4-(1,1,3,3-Tetramethylbutyl)-phenol (BioDeep_00000002410)
Secondary id: BioDeep_00001873574
human metabolite PANOMIX_OTCML-2023 Endogenous Industrial Pollutants
代谢物信息卡片
化学式: C14H22O (206.1671)
中文名称: 4-叔辛基苯酚, 4-(1,1,3,3-四甲基丁基)苯酚
谱图信息:
最多检出来源 Homo sapiens(feces) 7.91%
分子结构信息
SMILES: CC(C)(C)CC(C)(C)C1=CC=C(C=C1)O
InChI: InChI=1S/C14H22O/c1-13(2,3)10-14(4,5)11-6-8-12(15)9-7-11/h6-9,15H,10H2,1-5H3
描述信息
4-(1,1,3,3-Tetramethylbutyl)-phenol is manufactured via a catalytic reaction of phenol with diisobutylene. It is a member of the class of compounds known as phenylpropanes. Phenylpropanes are organic compounds that contain a phenylpropane moiety. 4-(1,1,3,3-Tetramethylbutyl)-phenol can be found primarily in feces and urine. Within the cell, 4-(1,1,3,3-Tetramethylbutyl)-phenol is primarily located in the membrane (predicted from logP). It is a non-carcinogenic (not listed by IARC) potentially toxic compound. 4-(1,1,3,3-Tetramethylbutyl)-phenol is biodegradable, and in the surface layer of natural waters, 30\\\% of OP can be degraded within one day. 4-(1,1,3,3-Tetramethylbutyl)-phenol is acutely very toxic to aquatic organisms and may cause long-term adverse effects in the aquatic environment. It is not acutely toxic to human health, but it is slightly irritating to the skin and highly irritating to the eyes. It is not genotoxic, but it may cause depigmentation of the skin. 4-(1,1,3,3-Tetramethylbutyl)-phenol is used as a food additive (EAFUS: Everything Added to Food in the United States).
CONFIDENCE standard compound; INTERNAL_ID 939; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5475; ORIGINAL_PRECURSOR_SCAN_NO 5474
CONFIDENCE standard compound; INTERNAL_ID 939; 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 939; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5472; ORIGINAL_PRECURSOR_SCAN_NO 5470
CONFIDENCE standard compound; INTERNAL_ID 939; DATASET 20200303_ENTACT_RP_MIX501; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5015; ORIGINAL_PRECURSOR_SCAN_NO 5012
CONFIDENCE standard compound; INTERNAL_ID 939; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5452; ORIGINAL_PRECURSOR_SCAN_NO 5448
CONFIDENCE standard compound; INTERNAL_ID 939; 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
D013501 - Surface-Active Agents
It is used as a food additive .
4-tert-Octylphenol, a endocrine-disrupting chemical, is an estrogenic agent. 4-tert-Octylphenol induces apoptosis in neuronal progenitor cells in offspring mouse brain. 4-tert-Octylphenol reduces bromodeoxyuridine (BrdU), mitotic marker Ki67, and phospho-histone H3 (p-Histone-H3), resulting in a reduction of neuronal progenitor proliferation. 4-tert-Octylphenol disrupts brain development and behavior in mice[1].
同义名列表
23 个代谢物同义名
alpha-(p-(1,1,3,3-Tetramethylbutyl)phenyl)-omega-hydroxypoly(oxyethylene); a-(p-(1,1,3,3-Tetramethylbutyl)phenyl)-omega-hydroxypoly(oxyethylene); Α-(p-(1,1,3,3-tetramethylbutyl)phenyl)-omega-hydroxypoly(oxyethylene); 4-(1,1,3,3-Tetramethylbutyl)phenol (acd/name 4.0); 4-(2,4,4-trimethylpentan-2-yl)phenol; P-(1,1,3, 3-Tetramethylbutyl)phenol; 4-(1,1,3,3-Tetramethylbutyl)-phenol; p-(1,1,3,3-Tetramethylbutyl)-phenol; P-(1,1,3,3-Tetramethylbutyl)phenol; 4-(1,1,3,3-Tetramethylbutyl)phenol; Tert-octylphenol, flaked; 4-Tertiary-octylphenol; Para-tert-octylphenol; P-(Tert-octyl)-phenol; p-Tert-octylphenol; 4-tert-Octylphenol; P-Terc.oktylfenol; 4-t-Octylphenol; Octylphenol PT; P-Octylphenol; 4-tOP; 4-tert-Octylphenol; 4-tert-Octylphenol
数据库引用编号
22 个数据库交叉引用编号
- ChEBI: CHEBI:34445
- KEGG: C14205
- PubChem: 8814
- HMDB: HMDB0013825
- Metlin: METLIN69877
- ChEMBL: CHEMBL259327
- foodb: FDB010381
- chemspider: 8483
- CAS: 140-66-9
- MoNA: LU093956
- MoNA: LU093951
- MoNA: LU093955
- MoNA: LU093952
- MoNA: LU093954
- MoNA: LU093953
- PMhub: MS000002540
- PubChem: 7847015
- PDB-CCD: 27L
- NIKKAJI: J1.190H
- RefMet: alpha-(p-(1,1,3,3-Tetramethylbutyl)phenyl)-omega-hydroxypoly(oxyethylene)
- medchemexpress: HY-B1941
- KNApSAcK: 34445
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。
文献列表
- 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] - Katarzyna Knapczyk-Stwora, Anna Nynca, Renata E Ciereszko, Lukasz Paukszto, Jan P Jastrzebski, Elzbieta Czaja, Patrycja Witek, Marek Koziorowski, Maria Slomczynska. Transcriptomic profiles of the ovaries from piglets neonatally exposed to 4-tert-octylphenol.
