Oxybenzone (BioDeep_00000018188)

 

Secondary id: BioDeep_00000002574

human metabolite blood metabolite natural product Volatile Flavor Compounds


代谢物信息卡片


4-Methoxy-2-hydroxybenzophenone butyric acid

化学式: C14H12O3 (228.0786402)
中文名称: 2-羟基-4-甲氧基二苯甲酮
谱图信息: 最多检出来源 Homo sapiens(blood) 4.11%

分子结构信息

SMILES: COC1=CC(=C(C=C1)C(=O)C2=CC=CC=C2)O
InChI: InChI=1S/C14H12O3/c1-17-11-7-8-12(13(15)9-11)14(16)10-5-3-2-4-6-10/h2-9,15H,1H3

描述信息

Oxybenzone is an organic compound used in sunscreens. It is a derivative of benzophenone. It forms colorless crystals that are readily soluble in most organic solvents. It is used as an ingredient in sunscreen and other cosmetics because it absorbs UV-A ultraviolet rays.
D020011 - Protective Agents > D011837 - Radiation-Protective Agents > D013473 - Sunscreening Agents
C1892 - Chemopreventive Agent > C851 - Sunscreen
D003879 - Dermatologic Agents
D003358 - Cosmetics
Same as: D05309

同义名列表

16 个代谢物同义名

4-Methoxy-2-hydroxybenzophenone butyric acid; (2-Hydroxy-4-methoxyphenyl)phenylmethanone; 4-Methoxy-2-hydroxybenzophenone; 2-Hydroxy-4-methoxybenzophenone; 2-Hydroxy-4-methoxybenzone; 2-Benzoyl-5-methoxyphenol; Benzophenone-3; Eusolex 4360; Eusolex-4360; Oxybenzonum; Oxibenzona; oxybenzone; Uvinul 40; HMBP CPD; Solbar; 2-Hydroxy-4-methoxybenzophenone



数据库引用编号

15 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)

