Lapachol

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| verifiedrevid = 401250545

| Reference=[http://www.rdchemicals.com/chemicals.php?mode=details&mol_id=7988] Lapochol at R&D Chemicals.{{cite web |url=http://www.chromadex.com/chemicals/CDXProductPageH8r2mS8767c.html |title=ChromaDex Incorporated General Product Information for LAPACHOL(RG) |access-date=2007-07-06 |url-status=dead |archive-url=https://web.archive.org/web/20070928020707/http://www.chromadex.com/chemicals/CDXProductPageH8r2mS8767c.html |archive-date=2007-09-28 }} Lapochol at CromaDex.

| ImageFile=Lapachol.png

| ImageSize=200px

| ImageFile1 = Lapachol molecule ball.png

| ImageSize1 = 230

| ImageAlt1 = Ball-and-stick model of lapachol

| PIN=2-Hydroxy-3-(3-methylbut-2-en-1-yl)naphthalene-1,4-dione

| OtherNames=

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|??}}

| CASNo=84-79-7

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 15193

| PubChem=3884

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = B221938VB6

| SMILES=CC(=CCC1=C(C2=CC=CC=C2C(=O)C1=O)O)C

| EINECS = 201-563-7

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 10770962

| ChEBI = 6377

| 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

| InChIKey = CIEYTVIYYGTCCI-UHFFFAOYAS

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = CIEYTVIYYGTCCI-UHFFFAOYSA-N

}}

|Section2={{Chembox Properties

| Formula=C₁₅H₁₄O₃

| MolarMass=242.27

| Appearance=Yellow crystals

| Density=

| MeltingPtC=140

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|Section3={{Chembox Hazards

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Lapachol is a natural phenolic compound isolated from the bark of the lapacho tree.Record, Samuel J.. "Lapachol" pages 17-19. In: Tropical Woods (1925). This tree is known botanically as Handroanthus impetiginosus, but was formerly known by various other botanical names such as Tabebuia avellanedae.{{cite journal | vauthors = Grose SO, Olmstead RG | year = 2007 | title = Evolution of a Charismatic Neotropical Clade: Molecular Phylogeny of Tabebuia s.l., Crescentieae, and Allied Genera (Bignoniaceae) | journal = Systematic Botany | volume = 32 | issue = 3| pages = 650–659 | doi=10.1600/036364407782250553| s2cid = 8824926 }} 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.Louis F.Fieser. The Scientific Method pages 163-191. Reinhold Publishing Corporation, New York, 1964

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.{{cite journal |vauthors=Felício AC, Chang CV, Brandão MA, Peters VM, Guerra Mde O |title=Fetal growth in rats treated with lapachol |journal=Contraception |volume=66 |issue=4 |pages=289–93 |year=2002 |pmid=12413627 |doi=10.1016/S0010-7824(02)00356-6}}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.{{cite journal |vauthors=Guerra Mde O, Mazoni AS, Brandão MA, Peters VM |title=Toxicology of Lapachol in rats: embryolethality |journal=Brazilian Journal of Biology |volume=61 |issue=1 |pages=171–4 |year=2001 |pmid=11340475 |doi=10.1590/s0034-71082001000100021|doi-access=free }}{{cite journal |vauthors=((de Cássia da Silveira E)), Sá R, de Oliveira Guerra M |title=Reproductive toxicity of lapachol in adult male Wistar rats submitted to short-term treatment |journal=Phytotherapy Research |volume=21 |issue=7 |pages=658–62 |year=2007 |pmid=17421057 |doi=10.1002/ptr.2141}}

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.{{cite journal|vauthors=((Draelos Z)) |title=The Clinical Efficacy of Lapachol in Facial Redness Reduction |journal=Journal of Cosmetic Dermatology |year=2024 |doi=10.1111/jocd.16602|doi-access=free }}