Octinoxate (BioDeep_00000409823)
Secondary id: BioDeep_00000017475
natural product PANOMIX_OTCML-2023 Industrial Pollutants
代谢物信息卡片
化学式: C18H26O3 (290.1882)
中文名称: 4-甲氧基肉桂酸-2-乙基己酯, 对甲氧基肉桂酸异辛酯, 甲氧基肉桂酸乙基己酯
谱图信息:
最多检出来源 Chinese Herbal Medicine(otcml) 71.05%
分子结构信息
SMILES: CCCCC(CC)COC(=O)C=CC1=CC=C(C=C1)OC
InChI: InChI=1S/C18H26O3/c1-4-6-7-15(5-2)14-21-18(19)13-10-16-8-11-17(20-3)12-9-16/h8-13,15H,4-7,14H2,1-3H3/b13-10+
描述信息
D - Dermatologicals > D02 - Emollients and protectives > D02B - Protectives against uv-radiation > D02BA - Protectives against uv-radiation for topical use
D020011 - Protective Agents > D011837 - Radiation-Protective Agents > D013473 - Sunscreening Agents
C1892 - Chemopreventive Agent > C851 - Sunscreen
D003879 - Dermatologic Agents
D003358 - Cosmetics
CONFIDENCE standard compound; INTERNAL_ID 2502
Octinoxate is an organic compound that is a component of sunscreen and lipstick. It is mainly used in cosmetics such as sunscreen to absorb UV-B rays from the sun and protect the skin from damage. It can also be used to reduce the appearance of scars.
同义名列表
数据库引用编号
17 个数据库交叉引用编号
- ChEBI: CHEBI:88667
- KEGGdrug: D95744
- KEGGdrug: D05225
- PubChem: 5355130
- Metlin: METLIN43282
- DrugBank: DB09496
- ChEMBL: CHEMBL1200608
- CAS: 83834-59-7
- CAS: 5466-77-3
- MoNA: CCMSLIB00005720266
- MoNA: AU250206
- MoNA: AU250205
- MoNA: AU250204
- MoNA: AU250203
- MoNA: AU250202
- MoNA: AU250201
- medchemexpress: HY-B1234
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 |
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文献列表
- Jiabo He, Zhi Chen, Chen Jing, Weiwei Zhang, Hangke Peng, Honglei Zhou, Fengxiao Hu. Behavioral and biochemical responses of the marine polychaete Perinereis aibuhitensis to 2-ethylhexyl-4-methoxycinnamate (EHMC) exposure.
Comparative biochemistry and physiology. Toxicology & pharmacology : CBP.
2024 May; 279(?):109868. doi:
10.1016/j.cbpc.2024.109868
. [PMID: 38423197] - Andrei Iulian Slabu, Laura Miu, Emilian Ghibu, Cristina Elena Stavarache, Raluca Stan, Florina Teodorescu. Bioconjugation of Vegetable Oils with UV Absorbers: New Approach in Skin Photoprotection.
Molecules (Basel, Switzerland).
2023 Nov; 28(22):. doi:
10.3390/molecules28227550
. [PMID: 38005272] - Emily E Burns, Kyle S Roush, Susan A Csiszar, Iain A Davies. Freshwater Environmental Risk Assessment of Down-the-Drain Octinoxate Emissions in the United States.
Environmental toxicology and chemistry.
2022 12; 41(12):3116-3124. doi:
10.1002/etc.5488
. [PMID: 36148933] - Seoyoon Chu, Ba Reum Kwon, Young-Min Lee, Kyung-Duk Zoh, Kyungho Choi. Effects of 2-ethylhexyl-4-methoxycinnamate (EHMC) on thyroid hormones and genes associated with thyroid, neurotoxic, and nephrotoxic responses in adult and larval zebrafish (Danio rerio).
Chemosphere.
2021 Jan; 263(?):128176. doi:
10.1016/j.chemosphere.2020.128176
. [PMID: 33297144] - Alice Haddad do Prado, Victor Hugo Sousa Araújo, Josimar O Eloy, Bruno Fonseca-Santos, Marcelo A Pereira-da-Silva, Rosângela Gonçalves Peccinini, Marlus Chorilli. Synthesis and Characterization of Nanostructured Lipid Nanocarriers for Enhanced Sun Protection Factor of Octyl p-methoxycinnamate.
AAPS PharmSciTech.
2020 Apr; 21(4):125. doi:
10.1208/s12249-019-1547-0
. [PMID: 32350635] - 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] - Leslie J Saunders, Alex D Hoffman, John W Nichols, Frank A P C Gobas. Dietary Bioaccumulation and Biotransformation of Hydrophobic Organic Sunscreen Agents in Rainbow Trout.
