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

CAS: 83-72-7 Cat. No.: H121701 Molecular Weight: 174.15 Beilstein Registry Number: 1565260 EC Number: 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

Overview

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

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- |

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

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

Storage

Room temperature

Shipped In

Normal

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 488180149
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488180149
• Canonical Smiles: 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
• Isomeric SMILES: C1=CC=C2C(=C1)C(=CC(=O)C2=O)O
• WGK Germany: 3
• RTECS: QL8200000
• Molecular Weight: 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
    • Class Naphthalenes
      • Subclass Naphthoquinones

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: 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
• 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: 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

Associated Targets(Human)

ALOX5 Tclin Arachidonate 5-lipoxygenase (6568 Activities)

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VDR Tclin Vitamin D receptor (26531 Activities)

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TYR Tclin Tyrosinase (717 Activities)

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DHODH Tclin Dihydroorotate dehydrogenase (2737 Activities)

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P2RX7 Tchem P2X purinoceptor 7 (5534 Activities)

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MMP3 Tchem Matrix metalloproteinase 3 (3433 Activities)

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MMP8 Tchem Matrix metalloproteinase 8 (1942 Activities)

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ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)

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

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MMP1 Tchem Matrix metalloproteinase-1 (7046 Activities)

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CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

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LoVo (4724 Activities)

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MCF7 (126967 Activities)

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PC-3 (62116 Activities)

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SK-BR-3 (5175 Activities)

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SK-MEL-28 (48833 Activities)

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A549 (127892 Activities)

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KB (17409 Activities)

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HeLa (62764 Activities)

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MDA-MB-231 (73002 Activities)

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

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SETD7 Tchem Histone-lysine N-methyltransferase SETD7 (390 Activities)

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POLK Tbio DNA polymerase kappa (8653 Activities)

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TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

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SAS (201 Activities)

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

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

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SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

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SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)

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USP1 Tchem Ubiquitin carboxyl-terminal hydrolase 1 (22556 Activities)

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HFF-1 (186 Activities)

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Associated Targets(non-human)

pol Human immunodeficiency virus type 1 protease (9113 Activities)

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Papain (844 Activities)

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Cruzipain (33337 Activities)

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Mapk1 MAP kinase ERK2 (650 Activities)

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Mmp2 Matrix metalloproteinase-2 (12 Activities)

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Mmp9 Matrix metalloproteinase 9 (38 Activities)

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pol Human immunodeficiency virus type 1 integrase (9041 Activities)

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protease Human rhinovirus A protease (1343 Activities)

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Pseudomonas aeruginosa (123386 Activities)

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Porphyromonas gingivalis (651 Activities)

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Staphylococcus aureus (210822 Activities)

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Streptococcus mutans (2687 Activities)

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Candida albicans (78123 Activities)

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Trypanosoma cruzi (99888 Activities)

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Mus musculus (284745 Activities)

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Vero (26788 Activities)

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HT-22 (3261 Activities)

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rhodesain Rhodesain (1463 Activities)

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lef Anthrax lethal factor (7585 Activities)

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Trpa1 Transient receptor potential cation channel subfamily A member 1 (1003 Activities)

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Erwinia amylovora (182 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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CELA2A Pancreatic elastase (395 Activities)

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Dihydroorotate dehydrogenase (quinone), mitochondrial (90 Activities)

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groL GroEL/GroES (1042 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in water. 2 g/L at 20°C
• Melt Point(°C): 193°C
• Molecular Weight: 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

References

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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]

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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]

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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]