| Revision as of 13:06, 15 December 2010 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: InChI1->InChI StdInChI StdInChIKey.← Previous edit |
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{{chembox |
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{{chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 394804247 |
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| Watchedfields = changed |
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| ImageFile = Nonylphenolnew.png |
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| verifiedrevid = 402508915 |
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| ImageSize = 160 px |
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| ImageFile = Nonylphenoles V.svg |
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| ImageSize = 200 px |
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| IUPACName = 4-(2,4-dimethylheptan-3-yl)phenol |
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| IUPACName = 4-(2,4-dimethylheptan-3-yl)phenol |
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| OtherNames = Phenol, nonyl- |
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| OtherNames = Phenol, nonyl- |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 60628 |
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| ChemSpiderID = 60628 |
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| InChI = 1/C15H24O/c1-2-3-4-5-6-7-8-11-14-12-9-10-13-15(14)16/h9-10,12-13,16H,2-8,11H2,1H3 |
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| InChI = 1/C15H24O/c1-2-3-4-5-6-7-8-11-14-12-9-10-13-15(14)16/h9-10,12-13,16H,2-8,11H2,1H3 |
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| InChIKey = SNQQPOLDUKLAAF-UHFFFAOYAP |
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| InChIKey = SNQQPOLDUKLAAF-UHFFFAOYAP |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C15H24O/c1-2-3-4-5-6-7-8-11-14-12-9-10-13-15(14)16/h9-10,12-13,16H,2-8,11H2,1H3 |
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| StdInChI = 1S/C15H24O/c1-2-3-4-5-6-7-8-11-14-12-9-10-13-15(14)16/h9-10,12-13,16H,2-8,11H2,1H3 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = SNQQPOLDUKLAAF-UHFFFAOYSA-N |
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| StdInChIKey = SNQQPOLDUKLAAF-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 25154-52-3 |
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| CASNo = 25154-52-3 |
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| CASNo_Comment = (general class) |
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| CASOther = (also: 104-40-5, 84852-15-3, 11066-49-2) |
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| CASNo1_Ref = {{cascite|correct|CAS}} |
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| PubChem = 67296 |
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| CASNo1 = 104-40-5 |
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| SMILES = Oc1ccccc1CCCCCCCCC |
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| CASNo1_Comment = (]) |
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| CASNo2_Ref = {{cascite|correct|CAS}} |
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| CASNo2 = 84852-15-3 |
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| CASNo2_Comment = (branched 4-Nonyl phenols) |
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| CASNo3_Ref = {{cascite|changed|??}} |
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| CASNo3 = 11066-49-2 |
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| CASNo3_Comment = (isononylphenols) |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 79F6A2ILP5 |
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| UNII_Comment = (general class) |
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| UNII1 = I03GBV4WEL |
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| UNII1_Ref = {{fdacite|correct|FDA}} |
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| UNII1_Comment = (4-''n''-Nonyl phenol) |
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| UNII2 = JRW3Q994VG |
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| UNII2_Ref = {{fdacite|correct|FDA}} |
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| UNII2_Comment = (branched 4-Nonyl phenols) |
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| PubChem = 67296 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 153062 |
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| SMILES = Oc1ccccc1CCCCCCCCC |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>15</sub>H<sub>24</sub>O |
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| Formula = C<sub>15</sub>H<sub>24</sub>O |
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| MolarMass = 220.35 g/mol |
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| MolarMass = 220.35 g/mol |
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| Appearance = Light yellow viscous liquid with phenolic smell <ref name="GESTIS">{{GESTIS|ZVG=20610|Name=Nonylphenol, mixed isomers|Date=6 April 2011}}</ref> |
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| Appearance = White crystals |
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| Density = 0.953 |
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| Density = 0.953 |
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| MeltingPt = –8 - 2 °C |
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| MeltingPtC = −8 to 2 |
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| MeltingPt_notes = |
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| BoilingPt = 293 to 297 °C |
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| Solubility = 6 mg/L (pH 7) |
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| BoilingPtC = 293 to 297 |
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| Solubility = 6 mg/L (pH 7) |
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| Section3 = {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| MainHazards = low level endrocrine disruptor |
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| MainHazards = low level endrocrine disruptor |
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| FlashPt = |
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| FlashPt = |
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| Autoignition = |
