1,2-Naphthoquinone - ≥95% , CAS No.524-42-5

CAS: 524-42-5 Cat. No.: N113473 Molecular Weight: 158.15 Beilstein Registry Number: 606546 EC Number: 208-360-2

GRADE & PURITY ≥95%

Synonyms

BBL027354 | 1,2-Naphthalenedione | HSDB 2036 | NAPHTHOQUINONE, 1,2- | 1,2-Dihydro-1,2-diketo-naphthalene | F30116 | 1,2-NAPHTHOQUINONE | AM85414 | BRN 0606546 | Z324553598 | DTXSID2060171 | 1,2-Naphthaquinone | 1,2-NAPHTHOQUINONE [MI] | 4-07-00-02417 (Bei

Storage

Protected from light,Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

product description：

1,2-Naphthoquinone is one of the major metabolite of naphthalene, which is responsible for the cytotoxicity and genotoxicity associated with it. 1,2-Naphthoquinone is an atmospheric contaminant. It causes the contraction of trachea smooth muscles in guinea pig through the activation of epidermal growth factor receptor. 1,2-Naphthoquinone has been reported as an environmental quinone in diesel exhaust particles (DEP) and atmospheric particulate matter.

application：

1,2-Naphthoquinone was employed as mediator during electrochemical mapping of redox activity in normal human breast (MCF-10A) cells by scanning electrochemical microscopy (SECM).

Specifications

Synonyms

BBL027354 | 1, 2-Naphthalenedione | HSDB 2036 | NAPHTHOQUINONE, 1, 2- | 1, 2-Dihydro-1, 2-diketo-naphthalene | F30116 | 1, 2-NAPHTHOQUINONE | AM85414 | BRN 0606546 | Z324553598 | DTXSID2060171 | 1, 2-Naphthaquinone | 1, 2-NAPHTHOQUINONE [MI] | 4-07-00-02417 (Bei

Specifications & Purity

≥95%

Storage

Protected from light, Store at -20°C, Argon charged

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥95%

Names and Identifiers

• Pubchem Sid: 504751983
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504751983
• Canonical Smiles: C1=CC=C2C(=C1)C=CC(=O)C2=O
• IUPAC Name: naphthalene-1,2-dione
• InChIKey: KETQAJRQOHHATG-UHFFFAOYSA-N
• INCHI: 1S/C10H6O2/c11-9-6-5-7-3-1-2-4-8(7)10(9)12/h1-6H
• Isomeric SMILES: C1=CC=C2C(=C1)C=CC(=O)C2=O
• WGK Germany: 3
• RTECS: QL7000000
• UN Number: 2811
• Packing Group: I
• Molecular Weight: 158.15
• Beilstein: 606546
• Reaxy-Rn: 606546
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=606546&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Naphthalenes
      • Subclass Naphthoquinones

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Naphthalenes
• Subclass: Naphthoquinones
• Intermediate Tree Nodes: Not available
• Direct Parent: Naphthoquinones
• Alternative Parents: Quinones Aryl ketones Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homopolycyclic compounds
• Substituents: Naphthoquinone - Aryl ketone - Quinone - Cyclic ketone - Ketone - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aromatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as naphthoquinones. These are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone).
• External Descriptors: a small molecule

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

CES1 Tchem Liver carboxylesterase 1 (1 Activities)

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ACHE Tclin Acetylcholinesterase (1 Activities)

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ACHE Tclin Acetylcholinesterase (18204 Activities)

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THRB Tclin Thyroid hormone receptor beta-1 (7926 Activities)

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POLB Tchem DNA polymerase beta (23632 Activities)

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BCHE Tclin Butyrylcholinesterase (7174 Activities)

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ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)

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CES1 Tchem Acyl coenzyme A:cholesterol acyltransferase (1029 Activities)

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ALOX15 Tchem Arachidonate 15-lipoxygenase (7108 Activities)

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PTPRC Tchem Leukocyte common antigen (2317 Activities)

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PTPN22 Tchem Hematopoietic cell protein-tyrosine phosphatase 70Z-PEP (1215 Activities)

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HL-60 (67320 Activities)

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HCT-116 (91556 Activities)

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IDO1 Tchem Indoleamine 2,3-dioxygenase (6650 Activities)

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HSD17B10 Tchem Endoplasmic reticulum-associated amyloid beta-peptide-binding protein (20669 Activities)

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APEX1 Tchem DNA-(apurinic or apyrimidinic site) lyase (38016 Activities)

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EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)

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KDM4E Tchem Lysine-specific demethylase 4D-like (40243 Activities)

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LMNA Tbio Prelamin-A/C (36751 Activities)

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RECQL Tbio ATP-dependent DNA helicase Q1 (5575 Activities)

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HPGD Tchem 15-hydroxyprostaglandin dehydrogenase [NAD+] (24926 Activities)

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GMNN Tbio Geminin (128009 Activities)

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KMT2A Tchem Histone-lysine N-methyltransferase MLL (17327 Activities)