Theriogenology.
2020 Sep; 153(?):102-111. doi:
10.1016/j.theriogenology.2020.04.027
. [PMID: 32450468] - Jiao Yang, Qingyi Huang, Huan Liu, Xiong Zhou, Zhuoquan Huang, Quansheng Peng, Chunhong Liu. 4-Nonylphenol and 4-tert-octylphenol induce anxiety-related behaviors through alternation of 5-HT receptors and transporters in the prefrontal cortex.
Comparative biochemistry and physiology. Toxicology & pharmacology : CBP.
2020 Apr; 230(?):108701. doi:
10.1016/j.cbpc.2020.108701
. [PMID: 31911191] - Lamidi W B Olaniyan, Omobola O Okoh, Noxolo T Mkwetshana, Anthony I Okoh. Environmental Water Pollution, Endocrine Interference and Ecotoxicity of 4-tert-Octylphenol: A Review.
Reviews of environmental contamination and toxicology.
2020; 248(?):81-109. doi:
10.1007/398_2018_20
. [PMID: 30460491] - 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] - Marjo Patama, Regina G Belz, Aki Sinkkonen. Realistic low-doses of two emerging contaminants change size distribution of an annual flowering plant population.
Ecotoxicology (London, England).
2019 Sep; 28(7):732-743. doi:
10.1007/s10646-019-02069-3
. [PMID: 31250287] - Yin-Zhi Lv, Li Yao, Li Wang, Wang-Rong Liu, Jian-Liang Zhao, Liang-Ying He, Guang-Guo Ying. Bioaccumulation, metabolism, and risk assessment of phenolic endocrine disrupting chemicals in specific tissues of wild fish.
Chemosphere.
2019 Jul; 226(?):607-615. doi:
10.1016/j.chemosphere.2019.03.187
. [PMID: 30954895] - Chien-Yu Lin, Yi-Ting Hwang, Pau-Chung Chen, Fung-Chang Sung, Ta-Chen Su. Association of serum levels of 4-tertiary-octylphenol with cardiovascular risk factors and carotid intima-media thickness in adolescents and young adults.
Environmental pollution (Barking, Essex : 1987).
2019 Mar; 246(?):107-113. doi:
10.1016/j.envpol.2018.11.110
. [PMID: 30529934] - Khaled M M Koriem, Mahmoud S S Arbid. Fertaric Acid Protects from Octylphenol-Related Hepatotoxicity in Rats: Biochemical, Molecular, and Histopathological Studies.
Journal of dietary supplements.
2019; 16(2):152-165. doi:
10.1080/19390211.2018.1443190
. [PMID: 29561242] - Kun Zhou, Xingwang Ding, Jing Yang, Yanhui Hu, Yun Song, Minjian Chen, Rongli Sun, Tianyu Dong, Bo Xu, Xiumei Han, Keqin Wu, Xiaoling Zhang, Xinru Wang, Yankai Xia. Metabolomics Reveals Metabolic Changes Caused by Low-Dose 4-Tert-Octylphenol in Mice Liver.
International journal of environmental research and public health.
2018 11; 15(12):. doi:
10.3390/ijerph15122686
. [PMID: 30487447] - Regina G Belz, Marjo Patama, Aki Sinkkonen. Low doses of six toxicants change plant size distribution in dense populations of Lactuca sativa.
The Science of the total environment.
2018 Aug; 631-632(?):510-523. doi:
10.1016/j.scitotenv.2018.02.336
. [PMID: 29529439] - Dinh Nam Tran, Eui-Man Jung, Changhwan Ahn, Jae-Hwan Lee, Yeong-Min Yoo, Eui-Bae Jeung. Effects of Bisphenol A and 4-tert-Octylphenol on Embryo Implantation Failure in Mouse.
International journal of environmental research and public health.
2018 07; 15(8):. doi:
10.3390/ijerph15081614
. [PMID: 30061528] - Katarzyna Knapczyk-Stwora, Malgorzata Grzesiak, Renata E Ciereszko, Elzbieta Czaja, Marek Koziorowski, Maria Slomczynska. The impact of sex steroid agonists and antagonists on folliculogenesis in the neonatal porcine ovary via cell proliferation and apoptosis.
Theriogenology.
