4-Octylphenol (BioDeep_00000003638)

 

Secondary id: BioDeep_00001873728

human metabolite blood metabolite


代谢物信息卡片


1-(p-Hydroxyphenyl)octane

化学式: C14H22O (206.1671)
中文名称: 4-辛基苯酚
谱图信息: 最多检出来源 Homo sapiens(blood) 52.57%

分子结构信息

SMILES: CCCCCCCCC1=CC=C(C=C1)O
InChI: InChI=1S/C14H22O/c1-2-3-4-5-6-7-8-13-9-11-14(15)12-10-13/h9-12,15H,2-8H2,1H3

描述信息

CONFIDENCE standard compound; INTERNAL_ID 938; DATASET 20200303_ENTACT_RP_MIX500; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4924; ORIGINAL_PRECURSOR_SCAN_NO 4922
CONFIDENCE standard compound; INTERNAL_ID 938; DATASET 20200303_ENTACT_RP_MIX500; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4929; ORIGINAL_PRECURSOR_SCAN_NO 4926
CONFIDENCE standard compound; INTERNAL_ID 938; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5507; ORIGINAL_PRECURSOR_SCAN_NO 5506
CONFIDENCE standard compound; INTERNAL_ID 938; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5486; ORIGINAL_PRECURSOR_SCAN_NO 5483
CONFIDENCE standard compound; INTERNAL_ID 938; DATASET 20200303_ENTACT_RP_MIX500; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4941; ORIGINAL_PRECURSOR_SCAN_NO 4939
CONFIDENCE standard compound; INTERNAL_ID 938; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5519; ORIGINAL_PRECURSOR_SCAN_NO 5518
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D004967 - Estrogens

同义名列表

9 个代谢物同义名

1-(p-Hydroxyphenyl)octane; 4-Octylphenol potassium; 4-Octylphenol barium; 4-Octylphenol sodium; 4-N-Octylphenol; P-Octylphenol; 4-OCTYLPHENOL; 4-Octylphenol; 4-Octylphenol



