18-7.5, <3.3 and <2.9-3.0 ng/g dry weight, respectively(2). Perfluoroheptanoic acid was detected in some of the 23 sediment samples collected Dec 29-30, 2008 from the Haihe River, China(3). Perfluoroheptanoic acid was detected in 1 of 7 sediment samples from the Guanting Reservoir, China at 0.35 ng/g dry weight; samples were collected May of 2008(4). Perfluoroheptanoic acid was not detected (detection limit 0.05 ng/g dry weight) in nine sediment samples collected from the Hudson Bay region of northeastern Canada, during the months of May to Sept between 1999 and 2003(5). SOIL: Perfluoroheptanoic acid was detected in 86 soil samples collected Dec 29-30, 2008 from suburban districts of Tianjin, China at <0.1-0.92 ng/g dry weight(3). Perfluoroheptanoic acid was detected in 2 of 7 soil samples from around the Guanting Reservoir, China at 0.11 and 1.2 ng/g dry weight; samples were collected May of 2008(4).

URBAN/SUBURBAN: Perfluoroheptanoic acid was detected in gas and particulate phase atmospheric samples from locations in Albany, NY at 0.13-0.42 and <0.12-0.81 pg/cu m, respectively; samples were taken May to July 2006(1). Perfluoroheptanoic acid was detected at 0.33-2.5 pg/cu m in outdoor air samples from six homes in Vancouver, Canada, samples were collected 2007 to 2008(2).|INDOOR: Perfluoroheptanoic acid was not detected in 40 indoor air samples from Oslo, Norway households(1). Perfluoroheptanoic acid was detected at <0.33-69 pg/cu m in indoor air samples from 59 homes in Vancouver, Canada; samples were collected 2007 to 2008(2). Perfluoroheptanoic acid was not detected in air samples from seven homes and one office; samples were collected the winter of 2007 to 2008 from locations in Tromso, Norway(3).

In food packaging materials collected from Greek markets, perfluoroheptanoic acid was not detected (detection limit 0.40 ng/g) in eight beverage cups, one ice cream cup, eight fast food paper boxes, two paper materials for baking and 14 foil bags/wrappers; it was detected at <0.40-10.02 and <0.40-5.19 ng/g in six fast food wrappers and three microwave bags, respectively(1). Perfluoroheptanoic acid was not detected in pre-treated carpet or thread sealant tapes and pastes purchased 2007-2011, but was detected in microwave cooking bags and mattress pads at respective averages of 1730 and 5.45 ng/g product(2). Perfluoroheptanoic acid was also detected at unreported concentrations in commercial carpet-care liquids, treated apparel, treated home textile and upholstery, treated non-woven medical garments, treated floor waxes and stone/wood sealants, treated food contact paper and membranes for apparel(2).|Dust samples were collected from 102 homes and 10 daycare centers in North Carolina and Ohio from 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, perfluoroheptanoic acid was detected in 74.1% of the samples at a mean, median and maximum concentration of 109, 50.2 and 1150 ng/g, respectively(1). Perfluoroheptanoic acid was detected at <0.55-1561 ng/g in dust samples from 140 homes in Vancouver, Canada, samples were collected 2007 to 2008(2). Perfluoroheptanoic acid was detected in 5 of 41 dust samples from Norwegian households at 4.5-28 ng/g(3). The mean concentration of perfluoroheptanoic acid in dust samples from seven homes and one office were 9.2 and 13.2 ng/g, respectively; samples were collected the winter of 2007 to 2008 from locations in Tromso, Norway(4). Perfluoroheptanoic acid was found in indoor dust samples with a mean value of 14 ng/g dry weight and a range of <0.17 to 43.1 ng/g dry weight, samples were collected Jan to Feb 2009 from 12 homes, 11 offices and five dorm rooms in Nanchang, Shanghai, Beijing and Tianjin, China(5). Perfluoroheptanoic acid was not detected on window film in a suburban area on an unsheltered window in the summer, but was detected on film from a sheltered window, it was detected at approximately the same unreported concentration on both sheltered and unsheltered window film in the winter(6).

