Determine the necessary mass, volume, or concentration for preparing a solution.
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Moligand™, ≥98%(GC) Moligand™ for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
Room temperature Ships Normal Check lot-specific COA for exact specifications.
SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
Cited in 21 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
Apocynin is a methoxy-substituted catechol that is commonly used as an inhibitor of Mox and Nox (NADPH oxidase) (IC50=10 μM). Because of Abocynin's inhibition of NADPH oxidase, ROS production is also inhibited. Studies show the compound's ability to decrease superoxide generation in bovine pulmonary arteries as well as neutrophils and macrophages (10 mM). In experimental rats, apocynin has displayed anti-inflammatory activity and can improve endothelial function by reducing oxidative stress and improved NO bioavailability. Reportedly prevents phagocytosis of MBP (myelin) by macrophages. Also has proven to be a useful product for studying NO-regulated processes in plants.
A methoxy-substituted catechol commonly used as an inhibitor of NADPH oxidase.
| Pubchem Sid | 488179678 |
|---|---|
| Pubchem Sid Url | https://pubchem.ncbi.nlm.nih.gov/substance/488179678 |
| Sonrisas canónicas | CC(=O)C1=CC(=C(C=C1)O)OC |
| IUPAC Name | 1-(4-hydroxy-3-methoxyphenyl)ethanone |
| InChIKey | DFYRUELUNQRZTB-UHFFFAOYSA-N |
| INCHI | 1S/C9H10O3/c1-6(10)7-3-4-8(11)9(5-7)12-2/h3-5,11H,1-2H3 |
| Isómeros SMILES | CC(=O)C1=CC(=C(C=C1)O)OC |
| WGK Alemania | 2 |
| RTECS | AM8800000 |
| Peso molecular | 166.18 |
| Beilstein | 637373 |
| Reaxy-Rn | 637373 |
| Reaxys-RN_link_address | https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=637373&ln= |
Comprehensive hazard, handling, storage, and regulatory compliance document.
Download SDS →Lot-specific quality data. Enter your lot number to retrieve the exact COA.
Look up COA →Full quality attributes and acceptance criteria for this grade.
View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organic oxygen compounds |
| Clase | Organooxygen compounds |
| Subclass | Carbonyl compounds |
| Intermediate Tree Nodes | Ketones - Aryl ketones - Phenylketones |
| Direct Parent | Alkyl-phenylketones |
| Alternative Parents | Methoxyphenols Acetophenones Phenoxy compounds Methoxybenzenes Benzoyl derivatives Aryl alkyl ketones Anisoles Alkyl aryl ethers 1-hydroxy-2-unsubstituted benzenoids Organic oxides Hydrocarbon derivatives |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Alkyl-phenylketone - Methoxyphenol - Acetophenone - Phenoxy compound - Methoxybenzene - Aryl alkyl ketone - Anisole - Phenol ether - Benzoyl - 1-hydroxy-2-unsubstituted benzenoid - Alkyl aryl ether - Phenol - Benzenoid - Monocyclic benzene moiety - Ether - Organic oxide - Hydrocarbon derivative - Aromatic homomonocyclic compound |
| Descripción | This compound belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. |
| External Descriptors | Flavans, Flavanols and Leucoanthocyanidins |
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Find and download the COA for your product by matching the lot number on the packaging.
