Plumbagin

Plumbagin
Names
	Preferred IUPAC name 5-Hydroxy-2-methylnaphthalene-1,4-dione
Identifiers
CAS Number	481-42-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:8273 ;
ChEMBL	ChEMBL295316 ;
ChemSpider	9790 ;
IUPHAR/BPS	7003;
KEGG	C10387 ;
PubChem CID	10205;
UNII	YAS4TBQ4OQ ;
	InChI InChI=1S/C11H8O3/c1-6-5-9(13)10-7(11(6)14)3-2-4-8(10)12/h2-5,12H,1H3 Key: VCMMXZQDRFWYSE-UHFFFAOYSA-N ; 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;
	SMILES Oc1c2C(=O)cc(C)C(=O)c2ccc1;
Properties
Chemical formula	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).
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	Infobox references

Plumbagin or 5-hydroxy-2-methyl-1,4-naphthoquinone is an organic compound with the chemical formula C₁₁H₈O₃. 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.

References

↑ ^1.0 ^1.1 Black Walnut. Drugs.com.
↑ 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.
↑ 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. PMID 2933393.
↑ 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.
↑ Wang, W.; Luo, X.; Li, H. (2010). "Terahertz and Infrared Spectra of Plumbagin, Juglone, and Menadione". Carnivorous Plant Newsletter 39 (3): 82–88.
↑ 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.

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[walnut-1] 1.0 ^1.1 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. 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.

[Rischer-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.

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Plumbagin

Topic: Chemistry

See also

References