Environmental toxicology and chemistry.
2020 03; 39(3):574-586. doi:
10.1002/etc.4638
. [PMID: 31749247] - 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] - Veerawat Teeranachaideekul, Boontida Morakul, Prapaporn Boonme, Warangkana Pornputtapitak, Varaporn Junyaprasert. Effect of Lipid and Oil Compositions on Physicochemical Properties and Photoprotection of Octyl Methoxycinnamate-loaded Nanostructured Lipid Carriers (NLC).
Journal of oleo science.
2020; 69(12):1627-1639. doi:
10.5650/jos.ess20093
. [PMID: 33268665] - Cristal Cerqueira, Fiammetta Nigro, Vânia E B Campos, André Rossi, Ralph Santos-Oliveira, Verônica Cardoso, Alane Beatriz Vermelho, Elisabete P Dos Santos, Claudia Regina E Mansur. Nanovesicle-based formulations for photoprotection: a safety and efficacy approach.
Nanotechnology.
2019 Aug; 30(34):345102. doi:
10.1088/1361-6528/ab177c
. [PMID: 30965299] - Timothy R Fennell, James M Mathews, Rodney W Snyder, Yan Hong, Scott L Watson, Sherry R Black, Barry S McIntyre, Suramya Waidyanatha. Metabolism and disposition of 2-ethylhexyl-p-methoxycinnamate following oral gavage and dermal exposure in Harlan Sprague Dawley rats and B6C3F1/N mice and in hepatocytes in vitro.
Xenobiotica; the fate of foreign compounds in biological systems.
2018 Nov; 48(11):1142-1156. doi:
10.1080/00498254.2017.1400129
. [PMID: 29111853] - Soo In Yang, Shuanghui Liu, Geoffrey J Brooks, Yves Lanctot, James V Gruber. Reliable and simple spectrophotometric determination of sun protection factor: A case study using organic UV filter-based sunscreen products.
Journal of cosmetic dermatology.
2018 Jun; 17(3):518-522. doi:
10.1111/jocd.12390
. [PMID: 28834040] - Newton Andréo-Filho, Antonio Vinicius Kosiski Bim, Telma Mary Kaneko, Nidia Ayumi Kitice, Isha N Haridass, Eman Abd, Patricia Santos Lopes, Sachin S Thakur, Harendra S Parekh, Michael S Roberts, Jeffrey E Grice, Heather A E Benson, Vânia Rodrigues Leite-Silva. Development and Evaluation of Lipid Nanoparticles Containing Natural Botanical Oil for Sun Protection: Characterization and in vitro and in vivo Human Skin Permeation and Toxicity.
Skin pharmacology and physiology.
2018; 31(1):1-9. doi:
10.1159/000481691
. [PMID: 29131088] - Petra Strajhar, David Tonoli, Fabienne Jeanneret, Raphaella M Imhof, Vanessa Malagnino, Melanie Patt, Denise V Kratschmar, Julien Boccard, Serge Rudaz, Alex Odermatt. Steroid profiling in H295R cells to identify chemicals potentially disrupting the production of adrenal steroids.
Toxicology.
2017 04; 381(?):51-63. doi:
10.1016/j.tox.2017.02.010
. [PMID: 28235592] - Yongtai Zhang, Lina Shen, Kai Zhang, Teng Guo, Jihui Zhao, Nana Li, Nianping Feng. Enhanced antioxidation via encapsulation of isooctyl p-methoxycinnamate with sodium deoxycholate-mediated liposome endocytosis.
International journal of pharmaceutics.
2015 Dec; 496(2):392-400. doi:
10.1016/j.ijpharm.2015.10.010
. [PMID: 26453790] - X-h Liu, X-z Liang, X Fang, W-P Zhang. Preparation and evaluation of novel octylmethoxycinnamate-loaded solid lipid nanoparticles.
International journal of cosmetic science.
2015 Aug; 37(4):446-53. doi:
10.1111/ics.12216
. [PMID: 25720757] - Franziska D Fleischli, Fabienne Morf, Christian Adlhart. Skin Concentrations of Topically Applied Substances in Reconstructed Human Epidermis (RHE) Compared with Human Skin Using in vivo Confocal Raman Microscopy.
Chimia.
2015; 69(3):147-51. doi:
10.2533/chimia.2015.147
. [PMID: 26507219] - Valentina Trotta, Filipa Goios, Helena Monteiro, Isabel F Almeida, Santo Scalia. Influence of lipid microparticle encapsulation on in vitro efficacy, photostability and water resistance of the sunscreen agents, octyl methoxycinnamate and butyl methoxydibenzoylmethane.
Drug development and industrial pharmacy.
