1092:
isomers, 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, 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.
709:, and it can take months or longer to degrade in surface waters, soils, and sediments. Nonbiological degradation is negligible. Nonylphenol is partially removed during municipal wastewater treatment due to sorption to suspended solids and biotransformation. 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. Nonylphenol
1096:
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. 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.
587:. This synthesis leads to a very complex mixture with diverse nonylphenols. Theoretically there are 211 constitutional isomers and this number rise to 550 isomers if we take the enantiomers into account. To make NPEs, manufacturers treat NP with ethylene oxide under basic conditions. Since its discovery in 1940, nonylphenol production has increased exponentially, and between 100 and 500 million pounds of nonylphenol are produced globally every year, meeting the definition of
757:
24:
420:
772:. Studies report that nonylphenol competitively displaces estrogen from its receptor site in rainbow trout. It has much less affinity for the estrogen receptor than estrogen in trout (5 x 10 relative binding affinity compared to estradiol) making it 100,000 times less potent than estradiol. Nonylphenol causes the
1229:
1127:
set criteria which recommends that nonylphenol concentration should not exceed 6.6 ug/L in fresh water and 1.7 ug/L in saltwater. 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
721:
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. Due to this bioaccumulation and persistence of nonylphenol, it has been suggested
978:(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. Finally, long-term exposure to nonylphenol has been shown to affect insulin signaling in the liver of adult male rats.
832:. 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
539:
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. The mixture of nonylphenol isomers is a pale yellow liquid, although the pure compounds
937:
properties. 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. Prenatal and perinatal exposure to nonylphenol has been linked with developmental abnormalities
1047:
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.
1039:
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. This is a large problem because breast milk is the main
803:
to produce the egg yolk. Males do not normally produce vitellogenin, but when exposed to nonylphenol they produce similar levels of vitellogenin to females. The concentration needed to induce vitellogenin production in fish is 10 ug/L for NP in water. Nonylphenol can also interfere with the
1091:
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. Industrially produced nonylphenol (the source most likely to be found in the environment) contains a mixture of structural
2416:
Vivacqua, Adele; Grazia
Recchia, Anna; Fasanella, Giovanna; Gabriele, Sabrina; Carpino, Amalia; Rago, Vittoria; Maria; Di Gioia, Luisa; Leggio, Antonella; Bonofiglio, Daniela; Liguori, Angelo; Maggiolini, Marcello (2003). "The Food Contaminants Bisphenol A and 4-Nonylphenol Act as Agonists for
965:
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. On the other hand, nonylphenol has been shown to increase food intake and have obesity enhancing properties by lowering the
1128:
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.
1095:
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. In a
1967:
1841:
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.
2998:
DIRECTIVE 2003/53/EC OF THE EUROPEAN PARLIAMENT AND OF THE COUNCIL of 18 June 2003 amending for the 26th time
Council Directive 76/769/EEC relating to restrictions on the marketing and use of certain dangerous substances and preparations (nonylphenol, nonylphenol ethoxylate and
2629:
Kim, Yun-Seok; Katase, Takao; Sekine, Sayaka; Inoue, Tadashi; Makino, Mitsuko; Uchiyama, Taketo; Fujimoto, Yasuo; Yamashita, Nobuyoshi (2004-02-01). "Variation in estrogenic activity among fractions of a commercial nonylphenol by high performance liquid chromatography".
598:, 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.
551:, 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
713:
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.
2736:
Moeder, M.; Martin, C.; Schlosser, D.; Harynuk, J.; Górecki, T. (2006-02-24). "Separation of technical 4-nonylphenols and their biodegradation products by comprehensive two-dimensional gas chromatography coupled to time-of-flight mass spectrometry".
717:
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.
2700:
Moeder, M.; Martin, C.; Harynuk, J.; Górecki, T.; Vinken, R.; Corvini, P. F. X. (2006-01-13). "Identification of isomeric 4-nonylphenol structures by gas chromatography–tandem mass spectrometry combined with cluster analysis".
1120:. 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. In 2013 nonylphenols were registered on the REACH candidate list.
1828:
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.
1075:, 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
1158:
2593:
Jeannot, R.; Sabik, H.; Sauvard, E.; Dagnac, T.; Dohrendorf, K. (2002-10-18). "Determination of endocrine-disrupting compounds in environmental samples using gas and liquid chromatography with mass spectrometry".
1040:
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
1027:
and a daily intake for an adult were calculated to be 7.5 μg/day. 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. In
2902:
Zhang, Haifeng; Oppel, Iris M.; Spiteller, Michael; Guenther, Klaus; Boehmler, Gabriele; Zuehlke, Sebastian (2009-02-01). "Enantiomers of a nonylphenol isomer: Absolute configurations and estrogenic potencies".
2511:
Raecker, Torsten; Thiele, Bjoern; Boehme, Roswitha M.; Guenther, Klaus (2011-03-01). "Endocrine disrupting nonyl- and octylphenol in infant food in
Germany: Considerable daily intake of nonylphenol for babies".
1792:
Benkendorff, K.; Beardmore, K.; Gooley, A. A.; Packer, N. H.; Tait, N. N. (1999). "Characterisation of the slime gland secretion from the peripatus, Euperipatoides kanangrensis (Onychophora: Peripatopsidae)".
2772:
Boehme, Roswitha M.; Andries, Thomas; Dötz, Karl Heinz; Thiele, Bjoern; Guenther, Klaus (2010-08-01). "Synthesis of defined endocrine-disrupting nonylphenol isomers for biological and environmental studies".
1899:
Soares, A.; Guieysse, B.; Jefferson, B.; Cartmell, E.; Lester, J.N. (2008). "Review article: Nonylphenol in the environment: A critical review on occurrence, fate, toxicity and treatment in wastewaters".
970:: an enzyme produced by the stomach that stimulates appetite. Ghrelin expression is positively regulated by estrogen signaling in the stomach, and it is also important in guiding the differentiation of
1655:
Ruß, Alexander S.; Vinken, Ralph; Schuphan, Ingolf; Schmidt, Burkhard (2005-09-01). "Synthesis of branched para-nonylphenol isomers: Occurrence and quantification in two commercial mixtures".
938:
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
840:
ERα and ERβ. 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
3814:
3809:
2078:
Bechi, Nicoletta; Ietta, Francesca; Romagnoli, Roberta; Jantra, Silke; Cencini, Marco; Galassi, Gianmichele; Serchi, Tommaso; Corsi, Ilaria; Focardi, Silvano; Paulesu, Luana (2009).
1739:
Fiege, Helmut; Voges, Heinz-Werner; Hamamoto, Toshikazu; Umemura, Sumio; Iwata, Tadao; Miki, Hisaya; Fujita, Yasuhiro; Buysch, Hans-Josef; Garbe, Dorothea; Paulus, Wilfried (2000).
575:
Nonylphenol can be produced industrially, naturally, and by the environmental degradation of alkylphenol ethoxylates. Industrially, nonylphenols are produced by the acid-catalyzed
1321:
Guenther, Klaus; Kleist, Einhard; Thiele, Bjoern (2005-12-10). "Estrogen-active nonylphenols from an isomer-specific viewpoint: a systematic numbering system and future trends".
2816:
Guether, Klaus; Kleist, Einhard; Thiele, Bjoern (2005-12-10). "Estrogen-active nonylphenols from an isomer-specific viewpoint: a systematic numbering system and future trends".
950:, 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
2460:
Guenther, Klaus; Heinke, Volkmar; Thiele, Bjoern; Kleist, Einhard; Prast, Hartmut; Raecker, Torsten (2002-04-15). "Endocrine disrupting nonylphenols are ubiquitous in food".
1194:
Soares, A.; Guieysse, B.; Jefferson, B.; Cartmell, E. (2008). "Nonylphenol in the
Environment: A Critical Review on Occurrence, Fate, Toxicity and Treatment in Wastewaters".
5695:
2235:"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"
1380:
2040:
Asimakopoulos, Alexandros G.; Thomaidis, Nikolaos S.; Koupparis, Michael A. (2012). "Recent Trends in
Biomonitoring of Bisphenol A, 4-t-octylphenol, and 4-nonylphenol".
2673:
Bhatt, B. D.; Prasad, J. V; Kalpana, G.; Ali, S. (1992-06-30). "Separation and
Characterization of Isomers of p-Nonylphenols by Capillary GC/GC-MS/GC-FTIR Techniques".
2323:
Kim, M.S.; Yoon, C.Y.; Jang, P.G.; Park, Y.J.; Shin, C.S.; Park, H.S.; Ryu, J.W.; Pak, Y.K.; Park, J.Y.; Lee, K.U.; Kim, S.Y.; Lee, H.K.; Kim, Y.B.; Park, K.S. (2004).
1604:
Thiele, Bjoern; Heinke, Volkmar; Kleist, Einhard; Guenther, Klaus (2004-06-01). "Contribution to the
Structural Elucidation of 10 Isomers of Technical p-Nonylphenol".
2859:
Zhang, Haifeng; Zuehlke, Sebastian; Guenther, Klaus; Spiteller, Michael (2007-01-01). "Enantioselective separation and determination of single nonylphenol isomers".
5927:
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1956:
WHO (World Health Organization). 2002. Integrated Risk Assessment: Nonylphenol Case Study. WHO/IPCS/IRA/12/04, World Health Organization, Geneva, Switzerland.
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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
3167:
796:
3446:
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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
1032:, 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.
605:, which was once used as intravaginal spermicide and condom lubricant, was found to metabolize into free nonylphenol when administered to lab animals.
433:
5842:
2946:
Acir, Ismail-Hakki; Wüst, Matthias; Guenther, Klaus (2016-05-28). "Enantioselective separation of defined endocrine-disrupting nonylphenol isomers".
1432:
Lu, Zhijiang; Gan, Jay (2014-01-21). "Isomer-Specific Biodegradation of Nonylphenol in River Sediments and Structure-Biodegradability Relationship".
5608:
1253:
883:(programmed cell death) in placental cells. These “low doses” ranged from 10-10 M, which is lower than what is generally found in the environment.
3799:
499:, personal care products, and plastics. Nonylphenol has attracted attention due to its prevalence in the environment and its potential role as an
5659:
5651:
787:, and decreases survival in young fish. Studies show that male fish exposed to nonylphenol have lower testicular weight. Nonylphenol can disrupt
3014:
David, A.; Fenet, H.; Gomez, E. (2009). "Alkylphenols in marine environments: distribution monitoring strategies and detection considerations".
