Wikipedia

Perfluorodecanoic acid

Perfluorodecanoic acid (PFDA) is a fluorosurfactant and has been used in industry.[2]

Perfluorodecanoic acid
Names
Preferred IUPAC name
Nonadecafluorodecanoic acid
Other names
PFDA
C10 PFCA
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.005.819 Edit this at Wikidata
EC Number
  • 206-400-3
35659
UNII
  • InChI=1S/C10HF19O2/c11-2(12,1(30)31)3(13,14)4(15,16)5(17,18)6(19,20)7(21,22)8(23,24)9(25,26)10(27,28)29/h(H,30,31)
    Key: PCIUEQPBYFRTEM-UHFFFAOYSA-N
  • C(=O)(C(C(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)O
Properties
C10HF19O2
Molar mass 514.086 g·mol−1
Melting point 77–81 °C (171–178 °F; 350–354 K)[1]
Boiling point 218 °C (424 °F; 491 K)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

It was recently linked to health concerns,[3] like other fluorosurfactants, leading to proposed restrictions on its use.[4] In 2020, a California bill banned its use as an intentionally added ingredient in cosmetics.[5]

It has been proposed as a chemical probe to study peroxisome proliferation.[6][7]

Perfluorodecanoic acid (PFDA) is a member of the group of polyfluoroalkyl substances (PFAS), more specific is it also a perfluoroalkyl acid (PFAA). PFAS, like PFDA, are man-made and are not naturally occurring in nature. Over the last decades they have been used in consumer products and industrial applications. It is a fluorosurfactant with a unique hydrophobicity and oleophobicity.[8] PFDA is well resistant to heat, oil, stains, grease and water, therefore it has been used in stain and greaseproof coating for furniture, packaging and carpet. Next to that, PFDA has also been found in nano-and impregnation-sprays, outdoor textiles, gloves, ski wax, leather, cosmetics, medical equipment and paper-based food containers.[8][9] PFDA has a relatively high toxicity and can promote tumor growth.[10]

Mechanism of action

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Via contaminated water or soil, plants can take up PFDA. This may lead to exposure and accumulation of PFDA in humans and other organisms.[10] In addition, exposure is possible via inhalation of indoor and outdoor air and ingestion of drinking water and food.[8] Direct dermal contact with PFDA-containing products is the main route of exposure.[10]

PFDA has been shown to increase the expression of two cytochrome P450 enzymes, namely Cyp2B10 and 4A14 in mouse liver.[11] In addition, it has been shown to activate the peroxisome proliferator-activated receptor alpha (PPARα). This receptor regulates lipid metabolism.[11]

A study looked at the harmful effects of PFDA on the antioxidative defense system in erythrocytes (red blood cells). Their results indicated that PFDA could influence the contents and activity of the biomolecules: GSH, MDA, SOD, CAT and GPx. This can lead to lipid peroxidation and oxidative injury of erythrocytes. The carbon chain length plays an important role, exposure to PFDA resulted in more obvious alterations of these biomolecules than shorter carbon chains of PFAA's.[12]

Further, has merging evidence showed that PFDA exposure can be associated with higher plasma triglyceride concentration in humans.[13] It is however unknown how PFDA might affect adipogenesis. HepG2 cells and 3T3-L1 differentiation model were used to detect the effects and mechanism of PFDA on lipid metabolism. PFDA showed to promote cellular triglyceride accumulation and triglyceride content in a concentration dependent manner. It also activated the NLP3 inflammasome. The inflammasome is crucial for induction of lipogenic genes expression in fatty acid synthase (FAS), hydroxymethyl glutaryl coenzyme A synthase (HMGCS) and stearoyl-CoA desaturase 1 (SCD1).[13] Besides, a suggestion can be made that PFDA may promote adipogenesis via an NLRP3 inflammasome-mediates SREBP1 pathway. Also, the expression of SREBP1, which is an important regulator of lipid metabolism, and its target genes were increased after PFDA treatment. The PFDA-induced SREBP1 enhanced expression can be terminated by caspase-1 inhibitor and by siNLRP3.[13]

Metabolism

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PFDA is resistant to hydrolysis, photolysis and biodegradation, this causes persistence of the compound in the environment.[14] With its long carbon chain and carboxylate group, PFDA has some similar structure to amino acids. But it does not biodegrade according to the route of fatty acid metabolism.[15]