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| AutoignitionPt = |
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'''Nonylphenols''' are a family of closely related ]s composed of phenol bearing a 9 carbon-tail. Nonylphenols can come in numerous structures, all of which may be considered ]s. They are used in manufacturing ]s, ] additives, laundry and dish ]s, ], and ].<ref name="Soares" /> They are used extensively in epoxy formulation in North America<ref>{{Cite web|title=Epoxy Nonyl Phenol Alert is it in your epoxy?|url=https://www.epoxyproducts.com/nonyl4u.html#:~:text=Nonyl%20Phenol%20is%20a%20common,both%20good%20and%20bad%20properties.&text=here%20-%20YouTube%20video.-,Nonyl%20Phenol%20is%20a%20common%20chemical%20additive%20in%20almost%20all,both%20good%20and%20bad%20properties.|access-date=2021-03-18|website=www.epoxyproducts.com}}</ref><ref>{{Cite web|title=para nonyl phenol|url=https://static1.squarespace.com/static/591c7e1086e6c0c8ce35371f/t/5971063b1e5b6c154c07cda0/1500579387753/PNP.pdf|website=squarespace}}</ref> but its use has been phased out in Europe.<ref>{{Cite web|title=No, no, nonyl(phenol)|url=https://healthybuilding.net/blog/273-no-no-nonylphenol|access-date=2021-03-18|website=Healthy Building Network|language=en}}</ref> These compounds are also ] to the commercially important ] alkylphenol ethoxylates and nonylphenol ethoxylates, which are used in ]s, paints, ]s, personal care products, and plastics. Nonylphenol has attracted attention due to its prevalence in the environment and its potential role as an ] and ], due to its ability to act with ]-like activity.<ref name="maria" /> The estrogenicity and biodegradation heavily depends on the branching of the ] sidechain.<ref name=":0">{{Cite journal |last1=Guenther |first1=Klaus |last2=Kleist |first2=Einhard |last3=Thiele |first3=Bjoern |date=2005-12-10 |title=Estrogen-active nonylphenols from an isomer-specific viewpoint: a systematic numbering system and future trends |journal=Analytical and Bioanalytical Chemistry |language=en |volume=384 |issue=2 |pages=542–546 |doi=10.1007/s00216-005-0181-8 |pmid=16341851 |s2cid=39833642 |issn=1618-2642}}</ref><ref name=":1">{{Cite journal |vauthors=Gabriel FL, Routledge EJ, Heidelberger A, Rentsch D, Guenther K, ] et al. |year=2008 |title=Isomer-specific degradation and endocrine disrupting activity of nonylphenols |journal=Environ Sci Technol |volume=42 |issue=17 |pages=6399–408 |doi=10.1021/es800577a|pmid=18800507 |bibcode=2008EnST...42.6399G |url=https://juser.fz-juelich.de/record/432/files/Gabriel-2008-Isomer-specific_degradation_and_endocrine_disrupting-%28accepted_version%29.pdf }}</ref><ref name=":2">{{Cite journal |last1=Lu |first1=Zhijiang |last2=Gan |first2=Jay |date=2014-01-21 |title=Isomer-Specific Biodegradation of Nonylphenol in River Sediments and Structure-Biodegradability Relationship |journal=Environmental Science & Technology |volume=48 |issue=2 |pages=1008–1014 |doi=10.1021/es403950y |pmid=24345275 |bibcode=2014EnST...48.1008L |issn=0013-936X}}</ref> Nonylphenol has been found to act as an ] of the ] (GPR30).<ref name="ProssnitzBarton2014">{{cite journal |last1=Prossnitz |first1=Eric R. |last2=Barton |first2=Matthias |title=Estrogen biology: New insights into GPER function and clinical opportunities |journal=Molecular and Cellular Endocrinology |volume=389 |issue=1–2 |year=2014 |pages=71–83 |issn=0303-7207 |doi=10.1016/j.mce.2014.02.002 |pmid=24530924 |pmc=4040308}}</ref> |
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==Structure and basic properties== |
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'''Nonylphenol''' is a family of ]s, a subset of the ]s. It is a useful precursor to certain detergents. These compounds are classified as a ] and are controversial pollutants.<ref>C. A. Staples, G. M. Klecka, C. G. Naylor, and B. S. Losey "C8- and C9-Alkylphenols and Ethoxylates: I. Identity, Physical Characterization, and Biodegradation Pathways Analysis" Human and Ecological Risk Assessment, 14: 1007–1024, 2008 |
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Nonylphenols fall into the general chemical category of ]s.<ref name="Sonnenschein">{{cite journal |last1=Sonnenschein |first1=Carlos |last2=Soto |first2=Ana M. |year=1998 |title=An Updated Review of Environmental Estrogen and Androgen Mimics and Antagonists |journal=The Journal of Steroid Biochemistry and Molecular Biology |volume=65 |issue=1–6 |pages=143–50 |doi=10.1016/s0960-0760(98)00027-2|pmid=9699867 |s2cid=16158451 }}</ref> The structure of NPs may vary. The nonyl group can be attached to the ] ring at various locations, usually the 4- and, to lesser extent, the 2-positions, and can be either branched or linear. A branched nonylphenol, 4-nonylphenol, is the most widely produced and marketed nonylphenol.<ref name="EPA">EPA. 2010. Nonylphenol (NP) and Nonylphenal Ethoxylates (NPEs) Action Plan. February, 2014.</ref> The mixture of nonylphenol isomers is a pale yellow liquid, although the pure compounds are colorless. The nonylphenols are moderately soluble in water <ref name="EPA"/> but soluble in alcohol. |
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{{DOI|10.1080/10807030802387705}}</ref> |
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Nonylphenol arises from the ] of ], which are the metabolites of commercial detergents called alkylphenol ethoxylates. NPEs are a clear to light orange color liquid. Nonylphenol ethoxylates are nonionic in water, which means that they have no charge. Because of this property they are used as ]s, cleaners, emulsifiers, and a variety of other applications. They are ], meaning they have both ] and ] properties, which allows them to surround non-polar substances like oil and grease, isolating them from water.<ref name="Soares">{{cite journal |last1=Soares |first1=A. |last2=Guieysse |first2=B. |last3=Jefferson |first3=B. |last4=Cartmell |first4=E. |year=2008 |title=Nonylphenol in the Environment: A Critical Review on Occurrence, Fate, Toxicity and Treatment in Wastewaters |journal=Environment International |volume=34 |issue=7 |pages=1033–049 |doi=10.1016/j.envint.2008.01.004 |pmid=18282600}}</ref> |
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==Production and basic properties== |
