Plumbagin

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Plumbagin
Plumbagin.PNG
Plumbagin-3D-balls.png
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
11
H
8
O
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

Related Research Articles

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Barbigerone Chemical compound

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Pterocarpan

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1,4-Naphthoquinone Chemical compound

1,4-Naphthoquinone or para-naphthoquinone is an quinone derived from naphthalene. It forms volatile yellow triclinic crystals and has a sharp odor similar to benzoquinone. It is almost insoluble in cold water, slightly soluble in petroleum ether, and more soluble in polar organic solvents. In alkaline solutions it produces a reddish-brown color. Vitamin K is a derivative of 1,4-naphthoquinone. It is a planar molecule with one aromatic ring fused to a quinone subunit. It is an isomer of 1,2-naphthoquinone.

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1,4-dihydroxy-2-naphthoyl-CoA hydrolase (EC 3.1.2.28) is an enzyme with systematic name 1,4-dihydroxy-2-naphthoyl-CoA hydrolase. This enzyme catalyses the following chemical reaction

Pisatin Chemical compound

Pisatin (3-hydroxy-7-methoxy-4′,5′-methylenedioxy-chromanocoumarane) is the major phytoalexin made by the pea plant Pisum sativum. It was the first phytoalexin to be purified and chemically identified. The molecular formula is C17H14O6.

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. 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. 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.
  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. doi:10.1016/S0031-9422(02)00003-1. PMID   11867092.