Toxicity

IDENTIFICATION AND USE: Perfluoroheptanoic acid (PFHpA) is a beige crystalline solid. It is categorized as a long-chain perfluoroalkanecarboxylic acid. These acids and derivatives are used as wetting, dispersing, emulsifying, and foaming agents. HUMAN EXPOSURE AND TOXICITY: Researchers studied 105 men and determined that there was no difference in mean PFHpA levels between those with high testosterone and those with low testosterone. In children, a significant difference in serum levels of PFHpA between those with or without asthma was reported, although median levels were the same. No difference in mean serum levels of PFHpA were reported in women with or without endometriosis. In a study in South Korea, PFHpA was not detected in maternal sera, cord sera, or human milk. ANIMAL STUDIES: The cytotoxicity of PFHpA (among other perfluorinated carboxylic acids) towards two different types of mammalian cell lines and one marine bacteria was investigated. The results show these compounds have a very low acute biological activity. Perfluoroheptanoic acid had no effect on the potency to accumulate triglyceride and induction of peroxisomal beta-oxidation in the liver of male and female rats.

Perfluorochemicals like perfluoroheptanoic 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). Perfluoroheptanoic 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), reported log Koc values of 1.52-2.82(2), indicate that perfluoroheptanoic acid is expected to have very high to low mobility in soil depending on the soil composition(SRC). The estimated pKa of perfluoroheptanoic acid is -2.29(3), indicating that this compound will exist entirely in the anion form in the environment and, therefore, volatilization from moist soil surfaces is not expected to be an important fate process(SRC). Perfluoroheptanoic acid is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.133 mm Hg at 25 °C(4). The concentration of perfluoroheptanoic acid decreased 40% from day 497 to day 546 in soil containing endogenous microbes incubated at 25 °C, indicating degradation may occur(5).|AQUATIC FATE: Based on a classification scheme(1), log Koc values of 1.52-2.82(2), indicate that perfluoroheptanoic acid is expected to adsorb to suspended solids and sediment(SRC). An estimated pKa of -2.29(3) indicates perfluoroheptanoic 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). Perfluoroheptanoic acid is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(4). According to a classification scheme(5), a reported BCF of 0.62 in rainbow trout(6), suggests bioconcentration in aquatic organisms is low(SRC). Perfluoroheptanoic acid biodegraded 40% in soil containing endogenous microbes incubated at 25 °C from day 497 to day 546, indicating that degradation in water may occur(7).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), perfluoroheptanoic acid, which has a vapor pressure of 0.133 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase perfluoroheptanoic 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 5.2X10-13 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Perfluoroheptanoic 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 perfluoroheptanoic acid with photochemically-produced hydroxyl radicals has been estimated as 5.2X10-13 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). Perfluoroheptanoic acid is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). Perfluoroheptanoic 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).

Perfluoroheptanoic acid was not found to bioaccumulate in laboratory experiments using rainbow trout (Onchorynchus mykiss) with a reported BCF of 0.62(1). The predicted biomagnification factor of 0.03 in fish was reported(2). The log BAFs of four whole common shiner (Notropis cornutus) and livers of 16 fish were 1.72-2.63 and 0.49-3.46 L/kg, respectively(3). Based on Arctic food web data collected from the Hudson Bay region of northeastern Canada, during the months of May to Sept between 1999 and 2003, the tropic magnification factor for perfluoroheptanoic acid is 0.75 ng/g protein(4).

The log Koc of perfluoroheptanoic acid was measured in three soils amended with municipal biosolids.The log Koc was 2.22 for a silty clay loam having 3 years of biosold application, log Koc of 2.82 for a fine sand with 3 years of biosolis application, and a log Koc of 1.52 for a silt loam with 1-20 years of biosolid application(1). According to a classification scheme(2), this Koc range suggests that perfluoroheptanoic acid is expected to have very high to low mobility in soil, depending on soil composition. The log Kd in sediment samples was reported as 0.96-1.03(3). The log Koc and log Kd were reported as 2.4-4.0 and 1.1-2.9, respectively, in 26 sediment samples collected along the Haihe River, China; samples were collected April to May 2010(4).

