perfluorononanoic acid

Synonyms: "perfluorononanoic acid", "heptadecafluorononanoic acid", "perfluoro-n-nonanoic acid", "PFNA", "perfluorononan-1-oic acid", "heptadecafluoropelargonic Acid", "2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-Heptadecafluorononanoic acid", "n-heptadecafluorononanoic acid".

Source: perfluorononanoic acid is a member of a class of perfluorinated alkanoic acids commonly used as lubricants, plasticizers, wetting agents and corrosion, as well as emulsifiers and surfactants in fluoropolymer manufacturing.


IUPAC Name: 2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-heptadecafluorononanoic acid
CAS Number: 375-95-1
PubChem ID: 67821
Canonical SMILES: C(=O)(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)O

Structural Properties:

Molecular Formula: C9HF17O2
Molecular Weight: 464.078

Pharmacophore Features:

Number of bond donors: 1
Number of bond acceptors: 19
Number of atoms different from hydrogen: 28


2D structure (.sdf)
3D structure (.sdf)
3D structure (.mol2)
3D structure (.pdb)
3D structure (.pdbqt)

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Evidence Supporting This Chemical as an Endocrine Disruptor
TEDX List of Potential Endocrine Disruptors

Kjeldsen LS and Bonefeld-Jorgensen EC. 2013. Perfluorinated compounds affect the function of sex hormone receptors. Environ Sci Pollut Res Int 20(11):8031-8044. DOI: 10.1007/s11356-013-1753-3. URL:
Long M, Ghisari M and Bonefeld-Jorgensen EC. 2013. Effects of perfluoroalkyl acids on the function of the thyroid hormone and the aryl hydrocarbon receptor. Environ Sci Pollut Res Int 20(11):8045-8056. DOI: 10.1007/s11356-013-1628-7. URL:

Rosenmai AK, Ahrens L, Godec T, Lundqvist J and Oskarsson A. 2017. Relationship between peroxisome proliferator?activated receptor alpha activity and cellular concentration of 14 perfluoroalkyl substances in HepG2 cells. J Appl Toxicol 38(2):219-226. DOI: 10.1002/jat.3515. URL:
Shah-Kulkarni, S., Kim, B.M., Hong, Y.C., Kim, H.S., Kwon, E.J., Park, H., Kim, Y.J. and Ha, E.H., 2016. Prenatal exposure to perfluorinated compounds affects thyroid hormone levels in newborn girls. Environment international, 94, pp.607-613. DOI: 10.1016/j.envint.2016.06.024. URL:
Vongphachan V, Cassone CG, Wu D, Chiu S, Crump D, Kennedy SW. 2011. Effects of perfluoroalkyl compounds on mRNA expression levels of thyroid hormone-responsive genes in primary cultures of avian neuronal cells. Toxicol Sci 120(2):392-402. DOI: 10.1093/toxsci/kfq395. URL:
Wang Y, Rogan WJ, Chen PC, Lien GW, Chen HY, Tseng YC, Longnecker MP and Wang SL. 2014. Association between maternal serum perfluoroalkyl substances during pregnancy and maternal and cord thyroid hormones: Taiwan maternal and infant cohort study. Environ Health Perspect 122(5):529-534. DOI: 10.1289/ehp.1306925. URL:
Wolf CJ, Takacs ML, Schmid JE, Lau C, Abbott BD. 2008. Activation of mouse and human peroxisome proliferator-activated receptor alpha by perfluoroalkyl acids of different functional groups and chain lengths. Toxicol Sci 106(1):162-171. DOI: 10.1093/toxsci/kfn166. URL:

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