Lapachol
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| Names | |
|---|---|
| IUPAC name
2-Hydroxy-3-(3-methylbut-2-enyl)naphthalene-1,4-dione | |
| Identifiers | |
84-79-7  | |
| ChEMBL | ChEMBL15193  |
| ChemSpider | 10770962 |
| EC number | 201-563-7 |
| |
| Jmol-3D images | Image |
| PubChem | 3884 |
| |
| UNII | B221938VB6 |
| Properties | |
| C15H14O3 | |
| Molar mass | 242.27 |
| Appearance | Yellow crystals |
| Melting point | 140 °C (284 °F; 413 K) |
| Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
| verify (what is: /?) | |
| Infobox references | |
Lapachol is a natural phenolic compound isolated from the bark of the lapacho tree.[3] This tree is known botanically as Handroanthus impetiginosus, but was formerly known by various other botanical names such as Tabebuia avellanedae.[4] Lapachol is also found in other species of Handroanthus.
Lapachol is usually encountered as a yellow, skin-irritating powder from wood. Chemically, it is a derivative of naphthoquinone, related to vitamin K[5]
Once studied as a possible treatment for some types of cancer, lapachol's potential is now considered low due to its toxic side effects.[6][7][8][9]
See also
References
- ↑ Lapochol at R&D Chemicals.
- ↑ Lapochol at CromaDex.
- ↑ Record, Samuel J.. "Lapachol" pages 17-19. In: Tropical Woods (1925).
- ↑ Susan O. Grose and Richard G. Olmstead. 2007. "Evolution of a Charismatic Neotropical Clade: Molecular Phylogeny of Tabebuia s.l., Crescentieae, and Allied Genera (Bignoniaceae)". Systematic Botany 32(3):650-659.
- ↑ Louis F.Fieser. The Scientific Method pages 163-191. Reinhold Publishing Corporation, New York, 1964
- ↑ Felício AC, Chang CV, Brandão MA, Peters VM, Guerra Mde O (2002). "Fetal growth in rats treated with lapachol". Contraception 66 (4): 289–93. doi:10.1016/S0010-7824(02)00356-6. 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.