Lapachol

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^[1][2]

Names
Preferred IUPAC name 2-Hydroxy-3-(3-methylbut-2-en-1-yl)naphthalene-1,4-dione
Identifiers
CAS Number	84-79-7 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:6377
ChEMBL	ChEMBL15193 N
ChemSpider	10770962 N
ECHA InfoCard	100.001.421
EC Number	201-563-7
PubChem CID	3884
UNII	B221938VB6 N
CompTox Dashboard (EPA)	DTXSID6049430
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 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
Chemical formula	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.^[5]

Once studied as a possible treatment for some types of cancer, the levels of lapachol required for cancer treatment are considered too toxic for use as an in vivo chemotherapy treatment.^[6][7][8][9]

In 2024, A clinical trial published in the Journal of Cosmetic Dermatology determined that lower concentrations of lapachol were safe and efficacious in Facial Redness Reduction.^[10]

See also

§Hooker-Oxidation§