6 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

  • Junnan Li, Luhua You, Zichen Xu, Karina Yew-Hoong Gin, Yiliang He. Nano-scale and micron-scale plastics amplify the bioaccumulation of benzophenone-3 and ciprofloxacin, as well as their co-exposure effect on disturbing the antioxidant defense system in mussels, Perna viridis. Environmental pollution (Barking, Essex : 1987). 2024 Apr; 346(?):123547. doi: 10.1016/j.envpol.2024.123547. [PMID: 38387549]
  • Yaoyao Nie, Houpu Liu, Runtao Wu, Jiayao Fan, Ye Yang, Wenxia Zhao, Jiapeng Bao, Zhenqiang You, Fan He, Yingjun Li. Interference with SPARC inhibits Benzophenone-3 induced ferroptosis in osteoarthritis: Evidence from bioinformatics analyses and biological experimentation. Ecotoxicology and environmental safety. 2024 Apr; 274(?):116217. doi: 10.1016/j.ecoenv.2024.116217. [PMID: 38489904]
  • Daniela Giovana da Cunha Barros, Gabrielle Cristina Dos Santos Gonçalves do Nascimento, Caio Okon, Mylena Bathke Rocha, Diego Espirito Santo, Lidiane de Lima Feitoza, Osvaldo Valarini Junior, Regiane da Silva Gonzalez, Débora Cristina de Souza, Ana Paula Peron. Benzophenone-3 sunscreen causes phytotoxicity and cytogenotoxicity in higher plants. Environmental science and pollution research international. 2023 Nov; 30(52):112788-112798. doi: 10.1007/s11356-023-30365-3. [PMID: 37840079]
  • Alicja Maciejska, Bartosz Pomierny, Weronika Krzyżanowska, Beata Starek-Świechowicz, Alicja Skórkowska, Bogusława Budziszewska. Mechanism of microglial cell activation in the benzophenone-3 exposure model. Neuroscience. 2023 Oct; ?(?):. doi: 10.1016/j.neuroscience.2023.10.002. [PMID: 37827357]
  • Shuhao Li, Shengxiang Ran, Craig A Downs, Ru Xu, Qingming Li, Xin Zhong, Fenglin Zhong. A combined proteomics and metabolomics analysis reveals the invisible regulation of plant root responses to oxybenzone (benzophenone-3) stress. The Science of the total environment. 2023 Jun; ?(?):164951. doi: 10.1016/j.scitotenv.2023.164951. [PMID: 37331386]
  • Shuhao Li, Yuqi Zhou, Craig A Downs, Song Yuan, Maomao Hou, Qingming Li, Xin Zhong, Fenglin Zhong. Proteomics and Lysine Acetylation Modification Reveal the Responses of Pakchoi (Brassica rapa L. ssp. chinensis) to Oxybenzone Stress. Journal of agricultural and food chemistry. 2023 May; ?(?):. doi: 10.1021/acs.jafc.2c07852. [PMID: 37216206]
  • Alexis Scheele, Kimberly Sutter, Osman Karatum, Ashley A Danley-Thomson, Lauren K Redfern. Environmental impacts of the ultraviolet filter oxybenzone. The Science of the total environment. 2023 Mar; 863(?):160966. doi: 10.1016/j.scitotenv.2022.160966. [PMID: 36535482]
  • Yan-Kun Zhang, Huai-Yang Ke, Yong-Qiang Qin, Han-Ye Ju, Yu-Mei Chen, Fang Lin, Ji-Liang Zhang, Xiao-Ping Diao. Environmental concentrations of benzophenone-3 disturbed lipid metabolism in the liver of clown anemonefish (Amphiprion ocellaris). Environmental pollution (Barking, Essex : 1987). 2023 Jan; 317(?):120792. doi: 10.1016/j.envpol.2022.120792. [PMID: 36473638]
  • Wenjing Wang, Anran Liu, Xiancao Chen, Xiaoyan Zheng, Wenting Fu, Gang Wang, Jing Ji, Chao Jin, Chunfeng Guan. The potential role of betaine in enhancement of microbial-assisted phytoremediation of benzophenone-3 contaminated soil. Chemosphere. 2022 Nov; 307(Pt 1):135783. doi: 10.1016/j.chemosphere.2022.135783. [PMID: 35868529]
  • Laura Anido-Varela, Marta Seoane, Marta Esperanza, Ángeles Cid, Carmen Rioboo. Cytotoxicity of BP-3 and BP-4: Blockage of extrusion pumps, oxidative damage and programmed cell death on Chlamydomonas reinhardtii. Aquatic toxicology (Amsterdam, Netherlands). 2022 Oct; 251(?):106285. doi: 10.1016/j.aquatox.2022.106285. [PMID: 36087491]