数据库引用编号

22 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

1 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。

亚细胞结构定位 关联基因列表
Cytoplasm 7 AR, BAX, ESR1, IL18, IL1A, SOX10, TLR7
Peripheral membrane protein 2 ESR1, SOX10
Endosome membrane 1 TLR7
Endoplasmic reticulum membrane 3 BAX, CYP17A1, TLR7
Nucleus 7 AR, BAX, ESR1, IL1A, NR5A1, SOX10, SOX9
cytosol 6 AR, BAX, ESR1, IL18, IL1A, NR5A1
nucleoplasm 5 AR, ESR1, NR5A1, SOX10, SOX9
RNA polymerase II transcription regulator complex 1 NR5A1
Cell membrane 5 C3AR1, C5AR1, CD86, ESR1, TNF
Cytoplasmic side 2 ESR1, SOX10
Multi-pass membrane protein 2 C3AR1, C5AR1
cell surface 5 C3, CD86, ICAM1, IL1A, TNF
Golgi apparatus 1 ESR1
Golgi membrane 1 TLR7
neuronal cell body 2 CYP17A1, TNF
Cytoplasm, cytosol 1 IL18
Lysosome 1 TLR7
endosome 1 TLR7
plasma membrane 9 AR, C3, C3AR1, C5AR1, CD86, ESR1, ICAM1, TLR7, TNF
Membrane 6 AR, BAX, CD86, ESR1, ICAM1, TLR7
axon 1 CYP17A1
basolateral plasma membrane 1 C5AR1
extracellular exosome 4 BAX, C3, CD86, ICAM1
endoplasmic reticulum 3 BAX, CYP17A1, TLR7
extracellular space 7 C3, COL2A1, CXCL8, ICAM1, IL18, IL1A, TNF
mitochondrion 1 BAX
protein-containing complex 4 AR, C3, ESR1, SOX9
Microsome membrane 1 CYP17A1
Single-pass type I membrane protein 3 CD86, ICAM1, TLR7
Secreted 5 C3, COL2A1, CXCL8, IL18, IL1A
extracellular region 6 C3, COL2A1, CXCL8, IL18, IL1A, TNF
Mitochondrion outer membrane 1 SOX10
Single-pass membrane protein 1 BAX
mitochondrial outer membrane 2 BAX, SOX10
transcription regulator complex 2 ESR1, SOX9
BAK complex 1 BAX
centriolar satellite 1 CD86
Bcl-2 family protein complex 1 BAX
external side of plasma membrane 3 CD86, ICAM1, TNF
Secreted, extracellular space, extracellular matrix 1 COL2A1
cytoplasmic vesicle 1 C5AR1
apical part of cell 1 C5AR1
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Membrane raft 2 ICAM1, TNF
pore complex 1 BAX
focal adhesion 1 ICAM1
basement membrane 1 COL2A1
collagen trimer 1 COL2A1
collagen-containing extracellular matrix 2 COL2A1, ICAM1
nuclear speck 1 AR
receptor complex 1 TLR7
chromatin 5 AR, ESR1, NR5A1, SOX10, SOX9
phagocytic cup 1 TNF
blood microparticle 1 C3
nuclear envelope 1 BAX
Endomembrane system 1 TLR7
specific granule membrane 1 C3AR1
euchromatin 1 ESR1
secretory granule lumen 1 C3
secretory granule membrane 1 C5AR1
endoplasmic reticulum lumen 2 C3, COL2A1
azurophil granule membrane 1 C3AR1
azurophil granule lumen 1 C3
immunological synapse 1 ICAM1
[Isoform 1]: Nucleus 1 ESR1
endolysosome membrane 1 TLR7
early phagosome 1 TLR7
Cytoplasmic vesicle, phagosome 1 TLR7
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
collagen type II trimer 1 COL2A1
collagen type XI trimer 1 COL2A1
mitochondrial permeability transition pore complex 1 BAX
[Isoform Alpha]: Mitochondrion outer membrane 1 BAX
[Isoform Delta]: Cytoplasm 1 BAX
BAX complex 1 BAX
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Yang Xu, Seung Hyun Park, Myung Chan Gye. Head dysgenesis and disruption of cranial neural crest stem cells behaviour by 4-octylphenol in fire-bellied toad Bombina orientalis embryos. Environmental pollution (Barking, Essex : 1987). 2023 Oct; 338(?):122697. doi: 10.1016/j.envpol.2023.122697. [PMID: 37804908]
  • Guowen Zhang, Na Li, Ying Zhang, Junhui Pan, Deming Gong. Binding mechanism of 4-octylphenol with human serum albumin: Spectroscopic investigations, molecular docking and dynamics simulation. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2021 Jul; 255(?):119662. doi: 10.1016/j.saa.2021.119662. [PMID: 33780895]
  • Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
  • Yang Xu, Ji Hyun Jang, Myung Chan Gye. 4-Octylphenol induces developmental abnormalities and interferes the differentiation of neural crest cells in Xenopus laevis embryos. Environmental pollution (Barking, Essex : 1987). 2021 Apr; 274(?):116560. doi: 10.1016/j.envpol.2021.116560. [PMID: 33524650]
  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
  • Muhammad Ashfaq, Yan Li, Yuwen Wang, Dan Qin, Muhammad Saif Ur Rehman, Azhar Rashid, Chang-Ping Yu, Qian Sun. Monitoring and mass balance analysis of endocrine disrupting compounds and their transformation products in an anaerobic-anoxic-oxic wastewater treatment system in Xiamen, China. Chemosphere. 2018 Aug; 204(?):170-177. doi: 10.1016/j.chemosphere.2018.04.028. [PMID: 29655110]
  • Weiyue Hu, Minjian Chen, Juan Ji, Yufeng Qin, Feng Zhang, Miaofei Xu, Wei Wu, Guizhen Du, Di Wu, Xiumei Han, Li Jin, Yankai Xia, Chuncheng Lu, Xinru Wang. Interaction between Y chromosome haplogroup O3* and 4-n-octylphenol exposure reduces the susceptibility to spermatogenic impairment in Han Chinese. Ecotoxicology and environmental safety. 2017 Oct; 144(?):450-455. doi: 10.1016/j.ecoenv.2017.06.038. [PMID: 28667856]
  • Hyejin Park, Kisok Kim. Urinary Levels of 4-Nonylphenol and 4-t-Octylphenol in a Representative Sample of the Korean Adult Population. International journal of environmental research and public health. 2017 08; 14(8):. doi: 10.3390/ijerph14080932. [PMID: 28820486]