5234:
689:, personal care products, and plastics. Nonylphenol and nonylphenol ethoxylates are only used as components of household detergents outside of
5994:
5989:
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5482:
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In other Asian and South American countries nonylphenol is still widely available in commercial detergents, and there is little regulation.
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due to its effects on health and the environment. In Europe, due to environmental concerns, they also have been replaced by more expensive
282:
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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
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3739:
3182:
1991:
Liney, Katherine E.; Hagger, Josephine A.; Tyler, Charles R.; Depledge, Michael H.; Galloway, Tamara S.; Jobling, Susan (April 2006).
483:. They are used extensively in epoxy formulation in North America but its use has been phased out in Europe. These compounds are also
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5888:
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that nonylphenol could be transported over long distances and have a global reach that stretches far from the site of contamination.
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5633:
5628:
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5532:
5457:
4469:
2180:"Endocrine Disruption Fact Sheet." Endocrinedisruption.org. TEDX the Endocrine Disruption Exchange, 7 Nov. 2011. Web. 25 Apr. 2014.
1002:(estrogen receptor α) in estrogen-dependent and estrogen-independent breast cancer cells. Some argue that nonylphenol's suggested
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897:
of human placenta during the first trimester were treated with nonylphenol, which increase the secretion of cytokines including
5248:
1545:
Sonnenschein, Carlos; Soto, Ana M. (1998). "An Updated Review of Environmental Estrogen and Androgen Mimics and Antagonists".
6050:
3732:
2558:
Ademollo, N.; Ferrara, F.; Delise, M.; Fabietti, F.; Funari, E. (2008). "Nonylphenol and octylphenol in human breast milk".
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composed of phenol bearing a 9 carbon-tail. Nonylphenols can come in numerous structures, all of which may be considered
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effect coupled with its widespread human exposure could potentially influence hormone-dependent breast cancer disease.
428:
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1112:, which are less problematic for the environment due to their ability to degrade more quickly than nonylphenols. The
247:
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588:
4623:
4189:
440:
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Pesticide Action Network North America. PANNA. Nonylphenol Etoxylates.. Accessed 9/30/2011. UK Environment Agency
1855:
Thiele B, Guenther K, Schwuger MJ (1997). "Alkylphenol ethoxylates: trace analysis and environmental behaviour".
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properties, which allows them to surround non-polar substances like oil and grease, isolating them from water.
390:
1306:
Mergel, Maria. "Nonylphenol and Nonylphenol Ethoxylates." Toxipedia.org. N.p., 1 Nov. 2011. Web. 27 Apr. 2014.
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The production and use of nonylphenol and nonylphenol ethoxylates is prohibited for certain situations in the
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1819:
Nonylphenol and nonylphenol ethoxylates action plan. U.S. Environmental Protection Agency (EPA). August 2010.
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expression of these anorexigenic neurons in the brain. Additionally, nonylphenol affects the expression of
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147:
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Minnesota Pollution Control Agency Statewide Endocrine Disrupting Compound Monitoring Study, 2007 - 2008
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Gao, Q.; Horvath, T.L. (2008). "Cross-talk between estrogen and leptin signaling in the hypothalamus".
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in affected organisms. The effect is weak because nonylphenols are not very close structural mimics of
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2080:"Environmental Levels of Para-Nonylphenol Are Able to Affect Cytokine Secretion in Human Placenta"
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1700:"Mass Spectral Characterization of p-Nonylphenol Isomers Using High-Resolution Capillary GC—MS"
852:
812:. Concentrations of NP that inhibit reproductive development and function in fish also damages
773:
658:
3939:
913:. This unbalanced cytokine profile at this part of pregnancy has been documented to result in
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2366:"Long-term exposure to nonylphenol affects insulin signaling in the liver of adult male rats"
511:-like activity. The estrogenicity and biodegradation heavily depends on the branching of the
484:
36:
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in the liver. One function of endogenous estrogen in fish is to stimulate the liver to make
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1993:"Health Effects in Fish of Long-Term Exposure to Effluents from Wastewater Treatment Works"
1968:"ARCHIVED - Priority Substances List Assessment Report for Nonylphenol and its Ethoxylates"
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EPA. 2010. Nonylphenol (NP) and Nonylphenal Ethoxylates (NPEs) Action Plan. February, 2014.
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has also included NP on the list of priority hazardous substances for surface water in the
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102:
94:
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Diet seems the most significant source of exposure of nonylphenol to humans. For example,
8:
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are colorless. The nonylphenols are moderately soluble in water but soluble in alcohol.
500:
78:
60:
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2284:"Gastric estrogen directly induces ghrelin expression and production in the rat stomach"
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256:
InChI=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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2017:
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were found with concentrations ranging from 0.1 to 19.4 μg/kg in a diet survey in
991:
674:
266:
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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Microgram amounts of nonylphenol have also been found in the saliva of patients with
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837:
769:
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633:. It can also be used to produce tris(4-nonyl-phenyl) phosphite (TNPP), which is an
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Wheeler, Todd F.; Heim, John R.; LaTorre, Maria R.; Janes, A. Blair (1997-01-01).
192:
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Sakata, I.; Tanaka, T.; Yamazaki, M.; Tanizaki, T.; Zheng, Z.; Sakai, T. (2006).
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809:
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799:. Vitellogenin is released by the maturing female and sequestered by developing
677:(PVC). Nonylphenol is also often used an intermediate in the manufacture of the
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3724:
3647:
3384:
3106:
3084:
2203:
1716:
1699:
1381:"Isomer-specific degradation and endocrine disrupting activity of nonylphenols"
1113:
1105:
1052:
955:
918:
906:
777:
630:
595:
594:
Nonylphenols are also produced naturally in the environment. One organism, the
480:
411:
2959:
2829:
2149:
1500:
1485:"Estrogen biology: New insights into GPER function and clinical opportunities"
1334:
6075:
5507:
5342:
5317:
5097:
5015:
4848:
4826:
4681:
4558:
4290:
4141:
4099:
3509:
3397:
3374:
3351:
2967:
2924:
2489:
2382:
2365:
1748:
1725:
1633:
1508:
1461:
1342:
1020:
987:
902:
829:
706:
646:
362:
352:
1067:. The metabolic pathways involved in its degradation are thought to involve
693:. Nonyl Phenol, is used in many epoxy formulations mainly in North America.
5675:
5647:
5623:
5492:
5417:
5327:
5322:
5312:
5115:
5081:
5071:
5067:
5002:
4996:
4928:
4424:
4414:
4389:
4253:
4206:
4060:
4048:
3607:
3460:
3250:
3215:
3076:
3035:
2975:
2932:
2888:
2837:
2802:
2758:
2722:
2659:
2615:
2579:
2541:
2497:
2438:
2391:
2350:
2309:
2260:
2211:
2167:
2113:
2061:
2026:
1921:
1876:
1684:
1641:
1526:
1469:
1415:
1376:
1350:
1215:
943:
939:
894:
792:
504:
1566:
512:
6020:
5948:
5908:
5868:
5838:
5824:
5814:
5809:
5638:
5582:
5577:
5472:
5467:
5447:
5397:
5372:
5367:
5292:
5282:
5199:
5195:
5191:
5183:
5173:
5169:
5137:
5125:
5111:
5103:
5043:
4976:
4920:
4892:
4726:
4701:
4573:
4474:
4349:
4273:
4243:
4094:
4074:
4024:
3978:
3874:
3592:
3557:
3552:
3547:
3532:
3473:
3468:
3441:
3314:
3260:
3200:
3192:
3116:
2341:
2325:"The mitogenic and antiapoptotic actions of ghrelin in 3T3-L1 adipocytes"
2324:
1036:
841:
825:
654:
634:
614:
564:
560:
556:
532:
464:
460:
2300:
2283:
2095:
753:, but the levels of nonylphenol can be sufficiently high to compensate.
535:. The structure of NPs may vary. The nonyl group can be attached to the
5963:
5943:
5918:
5765:
5710:
5665:
5643:
5552:
5547:
5517:
5502:
5497:
5462:
5352:
5307:
5287:
5165:
5159:
5063:
5051:
5011:
4992:
4968:
4952:
4862:
4858:
4832:
4818:
4771:
4766:
4761:
4751:
4721:
4691:
4686:
4666:
4603:
4524:
4504:
4489:
4484:
4429:
4379:
4280:
4221:
4154:
4149:
4126:
4064:
4039:
3642:
3597:
3587:
3582:
3436:
3369:
3341:
3328:
3111:
3101:
3093:
2916:
2415:
868:
756:
710:
678:
650:
576:
555:, cleaners, emulsifiers, and a variety of other applications. They are
491:
alkylphenol ethoxylates and nonylphenol ethoxylates, which are used in
488:
324:
158:
4464:
3959:
2481:
1868:
1625:
1453:
1407:
929:
Nonylphenol has been shown to act as an obesity enhancing chemical or
5958:
5938:
5878:
5858:
5700:
5537:
5412:
5407:
5392:
5377:
5337:
5219:
5187:
5145:
5093:
5089:
5085:
5075:
5055:
5039:
4988:
4964:
4960:
4948:
4940:
4936:
4896:
4884:
4868:
4854:
4844:
4840:
4796:
4656:
4630:
4618:
4593:
4583:
4568:
4548:
4499:
4399:
4394:
4369:
4359:
4324:
4184:
4159:
4121:
4079:
3415:
3336:
3304:
3299:
3281:
3230:
3220:
3144:
2008:
1063:
When humans orally ingest nonylphenol, it is rapidly absorbed in the
975:
971:
959:
880:
872:
864:
833:
784:
750:
686:
682:
622:
618:
602:
552:
496:
492:
472:
468:
3904:
410:
Except where otherwise noted, data are given for materials in their
5829:
5819:
5522:
5382:
5302:
5297:
5230:
5047:
4984:
4980:
4944:
4932:
4904:
4900:
4888:
4880:
4810:
4598:
4588:
4434:
4419:
4404:
4339:
4334:
4179:
4089:
3685:
3572:
3537:
3407:
3320:
3245:
3240:
3225:
3205:
3134:
3126:
1374:
1003:
951:
930:
891:
887:
876:
856:
836:, and it competes with the endogenous hormone for binding with the
780:
742:
725:
Nonylphenol is not persistent in air, as it is rapidly degraded by
626:
508:
476:
855:
of nonylphenol in late pregnancy causes the expression of certain
126:
23:
5984:
5730:
5542:
5442:
5432:
5427:
5207:
5151:
5141:
5033:
4908:
4716:
4711:
4613:
4578:
4509:
4409:
4258:
4226:
4164:
3617:
3602:
3478:
3392:
3361:
3272:
3210:
1375:
Gabriel FL, Routledge EJ, Heidelberger A, Rentsch D, Guenther K,
1024:
995:
967:
934:
746:
666:
638:
516:
342:
179:
3045:
1791:
5903:
5898:
5755:
5019:
5007:
4822:
4791:
4786:
4781:
4514:
4169:
3695:
3690:
3235:
2039:
1898:
1193:
1029:
947:
860:
813:
800:
760:
Structure of the hormone estradiol and one of the nonylphenols.
