Lawsone

• Catalog No.: Bio-0249
• CAS Number: 83-72-7
• M. F.: C10H6O3
• M. W.: 174.15284

SYNONYMS

• IUPAC name: 2-hydroxy-1,4-dihydronaphthalene-1,4-dione
• IUPAC Traditional name: 2-hydroxy-1,4-dihydronaphthalene-1,4-dione
• Synonyms: Natural Orange 6; Henna

DATABASE IDS

• CAS Number: 83-72-7

PROPERTIES

• Application(s): Antineoplastic
• Application(s): Antispasmodic agent, fungicide, bactericide and ingredient of sunscreen preparations
• Application(s): Possesses antiinflammatory, analgesic and antipyretic activity
• Biological Source: Isol. from Lawsonia spp., henna and seeds of Lomatia ferruginea. Also from Impatiens spp.
• Mechanism of Action: Inhibitor of NADPH-cytochrome C reductase

REFERENCES

• Aldrich Library of NMR Spectra, 2nd edn., 1983, 2, 86A, (nmr)
• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 79D, (ir)
• Fieser, L.F., J.A.C.S., 1948, 70, 3165, (synth)
• Amorosa, M., Gazz. Chim. Ital., 1954, 84, 602, (synth)
• Org. Synth., Coll. Vol., 3, 1955, 465
• Chen, D. et al., Can. J. Biochem., 1966, 44, 1389, (biosynth)
• Baillie, A.C. et al., J.C.S.(C), 1966, 2185, (synth)
• Fieser and Fieser's Reagents for Organic Synthesis, Wiley, 1967, 1, 484
• Japan. Pat., 1971, Mitsubishi Edogawa, 71 02 977; CA, 74, 141384, (synth)
• Japan. Pat., 1971, Mitsubishi Edogawa, 71 02 978; CA, 75, 48769h, (synth)
• Chapelle, J.P., Phytochemistry, 1974, 13, 662, (isol, deriv)
• Mehendale, A.R. et al., Phytochemistry, 1975, 14, 801, (isol)
• Yano, H. et al., Chem. Pharm. Bull., 1980, 28, 1207, (cmr)
• Munday, R. et al., J. Appl. Toxicol., 1991, 11, 85, (tox)
• Ali, B.H. et al., Pharmacology, 1995, 51, 356, (pharmacol)
• Dekkers, J. et al., Acta Cryst. C, 1996, 52, 2896-2899, (cryst struct)
• Martindale, The Extra Pharmacopoeia, 31st edn., Pharmaceutical Press, 1996, 1719
• Zinkham, W.H. et al., Pediatrics, 1996, 7, 707, (tox)
• Ishiguro, K. et al., J. Nat. Prod., 1998, 61, 1126-1129, (deriv, isol, pmr, cmr)