Plumbagin

Last updated
Plumbagin
Skeletal formula of plumbagin Plumbagin.PNG
Skeletal formula of plumbagin
Ball-and-stick model of plumbagin Plumbagin-3D-balls.png
Ball-and-stick model of plumbagin
Names
Preferred IUPAC name
5-Hydroxy-2-methylnaphthalene-1,4-dione
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.882 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C11H8O3/c1-6-5-9(13)10-7(11(6)14)3-2-4-8(10)12/h2-5,12H,1H3 Yes check.svgY
    Key: VCMMXZQDRFWYSE-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C11H8O3/c1-6-5-9(13)10-7(11(6)14)3-2-4-8(10)12/h2-5,12H,1H3
    Key: VCMMXZQDRFWYSE-UHFFFAOYAB
  • Oc1c2C(=O)cc(C)C(=O)c2ccc1
Properties
C11H8O3
Molar mass 188.17942 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Plumbagin or 5-hydroxy-2-methyl-1,4-naphthoquinone is an organic compound with the chemical formula C
11H
8O
3. It is regarded as a toxin [1] and it is genotoxic [2] and mutagenic. [3]

Plumbagin is a yellow dye, [1] formally derived from naphthoquinone.

It is named after the plant genus Plumbago , from which it was originally isolated. [4] It is also commonly found in the carnivorous plant genera Drosera and Nepenthes . [5] [6] It is also a component of the black walnut drupe.

See also

References

  1. 1 2 Black Walnut. Drugs.com.
  2. ↑ Jemal Demma; Karl Hallberg; Björn Hellman (2009). "Genotoxicity of plumbagin and its effects on catechol and NQNO-induced DNA damage in mouse lymphoma cells". Toxicology in Vitro. 23 (2): 266–271. Bibcode:2009ToxVi..23..266D. doi:10.1016/j.tiv.2008.12.007. PMID   19124069.
  3. ↑ S B Farr; D O Natvig & T Kogoma (1985). "Toxicity and mutagenicity of plumbagin and the induction of a possible new DNA repair pathway in Escherichia coli". J Bacteriol. 164 (3): 1309–1316. doi:10.1128/JB.164.3.1309-1316.1985. PMC   219331 . PMID   2933393.
  4. ↑ van der Vijver; L. M. (1972). "Distribution of Plumbagin in the Plumbaginaceae". Phytochemistry. 11 (11): 3247–3248. Bibcode:1972PChem..11.3247V. doi:10.1016/S0031-9422(00)86380-3.
  5. ↑ Wang, W.; Luo, X.; Li, H. (2010). "Terahertz and Infrared Spectra of Plumbagin, Juglone, and Menadione". Carnivorous Plant Newsletter . 39 (3): 82–88. doi:10.55360/cpn393.ww544.
  6. ↑ Rischer, H.; Hamm, A.; Bringmann, G. (2002). "Nepenthes insignis Uses a C2-Portion of the Carbon Skeleton of L-Alanine Acquired via its Carnivorous Organs, to Build up the Allelochemical Plumbagin". Phytochemistry. 59 (6): 603–609. Bibcode:2002PChem..59..603R. doi:10.1016/S0031-9422(02)00003-1. PMID   11867092.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.