701:
Nonylphenol persists in aquatic environments and is moderately
690:
662:
642:
584:
580:
536:
138:
5249:
5979:
5853:
5735:
5705:
4924:
4806:
4635:
3268:
2858:
2557:
1080:
1076:
116:
2735:
2363:
2281:
5999:
5780:
5690:
5059:
4814:
2901:
2510:
954:. Nonylphenol has been shown mimic the action of leptin on
520:
367:
293 to 297 °C (559 to 567 °F; 566 to 570 K)
2699:
2459:
1603:
879:
exposure to low doses of nonylphenol cause an increase in
5834:
2592:
2077:
1738:
1547:
The Journal of Steroid Biochemistry and Molecular Biology
1124:
1990:
1654:
816:, decreases body weight, and induces stressed behavior.
531:
Nonylphenols fall into the general chemical category of
2771:
1697:
828:
have estrogenic effects in the body. They are known as
4150:
Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol)
1854:
933:, though it has paradoxically been shown to have anti-
357:−8 to 2 °C (18 to 36 °F; 265 to 275 K)
2672:
890:
signaling molecule secretions in the human placenta.
2628:
2232:
1320:
2815:
2233:Masuo, Y.; Morita, M.; Oka, S.; Ishido, M. (2004).
1476:
986:Nonylphenol exposure has also been associated with
515:sidechain. Nonylphenol has been found to act as an
2417:Estrogen Receptor α in MCF7 Breast Cancer Cells".
526:
337:Light yellow viscous liquid with phenolic smell
6073:
3754:
2945:
1544:
696:
191:
3013:
2322:
1785:
1540:
1538:
1536:
1482:
1230:"Epoxy Nonyl Phenol Alert is it in your epoxy?"
1009:
101:
93:
77:
69:
5254:Tooltip Selective estrogen receptor modulators
4609:Furostilbestrol (diethylstilbestrol difuroate)
3970:16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)
2364:Jubendradass, R; D'Cruz, S; Mathur, P (2012).
3800:3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol
3740:
3061:
1483:Prossnitz, Eric R.; Barton, Matthias (2014).
3910:10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED)
2131:
1533:
1159:Institute for Occupational Safety and Health
847:
5785:Tooltip G protein-coupled estrogen receptor
4604:Fosfestrol (diethylstilbestrol diphosphate)
2553:
2551:
2411:
2409:
745:and in turn disrupt the natural balance of
681:nonylphenol ethoxylates, which are used in
4747:Triphenylmethylethylene (triphenylpropene)
4071:, many others; via estrogenic metabolites)
3995:17α-Epiestriol (16α-hydroxy-17α-estradiol)
3747:
3733:
3502:
3068:
3054:
2189:
886:Nonylphenol has also been shown to affect
166:
3767:
2381:
2340:
2299:
2250:
2157:
2103:
2016:
1795:Comparative Biochemistry and Physiology B
1715:
1516:
1189:
1187:
231:
219:
211:
3009:
3007:
2996:Official Journal of the European Union:
2548:
2406:
2073:
2071:
1185:
1183:
1181:
1179:
1177:
1175:
1173:
1171:
1169:
1167:
924:
755:
732:
2127:
2125:
2123:
1302:
1300:
1298:
1296:
1294:
819:
6074:
2948:Analytical and Bioanalytical Chemistry
2818:Analytical and Bioanalytical Chemistry
2462:Environmental Science & Technology
1965:
1952:
1950:
1948:
1946:
1944:
1942:
1940:
1606:Environmental Science & Technology
1590:
1588:
1586:
1584:
1434:Environmental Science & Technology
1323:Analytical and Bioanalytical Chemistry
669:salts of nonylphenol are also used as
3728:
3049:
3004:
2132:Grün, Felix; Blumberg, Bruce (2009).
2068:
1431:
1164:
1141:
613:Nonylphenol is used in manufacturing
259:Key: SNQQPOLDUKLAAF-UHFFFAOYSA-N
146:
2138:Molecular and Cellular Endocrinology
2120:
1489:Molecular and Cellular Endocrinology
1427:
1425:
1370:
1368:
1316:
1314:
1312:
1291:
2134:"Endocrine Disrupters as Obesogens"
1937:
1581:
994:of breast cancer cells, due to its
990:. It has been shown to promote the
737:Nonylphenol is considered to be an
269:Key: SNQQPOLDUKLAAF-UHFFFAOYAP
182:
13:
2675:Journal of Chromatographic Science
1704:Journal of Chromatographic Science
824:Alkylphenols like nonylphenol and
14:
6108:
5146:taleranol (teranol, β-zearalanol)
4061:metandienone (methandrostenolone)
3075:
2881:10.1016/j.chemosphere.2006.08.012
2795:10.1016/j.chemosphere.2010.03.064
2652:10.1016/j.chemosphere.2003.09.024
2534:10.1016/j.chemosphere.2010.11.065
2192:Am. J. Physiol. Endocrinol. Metab
2084:Environmental Health Perspectives
1677:10.1016/j.chemosphere.2005.02.046
1422:
1365:
1309:
507:, due to its ability to act with
463:. They are used in manufacturing
40:4-(2,4-dimethylheptan-3-yl)phenol
6056:Progesterone receptor modulators
5810:Afimoxifene (4-hydroxytamoxifen)
4692:Prinaberel (ERB-041, WAY-202041)
589:High Production Volume Chemicals
455:are a family of closely related
418:
236: (branched 4-Nonyl phenols)
98: (branched 4-Nonyl phenols)
22:
5753:Coregulator-binding modulators:
4020:17β-Methyl-17α-dihydroequilenin
3028:10.1016/j.marpolbul.2009.04.021
2990:
2939:
2895:
2852:
2809:
2765:
2729:
2693:
2666:
2622:
2586:
2504:
2453:
2357:
2316:
2275:
2226:
2183:
2174:
2033:
1984:
1959:
1928:
1892:
1883:
1848:
1835:
1822:
1813:
1732:
1691:
1648:
1597:
1044:, growth, and memory function.
909:, and reduced the secretion of
608:
414:(at 25 °C , 100 kPa).
404:low level endrocrine disruptor
4584:Erteberel (SERBA-1, LY-500307)
1267:
1246:
1222:
527:Structure and basic properties
487:to the commercially important
391:Occupational safety and health
1:
6041:Receptor/signaling modulators
4005:17α-Ethynyl-3β-androstanediol
4000:17α-Ethynyl-3α-androstanediol
2608:10.1016/s0021-9673(02)01240-2
1966:Canada, Health (2004-07-26).
1807:10.1016/S0305-0491(99)00145-5
1559:10.1016/s0960-0760(98)00027-2
1134:
1099:
697:Prevalence in the environment
570:
6051:Androgen receptor modulators
4355:Lynestrenol phenylpropionate
2751:10.1016/j.chroma.2005.12.092
2715:10.1016/j.chroma.2005.10.031
2572:10.1016/j.envint.2008.03.001
2252:10.1016/j.regpep.2004.05.010
2054:10.1016/j.toxlet.2011.07.032
1914:10.1016/j.envint.2008.01.004
1208:10.1016/j.envint.2008.01.004
1161:, accessed on 6 April 2011.
1086:
1058:
1010:Human exposure and breakdown
806:follicle-stimulating hormone
741:due to its ability to mimic
621:additives, laundry and dish
543:Nonylphenol arises from the
471:additives, laundry and dish
7:
6046:Estrogens and antiestrogens
5696:Oxabicycloheptene sulfonate
5383:Etacstil (GW-5638, DPC-974)
4559:Doisynoestrol (fenocycline)
4303:Ethinylestradiol 3-benzoate
3815:3β,5α-Dihydrolevonorgestrel
3810:3α,5α-Dihydrolevonorgestrel
2739:Journal of Chromatography A
2703:Journal of Chromatography A
2596:Journal of Chromatography A
1014:
921:, and other complications.
911:tumor necrosis factor alpha
661:in plastic food packaging.
10:
6113:
5763:Noncompetitive inhibitors:
5388:Ethamoxytriphetol (MER-25)
4549:Dimestrol (dianisylhexene)
4308:Ethinylestradiol sulfonate
2204:10.1152/ajpendo.00733.2007
1150:Nonylphenol, mixed isomers
808:) being released from the
601:Another surfactant called
329:220.35 g/mol
6033:
6008:
5972:
5805:7β-Hydroxyepiandrosterone
5792:
5778:
5591:
5363:Desmethylchlorotrianisene
5244:
4542:Diethylstilbestrol esters
4495:Bisdehydrodoisynolic acid
3915:11β-Chloromethylestradiol
3890:7β-Hydroxyepiandrosterone
3779:
3772:Tooltip Estrogen receptor
3765:
3661:
3525:
3459:
3424:
3406:
3383:
3360:
3327:
3313:
3290:
3259:
3191:
3153:
3125:
3092:
3083:
2960:10.1007/s00216-016-9661-2
2830:10.1007/s00216-005-0181-8
2687:10.1093/chromsci/30.6.203
2150:10.1016/j.mce.2009.02.018
1902:Environment International
1501:10.1016/j.mce.2014.02.002
1335:10.1007/s00216-005-0181-8
1196:Environment International
1155:GESTIS Substance Database
1118:Water Framework Directive
981:
848:Effects in pregnant women
559:, meaning they have both
545:environmental degradation
408:
388:
383:
298:
278:
243:
53:
45:
35:
30:
21:
5869:Fulvestrant (ICI-182780)
5686:Methylpiperidinopyrazole
5639:Fulvestrant (ICI-182780)
5122:Resorcylic acid lactones
4345:Hydroxyestrone diacetate
4281:Etamestrol (eptamestrol)
2383:10.1177/0960327111426587
1749:10.1002/14356007.a19_313
1717:10.1093/chromsci/35.1.19
1279:Healthy Building Network
1042:neurological development
946:responds to the hormone
5180:Synthetic xenoestrogens
4737:Triphenylchloroethylene
4672:Methestrol dipropionate
4200:Polyestradiol phosphate
3653:Perfluorinated compound
1997:Environ Health Perspect
1844:Stasinakis et al., 2013
1275:"No, no, nonyl(phenol)"
853:Subcutaneous injections
657:in addition to being a
549:nonylphenol ethoxylates
106: (isononylphenols)
5273:4'-Hydroxynorendoxifen
5268:2-Phenylbenzothiophene
5142:zeranol (α-zearalanol)
4845:phlorizin (phloridzin)
4732:Triphenylbromoethylene
4631:ICI-85966 (Stilbostat)
4212:Estramustine phosphate
4085:Bolandiol dipropionate
3479:α-Zearalanol (zeranol)
3347:Desmethylwedelolactone
3178:6,8-Diprenylnaringenin
1379:, et al. (2008).