An estimated pKa of -2.29(1) indicates perfluoroheptanoic 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). Perfluoroheptanoic acid is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.133 mm Hg(2).

GROUNDWATER: Perfluoroheptanoic acid was detected at 18 and 149 ug/L in two of four well water samples from fire-training facilities located on Naval Air Station Fallon, NV and at 19, 22 and 38 ug/L in three of four samples from Tyndall Air Force Base, FL(1). Perfluoroheptanoic acid was detected in four of 19 well water samples at 77.2-5220 ng/L, samples were taken around Decatur, AL, from area farms that have a history of being treated with fluorochemical industry impacted biosolids(2). Perfluoroheptanoic acid was detected in 53 samples collected Oct 2007 to Oct 2009 from wells in Tokyo, Japan at <0.25-61 ng/L(3). Perfluoroheptanoic acid was detected in 30% of groundwater samples in Europe(4).|DRINKING WATER: Perfluoroheptanoic acid was detected in 5 samples collected Oct 2007 to Oct 2009 from public sources in Tokyo, Japan at <1.0-4.6 ng/L(1). The concentration of perfluoroheptanoic acid was monitored through a water treatment facility in Amsterdam, The Netherlands; intake concentration from Lek canal was 1.0-2.0 ng/L, finished water concentration was 1.4-3.8 ng/L, concentrations at monitored steps ranged from 0.9 to 4.1 ng/L(2). Perfluoroheptanoic acid was detected in four tap water samples from Amsterdam, The Netherlands at 0.9-1.4 ng/L(3). Perfluoroheptanoic acid was detected at <0.12-0.76 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(4). Perfluoroheptanoic acid was detected in 83% 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(5). Municipal drinking water samples were collected Feb 2008 at 40 different locations from five different zones of Catalonia, Spain, perfluoroheptanoic acid was detected in 17 of the 40 samples at <0.47-18.40 ng/L(6). Perfluoroheptanoic acid concentrations in drinking water samples collected from residential homes and shopping centers in 12 districts of southeastern Brazil were <0.1-2.21 ng/L(7). Perfluoroheptanoic acid was detected in 62% of drinking water samples collected Aug-Nov 2010 from 34 locations across Australia at <0.15-2.54 ng/L(8).|DRINKING WATER: The USEPA Unregulated Contaminant Monitoring Rule (UCMR3) program monitors for 30 contaminants (including perfluoroheptanoic acid) in PWSs (public water systems)(1). All PWSs serving more than 10,000 people and 800 representative PWSs serving 10,000 or fewer people were monitored beginning in January 2013. The April 2016 Data Summary reports that 4,864 systems contained perfluorheptanoic acid, 84 of which were at or above the minimum reporting level (MRL) of 0.01 ug/L(2).|SURFACE WATER: Perfluoroheptanoic acid was detected in lake water samples from locations in Albany, NY at 1.15-12.7 ng/L; samples were taken Feb to Nov 2006(1). Perfluoroheptanoic acid was detected in 16 of 32 surface water samples at 30-8250 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(2). Perfluoroheptanoic acid was 36.8 and 41.2% of the total perfluorocarbon concentration (7.8 and 3.6 ng/L) in 10 Washington state rivers sampled May 6-12 and Sept 8-12, 2008, respectively(3). Perfluoroheptanoic acid was detected in 55.7% of samples from 80 locations throughout the Cape Fear water shed, North Carolina at <0.10-329 ng/L; samples were collected the spring of 2006 and included samples from the Haw, Little, Deep and Cape Fear rivers(4). Perfluoroheptanoic acid was detected at <0.25-10.23 ng/L in samples from 12 locations in Minnesota, Wisconsin and Lake Michigan(5). Perfluoroheptanoic acid was detected in water samples collected in 2003, 2006 and 2009 from Etobicoke Creek, (Toronto, Canada) at 3.8-34.0, <1.0-64.0 and 2.4-9.5 ng/L, respectively(6).|For more Environmental Water Concentrations (Complete) data for Perfluoroheptanoic acid (11 total), please visit the HSDB record page.