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The material known collectively as nonylphenol is produced by acid-catalyzed ] of ] with a mixture of ]s. Millions of kilograms are produced annually.<ref>Helmut Fiege, Heinz-Werner Voges, Toshikazu Hamamoto, Sumio Umemura, Tadao Iwata, Hisaya Miki, Yasuhiro Fujita, Hans-Josef Buysch, Dorothea Garbe, Wilfried Paulus "Phenol Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim.{{DOI|10.1002/14356007.a19_313}}.</ref>The nonyl group, which is highly branched, attaches to the phenol ring via the 4- and, to lesser extent, the 2-positions. This mixture of isomers is usually available as a pale yellow liquid although the pure compounds are white. The organic compound ] is not normally a component of what is marketed as nonylphenol. The nonylphenols are poorly soluble in water but soluble in alcohol. |
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==Production== |
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In the environment, nonylphenols arise from the degradation of the nonaphenol ethoxylates, which are detergents. |
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Nonylphenol can be produced industrially, naturally, and by the environmental degradation of alkylphenol ethoxylates. Industrially, nonylphenols are produced by the acid-catalyzed ] of ] with a mixture of ]s. This synthesis leads to a very complex mixture with diverse nonylphenols.<ref>{{Cite journal |last1=Thiele |first1=Bjoern |last2=Heinke |first2=Volkmar |last3=Kleist |first3=Einhard |last4=Guenther |first4=Klaus |date=2004-06-01 |title=Contribution to the Structural Elucidation of 10 Isomers of Technical p-Nonylphenol |journal=Environmental Science & Technology |volume=38 |issue=12 |pages=3405–3411 |doi=10.1021/es040026g |pmid=15260341 |bibcode=2004EnST...38.3405T |issn=0013-936X}}</ref><ref>{{Cite journal |last1=Ruß |first1=Alexander S. |last2=Vinken |first2=Ralph |last3=Schuphan |first3=Ingolf |last4=Schmidt |first4=Burkhard |date=2005-09-01 |title=Synthesis of branched para-nonylphenol isomers: Occurrence and quantification in two commercial mixtures |journal=Chemosphere |volume=60 |issue=11 |pages=1624–1635 |doi=10.1016/j.chemosphere.2005.02.046 |pmid=16083769|bibcode=2005Chmsp..60.1624R }}</ref><ref>{{Cite journal |last1=Wheeler |first1=Todd F. |last2=Heim |first2=John R. |last3=LaTorre |first3=Maria R. |last4=Janes |first4=A. Blair |date=1997-01-01 |title=Mass Spectral Characterization of p-Nonylphenol Isomers Using High-Resolution Capillary GC—MS |journal=Journal of Chromatographic Science |language=en |volume=35 |issue=1 |pages=19–30 |doi=10.1093/chromsci/35.1.19 |issn=0021-9665|doi-access=free }}</ref> Theoretically there are 211 constitutional isomers and this number rise to 550 isomers if we take the enantiomers into account.<ref name=":0" /> To make NPEs, manufacturers treat NP with ethylene oxide under basic conditions.<ref name="EPA"/> Since its discovery in 1940, nonylphenol production has increased exponentially, and between 100 and 500 million pounds of nonylphenol are produced globally every year,<ref name="EPA"/><ref>{{Cite book |last1=Fiege |first1=Helmut |last2=Voges |first2=Heinz-Werner |last3=Hamamoto |first3=Toshikazu |last4=Umemura |first4=Sumio |last5=Iwata |first5=Tadao |last6=Miki |first6=Hisaya |last7=Fujita |first7=Yasuhiro |last8=Buysch |first8=Hans-Josef |last9=Garbe |first9=Dorothea |last10=Paulus |first10=Wilfried |title=Phenol Derivatives |journal=Ullmann's Encyclopedia of Industrial Chemistry |date=2000 |doi=10.1002/14356007.a19_313 |language=en|isbn=978-3527306732 }}</ref> meeting the definition of ]. |
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Nonylphenols are also produced naturally in the environment. One organism, the ], produces nonylphenol as a component of its defensive slime. The nonylphenol coats the ejection channel of the slime, stopping it from sticking to the organism when it is secreted. It also prolongs the drying process long enough for the slime to reach its target.<ref name=Benkendorff1999>{{Cite journal |first1=K. |title=Characterisation of the slime gland secretion from the peripatus, Euperipatoides kanangrensis (Onychophora: Peripatopsidae) |last1=Benkendorff |journal=Comparative Biochemistry and Physiology B |volume=124 |issue=4 |pages=457–465 |year=1999 |doi=10.1016/S0305-0491(99)00145-5 |last2=Beardmore |first2=K. |last3=Gooley |first3=A. A. |last4=Packer |first4=N. H. |last5=Tait |first5=N. N.}}</ref> |
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Another surfactant called ], which was once used as intravaginal spermicide and condom lubricant, was found to metabolize into free nonylphenol when administered to lab animals.<ref name="Sonnenschein" /> |
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==Applications== |
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==Applications== |
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Nonylphenol is used in manufacturing ]s, ] additives, laundry and dish ]s, ], and ].<ref name="Soares" /> It can also be used to produce tris(4-nonyl-phenyl) phosphite (TNPP), which is an ] used to protect ]s, such as ], ]s, ]s, and ]s in addition to being a ] in plastic food packaging. ] and ] salts of nonylphenol are also used as ]s for ] (PVC).<ref>Nonylphenol and nonylphenol ethoxylates action plan. U.S. Environmental Protection Agency (EPA). August 2010.</ref> Nonylphenol is also often used an intermediate in the manufacture of the ] nonylphenol ethoxylates, which are used in ]s, paints, ]s, personal care products, and plastics. Nonylphenol and nonylphenol ethoxylates are only used as components of household detergents outside of ].<ref name="Soares" /> Nonyl Phenol, is used in many epoxy formulations mainly in North America. |
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Alkylphenols are subjected to ] to give alkylphenol ethoxylates (APEs), which are widely used as industrial ]s. They are used in the processing of wool and metals, as ]s for ], as laboratory ]s, and as ]s. APEs are a component of some household detergents outside of Europe. In Europe, due to environmental concerns, they have been replaced by more expensive alcohol ethoxylates, which are less problematic environmentally. ], one of the APEs, is used as a surfactant in cleaning and cosmetic products, and as a ] in ]s. |