1065:gastrointestinal tract
942:appetite control. The
761:
5453:Miproxifene phosphate
5278:27-Hydroxycholesterol
4742:Triphenyliodoethylene
4286:Ethinylandrostenediol
4249:Estrogenic substances
4237:Polyestriol phosphate
4105:Cloxestradiol acetate
2431:10.1385/endo:22:3:275
1234:www.epoxyproducts.com
925:Effects on metabolism
875:. In addition, early
759:
733:Environmental hazards
679:non-ionic surfactants
489:non-ionic surfactants
216: (general class)
74: (general class)
6082:Endocrine disruptors
4767:WAY-204688 (SIM-688)
4579:ERB-196 (WAY-202196)
4530:Dienestrol diacetate
4269:Estrone methyl ether
4175:Esterified estrogens
4117:Conjugated estrogens
4010:17β-Dihydroequilenin
3985:17α-Dihydroequilenin
3925:15α-Hydroxyestradiol
3920:11β-Methoxyestradiol
3895:8,9-Dehydroestradiol
3140:7,8-Dihydroxyflavone
2342:10.1210/me.2003-0459
1831:Samaras et al., 2013
915:implantation failure
820:Human health hazards
705:. It is not readily
5934:Propylpyrazoletriol
5849:Diarylpropionitrile
4697:Propylpyrazoletriol
4554:Dimethylstilbestrol
4520:Diarylpropionitrile
4330:Etynodiol diacetate
4030:Abiraterone acetate
3940:16α-Fluoroestradiol
3173:8-Geranylnaringenin
2873:2007Chmsp..66..594Z
2787:2010Chmsp..80..813B
2644:2004Chmsp..54.1127K
2526:2011Chmsp..82.1533R
2474:2002EnST...36.1676G
2301:10.1677/joe.1.06808
2096:10.1289/ehp.0900882
1669:2005Chmsp..60.1624R
1618:2004EnST...38.3405T
1446:2014EnST...48.1008L
1400:2008EnST...42.6399G
1388:Environ Sci Technol
1254:"para nonyl phenol"
1110:alcohol ethoxylates
1073:sulfate conjugation
739:endocrine disruptor
501:endocrine disruptor
374:Solubility in water
18:
6016:Diethylstilbestrol
5800:2-Methoxyestradiol
5731:TAS-108 (SR-16234)
5681:Methylepitiostanol
5619:EM-800 (SCH-57050)
5543:TAS-108 (SR-16234)
5263:2-Phenylbenzofuran
4877:8-prenylnaringenin
4537:Diethylstilbestrol
4195:Lipoidal estradiol
4170:ERA-63 (ORG-37663)
4112:Conjugated estriol
4057:methyltestosterone
4015:17β-Dihydroequilin
3990:17α-Dihydroequilin
3965:16β-Hydroxyestrone
3950:16α-Hydroxyestrone
3900:8,9-Dehydroestrone
3885:7α-Methylestradiol
3860:4-Methoxyestradiol
3850:4-Hydroxyestradiol
3825:3β-Hydroxytibolone
3820:3α-Hydroxytibolone
3790:2-Hydroxyestradiol
3168:6-Prenylnaringenin
3163:8-Prenylnaringenin
2917:10.1002/chir.20556
2042:Toxicology Letters
2003:(Suppl 1): 81–89.
1741:Phenol Derivatives
867:placenta than the
838:estrogen receptors
797:phospholipoprotein
770:androgen receptors
766:estrogen receptors
762:
675:polyvinyl chloride
583:with a mixture of
441:Infobox references
290:Oc1ccccc1CCCCCCCCC
16:
6069:
6068:
6061:List of estrogens
6029:
6028:
5774:
5773:
5614:Cytestrol acetate
4837:isoliquiritigenin
4779:Unknown/unsorted:
4465:β-LGND2 (GTx-878)
4045:Anabolic steroids
3955:16α-Iodoestradiol
3845:4-Fluoroestradiol
3840:4-Androstenedione
3830:3β-Androstanediol
3805:3α-Androstanediol
3756:Estrogen receptor
3722:
3721:
3633:Pentachlorophenol
3521:
3520:
3512:
3455:
3454:
3016:Mar. Pollut. Bull
2954:(20): 5601–5607.
2520:(11): 1533–1540.
2482:10.1021/es010199v
2370:Hum. Exp. Toxicol
1869:10.1021/cr970323m
1663:(11): 1624–1635.
1626:10.1021/es040026g
1612:(12): 3405–3411.
1454:10.1021/es403950y
1408:10.1021/es800577a
783:, decreases male
727:hydroxyl radicals
457:organic compounds
449:Chemical compound
447:
446:
128:Interactive image
6104:
5928:2,2',5'-PCB-4-OH
5864:Ethinylestradiol
5790:
5789:
5786:
5782:
5523:Rimostil (P-081)
5333:Chlorotrianisene
5255:
5251:
5030:Metalloestrogens
4809:-related (e.g.,
4624:Hexestrol esters
4298:Ethinylestradiol
4190:Estradiol esters
3945:16α-Hydroxy-DHEA
3930:16-Ketoestradiol
3870:5-Androstenediol
3865:4-Methoxyestrone
3855:4-Hydroxyestrone
3835:4-Androstenediol
3795:2-Hydroxyestrone
3777:
3776:
3773:
3769:
3749:
3742:
3735:
3726:
3725:
3663:Metalloestrogens
3510:
3500:
3499:
3292:Dihydrochalcones
3155:Prenylflavonoids
3090:
3089:
3070:
3063:
3056:
3047:
3046:
3040:
3039:
3011:
3002:
2994:
2988:
2987:
2943:
2937:
2936:
2899:
2893:
2892:
2856:
2850:
2849:
2813:
2807:
2806:
2769:
2763:
2762:
2745:(1–2): 233–239.
2733:
2727:
2726:
2709:(1–2): 245–255.
2697:
2691:
2690:
2670:
2664:
2663:
2638:(8): 1127–1134.
2626:
2620:
2619:
2602:(1–2): 143–159.
2590:
2584:
2583:
2555:
2546:
2545:
2508:
2502:
2501:
2468:(8): 1676–1680.
2457:
2451:
2450:
2413:
2404:
2403:
2385:
2361:
2355:
2354:
2344:
2335:(9): 2291–2301.
2320:
2314:
2313:
2303:
2279:
2273:
2272:
2254:
2245:(1–3): 225–234.
2230:
2224:
2223:
2198:(5): E817–E826.
2187:
2181:
2178:
2172:
2171:
2161:
2129:
2118:
2117:
2107:
2075:
2066:
2065:
2037:
2031:
2030:
2020:
2009:10.1289/ehp.8058
1988:
1982:
1981:
1979:
1978:
1963:
1957:
1954:
1935:
1932:
1926:
1925:
1908:(7): 1033–1049.
1896:
1890:
1887:
1881:
1880:
1852:
1846:
1839:
1833:
1826:
1820:
1817:
1811:
1810:
1789:
1783:
1782:
1776:
1772:
1770:
1762:
1736:
1730:
1729:
1719:
1695:
1689:
1688:
1652:
1646:
1645:
1601:
1595:
1592:
1579:
1578:
1542:
1531:
1530:
1520:
1480:
1474:
1473:
1440:(2): 1008–1014.
1429:
1420:
1419:
1394:(17): 6399–408.
1385:
1372:
1363:
1362:
1318:
1307:
1304:
1289:
1288:
1286:
1285:
1271:
1265:
1264:
1258:
1250:
1244:
1243:
1241:
1240:
1226:
1220:
1219:
1191:
1162:
1145:
899:interferon gamma
671:heat stabilizers
637:used to protect
431:
425:
422:
421:
306:Chemical formula
235:
223:
215:
195:
184:
170:
150:
130:
105:
97:
81:
73:
26:
19:
15:
6112:
6111:
6107:
6106:
6105:
6103:
6102:
6101:
6072:
6071:
6070:
6065:
6025:
6004:
5968:
5784:
5770:
5604:7β-Hydroxy-DHEA
5587:
5423:Levormeloxifene
5253:
5246:
5240:
5156:deoxymiroestrol
5024:-hinokiresinol)
4662:Methallenestril
4564:Doisynolic acid
4365:Methylestradiol
3880:7α-Hydroxy-DHEA
3771:
3761:
3753:
3723:
3718:
3657:
3517:
3498:
3451:
3432:Deoxymiroestrol
3420:
3402:
3379:
3356:
3323:
3309:
3286:
3255:
3187:
3149:
3121:
3079:
3074:
3044:
3043:
3012:
3005:
3001:, July 17, 2003
2995:
2991:
2944:
2940:
2900:
2896:
2857:
2853:
2814:
2810:
2770:
2766:
2734:
2730:
2698:
2694:
2671:
2667:
2627:
2623:
2591:
2587:
2556:
2549:
2509:
2505:
2458:
2454:
2414:
2407:
2362:
2358:
2329:Mol. Endocrinol
2321:
2317:
2280:
2276:
2231:
2227:
2188:
2184:
2179:
2175:
2130:
2121:
2076:
2069:
2038:
2034:
1989:
1985:
1976:
1974:
1964:
1960:
1955:
1938:
1933:
1929:
1897:
1893:
1888:
1884:
1853:
1849:
1840:
1836:
1827:
1823:
1818:
1814:
1790:
1786:
1774:
1773:
1764:
1763:
1759:
1737:
1733:
1696:
1692:
1653:
1649:
1602:
1598:
1593:
1582:
1553:(1–6): 143–50.