Perfluoroheptanoic acid was detected in one of three popcorn packaging paper before and after cooking at 3.2 and 4.3 ng/sq cm, respectively; popcorn was purchased at retail stores in New York, NY in 2005(1). Perfluoroheptanoic acid in was not detected in traditional aquatic (ringed seal, polar bear, beluga, narwhal, bearded seal, walrus, eider duck, black duck, Arctic char, lake trout, clams, seaweed) or terrestrial (caribou, ptarmigan, Arctic hare, snow goose) Inuit foods collected between 1997 and 1999 in Nunavut, Canada(2). Perfluoroheptanoic acid was found at 0.015 ng/g fresh weight in whole milk; all other products (vegetables, pulses, cereals, white fish, seafood, tinned fish, blue fish, pork, chicken, veal, lamb, eggs, dairy products, semi-skimmed milk, fruits, margarine oil) were listed at less than detection limit (detection limits varied); samples were collected July 2006 from local markets, large supermarkets and grocery stores from different locations of Tarragona County, Spain(3). Perfluoroheptanoic acid was detected in four tap water samples from Amsterdam, The Netherlands at 0.9-1.4 ng/L; mixed cola and brewed coffee made from this tap water had perfluoroheptanoic acid concentrations of <0.07-0.71 and <0.11-2.4 ng/L, respectively(4). Perfluoroheptanoic acid was not detected (detection limit 0.13 ng/g) in chicken and duck eggs; not detected (detection limit 0.67ng/g) in pork, beef, duck or goat blood cakes; not detected (detection limit 0.70 ng/g) in pork, beef, chicken, duck or goat liver; not detected (detection limit 0.22 ng/g) in pork, chicken or goat meat; but was detected at 0.15 ng/g in beef meat; food samples were collected Jan to Feb 2009 from local markets and grocery stores in Nanchang, Shanghai, Beijing and Tianjin, China(5). Seven types of seafood were purchased from local markets in Zhoushan and Guangzhou, China in 2004, perfluoroheptanoic acid was only detected in Japanese mackerel from Guangzhou at 0.41 ng/g wet weight(6).|In Nov 2009, food products of 15 food categories were randomly purchased in several Dutch retail stores; perfluoroheptanoic acid was detected as follows(1):[Table#8303]|Perfluoroheptanoic acid was sampled for in food, tea and milk purchased in grocery stores in Oslo, Norway between Oct 2008 and Jan 2009; concentrations were (pg/g fresh weight)(1):[Table#8304]

Perfluoroheptanoic acid was not detected (detection limit 0.25 ng/g) in 12 raw and 49 retail milk samples collected at locations across the US(1). Perfluoroheptanoic acid was not detected (detection limit 1.2 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(2). Perfluoroheptanoic acid was not detected (detection limit 0.87 pg/g) in milk samples purchased at grocery stores in Oslo, Norway between Oct 2008 and Jan 2009(3). In Nov 2009, milk samples randomly purchased in several Dutch retail stores did not contain perfluoroheptanoic acid (detection limit <3 pg/g)(4). Perfluoroheptanoic acid was found at 0.015 ng/g fresh weight in whole milk but not detected in semi-skimmed milk (detection limit 0.004 ng/g fresh weight); samples were collected July 2006 from local markets, large supermarkets and grocery stores from different locations of Tarragona County, Spain(5).|Perfluoroheptanoic acid was detected at 0.074 ug/L in one of 48 breast milk samples collected November 2007, one month postpartum, from French women(1). Perfluoroheptanoic acid was detected at 0.007 ng/mL in pooled human milk samples collected 2003 to 2004 from women in the Kingston, Ontario, Canada region(2). Perfluoroheptanoic acid was not detected (detection limit 1.0 ng/mL) in two human milk samples, collection data were not provided(3).|Perfluoroheptanoic acid concentrations in breast milk samples, collected 1999 to 2005, from women primarily living in major cities from seven Asian Countries were reported as follows(1):[Table#8305]