2018 Jun; 113(?):19-26. doi:
10.1016/j.theriogenology.2018.02.008
. [PMID: 29452853] - Shuang-Hung Chung, Wang-Hsien Ding. Isotope-dilution gas chromatography-mass spectrometry coupled with injection-port butylation for the determination of 4-t-octylphenol, 4-nonylphenols and bisphenol A in human urine.
Journal of pharmaceutical and biomedical analysis.
2018 Feb; 149(?):572-576. doi:
10.1016/j.jpba.2017.11.063
. [PMID: 29197299] - Khaled M M Koriem, Mahmoud S S Arbid, Nawal E Gomaa. The Role of Chlorogenic Acid Supplementation in Anemia and Mineral Disturbances Induced by 4-Tert-Octylphenol Toxicity.
Journal of dietary supplements.
2018 Jan; 15(1):55-71. doi:
10.1080/19390211.2017.1321079
. [PMID: 28489956] - Punyanganie S de Silva, Xuan Yang, Joshua R Korzenik, Rose H Goldman, Kristopher L Arheart, Alberto J Caban-Martinez. Association of urinary phenolic compounds, inflammatory bowel disease and chronic diarrheal symptoms: Evidence from the National Health and Nutrition Examination Survey.
Environmental pollution (Barking, Essex : 1987).
2017 Oct; 229(?):621-626. doi:
10.1016/j.envpol.2017.06.023
. [PMID: 28689150] - Annisa' Bias Cahyanurani, Kuo-Hsun Chiu, Tsung-Meng Wu. Glutathione biosynthesis plays an important role against 4-tert-octylphenol-induced oxidative stress in Ceratophyllum demersum.
Chemosphere.
2017 Sep; 183(?):565-573. doi:
10.1016/j.chemosphere.2017.05.150
. [PMID: 28570900] - Elisabetta Loffredo, Eren Taskin. Adsorptive removal of ascertained and suspected endocrine disruptors from aqueous solution using plant-derived materials.
Environmental science and pollution research international.
2017 Aug; 24(23):19159-19166. doi:
10.1007/s11356-017-9595-z
. [PMID: 28664489] - O Carnevali, V Notarstefano, I Olivotto, M Graziano, P Gallo, I Di Marco Pisciottano, L Vaccari, A Mandich, E Giorgini, F Maradonna. Dietary administration of EDC mixtures: A focus on fish lipid metabolism.
Aquatic toxicology (Amsterdam, Netherlands).
2017 Apr; 185(?):95-104. doi:
10.1016/j.aquatox.2017.02.007
. [PMID: 28208108] - Oju R Ibor, Aina O Adeogun, Olusegun A Fagbohun, Augustine Arukwe. Gonado-histopathological changes, intersex and endocrine disruptor responses in relation to contaminant burden in Tilapia species from Ogun River, Nigeria.
Chemosphere.
2016 Dec; 164(?):248-262. doi:
10.1016/j.chemosphere.2016.08.087
. [PMID: 27591376] - Shenliang Lv, Chunhua Wu, Dasheng Lu, Xiaojuan Qi, Hao Xu, Jianqiu Guo, Weijiu Liang, XiuLi Chang, Guoquan Wang, Zhijun Zhou. Birth outcome measures and prenatal exposure to 4-tert-octylphenol.
Environmental pollution (Barking, Essex : 1987).
2016 May; 212(?):65-70. doi:
10.1016/j.envpol.2016.01.048
. [PMID: 26840518] - F Maradonna, V Nozzi, S Santangeli, I Traversi, P Gallo, E Fattore, D G Mita, A Mandich, O Carnevali. Xenobiotic-contaminated diets affect hepatic lipid metabolism: Implications for liver steatosis in Sparus aurata juveniles.
Aquatic toxicology (Amsterdam, Netherlands).
2015 Oct; 167(?):257-64. doi:
10.1016/j.aquatox.2015.08.006
. [PMID: 26382854] - 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] - Daryl N Bulloch, Eric D Nelson, Steve A Carr, Chris R Wissman, Jeffrey L Armstrong, Daniel Schlenk, Cynthia K Larive. Occurrence of halogenated transformation products of selected pharmaceuticals and personal care products in secondary and tertiary treated wastewaters from southern California.
Environmental science & technology.
2015 Feb; 49(4):2044-51. doi:
10.1021/es504565n
. [PMID: 25611547] - Shalini Saggu, Mohamed I Sakeran, Nahla Zidan, Ehab Tousson, Anand Mohan, Hasibur Rehman. Ameliorating effect of chicory (Chichorium intybus L.) fruit extract against 4-tert-octylphenol induced liver injury and oxidative stress in male rats.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
2014 Oct; 72(?):138-46. doi:
10.1016/j.fct.2014.06.029
. [PMID: 25010453] - Marta Staniszewska, Lucyna Falkowska, Paweł Grabowski, Justyna Kwaśniak, Stella Mudrak-Cegiołka, Andrzej R Reindl, Adam Sokołowski, Emilia Szumiło, Aleksandra Zgrundo. Bisphenol A, 4-tert-octylphenol, and 4-nonylphenol in the Gulf of Gdańsk (Southern Baltic).
Archives of environmental contamination and toxicology.