  • Lisa A Hamilton, Louis A Tremblay, Grant L Northcott, Michael Boake, Richard P Lim. The impact of variations of influent loading on the efficacy of an advanced tertiary sewage treatment plant to remove endocrine disrupting chemicals. The Science of the total environment. 2016 08; 560-561(?):101-9. doi: 10.1016/j.scitotenv.2016.04.003. [PMID: 27096490]
  • Pinggu Wu, Liqun Zhang, Dajin Yang, Jing Zhang, Zhengyan Hu, Liyuan Wang, Bingjie Ma. Isotope dilution gas chromatography with mass spectrometry for the analysis of 4-octyl phenol, 4-nonylphenol, and bisphenol A in vegetable oils. Journal of separation science. 2016 Mar; 39(5):904-9. doi: 10.1002/jssc.201500887. [PMID: 26698324]
  • N Salgueiro-González, I Turnes-Carou, L Viñas-Diéguez, S Muniategui-Lorenzo, P López-Mahía, D Prada-Rodríguez. Occurrence of endocrine disrupting compounds in five estuaries of the northwest coast of Spain: Ecological and human health impact. Chemosphere. 2015 Jul; 131(?):241-7. doi: 10.1016/j.chemosphere.2014.12.062. [PMID: 25648473]
  • Huixiao Hong, William S Branham, Hui Wen Ng, Carrie L Moland, Stacey L Dial, Hong Fang, Roger Perkins, Daniel Sheehan, Weida Tong. Human sex hormone-binding globulin binding affinities of 125 structurally diverse chemicals and comparison with their binding to androgen receptor, estrogen receptor, and α-fetoprotein. Toxicological sciences : an official journal of the Society of Toxicology. 2015 Feb; 143(2):333-48. doi: 10.1093/toxsci/kfu231. [PMID: 25349334]
  • Minjian Chen, Rong Tang, Guangbo Fu, Bin Xu, Pengfei Zhu, Shanlei Qiao, Xiaojiao Chen, Bo Xu, Yufeng Qin, Chuncheng Lu, Bo Hang, Yankai Xia, Xinru Wang. Association of exposure to phenols and idiopathic male infertility. Journal of hazardous materials. 2013 Apr; 250-251(?):115-21. doi: 10.1016/j.jhazmat.2013.01.061. [PMID: 23435201]
  • Yufeng Qin, Minjian Chen, Wei Wu, Bin Xu, Rong Tang, Xiaojiao Chen, Guizhen Du, Chuncheng Lu, John D Meeker, Zuomin Zhou, Yankai Xia, Xinru Wang. Interactions between urinary 4-tert-octylphenol levels and metabolism enzyme gene variants on idiopathic male infertility. PloS one. 2013; 8(3):e59398. doi: 10.1371/journal.pone.0059398. [PMID: 23555028]
  • M T Llorente, J M Parra, S Sánchez-Fortún, A Castaño. Cytotoxicity and genotoxicity of sewage treatment plant effluents in rainbow trout cells (RTG-2). Water research. 2012 Dec; 46(19):6351-8. doi: 10.1016/j.watres.2012.08.039. [PMID: 23022116]
  • Huixiao Hong, William S Branham, Stacey L Dial, Carrie L Moland, Hong Fang, Jie Shen, Roger Perkins, Daniel Sheehan, Weida Tong. Rat α-Fetoprotein binding affinities of a large set of structurally diverse chemicals elucidated the relationships between structures and binding affinities. Chemical research in toxicology. 2012 Nov; 25(11):2553-66. doi: 10.1021/tx3003406. [PMID: 23013281]
  • Minjian Chen, Pengfei Zhu, Bin Xu, Rencheng Zhao, Shanlei Qiao, Xiaojiao Chen, Rong Tang, Di Wu, Ling Song, Shoulin Wang, Yankai Xia, Xinru Wang. Determination of nine environmental phenols in urine by ultra-high-performance liquid chromatography-tandem mass spectrometry. Journal of analytical toxicology. 2012 Nov; 36(9):608-15. doi: 10.1093/jat/bks072. [PMID: 22989423]
  • Tanausú Vega-Morales, Rayco Guedes-Alonso, Zoraida Sosa-Ferrera, José Juan Santana-Rodríguez. Determination and assessment of estradiol-mimicking compounds in the dissolved and particulate phases of wastewater treatment plant samples. Journal of AOAC International. 2012 Jul; 95(4):1195-204. doi: 10.5740/jaoacint.11-219. [PMID: 22970591]
  • Griselda Genovese, Mariana Regueira, Yanina Piazza, David Walter Towle, Maria Cristina Maggese, Fabiana Lo Nostro. Time-course recovery of estrogen-responsive genes of a cichlid fish exposed to waterborne octylphenol. Aquatic toxicology (Amsterdam, Netherlands). 2012 Jun; 114-115(?):1-13. doi: 10.1016/j.aquatox.2012.02.005. [PMID: 22410082]
  • Alexandros G Asimakopoulos, Nikolaos S Thomaidis, Michael A Koupparis. Recent trends in biomonitoring of bisphenol A, 4-t-octylphenol, and 4-nonylphenol. Toxicology letters. 2012 Apr; 210(2):141-54. doi: 10.1016/j.toxlet.2011.07.032. [PMID: 21888958]
  • Qian Sun, Yan Li, Pei-Hsin Chou, Po-Yi Peng, Chang-Ping Yu. Transformation of bisphenol A and alkylphenols by ammonia-oxidizing bacteria through nitration. Environmental science & technology. 2012 Apr; 46(8):4442-8. doi: 10.1021/es204424t. [PMID: 22435736]
  • Philipp Hohenblum, Philipp Steinbichl, Wolfgang Raffesberg, Stefan Weiss, Wolfgang Moche, Birgit Vallant, Sigrid Scharf, Daniela Haluza, Hanns Moshammer, Michael Kundi, Brigitte Piegler, Peter Wallner, Hans-Peter Hutter. Pollution gets personal! A first population-based human biomonitoring study in Austria. International journal of hygiene and environmental health. 2012 Feb; 215(2):176-9. doi: 10.1016/j.ijheh.2011.08.015. [PMID: 21968335]