Occupational exposure to perfluoroheptanoic acid may occur through inhalation and dermal contact with this compound at workplaces where perfluoroheptanoic acid is produced or used. Monitoring data indicate that the general population may be exposed to perfluoroheptanoic acid via inhalation of dust, ingestion of food and drinking water, and dermal contact with consumer products containing perfluoroheptanoic acid. (SRC)

Perfluoroheptanoic acid was not detected (detection limit 0.4 ng/mL) in the serum of 31 Boston, MA office workers in samples collected winter of 2009(1). Perfluoroheptanoic acid was detected in the blood of 92% of California firefighters tested at 0.1-1 ng/g lipid weight(2). The concentration of perfluoroheptanoic acid in the serum of 2 of 20 Atlanta, GA residents was 1.2 and 8.5 ng/mL, samples were collected July 2003(3). Perfluoroheptanoic acid concentration was <0.050 ng/mL (1977), increased to 0.14 ng/mL (2000), and then stabilized at 0.061 to 0.14 ng/mL (2001-2006) in 24 pooled serum samples from men, age 40 to 50 years, representing 1977 to 2006(4). From 2006 to 2008, 233 human blood samples were taken from donors from the capital cities of 12 provinces or districts of China, perfluoroheptanoic acid was detected as follows - city (ng/mL): Harbin (0.399), Hohhot (0.655), Lanzhou (0.441), Taiyuan (<0.1), Shijiazhuang (0.695), Qingdao (<0.1), Ningbo (<0.1), Changsha (<0.1), Chengdu (0.694), Chongqing (0.244), Kumming (0.752) and Guizhou (0.693)(5). Human blood samples from volunteer donors from five Chinese cities (Shenyang, Beijing, Gulyang, Jintan, Nanjing) collected in 2004 had perfluoroheptanoic acid concentrations of <0.01-0.0906 ng/mL(6). Perfluoroheptanoic acid was detected at <0.004-2.25 ng/mL in 420 human blood samples collected from volunteer residents from Halle and Munster, Germany; samples were collected 1982 to 2009(7). Perfluoroheptanoic acid was not detected in blood samples from the population of Tarragona County, Spain(8). Perfluoroheptanoic acid was not detected (detection limit 1.0 ng/mL) in two human milk samples, collection data were not provided(3). Perfluoroheptanoic acid was detected at 0.007 ng/mL in pooled human milk samples collected 2003 to 2004 from women in the Kingston, Ontario, Canada region(9). Perfluoroheptanoic acid was detected at 0.074 ug/L in one of 48 breast milk samples collected November 2007, one month postpartum, from French women(10). Perfluoroheptanoic acid was not detected in 30 human hair samples(11).|Perfluoroheptanoic acid concentrations in breast milk samples, collected 1999 to 2005, from women primarily living in major cities from seven Asian Countries were reported as follows(1):[Table#8298]|Concentration of perfluoroheptanoic 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 collected July 2003(1). ;[Table#8299]|Perfluoroheptanoic acid was studied in wax technicians employed by the Swedish and US national cross-country ski teams. Whole blood samples were taken pre-season (pre) Sept 2007, during the World Cup season (during) Dec 2007 to Mar 2008 and post-season (post) April to Aug 2008. Number of years (years) working as a wax technician and occupations for the off season (April to Nov) are given, one technician is a full-time employee at Swedish Ski Association(1).[Table#8300]