2014 Oct; 67(3):335-47. doi:
10.1007/s00244-014-0023-9
. [PMID: 24752748] - Kaori Sadakane, Takamichi Ichinose, Hirohisa Takano, Rie Yanagisawa, Eiko Koike, Ken-ichiro Inoue. The alkylphenols 4-nonylphenol, 4-tert-octylphenol and 4-tert-butylphenol aggravate atopic dermatitis-like skin lesions in NC/Nga mice.
Journal of applied toxicology : JAT.
2014 Aug; 34(8):893-902. doi:
10.1002/jat.2911
. [PMID: 23983229] - 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] - XiaoYun Xie, WenJuan Lü, XingGuo Chen. Binding of the endocrine disruptors 4-tert-octylphenol and 4-nonylphenol to human serum albumin.
Journal of hazardous materials.
2013 Mar; 248-249(?):347-54. doi:
10.1016/j.jhazmat.2013.01.036
. [PMID: 23416871] - Hyunju Jung, Yonghee Hong, Donghwan Lee, Kijung Pang, Yunje Kim. The association between some endocrine disruptors in human plasma and the occurrence of congenital hypothyroidism.
Environmental toxicology and pharmacology.
2013 Mar; 35(2):278-83. doi:
10.1016/j.etap.2013.01.002
. [PMID: 23376177] - 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] - 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] - Sanka N Atapattu, Jack M Rosenfeld. Solid phase analytical derivatization of anthropogenic and natural phenolic estrogen mimics with pentafluoropyridine for gas chromatography-mass spectrometry.
Journal of chromatography. A.
2011 Dec; 1218(51):9135-41. doi:
10.1016/j.chroma.2011.10.060
. [PMID: 22104213] - Larry B Barber, Gregory K Brown, Todd G Nettesheim, Elizabeth W Murphy, Stephen E Bartell, Heiko L Schoenfuss. Effects of biologically-active chemical mixtures on fish in a wastewater-impacted urban stream.
The Science of the total environment.
2011 Oct; 409(22):4720-8. doi:
10.1016/j.scitotenv.2011.06.039
. [PMID: 21849205] - 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] - Tadashi Toyama, Manabu Murashita, Kazutaka Kobayashi, Shintaro Kikuchi, Kazunari Sei, Yasuhiro Tanaka, Michihiko Ike, Kazuhiro Mori. Acceleration of nonylphenol and 4-tert-octylphenol degradation in sediment by Phragmites australis and associated rhizosphere bacteria.
Environmental science & technology.
2011 Aug; 45(15):6524-30. doi:
10.1021/es201061a
. [PMID: 21736332] - Shabana I Khan, Jianping Zhao, Ikhlas A Khan, Larry A Walker, Asok K Dasmahapatra. Potential utility of natural products as regulators of breast cancer-associated aromatase promoters.
Reproductive biology and endocrinology : RB&E.
2011 Jun; 9(?):91. doi:
10.1186/1477-7827-9-91
. [PMID: 21693041] - Li You, Xiangzhu Zhu, Martha J Shrubsole, Hong Fan, Jing Chen, Jie Dong, Chuan-Ming Hao, Qi Dai. Renal function, bisphenol A, and alkylphenols: results from the National Health and Nutrition Examination Survey (NHANES 2003-2006).
Environmental health perspectives.
2011 Apr; 119(4):527-33. doi:
10.1289/ehp.1002572
. [PMID: 21147601] - Hui Zhang, Fan-Xiang Kong, Yang Yu, Xiao-Li Shi, Min Zhang, Hong-Er Tian. Assessing the combination effects of environmental estrogens in fish.
Ecotoxicology (London, England).
2010 Nov; 19(8):1476-86. doi:
10.1007/s10646-010-0533-9
. [PMID: 20711811] - Aki Sinkkonen, Mervi Myyrä, Olli-Pekka Penttinen, Anna-Lea Rantalainen. Selective toxicity at low doses: experiments with three plant species and toxicants.
Dose-response : a publication of International Hormesis Society.
2010 Jun; 9(1):130-43. doi:
10.2203/dose-response.09-045.sinkkonen
. [PMID: 21431082] - G Rey Vázquez, F J Meijide, R H Da Cuña, F L Lo Nostro, Y G Piazza, P A Babay, V L Trudeau, M C Maggese, G A Guerrero. Exposure to waterborne 4-tert-octylphenol induces vitellogenin synthesis and disrupts testis morphology in the South American freshwater fish Cichlasoma dimerus (Teleostei, Perciformes).
Comparative biochemistry and physiology. Toxicology & pharmacology : CBP.
2009 Aug; 150(2):298-306. doi:
10.1016/j.cbpc.2009.05.012
. [PMID: 19477298] - Nurhayat Barlas, Müfide Aydoğan. Histopathologic effects of maternal 4-tert-octylphenol exposure on liver, kidney and spleen of rats at adulthood.
Archives of toxicology.
