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2-Hydroxy-1,4-naphthoquinone (CAS 83-72-7)

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Alternate Names:
Lawsone
Application:
2-Hydroxy-1,4-naphthoquinone is an antimicrobial antioxidant dye isolated from Henna
CAS Number:
83-72-7
Purity:
≥98%
Molecular Weight:
174.15
Molecular Formula:
C10H6O3
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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2-Hydroxy-1,4-naphthoquinone, commonly known as lawsone, is a naturally occurring quinone found in the henna plant, *Lawsonia inermis*. This compound is distinguished by its naphthoquinone backbone and a hydroxyl group at the second position, which endows it with unique redox properties. Lawsone operates primarily through redox cycling, a process that involves its constant reduction and oxidation, enabling it to form strong complexes with proteins, which is essential for its use as a natural dye in the textile and cosmetic industries for hair and fabric coloring. Beyond its dyeing applications, lawsone has been a valuable subject in chemical research, particularly in studies related to organic synthesis and polymer chemistry. Its reactive quinone structure allows researchers to explore complex organic reactions and the development of synthetic pathways for advanced materials. Additionally, its interaction with metal ions offers insights into corrosion inhibition, suggesting potential applications in materials science for protecting metals against corrosion. This versatility makes lawsone a critical compound in both industrial applications and fundamental research, contributing significantly to advancements in materials science, textile engineering, and environmental sustainability.


2-Hydroxy-1,4-naphthoquinone (CAS 83-72-7) References

  1. An assessment of the genotoxicity of 2-hydroxy-1,4-naphthoquinone, the natural dye ingredient of Henna.  |  Kirkland, D. and Marzin, D. 2003. Mutat Res. 537: 183-99. PMID: 12787822
  2. Evidence for redox cycling of lawsone (2-hydroxy-1,4-naphthoquinone) in the presence of the hypoxanthine/xanthine oxidase system.  |  Osman, AM. and van Noort, PC. 2003. J Appl Toxicol. 23: 209-12. PMID: 12884402
  3. Antioxidant and immunomodulatory constituents of henna leaves.  |  Mikhaeil, BR., et al. 2004. Z Naturforsch C J Biosci. 59: 468-76. PMID: 15813363
  4. Cytotoxicity of lawsone and cytoprotective activity of antioxidants in catalase mutant Escherichia coli.  |  Sauriasari, R., et al. 2007. Toxicology. 235: 103-11. PMID: 17442476
  5. Natural ingredients for colouring and styling.  |  Dweck, AC. 2002. Int J Cosmet Sci. 24: 287-302. PMID: 18498522
  6. Detection of lawsone (2-hydroxy-1,4-naphthoquinone) in henna treated hair.  |  Petzel-Witt, S., et al. 2019. Forensic Sci Int. 297: 184-188. PMID: 30802647
  7. One-pot Synthesis of 2-Hydroxy-1,4-Naphthoquinone (Lawsone).  |  Sivakumar, D., et al. 2019. Curr Org Synth. 16: 431-434. PMID: 31984905
  8. Mechanisms of toxicity of 2- and 5-hydroxy-1,4-naphthoquinone; absence of a role for redox cycling in the toxicity of 2-hydroxy-1,4-naphthoquinone to isolated hepatocytes.  |  d'Arcy Doherty, M., et al. 1987. J Appl Toxicol. 7: 123-9. PMID: 3624767
  9. A fungitoxic principle from the leaves of lawsonia inermis lam.  |  Tripathi, RD., et al. 1978. Experientia. 34: 51-2. PMID: 620734
  10. Anti-inflammatory, antipyretic, and analgesic effects of Lawsonia inermis L. (henna) in rats.  |  Ali, BH., et al. 1995. Pharmacology. 51: 356-63. PMID: 8966192

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

2-Hydroxy-1,4-naphthoquinone, 10 g

sc-254254
10 g
$25.00

2-Hydroxy-1,4-naphthoquinone, 25 g

sc-254254A
25 g
$43.00