  • Satyanarayanan Senthil Kumaran, Chokkalingam Kavitha, Mathan Ramesh, Tamara Grummt. Toxicity studies of nonylphenol and octylphenol: hormonal, hematological and biochemical effects in Clarias gariepinus. Journal of applied toxicology : JAT. 2011 Nov; 31(8):752-61. doi: 10.1002/jat.1629. [PMID: 21404308]
  • Ting-ting Li, Liang-zhi Xu, Yong-heng Chen, Hong-mei Deng, Chun-ying Liang, Ying Liu, Xiao-fang Liu, Jing Zhang, De-ying Kang, Dong-sheng Qiu, Dai-wen Han, Rong Hu. [Effects of eight environmental endocrine disruptors on insulin resistance in patients with polycystic ovary syndrome: a preliminary investigation]. Nan fang yi ke da xue xue bao = Journal of Southern Medical University. 2011 Oct; 31(10):1753-6. doi: NULL. [PMID: 22027783]
  • T Vega-Morales, Z Sosa-Ferrera, J J Santana-Rodríguez. Determination of various estradiol mimicking-compounds in sewage sludge by the combination of microwave-assisted extraction and LC-MS/MS. Talanta. 2011 Sep; 85(4):1825-34. doi: 10.1016/j.talanta.2011.07.051. [PMID: 21872026]
  • Yumin Niu, Jing Zhang, Yongning Wu, Bing Shao. Simultaneous determination of bisphenol A and alkylphenol in plant oil by gel permeation chromatography and isotopic dilution liquid chromatography-tandem mass spectrometry. Journal of chromatography. A. 2011 Aug; 1218(31):5248-53. doi: 10.1016/j.chroma.2011.06.005. [PMID: 21708384]
  • Malgorzata Kotula-Balak, Ewa Pochec, Anna Hejmej, Malgorzata Duda, Barbara Bilinska. Octylphenol affects morphology and steroidogenesis in mouse tumor Leydig cells. Toxicology in vitro : an international journal published in association with BIBRA. 2011 Aug; 25(5):1018-26. doi: 10.1016/j.tiv.2011.03.021. [PMID: 21463676]
  • Aslı Korkmaz, Müfide Aydoğan, Dürdane Kolankaya, Nurhayat Barlas. Vitamin C coadministration augments bisphenol A, nonylphenol, and octylphenol induced oxidative damage on kidney of rats. Environmental toxicology. 2011 Aug; 26(4):325-37. doi: 10.1002/tox.20556. [PMID: 20014407]
  • Xian Zhang, Yajie Gao, Qingzhao Li, Guoxin Li, Qinghai Guo, Changzhou Yan. Estrogenic compounds and estrogenicity in surface water, sediments, and organisms from Yundang Lagoon in Xiamen, China. Archives of environmental contamination and toxicology. 2011 Jul; 61(1):93-100. doi: 10.1007/s00244-010-9588-0. [PMID: 20725718]
  • Zhaohan Zhang, Yujie Feng, Peng Gao, Ce Wang, Nanqi Ren. Occurrence and removal efficiencies of eight EDCs and estrogenicity in a STP. Journal of environmental monitoring : JEM. 2011 May; 13(5):1366-73. doi: 10.1039/c0em00597e. [PMID: 21390396]
  • Enzhong Li, Yuping Guo, Qianji Ning, Shiqing Zhang, Dexue Li. Research for the effect of octylphenol on spermatogenesis and proteomic analysis in octylphenol-treated mice testes. Cell biology international. 2011 Apr; 35(4):305-9. doi: 10.1042/cbi20100566. [PMID: 21108603]
  • S B Sainath, R Meena, C H Venkata Suneel Kumar, P Kalapana, K N Swetha, N Syamala Devi, P Sreenivasula Reddy. Embryonic exposure to octylphenol induces changes in testosterone levels and disrupts reproductive efficiency in rats at their adulthood. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2011 Apr; 49(4):983-90. doi: 10.1016/j.fct.2011.01.004. [PMID: 21219960]
  • Xiao Jing, Shao Bing, Wu Xiaoyan, Sun Xiaojie, Wu Yongning. A study on bisphenol A, nonylphenol, and octylphenol in human urine amples detected by SPE-UPLC-MS. Biomedical and environmental sciences : BES. 2011 Feb; 24(1):40-6. doi: 10.3967/0895-3988.2011.01.005. [PMID: 21440838]
  • Griselda Genovese, Rodrigo Da Cuña, David W Towle, María C Maggese, Fabiana Lo Nostro. Early expression of zona pellucida proteins under octylphenol exposure in Cichlasoma dimerus (Perciformes, Cichlidae). Aquatic toxicology (Amsterdam, Netherlands). 2011 Jan; 101(1):175-85. doi: 10.1016/j.aquatox.2010.09.017. [PMID: 21035200]
  • Chunying Wu, Wenchao Xue, Haidong Zhou, Xia Huang, Xianghua Wen. Removal of endocrine disrupting chemicals in a large scale membrane bioreactor plant combined with anaerobic-anoxic-oxic process for municipal wastewater reclamation. Water science and technology : a journal of the International Association on Water Pollution Research. 2011; 64(7):1511-8. doi: 10.2166/wst.2011.140. [PMID: 22179650]
  • Takeshi Matsui, Yuki Nomura, Mai Takano, Sofue Imai, Hideki Nakayama, Hitoshi Miyasaka, Hiroshi Okuhata, Satoshi Tanaka, Hideyuki Matsuura, Kazuo Harada, Takeshi Bamba, Kazumasa Hirata, Ko Kato. Molecular cloning and partial characterization of a peroxidase gene expressed in the roots of Portulaca oleracea cv., one potentially useful in the remediation of phenolic pollutants. Bioscience, biotechnology, and biochemistry. 2011; 75(5):882-90. doi: 10.1271/bbb.100823. [PMID: 21597193]
  • Zhen Mao, Yuan-Lin Zheng, Yan-Qiu Zhang. Behavioral impairment and oxidative damage induced by chronic application of nonylphenol. International journal of molecular sciences. 2010 Dec; 12(1):114-27. doi: 10.3390/ijms12010114. [PMID: 21339980]