  • Wenjing Wang, Anran Liu, Wenting Fu, Danliu Peng, Gang Wang, Jing Ji, Chao Jin, Chunfeng Guan. Tobacco-associated with Methylophilus sp. FP-6 enhances phytoremediation of benzophenone-3 through regulating soil microbial community, increasing photosynthetic capacity and maintaining redox homeostasis of plant. Journal of hazardous materials. 2022 06; 431(?):128588. doi: 10.1016/j.jhazmat.2022.128588. [PMID: 35248957]
  • Hyejin Ko, Seungchan An, Sungjin Ahn, In Guk Park, Junpyo Gong, Seok Young Hwang, Soyeon Oh, Min Won Ki, Sun Hee Jin, Won Jun Choi, Minsoo Noh. Sunscreen filter octocrylene is a potential obesogen by acting as a PPARγ partial agonist. Toxicology letters. 2022 Feb; 355(?):141-149. doi: 10.1016/j.toxlet.2021.12.001. [PMID: 34864131]
  • Luiza Abrahão Frank, Rafaela Pletsch Gazzi, Adriana Raffin Pohlmann, Silvia Stanisçuaski Guterres, Renata Vidor Contri. Evaluation of an Efficient and Skin-Adherent Semisolid Sunscreen Nanoformulation. Skin pharmacology and physiology. 2022; 35(5):291-298. doi: 10.1159/000525176. [PMID: 35705070]
  • Jinyoung Song, Joorim Na, Dahee An, Jinho Jung. Role of benzophenone-3 additive in chronic toxicity of polyethylene microplastic fragments to Daphnia magna. The Science of the total environment. 2021 Dec; 800(?):149638. doi: 10.1016/j.scitotenv.2021.149638. [PMID: 34426313]
  • Paulina Jedynak, Jörg Tost, Antonia M Calafat, Ekaterina Bourova-Flin, Florence Busato, Anne Forhan, Barbara Heude, Milan Jakobi, Sophie Rousseaux, Joel Schwartz, Rémy Slama, Daniel Vaiman, Claire Philippat, Johanna Lepeule. Pregnancy exposure to synthetic phenols and placental DNA methylation - An epigenome-wide association study in male infants from the EDEN cohort. Environmental pollution (Barking, Essex : 1987). 2021 Dec; 290(?):118024. doi: 10.1016/j.envpol.2021.118024. [PMID: 34523531]
  • Juan José Sandoval-Gío, Elsa Noreña-Barroso, Karla Escalante-Herrera, Gabriela Rodríguez-Fuentes. Effect of Benzophenone-3 to Acetylcholinesterase and Antioxidant System in Zebrafish (Danio rerio) Embryos. Bulletin of environmental contamination and toxicology. 2021 Nov; 107(5):814-819. doi: 10.1007/s00128-021-03277-6. [PMID: 34129062]
  • Emily E Burns, Susan A Csiszar, Kyle S Roush, Iain A Davies. National scale down-the-drain environmental risk assessment of oxybenzone in the United States. Integrated environmental assessment and management. 2021 Sep; 17(5):951-960. doi: 10.1002/ieam.4430. [PMID: 33913597]
  • Yueyang Zhang, Prachi Shah, Fan Wu, Peipei Liu, Jing You, Greg Goss. Potentiation of lethal and sub-lethal effects of benzophenone and oxybenzone by UV light in zebrafish embryos. Aquatic toxicology (Amsterdam, Netherlands). 2021 Jun; 235(?):105835. doi: 10.1016/j.aquatox.2021.105835. [PMID: 33887502]
  • 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]
  • Nageswara R Pilli, Suresh Narayanasamy, Jeffry Florian, Robbert Zusterzeel, Vikram Patel, David G Strauss, Murali K Matta. Novel simultaneous method for the determination of avobenzone and oxybenzone in human plasma by UHPLC-MS/MS with phospholipid removal pretreatment: An application to a sunscreen clinical trial. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2021 Apr; 1169(?):122615. doi: 10.1016/j.jchromb.2021.122615. [PMID: 33706185]
  • Ana Carvalhais, Bárbara Pereira, Mariangela Sabato, Rafaela Seixas, Marina Dolbeth, Ana Marques, Sofia Guilherme, Patrícia Pereira, Mário Pacheco, Cláudia Mieiro. Mild Effects of Sunscreen Agents on a Marine Flatfish: Oxidative Stress, Energetic Profiles, Neurotoxicity and Behaviour in Response to Titanium Dioxide Nanoparticles and Oxybenzone. International journal of molecular sciences. 2021 Feb; 22(4):. doi: 10.3390/ijms22041567. [PMID: 33557180]
