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]
Ball-and-stick model of 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
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
  • 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).
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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, it is now considered too toxic for use.[6][7][8][9]

See also

References
  1. Lapochol at R&D Chemicals.
  2. "ChromaDex Incorporated General Product Information for LAPACHOL(RG)". Archived from the original on 2007-09-28. Retrieved 2007-07-06. Lapochol at CromaDex.
  3. Record, Samuel J.. "Lapachol" pages 17-19. In: Tropical Woods (1925).
  4. Grose SO, Olmstead RG (2007). "Evolution of a Charismatic Neotropical Clade: Molecular Phylogeny of Tabebuia s.l., Crescentieae, and Allied Genera (Bignoniaceae)". Systematic Botany. 32 (3): 650–659. doi:10.1600/036364407782250553. S2CID 8824926.
  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. 61 (1): 171–4. doi:10.1590/s0034-71082001000100021. 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. 21 (7): 658–62. doi:10.1002/ptr.2141. PMID 17421057.
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