  • T Vega-Morales, Z Sosa-Ferrera, J J Santana-Rodríguez. Determination of alkylphenol polyethoxylates, bisphenol-A, 17α-ethynylestradiol and 17β-estradiol and its metabolites in sewage samples by SPE and LC/MS/MS. Journal of hazardous materials. 2010 Nov; 183(1-3):701-11. doi: 10.1016/j.jhazmat.2010.07.083. [PMID: 20724070]
  • Asli Korkmaz, Müfide Aydoğan Ahbab, Dürdane Kolankaya, Nurhayat Barlas. Influence of vitamin C on bisphenol A, nonylphenol and octylphenol induced oxidative damages in liver of male rats. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2010 Oct; 48(10):2865-71. doi: 10.1016/j.fct.2010.07.019. [PMID: 20643179]
  • Jaime Mendiola, Niels Jørgensen, Anna-Maria Andersson, Antonia M Calafat, Xiaoyun Ye, J Bruce Redmon, Erma Z Drobnis, Christina Wang, Amy Sparks, Sally W Thurston, Fan Liu, Shanna H Swan. Are environmental levels of bisphenol a associated with reproductive function in fertile men?. Environmental health perspectives. 2010 Sep; 118(9):1286-91. doi: 10.1289/ehp.1002037. [PMID: 20494855]
  • Ase Jespersen, Tina H Rasmussen, Majken Hirche, Kristine J K Sørensen, Bodil Korsgaard. Effects of exposure to the xenoestrogen octylphenol and subsequent transfer to clean water on liver and gonad ultrastructure during early development of Zoarces viviparus embryos. Journal of experimental zoology. Part A, Ecological genetics and physiology. 2010 Aug; 313(7):399-409. doi: 10.1002/jez.609. [PMID: 20623797]
  • Laura N Vandenberg, Ibrahim Chahoud, Jerrold J Heindel, Vasantha Padmanabhan, Francisco J R Paumgartten, Gilbert Schoenfelder. Urinary, circulating, and tissue biomonitoring studies indicate widespread exposure to bisphenol A. Environmental health perspectives. 2010 Aug; 118(8):1055-70. doi: 10.1289/ehp.0901716. [PMID: 20338858]
  • Müfide Aydoğan, Asli Korkmaz, Nurhayat Barlas, Dürdane Kolankaya. Pro-oxidant effect of vitamin C coadministration with bisphenol A, nonylphenol, and octylphenol on the reproductive tract of male rats. Drug and chemical toxicology. 2010 Apr; 33(2):193-203. doi: 10.3109/01480540903286468. [PMID: 19848444]
  • Gayathri Chandrasekar, Amena Archer, Jan-Ake Gustafsson, Monika Andersson Lendahl. Levels of 17beta-estradiol receptors expressed in embryonic and adult zebrafish following in vivo treatment of natural or synthetic ligands. PloS one. 2010 Mar; 5(3):e9678. doi: 10.1371/journal.pone.0009678. [PMID: 20300630]
  • Jorge Eduardo Loyo-Rosales, Clifford Paul Rice, Alba Torrents. Fate and distribution of the octyl- and nonylphenol ethoxylates and some carboxylated transformation products in the Back River, Maryland. Journal of environmental monitoring : JEM. 2010 Mar; 12(3):614-21. doi: 10.1039/b913229e. [PMID: 20445849]
  • Anastasia Arditsoglou, Dimitra Voutsa. Partitioning of endocrine disrupting compounds in inland waters and wastewaters discharged into the coastal area of Thessaloniki, Northern Greece. Environmental science and pollution research international. 2010 Mar; 17(3):529-38. doi: 10.1007/s11356-009-0172-y. [PMID: 19495820]
  • Terumi Midoro-Horiuti, Ruby Tiwari, Cheryl S Watson, Randall M Goldblum. Maternal bisphenol a exposure promotes the development of experimental asthma in mouse pups. Environmental health perspectives. 2010 Feb; 118(2):273-7. doi: 10.1289/ehp.0901259. [PMID: 20123615]
  • Kevin J Bisceglia, Jim T Yu, Mehmet Coelhan, Edward J Bouwer, A Lynn Roberts. Trace determination of pharmaceuticals and other wastewater-derived micropollutants by solid phase extraction and gas chromatography/mass spectrometry. Journal of chromatography. A. 2010 Jan; 1217(4):558-64. doi: 10.1016/j.chroma.2009.11.062. [PMID: 20015510]
  • Lili Qiao, Lixing Zheng, Depei Cai. [Study on the levels of the bisphenol A, octylphenol, 4-nonylphenol in serum of precocious girls]. Wei sheng yan jiu = Journal of hygiene research. 2010 Jan; 39(1):9-12. doi: NULL. [PMID: 20364578]
  • Beatrice Gagnaire, François Gagné, Chantale André, Christian Blaise, Khedidja Abbaci, Hélène Budzinski, Marie-Hélène Dévier, Jeanne Garric. Development of biomarkers of stress related to endocrine disruption in gastropods: alkali-labile phosphates, protein-bound lipids and vitellogenin-like proteins. Aquatic toxicology (Amsterdam, Netherlands). 2009 May; 92(3):155-67. doi: 10.1016/j.aquatox.2009.01.012. [PMID: 19269698]
  • Katalin Prokai-Tatrai, Laszlo Prokai, James W Simpkins, Marianna E Jung. Phenolic compounds protect cultured hippocampal neurons against ethanol-withdrawal induced oxidative stress. International journal of molecular sciences. 2009 Apr; 10(4):1773-1787. doi: 10.3390/ijms10041773. [PMID: 19468338]
  • Andrea N Edginton, Len Ritter. Predicting plasma concentrations of bisphenol A in children younger than 2 years of age after typical feeding schedules, using a physiologically based toxicokinetic model. Environmental health perspectives. 2009 Apr; 117(4):645-52. doi: 10.1289/ehp.0800073. [PMID: 19440506]
  • Monika D Jürgens, Andrew C Johnson, Tom G Pottinger, John P Sumpter. Do suspended sediments modulate the effects of octylphenol on rainbow trout?. Water research. 2009 Mar; 43(5):1381-91. doi: 10.1016/j.watres.2008.12.010. [PMID: 19138780]
