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Lapachol

Lapachol^[1]^[2]

IUPAC name	4-Hydroxy-3-(3-methylbut-2-enyl)naphthalene-1,2-dione
Identifiers
CAS number	84-79-7
PubChem	3884
SMILES	CC(=CCC1=C(C2=CC=CC=C2C(=O)C1=O)O)C
Properties
Molecular formula	C₁₅H₁₄O₃
Molar mass	242.27
Appearance	Yellow crystals
Melting point	140 °C, 413 K, 284 °F
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Lapachol is a natural organic compound isolated from the lapacho tree (Tabebuia avellandedae)^[3] Chemically, it is a derivative of naphthoquinone, related to vitamin K.

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Once studied as a possible treatment for some types of cancer, lapachol's potential is now considered low due to its toxic side effects.^[4]^[5]^[6]^[7]

References

^ [1] Lapochol at R&D Chemicals.
^ [2] Lapochol at CromaDex.
^ Record, Samuel J. Lapachol. Tropical Woods (1925), 1 7-9.
^ Felício AC, Chang CV, Brandão MA, Peters VM, Guerra Mde O (2002). "Fetal growth in rats treated with lapachol". Contraception 66 (4): 289-93. PMID 12413627.
^ Oral toxicology studies with lapachol. Morrison, Robert K.; Brown, Donald Emerson; Oleson, Jerome J.; Cooney, David A. Toxicology and Applied Pharmacology (1970), 17(1), 1-11.
^ Guerra Mde O, Mazoni AS, Brandão MA, Peters VM (2001). "Toxicology of Lapachol in rats: embryolethality". Brazilian journal of biology = Revista brasleira de biologia 61 (1): 171-4. PMID 11340475.
^ de Cássia da Silveira E Sá R, de Oliveira Guerra M (2007). "Reproductive toxicity of lapachol in adult male Wistar rats submitted to short-term treatment". Phytotherapy research : PTR 21 (7): 658-62. doi:10.1002/ptr.2141. PMID 17421057.