Lapachol

Lapachol^[1]^[2]
	200px
	Ball-and-stick model of lapachol
Names
	IUPAC name 2-Hydroxy-3-(3-methylbut-2-enyl)naphthalene-1,4-dione
Identifiers
CAS Number	84-79-7
ChEMBL	ChEMBL15193
ChemSpider	10770962
EC Number	201-563-7
Jmol 3D model	Interactive image
PubChem	3884
UNII	B221938VB6
	InChI InChI=1S/C15H14O3/c1-9(2)7-8-12-13(16)10-5-3-4-6-11(10)14(17)15(12)18/h3-7,18H,8H2,1-2H3 Key: CIEYTVIYYGTCCI-UHFFFAOYSA-N ; InChI=1/C15H14O3/c1-9(2)7-8-12-13(16)10-5-3-4-6-11(10)14(17)15(12)18/h3-7,18H,8H2,1-2H3 Key: CIEYTVIYYGTCCI-UHFFFAOYAS ;
	SMILES CC(=CCC1=C(C2=CC=CC=C2C(=O)C1=O)O)C ;
Properties
Chemical formula	C15H14O3
Molar mass	242.27
Appearance	Yellow crystals
Melting point	140 °C (284 °F; 413 K)
Vapor pressure	{{{value}}}
	Except where otherwise noted, data are 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 vitamin K^[5]

Once studied as a possible treatment for some types of cancer, it is now considered too toxic for use^[6]^[7]^[8]^[9]

References

↑ [1] Lapochol at R&D Chemicals.
↑ [2] 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
↑ Lua error in package.lua at line 80: module 'strict' not found.
↑ 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.
↑ Lua error in package.lua at line 80: module 'strict' not found.
↑ Lua error in package.lua at line 80: module 'strict' not found.