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MBNL1 Tbio Muscleblind-like protein 1 (34431 Activities)

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microRNA 21 (64692 Activities)

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BAZ2B Tchem Bromodomain adjacent to zinc finger domain protein 2B (56204 Activities)

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Associated Targets(non-human)

tat Human immunodeficiency virus type 1 Tat protein (75 Activities)

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Papain (844 Activities)

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Ptpn1 Protein-tyrosine phosphatase 1B (270 Activities)

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Pkm Pyruvate kinase isozymes M1/M2 (66 Activities)

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protease Human rhinovirus A protease (1343 Activities)

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Plasmodium falciparum (966862 Activities)

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Trichoplusia ni (986 Activities)

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dnaB Replicative DNA helicase (15 Activities)

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GCN5 Histone acetyltransferase GCN5 (89 Activities)

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Luciferin 4-monooxygenase (66902 Activities)

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pfk 6-phospho-1-fructokinase (7870 Activities)

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TGR Thioredoxin glutathione reductase (28579 Activities)

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Mapt Microtubule-associated protein tau (6 Activities)

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fba Putative fructose-1,6-bisphosphate aldolase (15559 Activities)

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ffp 4'-phosphopantetheinyl transferase ffp (24982 Activities)

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recA Protein RecA (2211 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Chloroform (Slightly), DMSO (Slightly)
• Sensitivity: Sensitive to heat, air, and light
• Melt Point(°C): 139-142 °C (dec.) (lit.)
• Molecular Weight: 158.150 g/mol
• XLogP3: 1.500
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 158.037 Da
• Monoisotopic Mass: 158.037 Da
• Topological Polar Surface Area: 34.100 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 253.000
• 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

References

1. Junqi Liu, Meng Wang, Saijin Wang, Yanli Zhao, Shi Zhou, Jinlian Li, Dongmei Wu.  (2023)  Assessment of oxygenated polycyclic aromatic hydrocarbon cytotoxicity using TiO2-MXene/MWCNTs/PDA/GCE electrochemical sensor.  ELECTROCHIMICA ACTA,      [PMID:] [10.1016/j.electacta.2023.143515]

2. Wenzhe Xu, Yang Chen, Ruixu Yang, Yiying Fu, Wanxin Zhuang, Yonggang Wang, Yi Liu, Hao Zhang.  (2023)  “Reaction”-Like Shaping of Self-Delivery Supramolecular Nanodrugs in the Nanoprecipitation Process.  ACS Nano,      [PMID:37668306] [10.1021/acsnano.3c05229]

3. Yitao Lv, Yi Zhang, Yunyin Yang, Jingyan Li, Jiacheng Wang, Xilin Xiao, Min Zhang.  (2023)  Strategy of In Situ Electrochemical Regulation for Highly Enhanced Nonenzymatic Sensing of Carbaryl.  ANALYTICAL CHEMISTRY,      [PMID:36802553] [10.1021/acs.analchem.2c04373]

4. Ning Xia, Fengli Gao, Gang Liu, Yong Chang, Lin Liu.  (2024)  Pyrroloquinoline quinone exhibiting peroxidase-mimicking property for colorimetric assays.  ANALYTICA CHIMICA ACTA,      [PMID:39643317] [10.1016/j.aca.2024.343468]

5. Kaineng Huang, Yi He, Xingyu Li, Yuanjiang Pan, Yuanji Gao.  (2024)  Unlocking the Mysteries of the Desorption–Ionization Mechanism via Separate Thermal and Charge Strategies.  ANALYTICAL CHEMISTRY,      [PMID:39568300] [10.1021/acs.analchem.4c03823]

6. Chenwei Sun, Guohua Wu, Di Wu, Lin Wu, Qingrui Lu, Wenqi Hu, Qijun Du, Jiashu Wang, Ao Xie, Mengjiao Xia, Haijie Hu, Bangchuan Hu, Jian Huang, Shuqi Wang.  (2025)  Determining the Optimal Transplantation Window in Hepatic Organoids via Real-Time Biosensing of Vascularization and Metabolic Maturation Utilizing the Integrated Organoid-on-a-Chip Platform.  BIOSENSORS & BIOELECTRONICS,      [PMID:41046609] [10.1016/j.bios.2025.118057]

7. Shuyan Zang, Bin Lian, Juan Wang, Yanjie Yang.  (2010)  Biodegradation of 2-naphthol and its metabolites by coupling Aspergillus niger with Bacillus subtilis.  Journal of Environmental Sciences,      [PMID:20608501] [10.1016/S1001-0742(09)60161-3]

8. Yixin Huang, Yihui Zhang, Mengzhe Zhao, Shuwen Yan, Daqiang Yin, Weihua Song.  (2025)  Solar-Induced Phototransformation of Peracetic Acid in Chromophoric Dissolved Organic Matter Solutions.  ENVIRONMENTAL SCIENCE & TECHNOLOGY,      [PMID:40313032] [10.1021/acs.est.5c00903]