Drug Information

Toxicokinetics was compared between perfluoroheptanoic acid (PFHA), perfluorooctanoic acid (PFOA), perfluorononanoic acid (PFNA) and perfluorodecanoic acid (PFDA) in male and female rats. Half lives (t(1/2)) in male and female rats were calculated to be 0.10 and 0.05 days, respectively, for PFHA, 5.63 and 0.08 days for PFOA, 29.5 and 2.44 days for PFNA and 39.9 and 58.6 days for PFDA. Total clearance (CL(tot)) of PFHA was higher than those of other perfluorocarboxylic acids (PFCAs) in both male and female rats. By contrast, CL(tot) of PFDA was extremely low in both sexes. PFCAs having shorter carbon chain length showed higher CL(tot). There was a significant sex-related difference in CL(tot) of PFOA and PFNA. Distribution volumes in steady state (V(ss)) were not much different between PFCAs and between sexes. To estimate the role of urinary excretion in plasma clearance of PFCA, renal clearance (CL(R)) was determined for PFCAs. CL(R) of PFCAs were in the order PFHA>PFOA>PFNA approximately equal PFDA and PFHA approximately equal PFOA>PDNA>PFDA in male and female rats, respectively. There was a close relationship between CL(tot) and CL(R) (r(2)=0.981). Plasma protein binding, estimated in vitro, was over 98% for all PFCAs tested. The results indicate that CL(R) is responsible for the difference in CL(tot) between PFCAs having different carbon chain length and between sexes.|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 >/= 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.|Elimination in urine and feces was compared between four perfluorinated fatty acids (PFCAs) with different carbon chain length. In male rats, perfluoroheptanoic acid (PFHA) was rapidly eliminated in urine with the proportion of 92% of the dose being eliminated within 120 hr after an intraperitoneal injection. Perfluorooctanoic acid (PFOA), perfluorononanoic acid (PFNA) and perfluorodecanoic acid (PFDA) was eliminated in urine with the proportions of 55, 2.0 and 0.2% of the dose, respectively. By contrast, four PFCAs were eliminated in feces with the proportion of less than 5% of the dose within 120 hr after an injection. In female rats, the proportions of PFOA and PFNA eliminated in urine within 120 hr were 80% and 51% of the dose, respectively, which were significantly higher compared with those in male rats. There was the tendency that PFCA with longer carbon chain length is less eliminated in urine in both male and female rats. Fecal elimination of PFCAs was not different between PFCAs in female rats and comparable to those in male rats. The rates of biliary excretion of PFCAs in male rats were slower than those in female rats. Sex-related difference in urinary elimination of PFOA was abolished when male rats had been castrated. On the contrary, treatment with testosterone suppressed the elimination of PFOA in urine in both castrated male rats and female rats. The effect of testosterone was in a time- and dose-dependent manner. These results suggest that PFCAs are distinguished by their carbon chain length by a renal excretion system, which is regulated by testosterone.

Rat (Wistar), adult, male. Route: IV. Dose: 17.7 mg/g. Exposure duration: 1 day. Elimination half-time: 2.4 hr (SD 1.2) (From table)|Rat (Wistar), adult, female. Route: IV. Dose: 17.7 mg/g. Exposure duration: 1 day. Elimination half-time: 1.2 hr (SD 0.2) (From table)

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/|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/|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 TKO /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) 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 (Valium) or lorazepam (Ativan) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

