Plumbagin

For the mineral known as plombagine, see Plumbago (mineral).
Plumbagin
Skeletal formula of plumbagin
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 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C11H8O3/c1-6-5-9(13)10-7(11(6)14)3-2-4-8(10)12/h2-5,12H,1H3 checkY
    Key: VCMMXZQDRFWYSE-UHFFFAOYSA-N checkY
  • 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).
☒N verify (what is checkY☒N ?)

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.

  1. ^ a b 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.