Structure and reactivity

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Perfluorodecanoic acid is a compound with a carbon chain of 10. At 9 of the carbons the hydrogens are replaced by all fluor atoms, the last carbon is the carboxylate group. The length of the PFDA carbon chain is greater than that of PFOAs (perfluorooctanoic acids) and PFOS (perfluorooctane sulfonic acid) indicating that it is possibly more toxic.[16]

Perfluorodecanoic acid is a chemically inert due to relatively high organic bond strength and fluorine's electron negativity, which makes it resistant to advanced oxidation processes.[17] It is also resistant to hydrolysis and has thermal and photochemical stability unless certain reaction conditions are introduced, e.g., PFDA can be decomposed in hot water in the presence of S2O82-.[18] Photochemical decomposition with Na2S is another way of breaking up PFDA molecules.[17]

Synthesis and reactions

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The first main road of perfluorochemicals (to which PFDA belongs) is electrochemical fluorination (ECF). This reaction occurs during an electrochemical hydrolysis of hydrofluoric acid (anhydrous) at a cell potential of 4.5 to 7 V. Several compounds can be used as starting material, for example, carboxylic acids (RCOOH), acyl chlorides (RCOCl) or sulfonic acid chlorides (RSO2Cl). The second step of the reaction is hydrolysis (addition of NaOH) to obtain the final products:[19]

RCOOH + nHF → RFCOOH + nH2O + by-products
RFCOOH + NaOH → RFCOONa + H2O
RCOCl + nHF → RFCO + nHCl + by-products
RFCO + NaOH→ RFCOONa+ H2O
RSO2Cl + nHF → RFSO2F + nHCl + by-products
RFSO2F + 2NaOH→ RFSO3Na+ NaF+ H2O

The second main synthesis road for perfluorodecanoic acid used commercially is telomerization.[20] Since PFDA has an even number of carbons, the starting material should be pentafluoroethyl iodide.[19] The process follows the general scheme:[20] 

              Telomerization
            Tetrafluoroethylene
                    ↓
           Perfluoroalkyl iodide
                    ↓
        Fluorotelomer alcohols (FTOH)
                    ↓
        Perfluorochemicals (e.g. PFDA)

Availability

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Studies have shown that, fortunately, there is a decreasing trend in the concentration of PFDA in Danish pregnant women from years of 2008- 2013. Germany and Denmark also follow this trend, while the concentration of this chemical is growing in Japan, Korea, Greenland, and Northern Norway.[21] Under normal conditions, the amount of PFDA (perfluorodecanoic acid) in European individuals was 0.8 ng/mL in 2013.[22]

Efficacy and side effects

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Efficacy

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Perfluorodecanoic Acid (PFDA) is a widely used industrial chemical that is persistent in the environment and can accumulate in the body. It has been detected in the blood of people and animals worldwide. The EPA has issued a lifetime health advisory for PFDA in drinking water of 70 parts per trillion (ppt). PFDA is not a medication and doesn't have any approved medical uses. It's a man-made chemical used in industrial applications and numerous studies point to its negative health effects.[23][24]

Side effects

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Perfluorodecanoic acid (PFDA) is a chemical of significant concern due to its classification as a Persistent, Bioaccumulative, and Toxic (PBT) substance. It has been identified as a potential carcinogen, with an acute oral toxicity estimate indicating a lethal dose for 50% of rats at 57 mg/kg. The substance is known to cause a range of acute symptoms as side effects such as a burning sensation, coughing, wheezing, and difficulty in breathing, which require immediate medical attention.[25]

There is little research done on the influence of PFDA on humans, most studies are done on animals. The human Reference Dose of PFDA can be calculated from mouse studies. In order to do that the NOAEL (no observed adverse effect level) should be divided by 10000.[22]

Toxicity

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Research has shown that PFDA inhibits peroxisomal β-oxidation, a crucial metabolic process for energy production from fatty acids and is associated with DNA damage. Even at low levels, can damage this DNA in ovarian cells. This damage comes in the form of double-strand breaks, which are like tears in the DNA. Our bodies have a built-in repair system to fix these tears, however, PFDA disrupts this repair system and induces genotoxicity. This unrepaired DNA damage can lead to mutations. The mistakes get copied during cell division, potentially leading to genomic instability. Over time, these mutations can accumulate, potentially leading to the uncontrolled growth characteristic of cancer. Since ovaries are involved in reproduction, damage to ovarian cells caused by PFDA might be a factor in reproductive health problems.[26] It is also a potent and long-lasting toxin that may contribute to tumor formation. Studies have linked PFDA exposure to exacerbated adiposity and hepatic lipid accumulation, especially when combined with a high-fat diet, indicating a risk factor for liver problems.[27]

