Lapachol

• Catalog No.: Bio-0237
• CAS Number: 84-79-7
• M. F.: C15H14O3
• M. W.: 242.26986

SYNONYMS

• IUPAC name: 2-hydroxy-3-(3-methylbut-2-en-1-yl)-1,4-dihydronaphthalene-1,4-dione
• IUPAC Traditional name: 2-hydroxy-3-(3-methylbut-2-en-1-yl)-1,4-dihydronaphthalene-1,4-dione
• Synonyms: Lapachoic acid; Groenhartin; Taiguic acid; Greenhartin

DATABASE IDS

• CAS Number: 84-79-7

PROPERTIES

• Application(s): Anticancer activity
• Application(s): Antibacterial
• Application(s): Antifungal agent
• Application(s): Anticoagulant
• Biological Source: Widespread occurrence in the plant world, particularly in heartwood, bark and roots, e.g. the Bignoniaceae and various Tabebuia, Tecomella and Tectona spp.
• Mechanism of Action: Inhibitor of DNA replication and RNA synthesis

REFERENCES

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 81D, (ir)
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 910A, (nmr)
• Hooker, S.C., J.A.C.S., 1936, 58, 1181, (synth, bibl)
• Burnett, A.R. et al., J.C.S.(C), 1967, 2100, (synth)
• Burnett, A.R. et al., Chem. Ind. (London), 1968, 1771, (synth)
• Pettit, G.R. et al., J.C.S.(C), 1971, 509, (synth)
• Jacobsen, N. et al., Acta Chem. Scand., 1973, 27, 3211, (synth)
• Rao, K.V., Cancer Chemother. Rep., Part 2, 1974, 4, 11, (use)
• Da Silveira, J.C. et al., Phytochemistry, 1975, 14, 1829, (isol)
• Sawnhey, S.S. et al., Indian J. Chem., 1976, 14, 295, (use)
• McDonald, I.A. et al., Aust. J. Chem., 1977, 30, 1727, (pmr, cmr)
• Sawnhey, S.S. et al., J. Indian Chem. Soc., 1977, 54, 403, (use)
• Kapoor, N.K. et al., Indian J. Chem., Sect. B, 1982, 21, 189, (synth)
• Ghera, E. et al., J.O.C., 1985, 50, 3355, (synth)
• Sun, J.S. et al., Tet. Lett., 1998, 39, 8221-8224, (synth)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, HLY500