2014 Sep; 40(9):1233-9. doi:
10.3109/03639045.2013.814062
. [PMID: 23837520] - Flavia F F Silva, Eduardo Ricci-Júnior, Claudia R E Mansur. Nanoemulsions containing octyl methoxycinnamate and solid particles of TiO₂: preparation, characterization and in vitro evaluation of the solar protection factor.
Drug development and industrial pharmacy.
2013 Sep; 39(9):1378-88. doi:
10.3109/03639045.2012.718787
. [PMID: 22998354] - Valeria Ambrogi, Loredana Latterini, Fabio Marmottini, Cinzia Pagano, Maurizio Ricci. Mesoporous silicate MCM-41 as a particulate carrier for octyl methoxycinnamate: Sunscreen release and photostability.
Journal of pharmaceutical sciences.
2013 May; 102(5):1468-75. doi:
10.1002/jps.23478
. [PMID: 23459857] - Muhammad Ihtisham Umar, Mohd Zaini Asmawi, Amirin Sadikun, Item J Atangwho, Mun Fei Yam, Rabia Altaf, Ashfaq Ahmed. Bioactivity-guided isolation of ethyl-p-methoxycinnamate, an anti-inflammatory constituent, from Kaempferia galanga L. extracts.
Molecules (Basel, Switzerland).
2012 Jul; 17(7):8720-34. doi:
10.3390/molecules17078720
. [PMID: 22825623] - M Krause, A Klit, M Blomberg Jensen, T Søeborg, H Frederiksen, M Schlumpf, W Lichtensteiger, N E Skakkebaek, K T Drzewiecki. Sunscreens: are they beneficial for health? An overview of endocrine disrupting properties of UV-filters.
International journal of andrology.
2012 Jun; 35(3):424-36. doi:
10.1111/j.1365-2605.2012.01280.x
. [PMID: 22612478] - Rachel Haywood, Arsen Volkov, Carima Andrady, Robert Sayer. Measuring sunscreen protection against solar-simulated radiation-induced structural radical damage to skin using ESR/spin trapping: development of an ex vivo test method.
Free radical research.
2012 Mar; 46(3):265-75. doi:
10.3109/10715762.2011.651719
. [PMID: 22236285] - Carmelo Puglia, Francesco Bonina, Luisa Rizza, Paolo Blasi, Aurelie Schoubben, Rosario Perrotta, Maria Stella Tarico, Elisabetta Damiani. Lipid nanoparticles as carrier for octyl-methoxycinnamate: in vitro percutaneous absorption and photostability studies.
Journal of pharmaceutical sciences.
2012 Jan; 101(1):301-11. doi:
10.1002/jps.22741
. [PMID: 21905033] - L Montenegro, M G Sarpietro, S Ottimo, G Puglisi, F Castelli. Differential scanning calorimetry studies on sunscreen loaded solid lipid nanoparticles prepared by the phase inversion temperature method.
International journal of pharmaceutics.
2011 Aug; 415(1-2):301-6. doi:
10.1016/j.ijpharm.2011.05.076
. [PMID: 21679757] - L Montenegro, C Carbone, G Puglisi. Vehicle effects on in vitro release and skin permeation of octylmethoxycinnamate from microemulsions.
International journal of pharmaceutics.
2011 Feb; 405(1-2):162-8. doi:
10.1016/j.ijpharm.2010.11.036
. [PMID: 21129459] - J Lademann, A Patzelt, S Schanzer, H Richter, I Gross, K H Menting, L Frazier, W Sterry, C Antoniou. Decontamination of the skin with absorbing materials.
Skin pharmacology and physiology.
2011; 24(2):87-92. doi:
10.1159/000322305
. [PMID: 21116121] - Carmelo Puglia, Francesco Bonina, Francesco Castelli, Dorotea Micieli, Maria Grazia Sarpietro. Evaluation of percutaneous absorption of the repellent diethyltoluamide and the sunscreen ethylhexyl p-methoxycinnamate-loaded solid lipid nanoparticles: an in-vitro study.
The Journal of pharmacy and pharmacology.
2009 Aug; 61(8):1013-9. doi:
10.1211/jpp/61.08.0004
. [PMID: 19703344] - N R Janjua, B Kongshoj, A-M Andersson, H C Wulf. Sunscreens in human plasma and urine after repeated whole-body topical application.
Journal of the European Academy of Dermatology and Venereology : JEADV.
2008 Apr; 22(4):456-61. doi:
10.1111/j.1468-3083.2007.02492.x
. [PMID: 18221342] - Holger Klammer, Christiane Schlecht, Wolfgang Wuttke, Cornelia Schmutzler, Inka Gotthardt, Josef Köhrle, Hubertus Jarry. Effects of a 5-day treatment with the UV-filter octyl-methoxycinnamate (OMC) on the function of the hypothalamo-pituitary-thyroid function in rats.