One important antioxidant molecule in the liver that helps protect cells from damage caused by free radicals is glutathione (GSH). PFDA exposure increases the total amount of GSH in the liver. This impact suggests an attempt by the body to counteract oxidative stress caused by the chemical.[28] Furthermore, exposure to PFDA has been associated with miscarriage,[29] liver damage, inflammation, and various negative effects on the heart, thyroid, and reproductive systems. It disrupts hormonal and immune system functions and can cause cellular damage through the activation of the PPARα receptor, affecting liver function and triggering oxidative stress, and the NLRP3 inflammasome pathway in both human cells and mouse tissues.[30]

PFDA interferes with the NF-κB pathway that induces the production of proinflammatory cytokines.[31] In gastric cells, PFDA has been found to increase the production of pro-inflammatory molecules IL-1β and IL-18, suggesting a role in stomach inflammation. Essentially, NLRP3 acts like a switch that turns on the production of mature IL-1β and IL-18. The active IL-1β and IL-18 are then released from the cell. They travel to nearby cells and trigger an inflammatory response.[32] It may also promote the proliferation of gastric epithelial cells, potentially preventing them from entering a state of senescence, which is a natural process to prevent uncontrolled cell growth. This increased growth could be a concern since uncontrolled cell growth is a hallmark of cancer.[33]

The toxicokinetic profile of PFDA reveals a long half-life in the body (52-66 days in rats), regardless of sex. Yet, female rats showed higher levels of PFDA accumulation in their bloodstream than males after exposure. Their bodies also showed slower clearance rates.[34] Similar to rats, PFDA in humans likely accumulates in the liver and triggers peroxisomal beta-oxidation. Data based on biomonitoring in Korea states that the margin of exposure of PFDA in human males was about two times higher than that of females (100.5, male; 27.7, female), indicating a lower risk for males.[35]

It's important to remember that most of the research on PFDA's health effects has been conducted on animals. While these studies’ findings raise concerns about the potential health risks of PFDA in humans, further investigation is needed to confirm these findings and fully understand the long-term health effects of PFDA exposure in humans.

Effects on animals

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A study on rats has shown that the administration of PFDA can cause certain changes in the thyroid gland function. While the concentration of hormone T3 (triiodothyronine) in blood remained the same, gland weight and levels of thyroxine have decreased. Interestingly, this has led to only an 8% reduction in the metabolic rate of these rats.[36]

A single dose of 5mg/kg of PFDA is enough to cause these symptoms in rodents, as well as harm to the rough endoplasmic reticulum in the hepatic cells as well as abnormal mitochondria. Except for its effect on the liver and thyroid gland, one study on pigs has shown that this chemical may prevent fertilization by causing oocyte death.[37]

Another study on fish has found that PFDA alters the production of sex hormones and thus leads to endocrine disturbance. This is done through increased levels of 17β-estradiol (E2) that lead to upregulation of the cyp19b and cyp19a gene. These genes are necessary for the production of aromatase and regulate the production of estrogen from androgen.[38]