  • Byung-Mi Kim, Mina Ha, Hye-Sook Park, Bo Eun Lee, Young Ju Kim, Yun-Chul Hong, Yangho Kim, Namsoo Chang, Young-Man Roh, Boong-Nnyun Kim, Se-young Oh, Eun-Hee Ha. The Mothers and Children's Environmental Health (MOCEH) study. European journal of epidemiology. 2009; 24(9):573-83. doi: 10.1007/s10654-009-9370-7. [PMID: 19629723]
  • Paraskevi Pothitou, Dimitra Voutsa. Endocrine disrupting compounds in municipal and industrial wastewater treatment plants in Northern Greece. Chemosphere. 2008 Dec; 73(11):1716-23. doi: 10.1016/j.chemosphere.2008.09.037. [PMID: 18954890]
  • Müfide Aydoğan, Asli Korkmaz, Nurhayat Barlas, Dürdane Kolankaya. The effect of vitamin C on bisphenol A, nonylphenol and octylphenol induced brain damages of male rats. Toxicology. 2008 Jul; 249(1):35-9. doi: 10.1016/j.tox.2008.04.002. [PMID: 18508178]
  • Hui Zhang, Fan-Xiang Kong, Shi-He Wang, Yang Yu, Min Zhang, Mei-Jun Chen, Xiao Tan, Shan-Qin Qian. [Mixture effects to vitellogenin induction by four environmental estrogens in freshwater fish]. Huan jing ke xue= Huanjing kexue. 2008 Jul; 29(7):2005-11. doi: NULL. [PMID: 18828392]
  • M M Santos, M A Reis-Henriques, R Guillot, D Lima, R Franco-Duarte, I Mendes, S Queirós, L Filipe C Castro. Anti-androgenic effects of sewage treatment plant effluents in the prosobranch gastropod Nucella lapillus. Comparative biochemistry and physiology. Toxicology & pharmacology : CBP. 2008 Jul; 148(1):87-93. doi: 10.1016/j.cbpc.2008.03.012. [PMID: 18450520]
  • Raquel Céspedes, Sílvia Lacorte, Antonio Ginebreda, Damià Barceló. Occurrence and fate of alkylphenols and alkylphenol ethoxylates in sewage treatment plants and impact on receiving waters along the Ter River (Catalonia, NE Spain). Environmental pollution (Barking, Essex : 1987). 2008 May; 153(2):384-92. doi: 10.1016/j.envpol.2007.08.026. [PMID: 18262317]
  • Hong Sun, Xiao-Lin Xu, Jian-Hua Qu, Xia Hong, Yu-Bang Wang, Li-Chun Xu, Xin-Ru Wang. 4-Alkylphenols and related chemicals show similar effect on the function of human and rat estrogen receptor alpha in reporter gene assay. Chemosphere. 2008 Mar; 71(3):582-8. doi: 10.1016/j.chemosphere.2007.09.031. [PMID: 18028983]
  • Kristin Quednow, Wilhelm Püttmann. Endocrine disruptors in freshwater streams of Hesse, Germany: changes in concentration levels in the time span from 2003 to 2005. Environmental pollution (Barking, Essex : 1987). 2008 Mar; 152(2):476-83. doi: 10.1016/j.envpol.2007.05.032. [PMID: 17698268]
  • Qingfeng Sun, Shubo Deng, Jun Huang, Gang Shen, Gang Yu. Contributors to estrogenic activity in wastewater from a large wastewater treatment plant in Beijing, China. Environmental toxicology and pharmacology. 2008 Jan; 25(1):20-6. doi: 10.1016/j.etap.2007.08.003. [PMID: 21783831]
  • Tanja Krüger, Philip S Hjelmborg, Bo A G Jönsson, Lars Hagmar, Aleksander Giwercman, Gian-Carlo Manicardi, Davide Bizzaro, Marcello Spanò, Anna Rignell-Hydbom, Henning S Pedersen, Gunnar Toft, Jens Peter Bonde, Eva C Bonefeld-Jørgensen. Xenoandrogenic activity in serum differs across European and Inuit populations. Environmental health perspectives. 2007 Dec; 115 Suppl 1(?):21-7. doi: 10.1289/ehp.9353. [PMID: 18174946]
  • J A van Meeuwen, W Ter Burg, A H Piersma, M van den Berg, J T Sanderson. Mixture effects of estrogenic compounds on proliferation and pS2 expression of MCF-7 human breast cancer cells. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2007 Nov; 45(11):2319-30. doi: 10.1016/j.fct.2007.06.011. [PMID: 17651883]
  • Manhai Long, Bente Deutch, Eva C Bonefeld-Jorgensen. AhR transcriptional activity in serum of Inuits across Greenlandic districts. Environmental health : a global access science source. 2007 Oct; 6(?):32. doi: 10.1186/1476-069x-6-32. [PMID: 17956617]
  • Suel-Kee Kim, Jong-Hoon Kim, Ho-Joon Lee, Yong-Dal Yoon. Octylphenol reduces the expressions of steroidogenic enzymes and testosterone production in mouse testis. Environmental toxicology. 2007 Oct; 22(5):449-58. doi: 10.1002/tox.20280. [PMID: 17696135]
  • Yasuko Yoshida, Azusa Ito, Masashi Murakami, Takayuki Murakami, Hideharu Fujimoto, Kikuo Takeda, Shigeru Suzuki, Masahiro Hori. Determination of nonylphenol ethoxylates and octylphenol ethoxylates in environmental samples using 13C-labeled surrogate compounds. Journal of the Air & Waste Management Association (1995). 2007 Oct; 57(10):1164-71. doi: 10.3155/1047-3289.57.10.1164. [PMID: 17972761]
  • K-E Tollefsen. Binding of alkylphenols and alkylated non-phenolics to the rainbow trout (Oncorhynchus mykiss) plasma sex steroid-binding protein. Ecotoxicology and environmental safety. 2007 Sep; 68(1):40-8. doi: 10.1016/j.ecoenv.2006.07.002. [PMID: 16945415]
  • Sofue Imai, Atsuhiko Shiraishi, Kazuaki Gamo, Ippei Watanabe, Hiroshi Okuhata, Hitoshi Miyasaka, Kazunori Ikeda, Takeshi Bamba, Kazumasa Hirata. Removal of phenolic endocrine disruptors by Portulaca oleracea. Journal of bioscience and bioengineering. 2007 May; 103(5):420-6. doi: 10.1263/jbb.103.420. [PMID: 17609156]