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==Prevalence in the environment== |
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==Health and environmental hazards== |
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Nonylphenol persists in aquatic environments and is moderately ]. It is not readily ], and it can take months or longer to degrade in surface waters, soils, and sediments. Nonbiological degradation is negligible.<ref name="maria">Mergel, Maria. "Nonylphenol and Nonylphenol Ethoxylates." Toxipedia.org. N.p., 1 Nov. 2011. Web. 27 Apr. 2014.</ref> Nonylphenol is partially removed during municipal wastewater treatment due to sorption to suspended solids and biotransformation.<ref>Samaras et al. 2013. Fate of selected pharmaceuticals and synthetic endocrine disruptive compounds during wastewater treatment and sludge anaerobic digestion. Journal of Hazardous Materials, vol. 244-245, January 2013, p. 259-267.</ref><ref>Stasinakis et al., 2013. Contribution of primary and secondary treatment on the removal of benzothiazoles, benzotriazoles, endocrine disruptors, pharmaceuticals and perfluorinated compounds in a sewage treatment plant. Sci. Total Environ. Vol. 463-464, October 2013, p. 1067-1075. </ref> Many products that contain nonylphenol have "down-the-drain" applications, such as laundry and dish soap, so the contaminants are frequently introduced into the water supply. In sewage treatment plants, nonylphenol ethoxylate degrades into nonylphenol, which is found in river water and sediments as well as soil and groundwater.<ref>{{Cite journal |vauthors=Thiele B, Guenther K, Schwuger MJ |year=1997 |title=Alkylphenol ethoxylates: trace analysis and environmental behaviour |journal=Chem Rev |volume=97 |issue=8 |pages=3247–72 |doi=10.1021/cr970323m|pmid=11851490 }}</ref> Nonylphenol ] in sunlight, but its half-life in sediment is estimated to be more than 60 years. Although the concentration of nonylphenol in the environment is decreasing, it is still found at concentrations of 4.1 μg/L in river waters and 1 mg/kg in sediments.<ref name="Soares" /> |
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Nonylphenol is considered to be an ] due to weak ability to mimic estrogen and in turn disrupt the natural balance of hormones in a given organism.<ref>“Review article: Nonylphenol in the environment: A critical review on occurrence, fate, toxicity and treatment in wastewaters” A. Soares, B. Guieysse, B. Jefferson, E. Cartmell, J.N. Lester Environment International 2008, Volume 34, Pages 1033-1049. {{DOI|10.1016/j.envint.2008.01.004}}</ref><ref>Minnesota Pollution Control Agency Statewide Endocrine Disrupting Compound Monitoring Study, 2007 - 2008</ref><ref>, ]</ref> The effect is weak because nonylphenols are not very close structural mimics of estradiol, but the levels of nonylphenol can be sufficiently high to compensate. |
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A major concern is that contaminated sewage sludge is frequently recycled onto agricultural land. The degradation of nonylphenol in soil depends on oxygen availability and other components in the soil. Mobility of nonylphenol in soil is low.<ref name="Soares" /> |
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===Occurrence in the environment=== |
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Nonylphenol has been detected widely in waste water streams across the globe, which is a concern since it is toxic to many aquatic organisms. For example, nonylphenol has been detected both in the Great Lakes and in the region of New York City.<ref>{{cite journal | journal = Science of the Total Environment | volume = 193 | issue = 3 | year = 1997 | pages = 263–275 | title = Occurrence of alkylphenols and alkylphenol mono- and diethoxylates in natural waters of the Laurentian Great Lakes and the upper St. Lawrence River | author = D. T. Bennie, C. A. Sullivan, H.-B. Lee, T. E. Peart and R. J. Maguire | doi = 10.1016/S0048-9697(96)05386-7}}</ref> In 1984, the formation of 4-nonylphenols from ] in ] was first discovered.<ref>{{cite journal | author = ], P. H. Brunner, C. Schaffner | title = 4-Nonylphenol in sewage sludge: accumulation of toxic metabolites from nonionic surfactants | journal = Science | volume = 225 | issue = 4662 |year = 1984 | pages = 623–625 | doi = 10.1126/science.6740328 | pmid = 6740328}}</ref> Nonylphenol is persistent in the environment,<ref>Dayue Y. Shang, Robie W. Macdonald, and Michael G. Ikonomou. 1999. Persistence of Nonylphenol Ethoxylate Surfactants and Their Primary Degradation Products in Sediments from near a Municipal Outfall in the Strait of Georgia, British Columbia, Canada, Environmental Science and Technology 33 (9), pp 1366–1372</ref> therefore lingers with the potential to negatively affect organisms it comes in contact with. Nonylphenol also bioaccumulates, which is dangerous to animals and humans who eat meat. |
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Bioaccumulation is significant in water-dwelling organisms and birds, and nonylphenol has been found in internal organs of certain animals at concentrations of 10 to 1,000 times greater than the surrounding environment.<ref name="maria" /> Due to this bioaccumulation and persistence of nonylphenol, it has been suggested that nonylphenol could be transported over long distances and have a global reach that stretches far from the site of contamination.<ref>Pesticide Action Network North America. PANNA. Nonylphenol Etoxylates.. Accessed 9/30/2011. UK Environment Agency</ref> |
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===Environmental protection policies=== |
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Nonylphenol and nonyphenol ethoxylates have been banned in the European Union as a hazard to human and environmental safety.<ref>Official Journal of the European Union: , July 17, 2003</ref> |
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Nonylphenol is not persistent in air, as it is rapidly degraded by ]s.<ref name="maria" /> |
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For freshwater ecosystems, the Environmental Protection Agency has set two types of standards: the first which is considered acute criteria is one-hour average concentration of nonylphenol does not exceed 28 μg/L more than once every three years on the average.<ref name=EPA>, ]</ref> |
