2-Hydroxy-1,4-naphthoquinone - ≥98% , CAS No.83-72-7

CAS: 83-72-7 Cat. No.: H121701 Peso molecular: 174.15 Beilstein Registry Number: 1565260 Número EC: 201-496-3

GRADE & PURITY ≥98%

Synonyms

2-Hydroxy-p-naphthoquinone | Mendi | Spectrum4_001697 | KBio1_001522 | 2-Hydroxy-1,4-naphthalenedione | FT-0612520 | H0285 | AKOS000120111 | NSC-52500 | TLH4A6LV1W | 2-hydroxyl-1,4-naphthoquinone | LAWSONE [INCI] | NQ-6 | 1,4-Naphthoquinone, 2-hydroxy- |

Storage

Room temperature

Shipped In

Normal

Descripción general

2-Hydroxy-1,4-naphthoquinone is one among the forensic reagents used for fingerprint detection 2-Hydroxy-1,4-naphthoquinone, produced from Lawsonia inermis, is an orange dye. It belongs to the class of naphthoquinone dyes. 2-Hydroxy-1,4-naphthoquinone is used to dye hair and to color textiles. It has antibacterial, antifungal, anti-inflammatory, antiviral and antineoplastic properties. 2-Hydroxy-1,4-naphthoquinone inhibits tumor cell growth. It stimulates the production of reactive oxygen species (ROS).[
An antimicrobial antioxidant dye isolated from Henna.

2-Hydroxy-1,4-naphthoquinone is used for preparing decorative hair and skin dyes. 2-Hydroxy-1,4-naphthoquinone also demonstrates antimicrobial and antioxidant effects. It also suppress the formation of hydrogen peroxide and superoxide radical anion by aldehyde oxidase-catalyzed reactions.

Specifications

Sinónimos

2-Hydroxy-p-naphthoquinone | Mendi | Spectrum4_001697 | KBio1_001522 | 2-Hydroxy-1, 4-naphthalenedione | FT-0612520 | H0285 | AKOS000120111 | NSC-52500 | TLH4A6LV1W | 2-hydroxyl-1, 4-naphthoquinone | LAWSONE [INCI] | NQ-6 | 1, 4-Naphthoquinone, 2-hydroxy- |

Especificaciones y pureza

≥98%

Mecanismos bioquímicos y fisiológicos

2-Hydroxy-1, 4-naphthoquinone (Lawsone) is a naphthoquinone dye isolated from leaves of Lawsonia inermis, the Henna plant used for preparing decorative hair and skin dyes. In addition to strong light interaction which underlies the aesthetic properties of

Condiciones de almacenamiento de almacenamiento

Room temperature

Enviado en

Normal

Pureza

≥98%

Nombres e identificadores

• Pubchem Sid: 488180149
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488180149
• Sonrisas canónicas: C1=CC=C2C(=C1)C(=CC(=O)C2=O)O
• IUPAC Name: 4-hydroxynaphthalene-1,2-dione
• InChIKey: WVCHIGAIXREVNS-UHFFFAOYSA-N
• INCHI: 1S/C10H6O3/c11-8-5-9(12)10(13)7-4-2-1-3-6(7)8/h1-5,11H
• Isómeros SMILES: C1=CC=C2C(=C1)C(=CC(=O)C2=O)O
• WGK Alemania: 3
• RTECS: QL8200000
• Peso molecular: 174.15
• Beilstein: 1565260
• Reaxy-Rn: 2575949
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2575949&ln=

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Clase: Naphthalenes
• Subclass: Naphthoquinones
• Intermediate Tree Nodes: Not available
• Direct Parent: Naphthoquinones
• Alternative Parents: Naphthols and derivatives Quinones Aryl ketones Vinylogous acids Enols Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homopolycyclic compounds
• Substituents: Naphthoquinone - 1-naphthol - Aryl ketone - Quinone - Vinylogous acid - Cyclic ketone - Ketone - Enol - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aromatic homopolycyclic compound
• Descripción: 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: Not available

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

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Mecanismos de acción

Propiedades químicas y físicas

• Solubilidad: Soluble in water. 2 g/L at 20°C
• Punto de fusión (°C): 193°C
• Peso molecular: 174.150 g/mol
• XLogP3: 0.900
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 174.032 Da
• Monoisotopic Mass: 174.032 Da
• Topological Polar Surface Area: 54.400 Ų
• Heavy Atom Count: 13
• Formal Charge: 0
• Complexity: 291.000
• 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

Referencias

1. 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]

2. Meng Li, Dong Wang, Xiaoduo Liu, Jingmei Sun.  (2019)  Evaluation and correction on quinones’ quantification errors: Derived from the coexistence of different quinone species and pH-sensitive feature.  CHEMOSPHERE,      [PMID:31102873] [10.1016/j.chemosphere.2019.04.146]

3. Yang Li, Cai Tianming, Ding Dahu, Cai Tianjin, Jiang Canlan, Li Hua, Yang Qian, Chen Liwei.  (2017)  Biodegradation of 2-hydroxyl-1,4 naphthoquinone (lawsone) by Pseudomonas taiwanensis LH-3 isolated from activated sludge.  Scientific Reports,  7  (1): (1-10).  [PMID:28754900] [10.1038/s41598-017-06338-1]

4. Lisong Xia, Lei Cheng, Wenni Xi, Xiliang Zhang, Xianyang Shi.  (2024)  Distinct influence of model electron shuttles on anaerobic mononitrophenols reduction in aquatic environments by Shewanella oneidensis MR-1.  JOURNAL OF HAZARDOUS MATERIALS,      [PMID:39079298] [10.1016/j.jhazmat.2024.135348]

5. Weifeng Wu, Mengke Li, Jiang Tian, Feng Li, Yun Liu.  (2024)  Passivation Performance and Mechanism of a Novel Self-Healing Composite Passivator on Pyrite.  Environmental Science-Nano,      [PMID:] [10.1039/D4EN00404C]

6. Yanpeng Huang, Qiong Wu, Jingfan Yan, Fumin Chu, Yuming Xu, Dongmin Li, Hongjia Zhang, Sen Yang.  (2024)  Efficient removal and recovery of phosphate by biochar loaded with ultrafine MgO nanoparticles.  ENVIRONMENTAL RESEARCH,      [PMID:39638027] [10.1016/j.envres.2024.120518]

7. Neng Guo, Shuaipeng Li, Dongdong Zhu, Yufan Wu, Dongjin Wang, Yaru Wang, Zhiguo Sun, Shengwen Chen, Jifen Wang.  (2025)  Preparation and Denitrification Performance of Sodium Humate/TiO₂ Composite Nanoparticles.  ChemistrySelect,  10  (22): (e01220).  [PMID:] [10.1002/slct.202501220]

8. Jinyang Chen, Xiaoyu Lin, Wei Wang, Li Gan, Zuliang Chen.  (2026)  Mediated electron transfer in the bio-reduction of graphene oxide by Lysinibacillus sphaericus: Mechanisms and facilitation.  JOURNAL OF POWER SOURCES,      [PMID:] [10.1016/j.jpowsour.2026.239646]