1543:
1534:
1481:
1477:
1430:
1423:
1383:
1373:
1366:
1319:
1310:
1305:
1292:
1283:
1281:
1273:
1272:
1268:
1256:
1252:
1251:
1247:
1238:
1236:
1228:
1227:
1223:
1202:(7): 1033–049.
1192:
1165:
1146:
1142:
1137:
1123:In the US, the
1102:
1089:
1061:
1053:dental sealants
1017:
1012:
984:
927:
865:first trimester
850:
822:
810:pituitary gland
789:steroidogenesis
735:
703:bioaccumulative
699:
619:lubricating oil
611:
573:
529:
469:lubricating oil
450:
443:
438:
437:
436: ?)
427:
423:
419:
415:
401:
376:
318:
314:
308:
294:
291:
286:
285:
274:
271:
270:
267:
261:
260:
257:
251:
250:
239:
198:
185:
173:
153:
133:
120:
109:
63:
49:
41:
12:
11:
5:
6110:
6100:
6099:
6094:
6089:
6084:
6067:
6066:
6064:
6063:
6058:
6053:
6048:
6043:
6038:
6034:
6031:
6030:
6027:
6026:
6024:
6023:
6018:
6012:
6010:
6006:
6005:
6003:
6002:
5997:
5992:
5987:
5982:
5976:
5974:
5970:
5969:
5967:
5966:
5961:
5956:
5951:
5946:
5941:
5936:
5931:
5921:
5916:
5911:
5906:
5901:
5896:
5894:Hydroxytyrosol
5891:
5886:
5881:
5876:
5871:
5866:
5861:
5856:
5851:
5846:
5832:
5827:
5822:
5817:
5812:
5807:
5802:
5796:
5794:
5787:
5776:
5775:
5772:
5771:
5769:
5768:
5759:
5758:
5749:
5748:
5743:
5738:
5733:
5728:
5723:
5718:
5713:
5708:
5703:
5698:
5693:
5688:
5683:
5678:
5673:
5668:
5663:
5641:
5636:
5631:
5626:
5621:
5616:
5611:
5609:Chloroindazole
5606:
5601:
5595:
5593:
5589:
5588:
5586:
5585:
5580:
5575:
5570:
5565:
5560:
5555:
5550:
5545:
5540:
5535:
5530:
5528:Spironolactone
5525:
5520:
5515:
5510:
5505:
5500:
5495:
5490:
5485:
5480:
5475:
5470:
5465:
5460:
5455:
5450:
5445:
5440:
5435:
5430:
5425:
5420:
5415:
5410:
5405:
5400:
5395:
5390:
5385:
5380:
5375:
5370:
5365:
5360:
5355:
5350:
5345:
5340:
5335:
5330:
5325:
5320:
5315:
5310:
5305:
5300:
5295:
5290:
5285:
5280:
5275:
5270:
5265:
5259:
5257:
5242:
5241:
5239:
5238:
5229:Others (e.g.,
5227:
5177:
5163:
5149:
5119:
5101:
5079:
5037:
5027:
5005:
5000:
4957:liquiritigenin
4866:
4852:
4830:
4804:Xenoestrogens:
4800:
4799:
4794:
4789:
4784:
4775:
4774:
4769:
4764:
4759:
4754:
4749:
4744:
4739:
4734:
4729:
4724:
4719:
4714:
4709:
4704:
4699:
4694:
4689:
4684:
4679:
4677:Paroxypropione
4674:
4669:
4664:
4659:
4654:
4646:
4638:
4633:
4628:
4627:
4626:
4616:
4611:
4606:
4601:
4596:
4591:
4589:Estrobin (DBE)
4586:
4581:
4576:
4571:
4566:
4561:
4556:
4551:
4546:
4545:
4544:
4534:
4533:
4532:
4522:
4517:
4512:
4507:
4502:
4497:
4492:
4487:
4482:
4480:Allenolic acid
4477:
4472:
4467:
4462:
4457:
4452:
4447:
4438:
4437:
4432:
4427:
4422:
4417:
4412:
4407:
4402:
4397:
4392:
4387:
4385:Norethisterone
4382:
4377:
4375:Mytatrienediol
4372:
4367:
4362:
4357:
4352:
4347:
4342:
4337:
4332:
4327:
4322:
4320:Ethylestradiol
4317:
4315:Ethinylestriol
4312:
4311:
4310:
4305:
4295:
4294:
4293:
4283:
4278:
4277:
4276:
4271:
4266:
4264:Estrone esters
4256:
4251:
4246:
4241:
4240:
4239:
4234:
4232:Estriol esters
4224:
4219:
4217:Estrapronicate
4214:
4209:
4204:
4203:
4202:
4197:
4192:
4182:
4177:
4172:
4167:
4162:
4157:
4152:
4147:
4139:
4134:
4129:
4124:
4119:
4114:
4109:
4108:
4107:
4097:
4092:
4087:
4082:
4077:
4072:
4042:
4037:
4035:Alestramustine
4032:
4027:
4022:
4017:
4012:
4007:
4002:
3997:
3992:
3987:
3982:
3972:
3967:
3962:
3957:
3952:
3947:
3942:
3937:
3935:16-Ketoestrone
3932:
3927:
3922:
3917:
3912:
3907:
3902:
3897:
3892:
3887:
3882:
3877:
3872:
3867:
3862:
3857:
3852:
3847:
3842:
3837:
3832:
3827:
3822:
3817:
3812:
3807:
3802:
3797:
3792:
3783:
3781:
3774:
3763:
3762:
3752:
3751:
3744:
3737:
3729:
3720:
3719:
3717:
3716:
3713:
3710:
3707:
3704:
3701:
3698:
3693:
3688:
3683:
3680:
3677:
3674:
3671:
3667:
3665:
3659:
3658:
3656:
3655:
3650:
3648:Propyl gallate
3645:
3640:
3635:
3630:
3625:
3620:
3615:
3610:
3605:
3600:
3595:
3590:
3585:
3580:
3575:
3570:
3565:
3560:
3555:
3550:
3545:
3540:
3535:
3529:
3527:
3523:
3522:
3519:
3518:
3516:
3515:
3513:-Penicillamine
3506:
3504:
3497:
3496:
3491:
3486:
3481:
3476:
3471:
3465:
3463:
3457:
3456:
3453:
3452:
3450:
3449:
3447:α-Isosparteine
3444:
3439:
3434:
3428:
3426:
3422:
3421:
3419:
3418:
3412:
3410:
3404:
3403:
3401:
3400:
3395:
3389:
3387:
3385:Flavonolignans
3381:
3380:
3378:
3377:
3372:
3366:
3364:
3358:
3357:
3355:
3354:
3349:
3344:
3339:
3333:
3331:
3325:
3324:
3319:
3317:
3311:
3310:
3308:
3307:
3302:
3296:
3294:
3288:
3287:
3285:
3284:
3279:
3265:
3263:
3257:
3256:
3254:
3253:
3248:
3243:
3238:
3233:
3228:
3223:
3218:
3213:
3208:
3203:
3197:
3195:
3189:
3188:
3186:
3185:
3180:
3175:
3170:
3165:
3159:
3157:
3151:
3150:
3148:
3147:
3142:
3137:
3131:
3129:
3123:
3122:
3120:
3119:
3114:
3109:
3107:Liquiritigenin
3104:
3098:
3096:
3087:
3085:Phytoestrogens
3081:
3080:
3073:
3072:
3065:
3058:
3050:
3042:
3041:
3022:(7): 953–960.
3003:
2989:
2938:
2911:(2): 271–275.
2894:
2867:(4): 594–602.
2851:
2824:(2): 542–546.
2808:
2781:(7): 813–821.
2764:
2728:
2692:
2681:(6): 203–210.
2665:
2621:
2585:
2566:(7): 984–987.
2547:
2503:
2452:
2405:
2376:(9): 868–876.
2356:
2315:
2294:(3): 749–757.
2274:
2225:
2182:
2173:
2144:(1–2): 19–29.
2119:
2067:
2032:
1983:
1958:
1936:
1927:
1891:
1882:
1863:(8): 3247–72.
1847:
1834:
1821:
1812:
1801:(4): 457–465.
1784:
1775:|journal=
1758:978-3527306732
1757:
1731:
1690:
1647:
1596:
1580:
1532:
1495:(1–2): 71–83.
1475:
1421:
1364:
1329:(2): 542–546.