2009 Apr; 83(4):341-9. doi:
10.1007/s00204-008-0354-2
. [PMID: 18754100] - T Randak, V Zlabek, J Pulkrabova, J Kolarova, H Kroupova, Z Siroka, J Velisek, Z Svobodova, J Hajslova. Effects of pollution on chub in the River Elbe, Czech Republic.
Ecotoxicology and environmental safety.
2009 Mar; 72(3):737-46. doi:
10.1016/j.ecoenv.2008.09.020
. [PMID: 19019432] - 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] - Guang-Wen Lien, Chia-Yang Chen, Gen-Shuh Wang. Comparison of electrospray ionization, atmospheric pressure chemical ionization and atmospheric pressure photoionization for determining estrogenic chemicals in water by liquid chromatography tandem mass spectrometry with chemical derivatizations.
Journal of chromatography. A.
2009 Feb; 1216(6):956-66. doi:
10.1016/j.chroma.2008.12.023
. [PMID: 19118834] - Poul Bjerregaard, Pernille R Hansen, Katrine J Larsen, Claudio Erratico, Bodil Korsgaard, Henrik Holbech. Vitellogenin as a biomarker for estrogenic effects in brown trout, Salmo trutta: laboratory and field investigations.
Environmental toxicology and chemistry.
2008 Nov; 27(11):2387-96. doi:
10.1897/08-148.1
. [PMID: 18611082] - Setsuya Kamei, Joji Miyawaki, Kenshi Sakayama, Haruyasu Yamamoto, Hiroshi Masuno. Perinatal and postnatal exposure to 4-tert-octylphenol inhibits cortical bone growth in width at the diaphysis in female mice.
Toxicology.
2008 Oct; 252(1-3):99-104. doi:
10.1016/j.tox.2008.08.008
. [PMID: 18790001] - Mary S Wolff, Stephanie M Engel, Gertrud S Berkowitz, Xiaoyun Ye, Manori J Silva, Chenbo Zhu, James Wetmur, Antonia M Calafat. Prenatal phenol and phthalate exposures and birth outcomes.
Environmental health perspectives.
2008 Aug; 116(8):1092-7. doi:
10.1289/ehp.11007
. [PMID: 18709157] - Y B Du, Y Y Li, Y J Zhen, C B Hu, W H Liu, W Z Chen, Z W Sun. Toxic Effects in Siganus oramin by dietary exposure to 4-tert-octylphenol.
Bulletin of environmental contamination and toxicology.
2008 Jun; 80(6):534-8. doi:
10.1007/s00128-008-9388-7
. [PMID: 18408878] - 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] - Michel Aubé, Christian Larochelle, Pierre Ayotte. 1,1-dichloro-2,2-bis(p-chlorophenyl)ethylene (p,p'-DDE) disrupts the estrogen-androgen balance regulating the growth of hormone-dependent breast cancer cells.
Breast cancer research : BCR.
2008; 10(1):R16. doi:
10.1186/bcr1862
. [PMID: 18275596] - Yucel Akgul, Raymond C Derk, Terence Meighan, K Murali Krishna Rao, Eisuke P Murono. The methoxychlor metabolite, HPTE, directly inhibits the catalytic activity of cholesterol side-chain cleavage (P450scc) in cultured rat ovarian cells.
Reproductive toxicology (Elmsford, N.Y.).
2008 Jan; 25(1):67-75. doi:
10.1016/j.reprotox.2007.10.007
. [PMID: 18065196] - Sung Ho Yoon, Yasuo Itoh, Gen Kaneko, Makiko Nakaniwa, Masataka Ohta, Shugo Watabe. Molecular characterization of Japanese sillago vitellogenin and changes in its expression levels on exposure to 17beta-estradiol and 4-tert-octylphenol.
Marine biotechnology (New York, N.Y.).
2008 Jan; 10(1):19-30. doi:
10.1007/s10126-007-9055-8
. [PMID: 18046605] - Antonia M Calafat, Xiaoyun Ye, Lee-Yang Wong, John A Reidy, Larry L Needham. Exposure of the U.S. population to bisphenol A and 4-tertiary-octylphenol: 2003-2004.
Environmental health perspectives.
2008 Jan; 116(1):39-44. doi:
10.1289/ehp.10753
. [PMID: 18197297] - Shiwei Jin, Fangxing Yang, Tao Liao, Yang Hui, Ying Xu. Seasonal variations of estrogenic compounds and their estrogenicities in influent and effluent from a municipal sewage treatment plant in China.
Environmental toxicology and chemistry.
2008 Jan; 27(1):146-53. doi:
10.1897/07-072.1
. [PMID: 18092861] - Guang-Guo Ying, Rai S Kookana, Anu Kumar. Fate of estrogens and xenoestrogens in four sewage treatment plants with different technologies.
Environmental toxicology and chemistry.
2008 Jan; 27(1):87-94. doi:
10.1897/07-046.1
. [PMID: 18092854] - S Baig, G Hansmann, B Paolini. Ozone oxidation of oestrogenic active substances in wastewater and drinking water.
Water science and technology : a journal of the International Association on Water Pollution Research.