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===Environmental hazards=== |
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For saltwater ecosystems, the standard is considered to be chronic criteria and is set to four-day average concentration of nonylphenol that does not exceed 6.6 μg/l more than once every three years on the average. <ref name=EPA/> |
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Nonylphenol is considered to be an ] due to its ability to mimic ] and in turn disrupt the natural balance of ]s in affected organisms.<ref name=":0" /><ref name=":1" /><ref name=":2" /><ref>{{cite journal |last1=Soares |first1=A. |last2=Guieysse |first2=B. |last3=Jefferson |first3=B. |last4=Cartmell |first4=E. |last5=Lester |first5=J.N. |year=2008 |title=Review article: Nonylphenol in the environment: A critical review on occurrence, fate, toxicity and treatment in wastewaters |journal=Environment International |volume=34 |issue=7|pages=1033–1049 |doi=10.1016/j.envint.2008.01.004 |pmid=18282600 }}</ref><ref>Minnesota Pollution Control Agency Statewide Endocrine Disrupting Compound Monitoring Study, 2007 - 2008</ref> The effect is weak because nonylphenols are not very close structural mimics of ], but the levels of nonylphenol can be sufficiently high to compensate. |
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The effects of nonylphenol in the environment are most applicable to aquatic species. Nonylphenol can cause endocrine disruption in fish by interacting with ]s and ]s. Studies report that nonylphenol competitively displaces estrogen from its receptor site in rainbow trout.<ref name="WHO">WHO (World Health Organization). 2002. Integrated Risk Assessment: Nonylphenol Case Study. WHO/IPCS/IRA/12/04, World Health Organization, Geneva, Switzerland.</ref> It has much less affinity for the estrogen receptor than estrogen in trout (5 x 10<sup>−5</sup> relative binding affinity compared to estradiol) making it 100,000 times less potent than estradiol.<ref name="WHO" /><ref>{{Cite web|url=https://www.canada.ca/en/health-canada/services/environmental-workplace-health/reports-publications/environmental-contaminants/canadian-environmental-protection-act-1999-priority-substances-list-assessment-report-nonylphenol-ethoxylates.html#a241|title=ARCHIVED - Priority Substances List Assessment Report for Nonylphenol and its Ethoxylates|last=Canada|first=Health|date=2004-07-26|website=aem|access-date=2019-10-03}}</ref> Nonylphenol causes the ] of ] ]s, decreases male ], and decreases survival in young fish.<ref name="Soares" /> Studies show that male fish exposed to nonylphenol have lower testicular weight.<ref name="WHO" /> Nonylphenol can disrupt ] in the liver. One function of endogenous estrogen in fish is to stimulate the liver to make ], which is a ].<ref name="WHO" /> Vitellogenin is released by the maturing female and sequestered by developing ]s to produce the egg yolk.<ref name="WHO" /> Males do not normally produce vitellogenin, but when exposed to nonylphenol they produce similar levels of vitellogenin to females.<ref name="WHO" /> The concentration needed to induce vitellogenin production in fish is 10 ug/L for NP in water.<ref name="WHO" /> Nonylphenol can also interfere with the level of FSH (]) being released from the ]. Concentrations of NP that inhibit reproductive development and function in fish also damages ]s, decreases body weight, and induces stressed behavior.<ref>{{cite journal |last1=Liney |first1=Katherine E. |last2=Hagger |first2=Josephine A. |last3=Tyler |first3=Charles R. |last4=Depledge |first4=Michael H. |last5=Galloway |first5=Tamara S. |last6=Jobling |first6=Susan |date=April 2006 |title=Health Effects in Fish of Long-Term Exposure to Effluents from Wastewater Treatment Works |journal=Environ Health Perspect |volume=114 |issue=Suppl 1 |pages=81–89 |doi=10.1289/ehp.8058 |pmid=16818251 |pmc=1874182 }}</ref> |
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==Human health hazards== |
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Alkylphenols like nonylphenol and ] have estrogenic effects in the body. They are known as ].<ref>{{cite journal | last1 = Asimakopoulos | first1 = Alexandros G. | last2 = Thomaidis | first2 = Nikolaos S. | last3 = Koupparis | first3 = Michael A. | year = 2012 | title = Recent Trends in Biomonitoring of Bisphenol A, 4-t-octylphenol, and 4-nonylphenol | journal = Toxicology Letters | volume = 210 | issue = 2| pages = 141–54 | doi=10.1016/j.toxlet.2011.07.032| pmid = 21888958 }}</ref> Estrogenic substances and other endocrine disruptors are compounds that have hormone-like effects in both wildlife and humans. Xenoestrogens usually function by binding to estrogen receptors and acting competitively against natural estrogens. Nonylphenol has been shown to mimic the natural hormone ], and it competes with the endogenous hormone for binding with the ]s ERα and ERβ.<ref name="Soares" /> Nonylphenol was discovered to have hormone-like effects by accident because it contaminated other experiments in laboratories that were studying natural estrogens that were using ] tubes.<ref name="Sonnenschein" /> |
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===Effects in pregnant women=== |
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]s of nonylphenol in late pregnancy causes the expression of certain ]l and ] proteins, namely CaBP-9k, which suggest it can be transferred through the placenta to the fetus. It has also been shown to have a higher potency on the ] placenta than the ] estrogen ]. In addition, early ] exposure to low doses of nonylphenol cause an increase in ] (programmed cell death) in placental cells. These “low doses” ranged from 10<sup>−13</sup>-10<sup>−9</sup> M, which is lower than what is generally found in the environment.<ref name="Bechi">{{cite journal |last1=Bechi |first1=Nicoletta |last2=Ietta |first2=Francesca |last3=Romagnoli |first3=Roberta |last4=Jantra |first4=Silke |last5=Cencini |first5=Marco |last6=Galassi |first6=Gianmichele |last7=Serchi |first7=Tommaso |last8=Corsi |first8=Ilaria |last9=Focardi |first9=Silvano |last10=Paulesu |first10=Luana |year=2009 |title=Environmental Levels of Para-Nonylphenol Are Able to Affect Cytokine Secretion in Human Placenta |journal=Environmental Health Perspectives |volume=118 |issue=3 |pages=427–31 |doi=10.1289/ehp.0900882|pmid=20194071 |pmc=2854774 }}</ref> |
