Plumbagin

{{for|the mineral known as plombagine|Plumbago (mineral)}}

{{Chembox

| Verifiedfields = changed

| verifiedrevid = 461751697

| Name = Plumbagin

| ImageFile = Plumbagin.PNG

| ImageClass = skin-invert-image

| ImageSize = 180

| ImageName = Skeletal formula of plumbagin

| ImageFile1 = Plumbagin-3D-balls.png

| ImageSize1 = 190

| ImageName1 = Ball-and-stick model of plumbagin

| PIN = 5-Hydroxy-2-methylnaphthalene-1,4-dione

| OtherNames =

| SystematicName =

| Section1 = {{Chembox Identifiers

| IUPHAR_ligand = 7003

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 9790

| PubChem = 10205

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = C10387

| InChI = 1/C11H8O3/c1-6-5-9(13)10-7(11(6)14)3-2-4-8(10)12/h2-5,12H,1H3

| InChIKey = VCMMXZQDRFWYSE-UHFFFAOYAB

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 295316

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C11H8O3/c1-6-5-9(13)10-7(11(6)14)3-2-4-8(10)12/h2-5,12H,1H3

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = VCMMXZQDRFWYSE-UHFFFAOYSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 481-42-5

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = YAS4TBQ4OQ

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 8273

| SMILES = Oc1c2C(=O)cc(C)C(=O)c2ccc1

}}

| Section2 = {{Chembox Properties

| Formula = C11H8O3

| MolarMass = 188.17942 g/mol

| Density =

| MeltingPt =

| BoilingPt =

| Solubility =

}}

| Section3 =

| Section4 =

| Section5 =

| Section6 =

}}

Plumbagin or 5-hydroxy-2-methyl-1,4-naphthoquinone is an organic compound with the chemical formula {{chem|C|11|H|8|O|3}}. It is regarded as a toxin and it is genotoxic{{Cite journal | journal = Toxicology in Vitro | volume = 23 | issue = 2 | year = 2009 | pages = 266–271 | title = Genotoxicity of plumbagin and its effects on catechol and NQNO-induced DNA damage in mouse lymphoma cells |author1=Jemal Demma |author2=Karl Hallberg |author3=Björn Hellman | doi = 10.1016/j.tiv.2008.12.007| pmid = 19124069 | bibcode = 2009ToxVi..23..266D }} and mutagenic.{{Cite journal | journal = J Bacteriol | year = 1985 | volume = 164 | issue = 3 | pages = 1309–1316 | pmc = 219331 | title = Toxicity and mutagenicity of plumbagin and the induction of a possible new DNA repair pathway in Escherichia coli |author1=S B Farr |author2=D O Natvig |author3=T Kogoma | doi = 10.1128/JB.164.3.1309-1316.1985 |name-list-style=amp | pmid=2933393}}

Plumbagin is a yellow dye,[https://www.drugs.com/npp/black-walnut.html Black Walnut]. Drugs.com. formally derived from naphthoquinone.

It is named after the plant genus Plumbago, from which it was originally isolated.{{ cite journal |author1=van der Vijver |author2=L. M. | title = Distribution of Plumbagin in the Plumbaginaceae | journal = Phytochemistry | year = 1972 | volume = 11 | issue = 11 | pages = 3247–3248 | doi = 10.1016/S0031-9422(00)86380-3 |bibcode=1972PChem..11.3247V }}

It is also commonly found in the carnivorous plant genera Drosera and Nepenthes.{{ cite journal |author1=Wang, W. |author2=Luo, X. |author3=Li, H. | title = Terahertz and Infrared Spectra of Plumbagin, Juglone, and Menadione | journal = Carnivorous Plant Newsletter | year = 2010 | volume = 39 | issue = 3 | pages = 82–88 |doi=10.55360/cpn393.ww544 |url=https://www.biodiversitylibrary.org/part/265979 }}{{ cite journal |author1=Rischer, H. |author2=Hamm, A. |author3=Bringmann, G. | title = Nepenthes insignis Uses a C2-Portion of the Carbon Skeleton of L-Alanine Acquired via its Carnivorous Organs, to Build up the Allelochemical Plumbagin | journal = Phytochemistry | year = 2002 | volume = 59 | issue = 6 | pages = 603–609 | doi = 10.1016/S0031-9422(02)00003-1 |pmid=11867092 |bibcode=2002PChem..59..603R }} It is also a component of the black walnut drupe.

See also

References