  • Azin Eftekhari, Jonathan T Hill, Glenn C Morrison. Transdermal uptake of benzophenone-3 from clothing: comparison of human participant results to model predictions. Journal of exposure science & environmental epidemiology. 2021 02; 31(1):149-157. doi: 10.1038/s41370-020-00280-7. [PMID: 33303958]
  • Joorim Na, Jinyoung Song, Jerry Collince Achar, Jinho Jung. Synergistic effect of microplastic fragments and benzophenone-3 additives on lethal and sublethal Daphnia magna toxicity. Journal of hazardous materials. 2021 01; 402(?):123845. doi: 10.1016/j.jhazmat.2020.123845. [PMID: 33254817]
  • Emelie Rietz Liljedahl, Gunnar Johanson, Helena Korres de Paula, Moosa Faniband, Eva Assarsson, Margareta Littorin, Malin Engfeldt, Carola Lidén, Anneli Julander, Karin Wahlberg, Christian Lindh, Karin Broberg. Filaggrin Polymorphisms and the Uptake of Chemicals through the Skin-A Human Experimental Study. Environmental health perspectives. 2021 01; 129(1):17002. doi: 10.1289/ehp7310. [PMID: 33439052]
  • Long Jin, Hai-Ying Zhu, Xiang-Jin Kang, Li-Ping Lin, Pu-Yao Zhang, Tao Tan, Yang Yu, Yong Fan. Melatonin protects against oxybenzone-induced deterioration of mouse oocytes during maturation. Aging. 2020 12; 13(2):2727-2749. doi: 10.18632/aging.202323. [PMID: 33373318]
  • Sushila Arya, Alok Kumar Dwivedi, Luis Alvarado, Sanja Kupesic-Plavsic. Exposure of U.S. population to endocrine disruptive chemicals (Parabens, Benzophenone-3, Bisphenol-A and Triclosan) and their associations with female infertility. Environmental pollution (Barking, Essex : 1987). 2020 Oct; 265(Pt A):114763. doi: 10.1016/j.envpol.2020.114763. [PMID: 32806428]
  • Sarit O'Donovan, Nélia C Mestre, Serena Abel, Tainá G Fonseca, Camilla C Carteny, Tim Willems, Els Prinsen, Bettie Cormier, Steffen S Keiter, Maria João Bebianno. Effects of the UV filter, oxybenzone, adsorbed to microplastics in the clam Scrobicularia plana. The Science of the total environment. 2020 Sep; 733(?):139102. doi: 10.1016/j.scitotenv.2020.139102. [PMID: 32446057]
  • Jeayoung C Shin, Eunyoung Lee, Seungchan An, Sun Hee Jin, Jaehyoun Ha, Won Jun Choi, Minsoo Noh. Benzophenone-3 and benzophenone-8 exhibit obesogenic activity via peroxisome proliferator-activated receptor γ pathway. Toxicology in vitro : an international journal published in association with BIBRA. 2020 Sep; 67(?):104886. doi: 10.1016/j.tiv.2020.104886. [PMID: 32407875]
  • Fernanda Chaves Lopes, Micheli Rosa de Castro, Sergiane Caldas Barbosa, Ednei Gilberto Primel, Camila de Martinez Gaspar Martins. Effect of the UV filter, Benzophenone-3, on biomarkers of the yellow clam (Amarilladesma mactroides) under different pH conditions. Marine pollution bulletin. 2020 Sep; 158(?):111401. doi: 10.1016/j.marpolbul.2020.111401. [PMID: 32753186]
  • Robin E Dodson, Katherine E Boronow, Herbert Susmann, Julia O Udesky, Kathryn M Rodgers, David Weller, Million Woudneh, Julia Green Brody, Ruthann A Rudel. Consumer behavior and exposure to parabens, bisphenols, triclosan, dichlorophenols, and benzophenone-3: Results from a crowdsourced biomonitoring study. International journal of hygiene and environmental health. 2020 09; 230(?):113624. doi: 10.1016/j.ijheh.2020.113624. [PMID: 33011057]
  • Clarisa Guillermina Santamaria, Nicole Meyer, Anne Schumacher, María Laura Zenclussen, Carla Mariela Teglia, María Julia Culzoni, Ana Claudia Zenclussen, Horacio Adolfo Rodriguez. Dermal exposure to the UV filter benzophenone-3 during early pregnancy affects fetal growth and sex ratio of the progeny in mice. Archives of toxicology. 2020 08; 94(8):2847-2859. doi: 10.1007/s00204-020-02776-5. [PMID: 32430675]