| Lot Number | Certificate Type | Fecha | Articulo |
|---|---|---|---|
| Certificate of Analysis | Oct 29, 2025 | H156885 | |
| Certificate of Analysis | Oct 29, 2025 | H156885 | |
| Certificate of Analysis | Oct 29, 2025 | H156885 | |
| Certificate of Analysis | Oct 29, 2025 | H156885 | |
| Certificate of Analysis | Aug 30, 2025 | H156885 | |
| Certificate of Analysis | Aug 30, 2025 | H156885 | |
| Certificate of Analysis | Aug 30, 2025 | H156885 | |
| Certificate of Analysis | Aug 30, 2025 | H156885 | |
| Certificate of Analysis | Aug 30, 2025 | H156885 | |
| Certificate of Analysis | Aug 30, 2025 | H156885 | |
| Certificate of Analysis | Jun 09, 2025 | H156885 | |
| Certificate of Analysis | Dec 16, 2024 | H156885 | |
| Certificate of Analysis | Dec 16, 2024 | H156885 | |
| Certificate of Analysis | Dec 16, 2024 | H156885 | |
| Certificate of Analysis | Dec 16, 2024 | H156885 | |
| Certificate of Analysis | Dec 16, 2024 | H156885 | |
| Certificate of Analysis | Dec 16, 2024 | H156885 | |
| Certificate of Analysis | Jun 09, 2023 | H156885 | |
| Certificate of Analysis | Dec 11, 2021 | H156885 | |
| Certificate of Analysis | Dec 11, 2021 | H156885 | |
| Certificate of Analysis | Sep 14, 2021 | H156885 | |
| Certificate of Analysis | Sep 14, 2021 | H156885 |
| Solubilidad | Soluble in hot water Solubility in other solvents: Soluble in ethanol, acetone, benzene Very soluble in diethyl ether, chloroform Practically insoluble in petroleum ether |
|---|---|
| Punto de inflamación (°F) | 235.4 °F |
| Punto de inflamación (°C) | 113 °C |
| Punto de ebullición (°C) | 263-265 °C/17 mmHg |
| Punto de fusión (°C) | 112-115 °C |
| Peso molecular | 166.170 g/mol |
| XLogP3 | 0.500 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 2 |
| Exact Mass | 166.063 Da |
| Monoisotopic Mass | 166.063 Da |
| Topological Polar Surface Area | 46.500 Ų |
| Heavy Atom Count | 12 |
| Formal Charge | 0 |
| Complexity | 167.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 1 |
| 1. Daihong Gao, Denghao Ouyang, Xuebing Zhao. (2023) Controllable oxidative depolymerization of lignin to produce aromatic aldehydes and generate electricity under mild conditions with direct biomass fuel cells as flexible reactors. CHEMICAL ENGINEERING JOURNAL, [PMID:] [10.1016/j.cej.2023.147874] |
| 2. Zhu Guodian, Shang Jingqi, Wen Weihong, Li Yuanyuan, Yin Guoqiang. (2023) Multilamellar spherical micelles of alkali lignin: dissipative particle dynamics simulations. JOURNAL OF MOLECULAR MODELING, 29 (2): (1-13). [PMID:36622451] [10.1007/s00894-023-05442-6] |
| 3. Yujie Qi, Xing Huang, Haoqi Zhai, Mengquan Shi, Yuxi Zhang, Yunlong Zhang, Yuxia Zhao. (2022) Synthesis and photoinitiation properties of lignin model compounds. PROGRESS IN ORGANIC COATINGS, [PMID:] [10.1016/j.porgcoat.2022.107210] |
| 4. Yang Guangxu, Gong Zhenggang, Luo Xiaolin, Shuai Li. (2022) Revisiting alkaline cupric oxide oxidation method for lignin structural analysis. Frontiers in Bioengineering and Biotechnology, [PMID:36159682] [10.3389/fbioe.2022.1002145] |
| 5. Zhijun Li, Xiaowen Lu, Weiwei Sun, Leipeng Leng, Mingyang Zhang, Honghong Li, Lu Bai, Dundong Yuan, J. Hugh Horton, Qian Xu, Jun Wang. (2021) One-step synthesis of single palladium atoms in WO2.72 with high efficiency in chemoselective hydrodeoxygenation of vanillin. APPLIED CATALYSIS B-ENVIRONMENTAL, [PMID:] [10.1016/j.apcatb.2021.120535] |
| 6. Keqin Yang, Li Hou, Zhifang Li, Tianran Lin, Jianniao Tian, Shulin Zhao. (2021) A mitochondria-targeted ratiometric fluorescent nanoprobe for imaging of peroxynitrite in living cells. TALANTA, [PMID:33965010] [10.1016/j.talanta.2021.122421] |
| 7. Bangrong Cai, Mengya Liu, Jinxing Li, Dujuan Xu, Jiansheng Li. (2021) Cigarette smoke extract amplifies NADPH oxidase-dependent ROS production to inactivate PTEN by oxidation in BEAS-2B cells. FOOD AND CHEMICAL TOXICOLOGY, [PMID:33577944] [10.1016/j.fct.2021.112050] |