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Nonylphenol has also been shown to affect ] signaling molecule secretions in the human placenta. ] ]s of human placenta during the first trimester were treated with nonylphenol, which increase the secretion of cytokines including ], ], and ], and reduced the secretion of ]. This unbalanced cytokine profile at this part of pregnancy has been documented to result in ], ], and other complications.<ref name="Bechi" /> |
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===Effects on metabolism=== |
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Nonylphenol has been shown to act as an obesity enhancing chemical or ], though it has paradoxically been shown to have anti-] properties.<ref name="Grun">{{cite journal |last1=Grün |first1=Felix |last2=Blumberg |first2=Bruce |year=2009 |title=Endocrine Disrupters as Obesogens |journal=Molecular and Cellular Endocrinology |volume=304 |issue=1–2 |pages=19–29 |doi=10.1016/j.mce.2009.02.018 |pmid=19433244 |pmc=2713042}}</ref> Growing embryos and newborns are particularly vulnerable when exposed to nonylphenol because low-doses can disrupt sensitive processes that occur during these important developmental periods.<ref>"Endocrine Disruption Fact Sheet." Endocrinedisruption.org. TEDX the Endocrine Disruption Exchange, 7 Nov. 2011. Web. 25 Apr. 2014.</ref> Prenatal and perinatal exposure to nonylphenol has been linked with developmental abnormalities in adipose tissue and therefore in metabolic hormone synthesis and release (Merrill 2011). Specifically, by acting as an estrogen mimic, nonylphenol has generally been shown to interfere with ] appetite control.<ref name="Grun" /> The ] responds to the hormone ], which signals the feeling of fullness after eating, and nonylphenol has been shown to both increase and decrease eating behavior by interfering with leptin signaling in the ].<ref name="Grun" /> Nonylphenol has been shown mimic the action of leptin on ] and ] ] neurons, which has an anti-obesity effect by decreasing eating behavior. This was seen when estrogen or estrogen mimics were injected into the ventromedial hypothalamus.<ref>{{cite journal |last1=Gao |first1=Q. |last2=Horvath |first2=T.L. |year=2008 |title=Cross-talk between estrogen and leptin signaling in the hypothalamus |journal=Am. J. Physiol. Endocrinol. Metab. |volume=294 |issue=5|pages=E817–E826 |doi=10.1152/ajpendo.00733.2007|pmid=18334610 |s2cid=20370652 }}</ref> On the other hand, nonylphenol has been shown to increase food intake and have obesity enhancing properties by lowering the expression of these anorexigenic neurons in the brain.<ref>{{cite journal |last1=Masuo |first1=Y. |last2=Morita |first2=M. |last3=Oka |first3=S. |last4=Ishido |first4=M. |year=2004 |title=Motor hyperactivity caused by a deficit in dopaminergic neurons and the effects of endocrine disruptors: a study inspired by the physiological roles of PACAP in the brain |journal=Regul. Pept. |volume=123 |issue=1–3|pages=225–234 |doi=10.1016/j.regpep.2004.05.010 |pmid=15518916|s2cid=9419249 |doi-access=free }}</ref> Additionally, nonylphenol affects the expression of ]: an enzyme produced by the stomach that stimulates appetite.<ref>{{cite journal |last1=Sakata |first1=I. |last2=Tanaka |first2=T. |last3=Yamazaki |first3=M. |last4=Tanizaki |first4=T. |last5=Zheng |first5=Z. |last6=Sakai |first6=T. |year=2006 |title=Gastric estrogen directly induces ghrelin expression and production in the rat stomach |journal=J. Endocrinol. |volume=190 |issue=3|pages=749–757 |doi=10.1677/joe.1.06808|pmid=17003276 |doi-access=free }}</ref> Ghrelin expression is positively regulated by estrogen signaling in the stomach, and it is also important in guiding the differentiation of ]s into ]s (fat cells). Thus, acting as an estrogen mimic, prenatal and perinatal exposure to nonylphenol has been shown to increase appetite and encourage the body to store fat later in life.<ref>{{cite journal |last1=Kim |first1=M.S. |last2=Yoon |first2=C.Y. |last3=Jang |first3=P.G. |last4=Park |first4=Y.J. |last5=Shin |first5=C.S. |last6=Park |first6=H.S. |last7=Ryu |first7=J.W. |last8=Pak |first8=Y.K. |last9=Park |first9=J.Y. |last10=Lee |first10=K.U. |last11=Kim |first11=S.Y. |last12=Lee |first12=H.K. |last13=Kim |first13=Y.B. |last14=Park |first14=K.S. |year=2004 |title=The mitogenic and antiapoptotic actions of ghrelin in 3T3-L1 adipocytes |journal=Mol. Endocrinol. |volume=18 |issue=9|pages=2291–2301 |doi=10.1210/me.2003-0459|pmid=15178745 |doi-access=free }}</ref> Finally, long-term exposure to nonylphenol has been shown to affect insulin signaling in the liver of adult male rats.<ref>{{cite journal |last1=Jubendradass |first1=R |last2=D'Cruz |first2=S |last3=Mathur |first3=P |year=2012 |title=Long-term exposure to nonylphenol affects insulin signaling in the liver of adult male rats |journal=Hum. Exp. Toxicol. |volume=31 |issue=9|pages=868–876 |doi=10.1177/0960327111426587|pmid=22076496 |s2cid=38257683 |doi-access=free }}</ref> |
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===Cancer=== |
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Nonylphenol exposure has also been associated with ].<ref name="Soares" /> It has been shown to promote the ] of breast cancer cells, due to its ]ic activity on ] (estrogen receptor α) in estrogen-dependent and estrogen-independent breast cancer cells. Some argue that nonylphenol's suggested ]ic effect coupled with its widespread human exposure could potentially influence hormone-dependent breast cancer disease.<ref name="vivacqua">{{cite journal |last1=Vivacqua |first1=Adele |last2=Grazia Recchia |first2=Anna |last3=Fasanella |first3=Giovanna |last4=Gabriele |first4=Sabrina |last5=Carpino |first5=Amalia |last6=Rago |first6=Vittoria |last7=Maria |last8=Di Gioia |first8=Luisa |last9=Leggio |first9=Antonella |last10=Bonofiglio |first10=Daniela |last11=Liguori |first11=Angelo |last12=Maggiolini |first12=Marcello |year=2003 |title=The Food Contaminants Bisphenol A and 4-Nonylphenol Act as Agonists for Estrogen Receptor α in MCF7 Breast Cancer Cells |journal=Endocrine |volume=22 |issue=3 |pages=275–84 |doi=10.1385/endo:22:3:275|pmid=14709801 |s2cid=24384354 }}</ref> |