1308:
1290:
1266:
1245:
1221:
1163:
1139:
1138:
1136:
1133:
1114:European Union
1106:European Union
1101:
1098:
1088:
1085:
1060:
1057:
1016:
1013:
1011:
1008:
983:
980:
956:neuropeptide Y
926:
923:
919:pregnancy loss
907:interleukin 10
849:
846:
821:
818:
804:level of FSH (
734:
731:
698:
695:
647:Vinyl polymers
610:
607:
572:
569:
528:
525:
448:
445:
444:
439:
417:
416:
412:standard state
409:
406:
405:
402:
399:
396:
395:
386:
385:
381:
380:
379:6 mg/L (pH 7)
377:
372:
369:
368:
365:
359:
358:
355:
349:
348:
345:
339:
338:
335:
331:
330:
327:
321:
320:
316:
312:
309:
304:
301:
300:
296:
295:
293:
292:
289:
281:
280:
279:
276:
275:
273:
272:
268:
265:
264:
262:
258:
255:
254:
246:
245:
244:
241:
240:
238:
237:
229:
228:-Nonyl phenol)
217:
208:
206:
200:
199:
197:
196:
188:
186:
178:
175:
174:
172:
171:
163:
161:
155:
154:
152:
151:
143:
141:
135:
134:
132:
131:
123:
121:
114:
111:
110:
108:
107:
99:
91:
75:
66:
64:
59:
56:
55:
51:
50:
48:Phenol, nonyl-
47:
43:
42:
39:
33:
32:
28:
27:
9:
6:
4:
3:
2:
6109:
6098:
6097:Xenoestrogens
6095:
6093:
6092:GPER agonists
6090:
6088:
6085:
6083:
6080:
6079:
6077:
6062:
6059:
6057:
6054:
6052:
6049:
6047:
6044:
6042:
6039:
6036:
6035:
6032:
6022:
6019:
6017:
6014:
6013:
6011:
6007:
6001:
5998:
5996:
5993:
5991:
5988:
5986:
5983:
5981:
5978:
5977:
5975:
5971:
5965:
5962:
5960:
5957:
5955:
5952:
5950:
5947:
5945:
5942:
5940:
5937:
5935:
5932:
5929:
5925:
5922:
5920:
5917:
5915:
5912:
5910:
5907:
5905:
5902:
5900:
5897:
5895:
5892:
5890:
5887:
5885:
5882:
5880:
5877:
5875:
5872:
5870:
5867:
5865:
5862:
5860:
5857:
5855:
5852:
5850:
5847:
5844:
5840:
5836:
5833:
5831:
5828:
5826:
5823:
5821:
5818:
5816:
5813:
5811:
5808:
5806:
5803:
5801:
5798:
5797:
5795:
5791:
5788:
5783:
5777:
5767:
5764:
5761:
5760:
5757:
5754:
5751:
5750:
5747:
5744:
5742:
5739:
5737:
5734:
5732:
5729:
5727:
5724:
5722:
5719:
5717:
5714:
5712:
5709:
5707:
5704:
5702:
5699:
5697:
5694:
5692:
5689:
5687:
5684:
5682:
5679:
5677:
5674:
5672:
5669:
5667:
5664:
5661:
5657:
5653:
5649:
5645:
5642:
5640:
5637:
5635:
5632:
5630:
5627:
5625:
5622:
5620:
5617:
5615:
5612:
5610:
5607:
5605:
5602:
5600:
5597:
5596:
5594:
5590:
5584:
5581:
5579:
5576:
5574:
5571:
5569:
5566:
5564:
5561:
5559:
5556:
5554:
5551:
5549:
5546:
5544:
5541:
5539:
5536:
5534:
5531:
5529:
5526:
5524:
5521:
5519:
5516:
5514:
5511:
5509:
5508:Pipendoxifene
5506:
5504:
5501:
5499:
5496:
5494:
5491:
5489:
5486:
5484:
5481:
5479:
5476:
5474:
5471:
5469:
5466:
5464:
5461:
5459:
5456:
5454:
5451:
5449:
5446:
5444:
5441:
5439:
5436:
5434:
5431:
5429:
5426:
5424:
5421:
5419:
5416:
5414:
5411:
5409:
5406:
5404:
5401:
5399:
5396:
5394:
5391:
5389:
5386:
5384:
5381:
5379:
5376:
5374:
5371:
5369:
5366:
5364:
5361:
5359:
5356:
5354:
5351:
5349:
5346:
5344:
5343:Clomifenoxide
5341:
5339:
5336:
5334:
5331:
5329:
5326:
5324:
5321:
5319:
5318:Brilanestrant
5316:
5314:
5311:
5309:
5306:
5304:
5301:
5299:
5296:
5294:
5291:
5289:
5286:
5284:
5281:
5279:
5276:
5274:
5271:
5269:
5266:
5264:
5261:
5260:
5258:
5252:
5243:
5236:
5232:
5228:
5225:
5221:
5217:
5213:
5209:
5205:
5201:
5197:
5193:
5189:
5185:
5181:
5178:
5175:
5171:
5167:
5164:
5161:
5157:
5154:-like (e.g.,
5153:
5150:
5147:
5143:
5139:
5135:
5131:
5127:
5123:
5120:
5117:
5113:
5109:
5105:
5102:
5099:
5098:guggulsterone
5095:
5091:
5087:
5083:
5082:Phytosteroids
5080:
5077:
5073:
5069:
5065:
5061:
5057:
5053:
5049:
5045:
5041:
5038:
5035:
5031:
5028:
5025:
5023:
5017:
5016:enterolactone
5013:
5009:
5006:
5004:
5001:
4998:
4994:
4990:
4986:
4982:
4978:
4974:
4970:
4966:
4962:
4958:
4954:
4950:
4946:
4942:
4938:
4934:
4930:
4926:
4922:
4918:
4914:
4910:
4906:
4902:
4898:
4894:
4890:
4886:
4882:
4878:
4874:
4870:
4867:
4864:
4860:
4856:
4853:
4850:
4849:wedelolactone
4846:
4842:
4838:
4834:
4831:
4828:
4827:photoanethole
4824:
4820:
4816:
4812:
4808:
4805:
4802:
4801:
4798:
4795:
4793:
4790:
4788:
4785:
4783:
4780:
4777:
4776:
4773:
4770:
4768:
4765:
4763:
4760:
4758:
4755:
4753:
4750:
4748:
4745:
4743:
4740:
4738:
4735:
4733:
4730:
4728:
4725:
4723:
4720:
4718:
4715:
4713:
4710:
4708:
4705:
4703:
4700:
4698:
4695:
4693:
4690:
4688:
4685:
4683:
4682:Pentafluranol
4680:
4678:
4675:
4673:
4670:
4668:
4665:
4663:
4660:
4658:
4655:
4653:
4651:
4647:
4645:
4643:
4639:
4637:
4634:
4632:
4629:
4625:
4622:
4621:
4620:
4617:
4615:
4612:
4610:
4607:
4605:
4602:
4600:
4597:
4595:
4592:
4590:
4587:
4585:
4582:
4580:
4577:
4575:
4572:
4570:
4567:
4565:
4562:
4560:
4557:
4555:
4552:
4550:
4547:
4543:
4540:
4539:
4538:
4535:
4531:
4528:
4527:
4526:
4523:
4521:
4518:
4516:
4513:
4511:
4508:
4506:
4503:
4501:
4498:
4496:
4493:
4491:
4488:
4486:
4483:
4481:
4478:
4476:
4473:
4471:
4468:
4466:
4463:
4461:
4458:
4456:
4453:
4451:
4448:
4446:
4443:
4442:Nonsteroidal:
4440:
4439:
4436:
4433:
4431:
4428:
4426:
4423:
4421:
4418:
4416:
4413:
4411:
4408:
4406:
4403:
4401:
4398:
4396:
4393:
4391:
4388:
4386:
4383:
4381:
4378:
4376:
4373:
4371:
4368:
4366:
4363:
4361:
4358:
4356:
4353:
4351:
4348:
4346:
4343:
4341:
4338:
4336:
4333:
4331:
4328:
4326:
4323:
4321:
4318:
4316:
4313:
4309:
4306:
4304:
4301:
4300:
4299:
4296:
4292:
4291:Ethandrostate
4289:
4288:
4287:
4284:
4282:
4279:
4275:
4272:
4270:
4267:
4265:
4262:
4261:
4260:
4257:
4255:
4252:
4250:
4247:
4245:
4242:
4238:
4235:
4233:
4230:
4229:
4228:
4225:
4223:
4220:
4218:
4215:
4213:
4210:
4208:
4205:
4201:
4198:
4196:
4193:
4191:
4188:
4187:
4186:
4183:
4181:
4178:
4176:
4173:
4171:
4168:
4166:
4163:
4161:
4158:
4156:
4153:
4151:
4148:
4146:
4144:
4140:
4138:
4135:
4133:
4130:
4128:
4125:
4123:
4120:
4118:
4115:
4113:
4110:
4106:
4103:
4102:
4101:
4100:Cloxestradiol
4098:
4096:
4093:
4091:
4088:
4086:
4083:
4081:
4078:
4076:
4073:
4070:
4066:
4062:
4058:
4054:
4050:
4046:
4043:
4041:
4038:
4036:
4033:
4031:
4028:
4026:
4023:
4021:
4018:
4016:
4013:
4011:
4008:
4006:
4003:
4001:
3998:
3996:
3993:
3991:
3988:
3986:
3983:
3980:
3976:
3975:17α-Estradiol
3973:
3971:
3968:
3966:
3963:
3961:
3958:
3956:
3953:
3951:
3948:
3946:
3943:
3941:
3938:
3936:
3933:
3931:
3928:
3926:
3923:
3921:
3918:
3916:
3913:
3911:
3908:
3906:
3903:
3901:
3898:
3896:
3893:
3891:
3888:
3886:
3883:
3881:
3878:
3876:
3873:
3871:
3868:
3866:
3863:
3861:
3858:
3856:
3853:
3851:
3848:
3846:
3843:
3841:
3838:
3836:
3833:
3831:
3828:
3826:
3823:
3821:
3818:
3816:
3813:
3811:
3808:
3806:
3803:
3801:
3798:
3796:
3793:
3791:
3788:
3785:
3784:
3782:
3778:
3775:
3770:
3764:
3760:
3757:
3750:
3745:
3743:
3738:
3736:
3731:
3730:
3727:
3714:
3711:
3708:
3705:
3702:
3699:
3697:
3694:
3692:
3689:
3687:
3684:
3681:
3678:
3675:
3672:
3669:
3668:
3666:
3664:
3660:
3654:
3651:
3649:
3646:
3644:
3641:
3639:
3636:
3634:
3631:
3629:
3626:
3624:
3621:
3619:
3616:
3614:
3611:
3609:
3606:
3604:
3601:
3599:
3596:
3594:
3591:
3589:
3586:
3584:
3581:
3579:
3576:
3574:
3571:
3569:
3566:
3564:
3561:
3559:
3556:
3554:
3551:
3549:
3546:
3544:
3541:
3539:
3536:
3534:
3531:
3530:
3528:
3524:
3514:
3508:
3507:
3505:
3501:
3495:
3492:
3490:
3487:
3485:
3482:
3480:
3477:
3475:
3472:
3470:
3467:
3466:
3464:
3462:
3461:Mycoestrogens
3458:
3448:
3445:
3443:
3440:
3438:
3435:
3433:
3430:
3429:
3427:
3423:
3417:
3414:
3413:
3411:
3409:
3405:
3399:
3398:Cinchonain-Ib
3396:
3394:
3391:
3390:
3388:
3386:
3382:
3376:
3375:Enterolactone
3373:
3371:
3368:
3367:
3365:
3363:
3359:
3353:
3352:Wedelolactone
3350:
3348:
3345:
3343:
3340:
3338:
3335:
3334:
3332:
3330:
3326:
3322:
3318:
3316:
3312:
3306:
3303:
3301:
3298:
3297:
3295:
3293:
3289:
3283:
3280:
3277:
3275:
3270:
3267:
3266:
3264:
3262:
3258:
3252:
3249:
3247:
3244:
3242:
3239:
3237:
3234:
3232:
3229:
3227:
3224:
3222:
3219:
3217:
3214:
3212:
3209:
3207:
3204:
3202:
3199:
3198:
3196:
3194:
3190:
3184:
3181:
3179:
3176:
3174:
3171:
3169:
3166:
3164:
3161:
3160:
3158:
3156:
3152:
3146:
3143:
3141:
3138:
3136:
3133:
3132:
3130:
3128:
3124:
3118:
3115:
3113:
3110:
3108:
3105:
3103:
3100:
3099:
3097:
3095:
3091:
3088:
3086:
3082:
3078:
3077:Xenoestrogens
3071:
3066:
3064:
3059:
3057:
3052:
3051:
3048:
3037:
3033:
3029:
3025:
3021:
3017:
3010:
3008:
3000:
2993:
2985:
2981:
2977:
2973:
2969:
2965:
2961:
2957:
2953:
2949:
2942:
2934:
2930:
2926:
2922:
2918:
2914:
2910:
2906:
2898:
2890:
2886:
2882:
2878:
2874:
2870:
2866:
2862:
2855:
2847:
2843:
2839:
2835:
2831:
2827:
2823:
2819:
2812:
2804:
2800:
2796:
2792:
2788:
2784:
2780:
2776:
2768:
2760:
2756:
2752:
2748:
2744:
2740:
2732:
2724:
2720:
2716:
2712:
2708:
2704:
2696:
2688:
2684:
2680:
2676:
2669:
2661:
2657:
2653:
2649:
2645:
2641:
2637:
2633:
2625:
2617:
2613:
2609:
2605:
2601:
2597:
2589:
2581:
2577:
2573:
2569:
2565:
2561:
2554:
2552:
2543:
2539:
2535:
2531:
2527:
2523:
2519:
2515:
2507:
2499:
2495:
2491:
2487:
2483:
2479:
2475:
2471:
2467:
2463:
2456:
2448:
2444:
2440:
2436:
2432:
2428:
2425:(3): 275–84.
