Lapachol

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Lapachol[1][2]
Lapachol.png
Identifiers
CAS number 84-79-7 YesY
PubChem 3884
ChemSpider 10770962 N
UNII B221938VB6 N
EC number 201-563-7
ChEMBL CHEMBL15193 N
Jmol-3D images Image 1
Properties
Molecular formula C15H14O3
Molar mass 242.27
Appearance Yellow crystals
Melting point 140 °C (284 °F; 413 K)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
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[edit]

References[edit]

  1. ^ [1] Lapochol at R&D Chemicals.
  2. ^ [2] Lapochol at CromaDex.
  3. ^ Record, Samuel J.. "Lapachol" pages 17-19. In: Tropical Woods (1925).
  4. ^ 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.
  5. ^ Louis F.Fieser. The Scientific Method pages 163-191. Reinhold Publishing Corporation, New York, 1964
  6. ^ 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. 
  7. ^ 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.
  8. ^ 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. 
  9. ^ 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.