Lapachol

Lapachol is a natural phenolic compound isolated from the bark of the lapacho tree. This tree is known botanically as Handroanthus impetiginosus, but was formerly known by various other botanical names such as Tabebuia avellanedae. Lapachol is also found in other species of Handroanthus.

Lapachol
Names
Preferred IUPAC name
2-Hydroxy-3-(3-methylbut-2-en-1-yl)naphthalene-1,4-dione
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.421
EC Number
  • 201-563-7
PubChem CID
UNII
  • 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 N
    Key: CIEYTVIYYGTCCI-UHFFFAOYSA-N 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
C15H14O3
Molar mass 242.27
Appearance Yellow crystals
Melting point 140 °C (284 °F; 413 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Lapachol is usually encountered as a yellow, skin-irritating powder from wood. Chemically, it is a derivative of vitamin K.

Once studied as a possible treatment for some types of cancer, it is now considered too toxic for use.

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