2424:
2420:
2412:
2410:
2401:
2397:
2393:
2389:
2384:
2379:
2375:
2371:
2367:
2360:
2352:
2348:
2343:
2338:
2334:
2330:
2326:
2319:
2311:
2307:
2302:
2297:
2293:
2289:
2288:J. Endocrinol
2285:
2278:
2270:
2266:
2262:
2258:
2253:
2248:
2244:
2240:
2236:
2229:
2221:
2217:
2213:
2209:
2205:
2201:
2197:
2193:
2186:
2177:
2169:
2165:
2160:
2155:
2151:
2147:
2143:
2139:
2135:
2128:
2126:
2124:
2115:
2111:
2106:
2101:
2097:
2093:
2090:(3): 427–31.
2089:
2085:
2081:
2074:
2072:
2063:
2059:
2055:
2051:
2048:(2): 141–54.
2047:
2043:
2036:
2028:
2024:
2019:
2014:
2010:
2006:
2002:
1998:
1994:
1987:
1973:
1969:
1962:
1953:
1951:
1949:
1947:
1945:
1943:
1941:
1931:
1923:
1919:
1915:
1911:
1907:
1903:
1895:
1886:
1878:
1874:
1870:
1866:
1862:
1858:
1851:
1845:
1838:
1832:
1825:
1816:
1808:
1804:
1800:
1796:
1788:
1780:
1768:
1760:
1754:
1750:
1746:
1742:
1735:
1727:
1723:
1718:
1713:
1709:
1705:
1701:
1694:
1686:
1682:
1678:
1674:
1670:
1666:
1662:
1658:
1651:
1643:
1639:
1635:
1631:
1627:
1623:
1619:
1615:
1611:
1607:
1600:
1591:
1589:
1587:
1585:
1576:
1572:
1568:
1564:
1560:
1556:
1552:
1548:
1541:
1539:
1537:
1528:
1524:
1519:
1514:
1510:
1506:
1502:
1498:
1494:
1490:
1486:
1479:
1471:
1467:
1463:
1459:
1455:
1451:
1447:
1443:
1439:
1435:
1428:
1426:
1417:
1413:
1409:
1405:
1401:
1397:
1393:
1389:
1382:
1378:
1371:
1369:
1360:
1356:
1352:
1348:
1344:
1340:
1336:
1332:
1328:
1324:
1317:
1315:
1313:
1303:
1301:
1299:
1297:
1295:
1280:
1276:
1270:
1262:
1255:
1249:
1235:
1231:
1225:
1217:
1213:
1209:
1205:
1201:
1197:
1190:
1188:
1186:
1184:
1182:
1180:
1178:
1176:
1174:
1172:
1170:
1168:
1160:
1156:
1152:
1151:
1144:
1140:
1132:
1129:
1126:
1121:
1119:
1115:
1111:
1107:
1097:
1093:
1084:
1082:
1078:
1074:
1070:
1066:
1056:
1054:
1049:
1045:
1043:
1038:
1033:
1031:
1026:
1022:
1007:
1005:
1001:
997:
993:
992:proliferation
989:
988:breast cancer
979:
977:
973:
969:
964:
961:
957:
953:
949:
945:
941:
936:
932:
922:
920:
916:
912:
908:
904:
903:interleukin 4
900:
896:
895:cell cultures
893:
889:
884:
882:
878:
874:
873:17β-estradiol
870:
866:
862:
858:
854:
845:
843:
839:
835:
834:17β-estradiol
831:
830:xenoestrogens
827:
817:
815:
811:
807:
802:
798:
795:, which is a
794:
790:
786:
782:
779:
775:
771:
767:
758:
754:
752:
748:
744:
740:
730:
728:
723:
719:
715:
712:
711:photodegrades
708:
707:biodegradable
704:
694:
692:
688:
684:
680:
676:
672:
668:
664:
660:
656:
655:polystyrenics
652:
648:
644:
640:
636:
632:
628:
624:
620:
616:
606:
604:
599:
597:
592:
590:
586:
582:
578:
568:
566:
562:
558:
554:
550:
546:
541:
538:
534:
524:
522:
518:
514:
510:
506:
502:
498:
494:
490:
486:
482:
478:
474:
470:
466:
462:
458:
454:
442:
435:
430:
413:
407:
403:
398:
397:
393:
392:
387:
382:
378:
375:
371:
370:
366:
364:
363:Boiling point
361:
360:
356:
354:
353:Melting point
351:
350:
346:
344:
341:
340:
336:
333:
332:
328:
326:
323:
322:
310:
307:
303:
302:
297:
288:
287:
284:
277:
263:
253:
252:
249:
242:
234:
230:
227:
222:
218:
214:
210:
209:
207:
205:
202:
201:
194:
190:
189:
187:
181:
177:
176:
169:
165:
164:
162:
160:
157:
156:
149:
145:
144:
142:
140:
137:
136:
129:
125:
124:
122:
118:
113:
112:
104:
100:
96:
92:
89:
88:-Nonyl phenol
87:
80:
76:
72:
68:
67:
65:
62:
58:
57:
52:
44:
38:
34:
29:
25:
20:
6087:Alkylphenols
5913:
5762:
5752:
5676:Mepitiostane
5624:Epitiostanol
5493:Ormeloxifene
5418:Lasofoxifene
5328:Camizestrant
5323:Broparestrol
5313:Bazedoxifene
5235:rotundifuran
5184:alkylphenols
5134:β-zearalenol
5130:α-zearalenol
5116:stigmasterol
5108:β-sitosterol
5104:Phytosterols
5072:triclocarban
5068:methoxychlor
5021:
5003:Lavender oil
4997:tectorigenin
4929:formononetin
4803:
4778:
4649:
4641:
4441:
4425:Quinestradol
4415:Promestriene
4390:Noretynodrel
4254:Estromustine
4207:Estramustine
4142:
4049:testosterone
3786:
3612:
3608:Methoxychlor
3533:Alkylphenols
3494:β-Zearalenol
3489:β-Zearalanol
3484:α-Zearalenol
3273:
3251:Tectorigenin
3216:Formononetin
3019:
3015:
2992:
2951:
2947:
2941:
2908:
2904:
2897:
2864:
2860:
2854:
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2599:
2595:
2588:
2563:
2560:Environ. Int
2559:
2517:
2513:
2506:
2465:
2461:
2455:
2422:
2418:
2373:
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2359:
2332:
2328:
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2242:
2238:
2228:
2195:
2191:
2185:
2176:
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2137:
2087:
2083:
2045:
2041:
2035:
2000:
1996:
1986:
1975:. Retrieved
1971:
1961:
1930:
1905:
1901:
1894:
1885:
1860:
1856:
1850:
1837:
1824:
1815:
1798:
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1787:
1740:
1734:
1710:(1): 19–30.