  • Esra Mutlu, C Edwin Garner, Christopher J Wegerski, Jacob D McDonald, Barry S McIntyre, Melanie Doyle-Eisele, Suramya Waidyanatha. Metabolism and disposition of 2-hydroxy-4-methoxybenzophenone, a sunscreen ingredient, in Harlan Sprague Dawley rats and B6C3F1/N mice; a species and route comparison. Xenobiotica; the fate of foreign compounds in biological systems. 2020 Jun; 50(6):689-704. doi: 10.1080/00498254.2019.1680906. [PMID: 31613170]
  • Zifan Wang, Lidia Mínguez-Alarcón, Paige L Williams, Andrea Bellavia, Jennifer B Ford, Myra Keller, John C Petrozza, Antonia M Calafat, Russ Hauser, Tamarra James-Todd. Perinatal urinary benzophenone-3 concentrations and glucose levels among women from a fertility clinic. Environmental health : a global access science source. 2020 04; 19(1):45. doi: 10.1186/s12940-020-00598-7. [PMID: 32345324]
  • Xin Zhong, Craig A Downs, Yuting Li, Zishan Zhang, Yiman Li, Binbin Liu, Huiyuan Gao, Qingming Li. Comparison of toxicological effects of oxybenzone, avobenzone, octocrylene, and octinoxate sunscreen ingredients on cucumber plants (Cucumis sativus L.). The Science of the total environment. 2020 Apr; 714(?):136879. doi: 10.1016/j.scitotenv.2020.136879. [PMID: 32018996]
  • Yingjun Li, Jiahao Zhu, Jiayao Fan, Shaofang Cai, Chunhong Fan, Yaohong Zhong, Lingling Sun. Associations of urinary levels of phenols and parabens with osteoarthritis among US adults in NHANES 2005-2014. Ecotoxicology and environmental safety. 2020 Apr; 192(?):110293. doi: 10.1016/j.ecoenv.2020.110293. [PMID: 32045785]
  • Alicja Skórkowska, Alicja Maciejska, Bartosz Pomierny, Weronika Krzyżanowska, Beata Starek-Świechowicz, Beata Bystrowska, Żaneta Broniowska, Grzegorz Kazek, Bogusława Budziszewska. Effect of Combined Prenatal and Adult Benzophenone-3 Dermal Exposure on Factors Regulating Neurodegenerative Processes, Blood Hormone Levels, and Hematological Parameters in Female Rats. Neurotoxicity research. 2020 Mar; 37(3):683-701. doi: 10.1007/s12640-020-00163-7. [PMID: 31970650]
  • Murali K Matta, Jeffry Florian, Robbert Zusterzeel, Nageswara R Pilli, Vikram Patel, Donna A Volpe, Yang Yang, Luke Oh, Edward Bashaw, Issam Zineh, Carlos Sanabria, Sarah Kemp, Anthony Godfrey, Steven Adah, Sergio Coelho, Jian Wang, Lesley-Anne Furlong, Charles Ganley, Theresa Michele, David G Strauss. Effect of Sunscreen Application on Plasma Concentration of Sunscreen Active Ingredients: A Randomized Clinical Trial. JAMA. 2020 01; 323(3):256-267. doi: 10.1001/jama.2019.20747. [PMID: 31961417]
  • Prabin Dhangada Majhi, Aman Sharma, Amy L Roberts, Elizabeth Daniele, Aliza R Majewski, Lynn M Chuong, Amye L Black, Laura N Vandenberg, Sallie S Schneider, Karen A Dunphy, D Joseph Jerry. Effects of Benzophenone-3 and Propylparaben on Estrogen Receptor-Dependent R-Loops and DNA Damage in Breast Epithelial Cells and Mice. Environmental health perspectives. 2020 01; 128(1):17002. doi: 10.1289/ehp5221. [PMID: 31939680]
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  • Joseph C DiNardo, Craig A Downs. Can oxybenzone cause Hirschsprung's disease?. Reproductive toxicology (Elmsford, N.Y.). 2019 06; 86(?):98-100. doi: 10.1016/j.reprotox.2019.02.014. [PMID: 30831214]
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  • Haizea Ziarrusta, Leire Mijangos, Rosa Montes, Rosario Rodil, Eneritz Anakabe, Urtzi Izagirre, Ailette Prieto, Nestor Etxebarria, Maitane Olivares, Olatz Zuloaga. Study of bioconcentration of oxybenzone in gilt-head bream and characterization of its by-products. Chemosphere. 2018 Oct; 208(?):399-407. doi: 10.1016/j.chemosphere.2018.05.154. [PMID: 29885506]
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