4'-Hydroxy-3'-methoxyacetophenone - Moligand™, 10mM in DMSO , CAS No.498-02-2

CAS: 498-02-2 Cat. No.: H424289 Peso molecular: 166.18 Beilstein Registry Number: 637373 Número EC: 207-854-5
Disponible para pedir
GRADE & PURITY Moligand™ ? Moligand™ — Aladdin's line of ligands and bioactive small molecules. Use for receptor, pathway, and binding studies needing defined small-molecule tools. 10mM in DMSO
Synonyms
1-(4-hydroxy-3-methoxyphenyl)ethan-1-one | 3-Methyl Methcathinone Hydrochloride | 3-Metoksy-4-hydroksyacetofenon | AKOS000120562 | 4-Acetyl-2-methoxyphenol | BRN 0637373 | 3-Metoksy-4-hydroksyacetofenon [Polish] | AA-504/20839006 | apocynin (acetovanillon
Storage
Store at -80°C
Shipped In
Dry ice packs + Cold packs
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Size
Estado
Price
Qty
1ml
H424289-1ml
2
49,90US$
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Why this grade

Moligand™, 10mM in DMSO Moligand™ for sensitive chromatographic and analytical workflows requiring minimal baseline interference.

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Storage & shipping

Store at -80°C Ships Dry ice packs + Cold packs Check lot-specific COA for exact specifications.

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Quality documents

SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.

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Literature proof

Cited in 21 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.

Descripción general

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.

Specifications

Sinónimos
1-(4-hydroxy-3-methoxyphenyl)ethan-1-one | 3-Methyl Methcathinone Hydrochloride | 3-Metoksy-4-hydroksyacetofenon | AKOS000120562 | 4-Acetyl-2-methoxyphenol | BRN 0637373 | 3-Metoksy-4-hydroksyacetofenon [Polish] | AA-504/20839006 | apocynin (acetovanillon
Especificaciones y pureza
Moligand™, 10mM in DMSO
Mecanismos bioquímicos y fisiológicos
Selective NADPH-oxidase inhibitor (IC 50 = 10 μM). Inhibits production of reactive oxygen species. Also elicits a range of in vitro and in vivo anti-inflammatory effects.
Condiciones de almacenamiento de almacenamiento
Store at -80°C
Enviado en
Dry ice packs + Cold packs
Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.
Grado
Moligand™
Tipo de acción
INHIBITOR
Nombres e identificadores
Sonrisas canónicasCC(=O)C1=CC(=C(C=C1)O)OC
IUPAC Name1-(4-hydroxy-3-methoxyphenyl)ethanone
InChIKeyDFYRUELUNQRZTB-UHFFFAOYSA-N
INCHI1S/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=

Documentation

📋 Safety Data Sheet (SDS)

Comprehensive hazard, handling, storage, and regulatory compliance document.

Download SDS →

✅ Certificate of Analysis (COA)

Lot-specific quality data. Enter your lot number to retrieve the exact COA.

Look up COA →

📊 Datasheet

Quick-reference summary of product specifications and applications.

View datasheet →

🔬 Specification Sheet

Full quality attributes and acceptance criteria for this grade.

View spec sheet →

Advanced Data

Taxonomic Classification

Taxonomy Tree

KingdomOrganic compounds
SuperclassOrganic oxygen compounds
ClaseOrganooxygen compounds
SubclassCarbonyl compounds
Intermediate Tree Nodes Ketones - Aryl ketones - Phenylketones
Direct ParentAlkyl-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 FrameworkAromatic 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
DescripciónThis 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
Estructura 3D
Modelo de Estructura Química Interactiva





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Mecanismos de acción
Certificados (CoA, COO, BSE/TSE y tabla de análisis)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Propiedades químicas y físicas
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 molecular166.170 g/mol
XLogP30.500
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count2
Exact Mass166.063 Da
Monoisotopic Mass166.063 Da
Topological Polar Surface Area46.500 Ų
Heavy Atom Count12
Formal Charge0
Complexity167.000
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
The total count of all stereochemical bonds0
Covalently-Bonded Unit Count1
Preguntas frecuentes y artículos
Citations of This Product
Referencias
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,  (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,  (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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