| 8. Jindong Wang, Wenzhi Li, Huizhen Wang, Ajibola Temitope Ogunbiyi, Xiaomeng Dou, Qiaozhi Ma. (2020) Effects of the novel catalyst Ni–S2O82−–K2O/TiO2 on efficient lignin depolymerization. RSC Advances, 10 (14): (8558-8567). [PMID:35497830] [10.1039/C9RA10675H] |
| 9. Shuli Man, Miao Li, Jin Zhou, Haiyue Wang, Jinyan Zhang, Long Ma. (2019) Polyethyleneimine coated Fe3O4 magnetic nanoparticles induce autophagy, NF-κB and TGF-β signaling pathway activation in HeLa cervical carcinoma cells via reactive oxygen species generation. Biomaterials Science, 8 (1): (201-211). [PMID:31664285] [10.1039/C9BM01563A] |
| 10. Dan Zhao, Xiaoqing Yi, Gongdao Yuan, Renxi Zhuo, Feng Li. (2017) Design and Construction of a Smart Targeting Drug Delivery System Based on Phototriggered Competition of Host–Guest Interaction. MACROMOLECULAR BIOSCIENCE, 17 (9): (1700150). [PMID:28683185] [10.1002/mabi.201700150] |
| 11. Y.N. Lin, R. Jia, Y.H. Liu, Y. Gao, L.L. Wang, J.P. Kou, B.Y. Yu. (2015) Ruscogenin suppresses mouse neutrophil activation: Involvement of protein kinase A pathway. JOURNAL OF STEROID BIOCHEMISTRY AND MOLECULAR BIOLOGY, [PMID:26134424] [10.1016/j.jsbmb.2015.06.003] |
| 12. Kissa R. Alunga, Yue-Yuan Ye, Shui-Rong Li, Duo Wang, Yun-Quan Liu. (2015) Catalytic oxidation of lignin–acetoderivatives: a potential new recovery route for value-added aromatic aldehydes from acetoderivatives. Catalysis Science & Technology, 5 (7): (3746-3753). [PMID:] [10.1039/C5CY00419E] |
| 13. Xinping Ouyang, Guodian Zhu, Xiangzhen Huang, Xueqing Qiu. (2015) Microwave assisted liquefaction of wheat straw alkali lignin for the production of monophenolic compounds. Journal of Energy Chemistry, [PMID:] [10.1016/S2095-4956(15)60286-8] |
| 14. Zhefan Yuan, Dan Zhao, Xiaoqing Yi, Renxi Zhuo, Feng Li. (2013) Steric Protected and Illumination-Activated Tumor Targeting Accessory for Endowing Drug-Delivery Systems with Tumor Selectivity. ADVANCED FUNCTIONAL MATERIALS, 24 (12): (1799-1807). [PMID:] [10.1002/adfm.201301309] |
| 15. Feng Chen, Xuebin Lin, Wei Chen, Na Wen, Yanqiao Jin. (2024) Double core–shell hollow nanocage CuO@Co3O4 for the selective hydrogenolysis of C–O bonds of lignin without external hydrogen. CHEMICAL ENGINEERING JOURNAL, [PMID:] [10.1016/j.cej.2024.152002] |
| 16. Shiyang Yu, Shanshan Tang, Jitao Lv, Feifei Li, Zichun Huang, Lixia Zhao, Dong Cao, Yawei Wang. (2024) High throughput identification of carbonyl compounds in natural organic matter by directional derivatization combined with ultra-high resolution mass spectrometry. WATER RESEARCH, [PMID:38759284] [10.1016/j.watres.2024.121769] |
| 17. Xia Zhang, Wenzhi Li, Yihang Jiang, Leyu Zhu, Liqun Wang. (2024) Valorization of waste lignin: Efficient and steady production of liquid fuels. INDUSTRIAL CROPS AND PRODUCTS, [PMID:] [10.1016/j.indcrop.2024.119400] |
| 18. Xiao Zhao, Baojie Liu, Hao Xu, Chengrong Qin, Shuangquan Yao, Chen Liang, Shuangfei Wang. (2025) A clean high-concentration chlorine dioxide bleaching process at room temperature facilitating the rapid degradation of lignin and its kinetic. INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES, [PMID:40334900] [10.1016/j.ijbiomac.2025.143966] |
| 19. Yu Wang, Teng Wang, Tianze Jiang, Bingjie Wang, Yanguo Su, Tiantian Gan, Xia Zhao. (2025) A cancer vaccine factory based on autophagy and efferocytosis to enhance tumor immunotherapy. CHEMICAL ENGINEERING JOURNAL, [PMID:] [10.1016/j.cej.2025.164943] |
| 20. Tianyin Huang, Yifan Yu, Wentao Zhang, Yue Zhao, Yiliang Tao, Wenguang Huang, Bingdang Wu. (2026) Molecular orbital-guided design of laccase–mediator systems for antibiotic removal in the presence of humic acid. BIORESOURCE TECHNOLOGY, [PMID:41513177] [10.1016/j.biortech.2026.133957] |
| 21. Feng Chen, Xiang Xia, Wei Chen, Wei Liu, Xinxin Liao, Lei Xiong, Yanqiao Jin. (2026) Highly efficient sea urchin-like N-doped CuCo bimetallic catalyst for selective cleavage of α-O-4 linkage in lignin. Journal of Environmental Chemical Engineering, 14 (3): (122374). [PMID:] [10.1016/j.jece.2026.122374] |
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