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===Human exposure and breakdown=== |
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====Exposure==== |
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Diet seems the most significant source of exposure of nonylphenol to humans. For example, ] were found with concentrations ranging from 0.1 to 19.4 μg/kg in a diet survey in ] and a daily intake for an adult were calculated to be 7.5 μg/day.<ref>{{Cite journal |last1=Guenther |first1=Klaus |last2=Heinke |first2=Volkmar |last3=Thiele |first3=Bjoern |last4=Kleist |first4=Einhard |last5=Prast |first5=Hartmut |last6=Raecker |first6=Torsten |date=2002-04-15 |title=Endocrine disrupting nonylphenols are ubiquitous in food |journal=Environmental Science & Technology |volume=36 |issue=8 |pages=1676–1680 |issn=0013-936X |pmid=11993862 |doi=10.1021/es010199v|bibcode=2002EnST...36.1676G }}</ref> Another study calculated a daily intake for the more exposed group of infants in the range of 0.23-0.65 μg per kg bodyweight per day.<ref>{{Cite journal |last1=Raecker |first1=Torsten |last2=Thiele |first2=Bjoern |last3=Boehme |first3=Roswitha M. |last4=Guenther |first4=Klaus |date=2011-03-01 |title=Endocrine disrupting nonyl- and octylphenol in infant food in Germany: Considerable daily intake of nonylphenol for babies |journal=Chemosphere |volume=82 |issue=11 |pages=1533–1540 |doi=10.1016/j.chemosphere.2010.11.065 |pmid=21185059|bibcode=2011Chmsp..82.1533R }}</ref> In ], nonylphenol concentrations in food ranged from 5.8 to 235.8 μg/kg. Seafood in particular was found to have a high concentration of nonylphenol.<ref name="Ademollo" /> |
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One study conducted in Italian women showed that nonylphenol was one of the highest contaminants at a concentration of 32 ng/mL in ] when compared to other alkyl phenols, such as octylphenol, nonylphenol monoethoxylate, and two octylphenol ethoxylates. The study also found a positive correlation between fish consumption and the concentration of nonylphenol in breast milk.<ref name="Ademollo">{{cite journal |last1=Ademollo |first1=N. |last2=Ferrara |first2=F. |last3=Delise |first3=M. |last4=Fabietti |first4=F. |last5=Funari |first5=E. |year=2008 |title=Nonylphenol and octylphenol in human breast milk |journal=Environ. Int. |volume=34 |issue=7|pages=984–987 |doi=10.1016/j.envint.2008.03.001|pmid=18410965 }}</ref> This is a large problem because breast milk is the main source of nourishment for newborns, who are in early stages of development where hormones are very influential. Elevated levels of endocrine disruptors in breast milk have been associated with negative effects on ], growth, and memory function. |
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Drinking water does not represent a significant source of exposure in comparison to other sources such as food packing materials, cleaning products, and various skin care products. Concentrations of nonylphenol in treated drinking water varied from 85 ng/L in Spain to 15 ng/L in Germany.<ref name="Soares" /> |
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Microgram amounts of nonylphenol have also been found in the saliva of patients with ]s.<ref name="vivacqua" /> |
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====Breakdown==== |
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When humans orally ingest nonylphenol, it is rapidly absorbed in the ]. The metabolic pathways involved in its degradation are thought to involve ] and ], and the metabolites are then concentrated in fat. There is inconsistent data on bioaccumulation in humans, but nonylphenol has been shown to bioaccumulate in water-dwelling animals and birds. Nonylphenol is excreted in ] and in ].<ref name="maria" /> |
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==Analytics== |
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There are standard GC-MS and HPLC protocols for the detection of nonylphenols within environmental sample matrices such as foodstuffs, drinking water and biological tissue.<ref>{{Cite journal |last1=Jeannot |first1=R. |last2=Sabik |first2=H. |last3=Sauvard |first3=E. |last4=Dagnac |first4=T. |last5=Dohrendorf |first5=K. |date=2002-10-18 |title=Determination of endocrine-disrupting compounds in environmental samples using gas and liquid chromatography with mass spectrometry |journal=Journal of Chromatography A |volume=974 |issue=1–2 |pages=143–159 |doi=10.1016/s0021-9673(02)01240-2|pmid=12458934 }}</ref><ref>{{Cite journal |last1=Kim |first1=Yun-Seok |last2=Katase |first2=Takao |last3=Sekine |first3=Sayaka |last4=Inoue |first4=Tadashi |last5=Makino |first5=Mitsuko |last6=Uchiyama |first6=Taketo |last7=Fujimoto |first7=Yasuo |last8=Yamashita |first8=Nobuyoshi |date=2004-02-01 |title=Variation in estrogenic activity among fractions of a commercial nonylphenol by high performance liquid chromatography |journal=Chemosphere |volume=54 |issue=8 |pages=1127–1134 |doi=10.1016/j.chemosphere.2003.09.024 |pmid=14664841|bibcode=2004Chmsp..54.1127K }}</ref> Industrially produced nonylphenol (the source most likely to be found in the environment) contains a mixture of structural isomers,<ref>{{Cite journal |last1=Bhatt |first1=B. D. |last2=Prasad |first2=J. V |last3=Kalpana |first3=G. |last4=Ali |first4=S. |date=1992-06-30 |title=Separation and Characterization of Isomers of p-Nonylphenols by Capillary GC/GC-MS/GC-FTIR Techniques |journal=Journal of Chromatographic Science |volume=30 |issue=6 |pages=203–210 |doi=10.1093/chromsci/30.6.203 }}</ref> and while these protocols are able to detect this mixture, they are typically unable to resolve the individual nonylphenol isomers within it. However, a methodological study has indicated that better isomeric resolution can be achieved in bulk nonylphenol samples using a GC-MS/MS (tandem mass-analyzer) system,<ref>{{Cite journal |last1=Moeder |first1=M. |last2=Martin |first2=C. |last3=Harynuk |first3=J. |last4=Górecki |first4=T. |last5=Vinken |first5=R. |last6=Corvini |first6=P. F. X. |date=2006-01-13 |title=Identification of isomeric 4-nonylphenol structures by gas chromatography–tandem mass spectrometry combined with cluster analysis |journal=Journal of Chromatography A |volume=1102 |issue=1–2 |pages=245–255 |doi=10.1016/j.chroma.2005.10.031|pmid=16271268 }}</ref> suggesting that this technique could also improve the resolution of nonylphenol isomers in environmental sample analyses; further improvements in the resolution of nonylphenol isomers have been achieved through the use of two-dimensional GC at the separation stage, as part of a GC x GC-TOF-MS system.