1707:
1703:
1693:
1660:
1656:
1650:
1609:
1605:
1599:
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1478:
1437:
1433:
1391:
1387:
1326:
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1282:. Retrieved
1278:
1269:
1260:
1248:
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1233:
1224:
1199:
1195:
1149:
1143:
1130:
1122:
1103:
1094:
1090:
1062:
1050:
1046:
1034:
1021:food samples
1018:
998:activity on
985:
944:hypothalamus
940:hypothalamic
928:
885:
851:
823:
793:vitellogenin
774:feminization
763:
736:
724:
720:
716:
700:
631:solubilizers
615:antioxidants
612:
609:Applications
600:
593:
574:
542:
533:alkylphenols
530:
505:xenoestrogen
481:solubilizers
465:antioxidants
461:alkylphenols
453:Nonylphenols
452:
451:
400:Main hazards
389:
225:
148:ChEMBL153062
85:
54:Identifiers
46:Other names
17:Nonylphenol
6021:Zearalenone
5973:Antagonists
5949:Resveratrol
5914:Nonylphenol
5909:Niacinamide
5825:Bisphenol A
5815:Aldosterone
5644:Glyceollins
5592:Antagonists
5583:Zuclomifene
5578:Zindoxifene
5488:NNC 45-1506
5483:NNC 45-0781
5478:NNC 45-0320
5473:NNC 45-0095
5468:Nitromifene
5448:Miproxifene
5398:Fispemifene
5373:Enclomifene
5368:Droloxifene
5348:CN-55945-27
5293:Afimoxifene
5283:Acefluranol
5174:rhaponticin
5170:resveratrol
5166:Stilbenoids
5138:zearalenone
5126:zearalanone
5112:campesterol
5044:alternariol
4977:pinocembrin
4921:epicatechin
4893:biochanin A
4833:Chalconoids
4727:Terfluranol
4702:Quadrosilan
4574:Elacestrant
4475:Allenestrol
4350:Lynestrenol
4274:Estropipate
4244:Estrofurate
4095:Clomestrone
4075:Atrimustine
4025:Abiraterone
3979:alfatradiol
3613:Nonylphenol
3593:Erythrosine
3558:Bisphenol S
3553:Bisphenol F
3548:Bisphenol A
3503:Derivatives
3474:Zearalenone
3469:Zearalanone
3442:Resveratrol
3315:Isoflavenes
3261:Isoflavanes
3201:Biochanin A
3193:Isoflavones
3117:Pinocembrin
2861:Chemosphere
2775:Chemosphere
2632:Chemosphere
2514:Chemosphere
2239:Regul. Pept
1657:Chemosphere
1261:squarespace
1069:glucuronide
1037:breast milk
842:polystyrene
826:bisphenol A
651:polyolefins
635:antioxidant
627:emulsifiers
596:velvet worm
565:hydrophobic
561:hydrophilic
557:amphipathic
477:emulsifiers
394:(OHS/OSH):
334:Appearance
299:Properties
6076:Categories
5964:Tectoridin
5944:Raloxifene
5919:Oleuropein
5766:Trilostane
5711:Prochloraz
5671:MDL-101906
5666:ICI-164384
5553:Trioxifene
5548:Toremifene
5518:Raloxifene
5503:Panomifene
5498:Ospemifene
5463:Nafoxidine
5353:Cyclofenil
5308:Arzoxifene
5288:Acolbifene
5220:phthalates
5188:bisphenols
5160:miroestrol
5064:methiocarb
5052:endosulfan
5040:Pesticides
5012:enterodiol
4993:tectoridin
4973:penduletin
4969:naringenin
4953:kaempferol
4869:Flavonoids
4863:psoralidin
4859:coumestrol
4855:Coumestans
4819:dianethole
4772:WAY-214156
4762:WAY-200070
4757:WAY-169916
4752:WAY-166818
4722:SKF-82,958
4687:Phenestrol
4667:Methestrol
4652:-Hexestrol
4644:-Butestrol
4525:Dienestrol
4505:Carbestrol
4490:Bifluranol
4485:Benzestrol
4430:Quinestrol
4380:Nilestriol
4222:Estrazinol
4155:Epimestrol
4145:-Estradiol
4127:Cyclotriol
4065:nandrolone
4040:Almestrone
3875:7-Oxo-DHEA
3787:Steroidal:
3759:modulators
3643:Phthalates
3598:Heptachlor
3588:Enzacamene
3583:Endosulfan
3437:Miroestrol
3370:Enterodiol
3342:Coumestrol
3329:Coumestans
3112:Naringenin
3102:Hesperetin
3094:Flavanones
1977:2019-10-03
1284:2021-03-18
1239:2021-03-18
1148:Record of
1135:References
1100:Regulation
1004:estrogenic
976:adipocytes
972:stem cells
869:endogenous
687:pesticides
685:, paints,
683:detergents
659:stabilizer
641:, such as
623:detergents
577:alkylation
571:Production
553:detergents
497:pesticides
495:, paints,
493:detergents
485:precursors
473:detergents
325:Molar mass
233:JRW3Q994VG
221:I03GBV4WEL
213:79F6A2ILP5
159:ChemSpider
115:3D model (
103:11066-49-2
95:84852-15-3
71:25154-52-3
61:CAS Number
37:IUPAC name
5959:Tamoxifen
5939:Quercetin
5879:Genistein
5859:Estradiol
5843:o',p'-DDE
5746:ZK-191703
5741:ZK-164015
5701:Phenytoin
5599:(R,R)-THC
5538:Tamoxifen
5513:Promensil
5438:LY-117018
5413:Idoxifene
5408:ICI-55548
5393:Femarelle
5378:Endoxifen
5338:Clomifene
5094:diosgenin
5090:digitalis
5086:digitoxin
5076:triclosan
5056:fenarimol
4989:quercetin
4965:myricetin
4961:mirificin
4949:glycitein
4941:genistein
4937:glabridin
4897:calycosin
4885:baicalein
4841:phloretin
4797:ZK-283197
4657:Mestilbol
4619:Hexestrol
4594:Fenestrel
4569:Efavirenz
4500:Butestrol
4455:2,8-DHHHC
4450:(S,S)-THC
4445:(R,R)-THC
4400:Pentolame
4395:Orestrate
4370:Moxestrol
4360:Mestranol
4325:Etynodiol
4185:Estradiol
4160:Equilenin
4122:Cyclodiol
4080:Bolandiol
3670:Aluminium
3526:Synthetic
3416:Quercetin
3408:Flavonols
3337:Coumestan
3305:Phlorizin
3300:Phloretin
3282:Glabridin
3231:Glycitein
3221:Genistein
3145:Mirificin
2968:1618-2642
2925:1520-636X
2905:Chirality
2490:0013-936X
2419:Endocrine
1777:ignored (
1767:cite book
1726:0021-9665
1634:0013-936X
1509:0303-7207
1462:0013-936X
1343:1618-2642
1087:Analytics
1059:Breakdown
996:agonistic
960:anorectic
881:apoptosis
871:estrogen
857:placental
785:fertility
781:organisms
751:estradiol
603:nonoxynol
523:(GPR30).
224: (4-
6037:See also
5839:p,p'-DDT
5830:Daidzein
5820:Atrazine
5793:Agonists
5721:RU-58668
5716:RU-39411
5563:U-11555A
5558:TZE-5323
5303:Anordrin
5298:Anordiol
5231:agnuside
5208:parabens
5048:dieldrin
5020:nyasol (
4985:puerarin
4981:prunetin
4945:genistin
4933:glabrene
4905:daidzein
4901:catechin
4889:baicalin
4881:apigenin
4811:anethole
4599:FERb 033
4435:Tibolone
4420:RU-16117
4405:Prodiame
4340:Hippulin
4335:Hexolame
4180:Estetrol
4090:Butolame
3780:Agonists
3715:Vanadate
3709:Selenite
3686:Chromium
3676:Arsenite
3673:Antimony
3618:Parabens
3573:Dieldrin
3538:Atrazine
3321:Glabrene
3246:Puerarin
3241:Prunetin
3226:Genistin
3206:Daidzein
3183:Icaritin
3135:Acacetin
3127:Flavones
3036:19476957
2984:11005914
2976:27236316
2933:18553459
2889:17027900
2846:39833642
2838:16341851
2803:20452641
2759:16427065
2723:16271268
2660:14664841
2616:12458934
2580:18410965
2542:21185059
2498:11993862
2447:24384354
2439:14709801
2400:38257683
2392:22076496
2351:15178745
2310:17003276
2261:15518916
2220:20370652
2212:18334610
2168:19433244
2114:20194071
2062:21888958
2027:16818251
1922:18282600
1877:11851490
1857:Chem Rev
1829:259-267.
1685:16083769
1642:15260341
1575:16158451
1527:24530924
1470:24345275
1416:18800507
1359:39833642
1351:16341851
1216:18282600
1015:Exposure
952:midbrain
931:obesogen
892:In vitro
888:cytokine
877:prenatal
747:hormones
743:estrogen
639:polymers
509:estrogen
384:Hazards
319:O
79:104-40-5
6009:Unknown
5985:Estriol
5889:GPER-L2
5884:GPER-L1
5568:U-11634
5443:Menerba
5433:LN-2299
5428:LN-1643
5403:GW-7604
5358:D-15413
5190:(e.g.,
5182:(e.g.,
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5152:Steroid
5124:(e.g.,
5106:(e.g.,
5084:(e.g.,
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5034:cadmium
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5008:Lignans
4909:daidzin
4873:7,8-DHF
4871:(incl.
4857:(e.g.,
4835:(e.g.,
4717:SERBA-2
4712:SC-4289
4707:SC-3296
4614:GTx-758
4510:D-15414
4460:β-LGND1
4410:Prolame
4259:Estrone
4227:Estriol
4165:Equilin
4047:(e.g.,
3960:16α-LE2
3703:Mercury
3682:Cadmium
3603:Lindane
3578:Dioxins
3393:Silybin
3362:Lignans
3211:Daidzin
2999:cement)
2869:Bibcode
2783:Bibcode
2640:Bibcode
2522:Bibcode
2470:Bibcode
2269:9419249
2159:2713042
2105:2854774
2018:1874182
1665:Bibcode
1614:Bibcode
1567:9699867
1518:4040308
1442:Bibcode
1396:Bibcode
1377:Giger W
1157:of the
1153:in the
1079:and in
1025:Germany
968:ghrelin
935:obesity
861:uterine
844:tubes.
814:kidneys
801:oocytes
778:aquatic
667:calcium
585:nonenes
519:of the
517:agonist
434:what is
432: (
343:Density
180:PubChem
82: (
5904:Niacin
5899:Kepone
5756:ERX-11
5726:SS1020
5634:ERB-88
5629:ERA-90
5533:SS1010
5458:MRL-37
4823:dianol
4792:ERB-79
4787:ERA-45
4782:ERB-26
4515:DCW234
4470:AC-186
4137:DHEA-S
4069:esters
4053:esters
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3706:Nickel
3696:Copper
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948:leptin
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691:Europe
663:Barium
653:, and
643:rubber
629:, and
581:phenol
537:phenol
479:, and
429:verify
426:
347:0.953
283:SMILES
139:ChEMBL
31:Names
5980:CCL18
5854:Equol
5736:ZB716
5706:PHTPP
5573:Y-134
5250:SERMs
5245:Mixed
4925:equol
4807:Anise
4636:M2613
3269:Equol
2980:S2CID
2842:S2CID
2443:S2CID
2396:S2CID
2265:S2CID
2216:S2CID
1571:S2CID
1384:(PDF)
1355:S2CID
1257:(PDF)
1081:urine
1077:feces
974:into
513:nonyl
248:InChI
193:67296
168:60628
117:JSmol
6000:MIBE
5995:G-36
5990:G-15
5924:PCBs
5781:GPER
5691:MIBE
5224:PCBs
5216:PHBA
5212:PBBs
5060:HPTE
4917:EGCG
4815:anol
4650:meso
4642:meso
4132:DHEA
4067:and
4051:and
3700:Lead
3638:PHBA
3628:PCBs
3623:PBBs
3032:PMID
2972:PMID
2964:ISSN
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2885:PMID
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2799:PMID
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1779:help
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859:and
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