  • J A van Meeuwen, M van den Berg, J T Sanderson, A Verhoef, A H Piersma. Estrogenic effects of mixtures of phyto- and synthetic chemicals on uterine growth of prepubertal rats. Toxicology letters. 2007 Apr; 170(2):165-76. doi: 10.1016/j.toxlet.2007.03.003. [PMID: 17428625]
  • Kaare Press-Kristensen, Anna Ledin, Jens Ejbye Schmidt, Mogens Henze. Identifying model pollutants to investigate biodegradation of hazardous XOCs in WWTPs. The Science of the total environment. 2007 Feb; 373(1):122-30. doi: 10.1016/j.scitotenv.2006.10.044. [PMID: 17196634]
  • Grantley D Charles, Chris Gennings, Belen Tornesi, H Lynn Kan, Timothy R Zacharewski, B Bhaskar Gollapudi, Edward W Carney. Analysis of the interaction of phytoestrogens and synthetic chemicals: an in vitro/in vivo comparison. Toxicology and applied pharmacology. 2007 Feb; 218(3):280-8. doi: 10.1016/j.taap.2006.11.029. [PMID: 17222880]
  • Robert Loos, Georg Hanke, Gunther Umlauf, Steven J Eisenreich. LC-MS-MS analysis and occurrence of octyl- and nonylphenol, their ethoxylates and their carboxylates in Belgian and Italian textile industry, waste water treatment plant effluents and surface waters. Chemosphere. 2007 Jan; 66(4):690-9. doi: 10.1016/j.chemosphere.2006.07.060. [PMID: 16949635]
  • Min Liu, Yuki Hashi, Fengyun Pan, Jianguo Yao, Guanqun Song, Jin-Ming Lin. Automated on-line liquid chromatography-photodiode array-mass spectrometry method with dilution line for the determination of bisphenol A and 4-octylphenol in serum. Journal of chromatography. A. 2006 Nov; 1133(1-2):142-8. doi: 10.1016/j.chroma.2006.08.009. [PMID: 16934275]
  • Gail F Jurgella, Ashok Marwah, Jeffrey A Malison, Richard Peterson, Terence P Barry. Effects of xenobiotics and steroids on renal and hepatic estrogen metabolism in lake trout. General and comparative endocrinology. 2006 Sep; 148(2):273-81. doi: 10.1016/j.ygcen.2006.03.011. [PMID: 16677648]
  • Lihua Yang, Chongyu Lan, Hongtao Liu, Jun Dong, Tiangang Luan. Full automation of solid-phase microextraction/on-fiber derivatization for simultaneous determination of endocrine-disrupting chemicals and steroid hormones by gas chromatography-mass spectrometry. Analytical and bioanalytical chemistry. 2006 Sep; 386(2):391-7. doi: 10.1007/s00216-006-0631-y. [PMID: 16865335]
  • Tiina F M Mikkilä, Jorma Toppari, Jorma Paranko. Effects of neonatal exposure to 4-tert-octylphenol, diethylstilbestrol, and flutamide on steroidogenesis in infantile rat testis. Toxicological sciences : an official journal of the Society of Toxicology. 2006 Jun; 91(2):456-66. doi: 10.1093/toxsci/kfj156. [PMID: 16537657]
  • Minne B Heringa, Chris Hogevonder, Frans Busser, Joop L M Hermens. Measurement of the free concentration of octylphenol in biological samples with negligible depletion-solid phase microextraction (nd-SPME): analysis of matrix effects. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2006 Apr; 834(1-2):35-41. doi: 10.1016/j.jchromb.2006.02.009. [PMID: 16513434]
  • Thomas H Hutchinson, Gerald T Ankley, Helmut Segner, Charles R Tyler. Screening and testing for endocrine disruption in fish-biomarkers as 'signposts,' not 'traffic lights,' in risk assessment. Environmental health perspectives. 2006 Apr; 114 Suppl 1(?):106-14. doi: 10.1289/ehp.8062. [PMID: 16818255]
  • Katherine E Liney, Josephine A Hagger, Charles R Tyler, Michael H Depledge, Tamara S Galloway, Susan Jobling. Health effects in fish of long-term exposure to effluents from wastewater treatment works. Environmental health perspectives. 2006 Apr; 114 Suppl 1(?):81-9. doi: 10.1289/ehp.8058. [PMID: 16818251]
  • Anunciación Lafuente, Teresa Cabaleiro, Pilar Cano, Ana I Esquifino. Toxic effects of methoxychlor on the episodic prolactin secretory pattern: possible mediated effects of nitric oxide production. Journal of circadian rhythms. 2006 Mar; 4(?):3. doi: 10.1186/1740-3391-4-3. [PMID: 16515688]
  • Lihua Yang, Tiangang Luan, Chongyu Lan. Solid-phase microextraction with on-fiber silylation for simultaneous determinations of endocrine disrupting chemicals and steroid hormones by gas chromatography-mass spectrometry. Journal of chromatography. A. 2006 Feb; 1104(1-2):23-32. doi: 10.1016/j.chroma.2005.11.108. [PMID: 16376914]
  • Li-Chun Xu, Hong Sun, Jian-Feng Chen, Qian Bian, Jie Qian, Ling Song, Xin-Ru Wang. Evaluation of androgen receptor transcriptional activities of bisphenol A, octylphenol and nonylphenol in vitro. Toxicology. 2005 Dec; 216(2-3):197-203. doi: 10.1016/j.tox.2005.08.006. [PMID: 16169144]
  • Grant W Feist, Molly A H Webb, Deke T Gundersen, Eugene P Foster, Carl B Schreck, Alec G Maule, Martin S Fitzpatrick. Evidence of detrimental effects of environmental contaminants on growth and reproductive physiology of white sturgeon in impounded areas of the Columbia River. Environmental health perspectives. 2005 Dec; 113(12):1675-82. doi: 10.1289/ehp.8072. [PMID: 16330346]
