Lapachol

Last updated
Lapachol [1] [2]
Lapachol.png
Lapachol molecule ball.png
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 OOjs UI icon edit-ltr-progressive.svg
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 X mark.svgN
    Key: CIEYTVIYYGTCCI-UHFFFAOYSA-N X mark.svgN
  • 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
AppearanceYellow 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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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]

See also

§Hooker-Oxidation§

Related Research Articles

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<i>Handroanthus chrysotrichus</i> Species of tree

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Handroanthus is a genus of flowering plants in the family Bignoniaceae. It consists of 30 species of trees, known in Latin America by the common names poui, pau d'arco, or ipê. The latter sometimes appears as epay or simply ipe (unaccented) in English. The large timber species are sometimes called lapacho or guayacan, but these names are more properly applied to the species Handroanthus lapacho and Handroanthus guayacan, respectively.

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<i>Handroanthus heptaphyllus</i> Species of tree

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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.