2008; 58(2):451-8. doi:
10.2166/wst.2008.665
. [PMID: 18701800] - L Balest, G Mascolo, C Di Iaconi, A Lopez. Removal of endocrine disrupter compounds from municipal wastewater by an innovative biological technology.
Water science and technology : a journal of the International Association on Water Pollution Research.
2008; 58(4):953-6. doi:
10.2166/wst.2008.711
. [PMID: 18776635] - Elisabete Silva, Martin Scholze, Andreas Kortenkamp. Activity of xenoestrogens at nanomolar concentrations in the E-Screen assay.
Environmental health perspectives.
2007 Dec; 115 Suppl 1(?):91-7. doi:
10.1289/ehp.9363
. [PMID: 18174956] - 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] - T Mayer, D Bennie, F Rosa, G Rekas, V Palabrica, J Schachtschneider. Occurrence of alkylphenolic substances in a Great Lakes coastal marsh, Cootes Paradise, ON, Canada.
Environmental pollution (Barking, Essex : 1987).
2007 Jun; 147(3):683-90. doi:
10.1016/j.envpol.2006.09.012
. [PMID: 17134807] - Migaku Kawaguchi, Rie Ito, Norihiro Sakui, Noriya Okanouchi, Koichi Saito, Yasuo Seto, Hiroyuki Nakazawa. Stir-bar-sorptive extraction, with in-situ deconjugation, and thermal desorption with in-tube silylation, followed by gas chromatography-mass spectrometry for measurement of urinary 4-nonylphenol and 4-tert-octylphenol glucuronides.
Analytical and bioanalytical chemistry.
2007 May; 388(2):391-8. doi:
10.1007/s00216-007-1225-z
. [PMID: 17356815] - Karsten Bangsgaard, Steffen S Madsen, Bodil Korsgaard. Effect of waterborne exposure to 4-tert-octylphenol and 17beta-estradiol on smoltification and downstream migration in Atlantic salmon, Salmo salar.
Aquatic toxicology (Amsterdam, Netherlands).
2006 Oct; 80(1):23-32. doi:
10.1016/j.aquatox.2006.07.009
. [PMID: 16949683] - 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] - Louise L Madsen, Bodil Korsgaard, Poul Bjerregaard. Oral single pulse exposure of flounder Platichthys flesus to 4-tert-octylphenol: Relations between tissue levels and estrogenic effects.
Marine environmental research.
2006 Apr; 61(3):352-62. doi:
10.1016/j.marenvres.2005.11.002
. [PMID: 16386298] - 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] - Yuqiu Wang, Wei Hu, Zhonghong Cao, Xueqi Fu, Tan Zhu. Occurrence of endocrine-disrupting compounds in reclaimed water from Tianjin, China.
Analytical and bioanalytical chemistry.
2005 Nov; 383(5):857-63. doi:
10.1007/s00216-005-0082-x
. [PMID: 16189677] - S A Myllymäki, M Karjalainen, T E Haavisto, J Toppari, J Paranko. Infantile 4-tert-octylphenol exposure transiently inhibits rat ovarian steroidogenesis and steroidogenic acute regulatory protein (StAR) expression.
Toxicology and applied pharmacology.
2005 Aug; 207(1):59-68. doi:
10.1016/j.taap.2004.12.001
. [PMID: 16054900] - Xiaoyun Ye, Zsuzsanna Kuklenyik, Larry L Needham, Antonia M Calafat. Automated on-line column-switching HPLC-MS/MS method with peak focusing for the determination of nine environmental phenols in urine.
Analytical chemistry.
2005 Aug; 77(16):5407-13. doi:
10.1021/ac050390d
. [PMID: 16097788] - Migaku Kawaguchi, Norihiro Sakui, Noriya Okanouchi, Rie Ito, Koichi Saito, Shun-ichiro Izumi, Tsunehisa Makino, Hiroyuki Nakazawa. Stir bar sorptive extraction with in situ derivatization and thermal desorption-gas chromatography--mass spectrometry for measurement of phenolic xenoestrogens in human urine samples.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2005 Jun; 820(1):49-57. doi:
10.1016/j.jchromb.2005.03.019
. [PMID: 15866492] - Tina H Rasmussen, Swee J Teh, Poul Bjerregaard, Bodil Korsgaard. Anti-estrogen prevents xenoestrogen-induced testicular pathology of eelpout (Zoarces viviparus).
Aquatic toxicology (Amsterdam, Netherlands).
2005 Apr; 72(3):177-94. doi:
10.1016/j.aquatox.2004.12.003
. [PMID: 15820099] - Thomas K Andreassen, Karsten Skjoedt, Bodil Korsgaard. Upregulation of estrogen receptor alpha and vitellogenin in eelpout (Zoarces viviparus) by waterborne exposure to 4-tert-octylphenol and 17beta-estradiol.
Comparative biochemistry and physiology. Toxicology & pharmacology : CBP.
2005 Mar; 140(3-4):340-6. doi:
10.1016/j.cca.2005.03.003
. [PMID: 15878695] - Suel-Kee Kim, Ho-Joon Lee, Hyunwon Yang, Ho-Seung Kim, Yong-Dal Yoon. Prepubertal exposure to 4-tert-octylphenol induces apoptosis of testicular germ cells in adult rat.