  • Paloma Alonso-Magdalena, Ouahiba Laribi, Ana B Ropero, Esther Fuentes, Cristina Ripoll, Bernat Soria, Angel Nadal. Low doses of bisphenol A and diethylstilbestrol impair Ca2+ signals in pancreatic alpha-cells through a nonclassical membrane estrogen receptor within intact islets of Langerhans. Environmental health perspectives. 2005 Aug; 113(8):969-77. doi: 10.1289/ehp.8002. [PMID: 16079065]
  • Richard Y Wang, Larry L Needham, Dana B Barr. Effects of environmental agents on the attainment of puberty: considerations when assessing exposure to environmental chemicals in the National Children's Study. Environmental health perspectives. 2005 Aug; 113(8):1100-7. doi: 10.1289/ehp.7615. [PMID: 16079085]
  • Matilde Carballo, Sonia Aguayo, Ana de la Torre, M Jesús Muñoz. Plasma vitellogenin levels and gonadal morphology of wild carp (Cyprinus carpio L.) in a receiving rivers downstream of sewage treatment plants. The Science of the total environment. 2005 Apr; 341(1-3):71-9. doi: 10.1016/j.scitotenv.2004.08.021. [PMID: 15833242]
  • Stewart M Rhind, Carol E Kyle, Gillian Telfer, Elizabeth I Duff, Alistair Smith. Alkyl phenols and diethylhexyl phthalate in tissues of sheep grazing pastures fertilized with sewage sludge or inorganic fertilizer. Environmental health perspectives. 2005 Apr; 113(4):447-53. doi: 10.1289/ehp.7469. [PMID: 15811823]
  • Antonia M Calafat, Zsuzsanna Kuklenyik, John A Reidy, Samuel P Caudill, John Ekong, Larry L Needham. Urinary concentrations of bisphenol A and 4-nonylphenol in a human reference population. Environmental health perspectives. 2005 Apr; 113(4):391-5. doi: 10.1289/ehp.7534. [PMID: 15811827]
  • Masayoshi Ohshima, Shuji Ohno, Shizuo Nakajin. Inhibitory effects of some possible endocrine-disrupting chemicals on the isozymes of human 11beta-hydroxysteroid dehydrogenase and expression of their mRNA in gonads and adrenal glands. Environmental sciences : an international journal of environmental physiology and toxicology. 2005; 12(4):219-30. doi: . [PMID: 16184081]
  • Chandana B Herath, Wanzhu Jin, Gen Watanabe, Koji Arai, Akira K Suzuki, Kazuyoshi Taya. Adverse effects of environmental toxicants, octylphenol and bisphenol A, on male reproductive functions in pubertal rats. Endocrine. 2004 Nov; 25(2):163-72. doi: 10.1385/endo:25:2:163. [PMID: 15711031]
  • Tina H Rasmussen, Bodil Korsgaard. Estrogenic octylphenol affects seminal fluid production and its biochemical composition of eelpout (Zoarces viviparus). Comparative biochemistry and physiology. Toxicology & pharmacology : CBP. 2004 Oct; 139(1-3):1-10. doi: 10.1016/j.cca.2004.08.016. [PMID: 15556059]
  • Sonia Aguayo, M Jesús Muñoz, Ana de la Torre, Jaime Roset, Eduardo de la Peña, Matilde Carballo. Identification of organic compounds and ecotoxicological assessment of sewage treatment plants (STP) effluents. The Science of the total environment. 2004 Jul; 328(1-3):69-81. doi: 10.1016/j.scitotenv.2004.02.013. [PMID: 15207574]
  • Justin G Teeguarden, Hugh A Barton. Computational modeling of serum-binding proteins and clearance in extrapolations across life stages and species for endocrine active compounds. Risk analysis : an official publication of the Society for Risk Analysis. 2004 Jun; 24(3):751-70. doi: 10.1111/j.0272-4332.2004.00473.x. [PMID: 15209943]
  • William L Gale, Reynaldo Patiño, Alec G Maule. Interaction of xenobiotics with estrogen receptors alpha and beta and a putative plasma sex hormone-binding globulin from channel catfish (Ictalurus punctatus). General and comparative endocrinology. 2004 May; 136(3):338-45. doi: 10.1016/j.ygcen.2004.01.009. [PMID: 15081833]
  • Barbara V Rutishauser, Maija Pesonen, Beate I Escher, Gabriele E Ackermann, Hans-Rudolf Aerni, Marc J F Suter, Rik I L Eggen. Comparative analysis of estrogenic activity in sewage treatment plant effluents involving three in vitro assays and chemical analysis of steroids. Environmental toxicology and chemistry. 2004 Apr; 23(4):857-64. doi: 10.1897/03-286. [PMID: 15095880]
  • Neil P Evans, Tom North, Sandra Dye, Torres Sweeney. Differential effects of the endocrine-disrupting compounds bisphenol-A and octylphenol on gonadotropin secretion, in prepubertal ewe lambs. Domestic animal endocrinology. 2004 Jan; 26(1):61-73. doi: 10.1016/j.domaniend.2003.09.005. [PMID: 14732453]
  • Zsuzsanna Kuklenyik, John Ekong, Caroline D Cutchins, Larry L Needham, Antonia M Calafat. Simultaneous measurement of urinary bisphenol A and alkylphenols by automated solid-phase extractive derivatization gas chromatography/mass spectrometry. Analytical chemistry. 2003 Dec; 75(24):6820-5. doi: 10.1021/ac0303158. [PMID: 14670041]
  • Hong Fang, Weida Tong, William S Branham, Carrie L Moland, Stacy L Dial, Huixiao Hong, Qian Xie, Roger Perkins, William Owens, Daniel M Sheehan. Study of 202 natural, synthetic, and environmental chemicals for binding to the androgen receptor. Chemical research in toxicology. 2003 Oct; 16(10):1338-58. doi: 10.1021/tx030011g. [PMID: 14565775]