References

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  1. ^ a b "Perfluorodecanoic acid 98%". Sigma-Aldrich.
  2. ^ Reich, Ieva L.; Reich, Hans J.; Menahan, Lawrence A.; Peterson, Richard E. (October 1987). "Synthesis of 14C-labeled perfluorooctanoic and perfluorodecanoic acids; purification of perfluorodecanoic acid". Journal of Labelled Compounds and Radiopharmaceuticals. 24 (10): 1235–1244. doi:10.1002/jlcr.2580241011.
  3. ^ "Danish study links perfluorinated chemicals to miscarriage". Chemical Watch. Retrieved 25 March 2019.
  4. ^ "Germany and Sweden propose restrictions on six PFASs". Chemical Watch. 14 May 2015. Retrieved 25 March 2019.
  5. ^ "Assembly Bill No. 2762". State of California. September 30, 2020. Retrieved 10 October 2020.
  6. ^ Vanden Heuvel, John P. (October 1996). "Perfluorodecanoic acid as a useful pharmacologic tool for the study of peroxisome proliferation". General Pharmacology: The Vascular System. 27 (7): 1123–1129. doi:10.1016/0306-3623(95)00126-3. PMID 8981056.
  7. ^ Chen, Li-Chuan; Tatum, Vickie; Glauert, Howard P.; Chow, Ching K. (2001). "Peroxisome proliferator perfluorodecanoic acid alters glutathione and related enzymes". Journal of Biochemical and Molecular Toxicology. 15 (2): 107–113. doi:10.1002/jbt.6. ISSN 1095-6670. PMID 11284052. S2CID 27570192.
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  29. ^ Xuping Gao, Wanze Ni, Sui Zhu, Yanxin Wu, Yunfeng Cui, Junrong Ma, Yanhua Liu, Jinlong Qiao, Yanbin Ye, Pan Yang, Chaoqun Liu, Fangfang Zeng,Per- and polyfluoroalkyl substances exposure during pregnancy and adverse pregnancy and birth outcomes: A systematic review and meta-analysis, Environmental Research, Volume 201, 2021, 111632, doi:10.1016/j.envres.2021.111632.
  30. ^ Dongxu Wang, Qiang Gao, Taotao Wang, Zhipeng Kan, Xin Li, Lizhen Hu, Chuan-yi Peng, Frank Qian, Yijun Wang, Daniel Granato, Green tea polyphenols and epigallocatechin-3-gallate protect against perfluorodecanoic acid induced liver damage and inflammation in mice by inhibiting NLRP3 inflammasome activation, Food Research International, Volume 127, 2020, 108628, doi:10.1016/j.foodres.2019.108628.
  31. ^ Rachel P. Frawley, Matthew Smith, Mark F. Cesta, Schantel Hayes-Bouknight, Chad Blystone, Grace E. Kissling, Shawn Harris & Dori Germolec (2018) Immunotoxic and hepatotoxic effects of perfluoro-n-decanoic acid (PFDA) on female Harlan Sprague–Dawley rats and B6C3F1/N mice when administered by oral gavage for 28 days, Journal of Immunotoxicology, 15:1, 41-52, doi:10.1080/1547691X.2018.1445145.
  32. ^ Zhou, X., Dong, T., Fan, Z. et al. Perfluorodecanoic acid stimulates NLRP3 inflammasome assembly in gastric cells. Sci Rep 7, 45468 (2017). doi:10.1038/srep45468.
  33. ^ Dong T., Peng Y., Zhong N., Liu F., Zhang H., Xu M., Liu R., Han M., Tian X., Jia J., Chang L., Guo L., Liu S. et al Perfluorodecanoic acid (PFDA) promotes gastric cell proliferation via sPLA2-IIA. Oncotarget. 2017; 8: 50911-50920. doi:10.18632/oncotarget.17284.
  34. ^ Dzierlenga AL, Robinson VG, Waidyanatha S, DeVito MJ, Eifrid MA, Gibbs ST, Granville CA, Blystone CR. Toxicokinetics of perfluorohexanoic acid (PFHxA), perfluorooctanoic acid (PFOA) and perfluorodecanoic acid (PFDA) in male and female Hsd:Sprague dawley SD rats following intravenous or gavage administration. Xenobiotica. 2020 Jun;50(6):722-732. doi:10.1080/00498254.2019.1683776.
  35. ^ Kim, SJ., Choi, EJ., Choi, GW. et al. Exploring sex differences in human health risk assessment for PFNA and PFDA using a PBPK model. Arch Toxicol 93, 311–330 (2019). doi:10.1007/s00204-018-2365-y.
  36. ^ Marc J. Van Rafelghem, Stanley L. Inhorn, Richard E. Peterson, Effects of perfluorodecanoic acid on thyroid status in rats, Toxicology and Applied Pharmacology, Volume 87, Issue 3, 1987, Pages 430-439, doi:10.1016/0041-008X(87)90248-1.
  37. ^ Domínguez, Z. Salazar, M. Betancourt, Y. Ducolomb, E. Casas, F. Fernández, I. Bahena, A. Salomón, M. Teteltitla, R. Martínez, A. Chaparro, P. Cuapio, C. Salazar-López, E. Bonilla, Effect of perfluorodecanoic acid on pig oocyte viability, intracellular calcium levels and gap junction intercellular communication during oocyte maturation in vitro, Toxicology in Vitro, Volume 58, 2019, Pages 224-229, doi:10.1016/j.tiv.2019.03.041.
  38. ^ Areum Jo, Kyunghee Ji, Kyungho Choi, Endocrine disruption effects of long-term exposure to perfluorodecanoic acid (PFDA) and perfluorotridecanoic acid (PFTrDA) in zebrafish (Danio rerio) and related mechanisms, Chemosphere, Volume 108, 2014, Pages 360-366, doi:10.1016/j.chemosphere.2014.01.080.
 
Scholia has a profile for perfluorodecanoic acid (Q27116511).
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