/EPIDEMIOLOGY STUDIES/ /Researchers/ noted in 105 men there was no difference in mean PFHpA between those with high testosterone (0.2 ng/mL) and those with low testosterone (0.3 ng/mL).|/EPIDEMIOLOGY STUDIES/ In /a/ study ... a significant difference in serum levels of PFHpA between children with (mean = 0.3 +/- 0.5 ng/mL) or without (mean = 0.2 +/- 0.3 ng/mL) asthma was reported, although median levels were the same (0.2 ng/mL). However, a greater proportion of samples were above the level of quantification (LOQ) in asthmatics (70.6 % compared with 53.3 %).|/EPIDEMIOLOGY STUDIES/ /Researchers/ explored the associations between PFASs and endometriosis in 495 women who were or were not seeking clinical care. PFASs investigated included PFOS, PFOA, PFNA, PFDA, PFHxS, PFHpA, PFUnDA, PFDODA and FOSA. No difference in mean serum levels of PFHpA were reported in women with (geometric mean (GM) = 0.05 ng/mL)) or without (GM = 0.05 ng/mL) endometriosis.|/BIOMONITORING/ In the recent years hair has been increasingly used as alternative matrix in human biomonitoring (HBM) of environmental pollutants. Sampling advantages and time integration of exposure assessment seem the most attractive features of hair matrix. In the current study, a novel miniaturized method was developed and validated for measuring 15 perfluoroalkyl substances (PFAS), including perfluoro n-butanoic acid (PFBA), perfluoro n-pentanoic acid (PFPeA), perfluoro n-hexanoic acid (PFHxA), perfluoro n-heptanoic acid (PFHpA), perfluoro n-octanoic acid (PFOA), perfluoro n-nonanoic acid (PFNA), perfluoro tetradecanoic acid (PFTeDA), perfluorobutane sulfonic acid (PFBS), perfluoro pentane sulfonic acid (PFPeS), perfluorohexane sulfonic acid (PFHxS), perfluoroheptane sulfonic acid (PFHpS), perfluorooctane sulfonic acid (PFOS), perfluorononane sulfonic acid (PFNS), perfluorodecane sulfonic acid (PFDS) and perfluorododecane sulfonic acid (PFDoS) in human hair by liquid chromatography tandem mass spectrometry (LC-MS/MS). After extraction using ethyl acetate, dispersive ENVI-Carb was used for clean-up. Good intra- and inter-day precision for low (LQ 5 ng/g hair) and high spike (HQ 15 ng/g) levels were achieved (in general RSD <10%). The accuracy was assessed using recoveries (%), which ranged between 68-118% (LQ) and 70-121% (HQ). The instrumental limit of detection (LODi) and limit of quantification (LOQi) were between 1-4 pg/g hair and 3-13 pg/g hair, respectively. The method limit of quantification (LOQm) ranged between 6 and 301 pg/g hair. The PFAS levels were measured in 30 human hair samples indicating that the levels are low (14-1534 pg/g hair). Some PFAS were not present in any hair sample (e.g. PFHpA, PFTeDA, PFNA, PFPeS, PFHpS, PFOS and PFNS), while other PFAS were frequently detected (PFBA, PFPeA, PFHxA, PFOA, PFBS, PFHxS, PFOS, PFDS and PFDoS) in human hair. Although levels in general were low, there is evidence of higher human exposure to some analytes, such as PFBA, PFPeA, PFHxA, PFOA, PFBS, PFHxS, and PFDoS. The current study shows that hair is a suitable alternative non-invasive matrix for exposure assessment of PFAS.|For more Human Toxicity Excerpts (Complete) data for Perfluoroheptanoic acid (7 total), please visit the HSDB record page.

Perfluoroheptanoic acid Use and Manufacturing

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/

Uses

Perfluorinated compounds (PFCs) have been detected in many environmental matrixes, biota, and nonoccupationally exposed populations in China recently. Being a persistent environmental pollutant, it can accumulate in human tissues via various exposure routes. PFHA may interfere in a toxic fashion on the immune system, liver, development, and endocrine systems.

Heptanoic acid, 2,2,3,3,4,4,5,5,6,6,7,7,7-tridecafluoro-: ACTIVE

Method: EPA-ORD/EPA-OST 537; Procedure: liquid chromatography/tandem mass spectrometry; Analyte: perfluoroheptanoic acid; Matrix: drinking water; Detection Limit: 0.5 nanogram/L.

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

Computed Properties

Molecular Weight:364.06
XLogP3:4.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:15
Rotatable Bond Count:5
Exact Mass:363.9768954
Monoisotopic Mass:363.9768954
Topological Polar Surface Area:37.3
Heavy Atom Count:22
Complexity:448
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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