<ref>{{Cite journal |last1=Moeder |first1=M. |last2=Martin |first2=C. |last3=Schlosser |first3=D. |last4=Harynuk |first4=J. |last5=Górecki |first5=T. |date=2006-02-24 |title=Separation of technical 4-nonylphenols and their biodegradation products by comprehensive two-dimensional gas chromatography coupled to time-of-flight mass spectrometry |journal=Journal of Chromatography A |volume=1107 |issue=1–2 |pages=233–239 |doi=10.1016/j.chroma.2005.12.092|pmid=16427065 }}</ref> |
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In contrast to environmental sample analyses, synthetic studies of nonylphenols have more control over sample state, concentration and preparation, simplifying the use of powerful structural identification techniques like NMR - capable of identifying the individual nonylphenol isomers.<ref>{{Cite journal |last1=Boehme |first1=Roswitha M. |last2=Andries |first2=Thomas |last3=Dötz |first3=Karl Heinz |last4=Thiele |first4=Bjoern |last5=Guenther |first5=Klaus |date=2010-08-01 |title=Synthesis of defined endocrine-disrupting nonylphenol isomers for biological and environmental studies |journal=Chemosphere |volume=80 |issue=7 |pages=813–821 |doi=10.1016/j.chemosphere.2010.03.064 |pmid=20452641|bibcode=2010Chmsp..80..813B }}</ref> In a preliminary investigation of the relationship between nonylphenol sidechain branching patterns and estrogenic potential, the authors identified 211 possible structural isomers of p-nonylphenol alone, which expanded to 550 possible p-nonylphenol compounds when taking chiral C-atoms into consideration.<ref>{{Cite journal |last1=Guether |first1=Klaus |last2=Kleist |first2=Einhard |last3=Thiele |first3=Bjoern |date=2005-12-10 |title=Estrogen-active nonylphenols from an isomer-specific viewpoint: a systematic numbering system and future trends |journal=Analytical and Bioanalytical Chemistry |volume=384 |issue=2 |pages=542–546 |doi=10.1007/s00216-005-0181-8|pmid=16341851 |s2cid=39833642 }}</ref> Because stereochemical factors are thought to contribute to the biological activity of nonylphenols, analytical techniques sensitive to chirality, such as enantioselective HPLC and certain NMR protocols, are desirable in order to further study these relationships.<ref>{{Cite journal |last1=Zhang |first1=Haifeng |last2=Zuehlke |first2=Sebastian |last3=Guenther |first3=Klaus |last4=Spiteller |first4=Michael |date=2007-01-01 |title=Enantioselective separation and determination of single nonylphenol isomers |journal=Chemosphere |volume=66 |issue=4 |pages=594–602 |doi=10.1016/j.chemosphere.2006.08.012|pmid=17027900 |bibcode=2007Chmsp..66..594Z }}</ref><ref>{{Cite journal |last1=Zhang |first1=Haifeng |last2=Oppel |first2=Iris M. |last3=Spiteller |first3=Michael |last4=Guenther |first4=Klaus |last5=Boehmler |first5=Gabriele |last6=Zuehlke |first6=Sebastian |date=2009-02-01 |title=Enantiomers of a nonylphenol isomer: Absolute configurations and estrogenic potencies |journal=Chirality |language=en |volume=21 |issue=2 |pages=271–275 |doi=10.1002/chir.20556 |pmid=18553459 |issn=1520-636X}}</ref><ref>{{Cite journal |last1=Acir |first1=Ismail-Hakki |last2=Wüst |first2=Matthias |last3=Guenther |first3=Klaus |date=2016-05-28 |title=Enantioselective separation of defined endocrine-disrupting nonylphenol isomers |journal=Analytical and Bioanalytical Chemistry |language=en |volume=408 |issue=20 |pages=5601–5607 |doi=10.1007/s00216-016-9661-2 |issn=1618-2642 |pmid=27236316|s2cid=11005914 }}</ref> |
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==Regulation== |
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The production and use of nonylphenol and nonylphenol ethoxylates is prohibited for certain situations in the ] due to its effects on health and the environment.<ref name="Soares" /><ref>Official Journal of the European Union: , July 17, 2003</ref> In Europe, due to environmental concerns, they also have been replaced by more expensive ], which are less problematic for the environment due to their ability to degrade more quickly than nonylphenols. The ] has also included NP on the list of priority hazardous substances for surface water in the ]. They are now implementing a drastic reduction policy of NP's in surface waterways. The Environmental quality standard for NP was proposed to be 0.3 ug/L.<ref name="Soares" /> In 2013 nonylphenols were registered on the REACH candidate list. |
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In the US, the ] set criteria which recommends that nonylphenol concentration should not exceed 6.6 ug/L in fresh water and 1.7 ug/L in saltwater.<ref name="david">{{cite journal |last1=David |first1=A. |last2=Fenet |first2=H. |last3=Gomez |first3=E. |year=2009 |title=Alkylphenols in marine environments: distribution monitoring strategies and detection considerations |journal=Mar. Pollut. Bull. |volume=58 |issue=7|pages=953–960 |doi=10.1016/j.marpolbul.2009.04.021|pmid=19476957 }}</ref> In order to do so, the EPA is supporting and encouraging a voluntary phase-out of nonylphenol in industrial laundry detergents. Similarly, the EPA is documenting proposals for a "significant new use" rule, which would require companies to contact the EPA if they decided to add nonylphenol to any new cleaning and detergent products. They also plan to do more risk assessments to ascertain the effects of nonylphenol on human health and the environment. |
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In other Asian and South American countries nonylphenol is still widely available in commercial detergents, and there is little regulation.<ref name="david" /> |
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==References== |
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==References== |
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