Toxicology.
2007 Sep; 238(2-3):192-9. doi:
10.1016/j.tox.2007.06.088
. [PMID: 17651886] - Dana Seidlová-Wuttke, Julie Christoffel, Guillermo Rimoldi, Hubertus Jarry, Wolfgang Wuttke. Comparison of effects of estradiol with those of octylmethoxycinnamate and 4-methylbenzylidene camphor on fat tissue, lipids and pituitary hormones.
Toxicology and applied pharmacology.
2006 Jul; 214(1):1-7. doi:
10.1016/j.taap.2005.11.002
. [PMID: 16368123] - Elisabetta Damiani, Paola Astolfi, Laura Cionna, Francesca Ippoliti, Lucedio Greci. Synthesis and application of a novel sunscreen-antioxidant.
Free radical research.
2006 May; 40(5):485-94. doi:
10.1080/10715760600590065
. [PMID: 16551575] - D Seidlová-Wuttke, H Jarry, J Christoffel, G Rimoldi, W Wuttke. Comparison of effects of estradiol (E2) with those of octylmethoxycinnamate (OMC) and 4-methylbenzylidene camphor (4MBC)--2 filters of UV light - on several uterine, vaginal and bone parameters.
Toxicology and applied pharmacology.
2006 Feb; 210(3):246-54. doi:
10.1016/j.taap.2005.05.006
. [PMID: 15979666] - Holger Klammer, Christiane Schlecht, Wolfgang Wuttke, Hubertus Jarry. Multi-organic risk assessment of estrogenic properties of octyl-methoxycinnamate in vivo A 5-day sub-acute pharmacodynamic study with ovariectomized rats.
Toxicology.
2005 Nov; 215(1-2):90-6. doi:
10.1016/j.tox.2005.06.026
. [PMID: 16112788] - Marjoke Heneweer, Martine Muusse, Martin van den Berg, J Thomas Sanderson. Additive estrogenic effects of mixtures of frequently used UV filters on pS2-gene transcription in MCF-7 cells.
Toxicology and applied pharmacology.
2005 Oct; 208(2):170-7. doi:
10.1016/j.taap.2005.02.006
. [PMID: 16183391] - Nadeem Rezaq Janjua, Brian Mogensen, Anna-Maria Andersson, Jørgen Holm Petersen, Mette Henriksen, Niels E Skakkebaek, Hans Christian Wulf. Systemic absorption of the sunscreens benzophenone-3, octyl-methoxycinnamate, and 3-(4-methyl-benzylidene) camphor after whole-body topical application and reproductive hormone levels in humans.
The Journal of investigative dermatology.
2004 Jul; 123(1):57-61. doi:
10.1111/j.0022-202x.2004.22725.x
. [PMID: 15191542] - Madoka Inui, Tetsuya Adachi, Shigeo Takenaka, Hiroshi Inui, Masami Nakazawa, Mitsuhiro Ueda, Hajime Watanabe, Chisato Mori, Taisen Iguchi, Kazutaka Miyatake. Effect of UV screens and preservatives on vitellogenin and choriogenin production in male medaka (Oryzias latipes).
Toxicology.
2003 Dec; 194(1-2):43-50. doi:
10.1016/s0300-483x(03)00340-8
. [PMID: 14636695] - Gülgün Yener, Tuba Incegül, Namýk Yener. Importance of using solid lipid microspheres as carriers for UV filters on the example octyl methoxy cinnamate.
International journal of pharmaceutics.
2003 Jun; 258(1-2):203-7. doi:
10.1016/s0378-5173(03)00203-5
. [PMID: 12753766] - Gülgün Yener, Tuba Incegül. Importance of protection from harmful effects of solar radiation by using solid lipid microspheres of UV filters.
Journal of cosmetic science.
2002 Sep; 53(5):317-19. doi:
"
. [PMID: 12392011] - Gerald J Smith, Ian J Miller, John F Clare, Brian L Diffey. The effect of UV absorbing sunscreens on the reflectance and the consequent protection of skin.
Photochemistry and photobiology.
2002 Feb; 75(2):122-5. doi:
10.1562/0031-8655(2002)075<0122:teouas>2.0.co;2
. [PMID: 11883599] - R Jiang, C G Hayden, R J Prankerd, M S Roberts, H A Benson. High-performance liquid chromatographic assay for common sunscreening agents in cosmetic products, bovine serum albumin solution and human plasma.
Journal of chromatography. B, Biomedical applications.
1996 Jun; 682(1):137-45. doi:
10.1016/0378-4347(96)00063-1
. [PMID: 8832434]