Archives of andrology.
2004 Nov; 50(6):427-41. doi:
10.1080/01485010490475093
. [PMID: 15669608] - K-E Tollefsen, J Ovrevik, J Stenersen. Binding of xenoestrogens to the sex steroid-binding protein in plasma from Arctic charr (Salvelinus alpinus L.).
Comparative biochemistry and physiology. Toxicology & pharmacology : CBP.
2004 Oct; 139(1-3):127-33. doi:
10.1016/j.cca.2004.10.003
. [PMID: 15556074] - M D Hernando, M Mezcua, M J Gómez, O Malato, A Agüera, A R Fernández-Alba. Comparative study of analytical methods involving gas chromatography-mass spectrometry after derivatization and gas chromatography-tandem mass spectrometry for the determination of selected endocrine disrupting compounds in wastewaters.
Journal of chromatography. A.
2004 Aug; 1047(1):129-35. doi:
10.1016/j.chroma.2004.06.123
. [PMID: 15481468] - Craig D Robinson, Elaine Brown, John A Craft, Ian M Davies, Colin F Moffat. Effects of prolonged exposure to 4-tert-octylphenol on toxicity and indices of oestrogenic exposure in the sand goby (Pomatoschistus minutus, Pallas).
Marine environmental research.
2004 Jul; 58(1):19-38. doi:
10.1016/j.marenvres.2003.12.001
. [PMID: 15046944] - P Diel, S Schmidt, G Vollmer, P Janning, A Upmeier, H Michna, H M Bolt, G H Degen. Comparative responses of three rat strains (DA/Han, Sprague-Dawley and Wistar) to treatment with environmental estrogens.
Archives of toxicology.
2004 Apr; 78(4):183-93. doi:
10.1007/s00204-003-0535-y
. [PMID: 14689164] - Jing-fu Liu, Yu-guang Chi, Gui-bin Jiang, Chao Tai, Jin-feng Peng, Jing-Tian Hu. Ionic liquid-based liquid-phase microextraction, a new sample enrichment procedure for liquid chromatography.
Journal of chromatography. A.
2004 Feb; 1026(1-2):143-7. doi:
10.1016/j.chroma.2003.11.005
. [PMID: 14763740] - S Jobling, D Casey, T Rogers-Gray, J Oehlmann, U Schulte-Oehlmann, S Pawlowski, T Baunbeck, A P Turner, C R Tyler. Comparative responses of molluscs and fish to environmental estrogens and an estrogenic effluent.
Aquatic toxicology (Amsterdam, Netherlands).
2004 Feb; 66(2):207-22. doi:
10.1016/j.aquatox.2004.01.002
. [PMID: 15046010] - Migaku Kawaguchi, Koichi Inoue, Norihiro Sakui, Rie Ito, Shun-ichiro Izumi, Tsunehisa Makino, Noriya Okanouchi, Hiroyuki Nakazawa. Stir bar sorptive extraction and thermal desorption-gas chromatography-mass spectrometry for the measurement of 4-nonylphenol and 4-tert-octylphenol in human biological samples.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2004 Jan; 799(1):119-25. doi:
10.1016/j.jchromb.2003.10.021
. [PMID: 14659443] - Charles A Blake, Fredric R Boockfor, Joyce U Nair-Menon, Clarke F Millette, Samir S Raychoudhury, George L McCoy. Effects of 4-tert-octylphenol given in drinking water for 4 months on the male reproductive system of Fischer 344 rats.
Reproductive toxicology (Elmsford, N.Y.).
2004 Jan; 18(1):43-51. doi:
10.1016/j.reprotox.2003.09.003
. [PMID: 15013063] - 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] - S Jobling, D Casey, T Rodgers-Gray, J Oehlmann, U Schulte-Oehlmann, S Pawlowski, T Baunbeck, A P Turner, C R Tyler. Comparative responses of molluscs and fish to environmental estrogens and an estrogenic effluent.
Aquatic toxicology (Amsterdam, Netherlands).
2003 Oct; 65(2):205-20. doi:
10.1016/s0166-445x(03)00134-6
. [PMID: 12946619] - Louise L Madsen, Bodil Korsgaard, Poul Bjerregaard. Estrogenic effects in flounder Platichthys flesus orally exposed to 4-tert-octylphenol.
Aquatic toxicology (Amsterdam, Netherlands).
2003 Sep; 64(4):393-405. doi:
10.1016/s0166-445x(03)00106-1
. [PMID: 12878410] - Alireza Hossaini, Majken Dalgaard, Anne Marie Vinggaard, Pirjo Pakarinen, Jens Jørgen Larsen. Male reproductive effects of octylphenol and estradiol in Fischer and Wistar rats.
Reproductive toxicology (Elmsford, N.Y.).
2003 Sep; 17(5):607-15. doi:
10.1016/j.reprotox.2003.05.001
. [PMID: 14555199] - Tapio E Haavisto, N Annika Adamsson, Sari A Myllymäki, Jorma Toppari, Jorma Paranko. Effects of 4-tert-octylphenol, 4-tert-butylphenol, and diethylstilbestrol on prenatal testosterone surge in the rat.
Reproductive toxicology (Elmsford, N.Y.).
2003 Sep; 17(5):593-605. doi:
10.1016/s0890-6238(03)00103-5
. [PMID: 14555198] - Anthony S Pait, Judd O Nelson. Vitellogenesis in male Fundulus heteroclitus (killifish) induced by selected estrogenic compounds.
Aquatic toxicology (Amsterdam, Netherlands).
2003 Aug; 64(3):331-42. doi:
10.1016/s0166-445x(03)00060-2
. [PMID: 12842596] - H Sabik, F Gagné, C Blaise, D J Marcogliese, R Jeannot. Occurrence of alkylphenol polyethoxylates in the St. Lawrence River and their bioconcentration by mussels (Elliptio complanata).
Chemosphere.
2003 May; 51(5):349-56. doi:
10.1016/s0045-6535(02)00862-7
. [PMID: 12598000] - Arthur Alan Karels, Steve Manning, Thea Hoexum Brouwer, Marius Brouwer. Reproductive effects of estrogenic and antiestrogenic chemicals on sheepshead minnows (Cyprinodon variegatus).
Environmental toxicology and chemistry.
2003 Apr; 22(4):855-65. doi:
NULL
. [PMID: 12685722] - Kristine H Pedersen, Søren N Pedersen, Knud L Pedersen, Bodil Korsgaard, Poul Bjerregaard. Estrogenic effect of dietary 4-tert-octylphenol in rainbow trout (Oncorhynchus mykiss).
Aquatic toxicology (Amsterdam, Netherlands).
2003 Feb; 62(4):295-303. doi:
10.1016/s0166-445x(02)00107-8
. [PMID: 12595169] - Tina H Rasmussen, Thomas K Andreassen, Søren N Pedersen, Leo T M Van der Ven, Poul Bjerregaard, Bodil Korsgaard. Effects of waterborne exposure of octylphenol and oestrogen on pregnant viviparous eelpout (Zoarces viviparus) and her embryos in ovario.
The Journal of experimental biology.
2002 Dec; 205(Pt 24):3857-76. doi:
10.1242/jeb.205.24.3857
. [PMID: 12432009] - Sirinmas Katchamart, Cristobal L Miranda, Marilyn C Henderson, Clifford B Pereira, Donald R Buhler. Effect of xenoestrogen exposure on the expression of cytochrome P450 isoforms in rainbow trout liver.
Environmental toxicology and chemistry.
2002 Nov; 21(11):2445-51. doi:
10.1002/etc.5620211125
. [PMID: 12389925] - Gabriele E Ackermann, Eva Brombacher, Karl Fent. Development of a fish reporter gene system for the assessment of estrogenic compounds and sewage treatment plant effluents.
Environmental toxicology and chemistry.
2002 Sep; 21(9):1864-75. doi:
. [PMID: 12206426]
- Louise L Madsen, Bodil Korsgaard, Poul Bjerregaard. 4-tert-octylphenol and 17beta-estradiol applied by feeding to flounder Platichthys flesus: induction of vitellogenin and accumulation in tissues.
Marine environmental research.
2002 Sep; 54(3-5):729-33. doi:
10.1016/s0141-1136(02)00111-3
. [PMID: 12408644] - Ragnor T Pedersen, Elizabeth M Hill. Tissue distribution and depuration of 4-tert-octylphenol residues in the cyprinid fish, Scardinius erythrophthalmus.
Environmental science & technology.
2002 Aug; 36(15):3275-83. doi:
10.1021/es010249w
. [PMID: 12188353] - K-E Tollefsen. Interaction of estrogen mimics, singly and in combination, with plasma sex steroid-binding proteins in rainbow trout (Oncorhynchus mykiss).
Aquatic toxicology (Amsterdam, Netherlands).
2002 Feb; 56(3):215-25. doi:
10.1016/s0166-445x(01)00154-0
. [PMID: 11792437] - K Van den Belt, R Verheyen, H Witters. Reproductive effects of ethynylestradiol and 4t-octylphenol on the zebrafish (Danio rerio).
Archives of environmental contamination and toxicology.
2001 Nov; 41(4):458-67. doi:
10.1007/s002440010272
. [PMID: 11598783] - M Fuerhacker, S Scharf, W Pichler, T Ertl, R Haberl. Sources and behaviour of bismuth active substances (BiAS) in a municipal sewage treatment plant.
The Science of the total environment.
2001 Sep; 277(1-3):95-100. doi:
10.1016/s0048-9697(00)00866-4
. [PMID: 11589412] - J Matthews, T Celius, R Halgren, T Zacharewski. Differential estrogen receptor binding of estrogenic substances: a species comparison.
The Journal of steroid biochemistry and molecular biology.
2000 Nov; 74(4):223-34. doi:
10.1016/s0960-0760(00)00126-6
. [PMID: 11162928]