Violacein

Violacein
Names
	IUPAC name (3E)-3-[5-(5-Hydroxy-1H-indol-3-yl)-2-oxo-1,2-dihydro-3H-pyrrol-3-ylidene]-1,3-dihydro-2H-indol-2-one
	Other names 3-(2-(5-Hydroxyindol-3-yl)-5-oxo-2-pyrrolin-4-ylidene)-2-indolinone
Identifiers
CAS Number	548-54-9 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:131914;
ChEMBL	ChEMBL1652263 ;
ChemSpider	8103672 ;
KEGG	C21136;
PubChem CID	11053;
UNII	QJH0DSQ3SG;
CompTox Dashboard (EPA)	DTXSID001028415 ;
	InChI InChI=1S/C20H13N3O3/c24-10-5-6-15-12(7-10)14(9-21-15)17-8-13(19(25)23-17)18-11-3-1-2-4-16(11)22-20(18)26/h1-9,21,23-25H Key: SHLJIZCPRXXHHZ-UHFFFAOYSA-N;
	SMILES C1=CC=C2C(=C1)/C(=C\3/C=C(NC3=O)C4=CNC5=C4C=C(C=C5)O)/C(=O)N2;
Properties
Chemical formula	C20H13N3O3
Molar mass	343.342 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Violacein is a naturally-occurring bis-indole pigment with antibiotic (anti-bacterial, anti-viral, anti-fungal and anti-tumor) properties.^[1]^[2]^[3]^[4] Violacein is produced by several species of bacteria, including Chromobacterium violaceum, and gives these organisms their striking purple hues. Violacein shows increasing commercially interesting uses, especially for industrial applications in cosmetics, medicines and fabrics.

^ Durán N, Justo GZ, Durán M, Brocchi M, Cordi L, Tasic L, et al. (2016). "Advances in Chromobacterium violaceum and properties of violacein-Its main secondary metabolite: A review". Biotechnology Advances. 34 (5): 1030–1045. doi:10.1016/j.biotechadv.2016.06.003. hdl:11336/49517. PMID 27288924.
^ Myeong NR, Seong HJ, Kim HJ, Sul WJ (April 2016). "Complete genome sequence of antibiotic and anticancer agent violacein producing Massilia sp. strain NR 4-1". Journal of Biotechnology. 223: 36–37. doi:10.1016/j.jbiotec.2016.02.027. PMID 26916415.
^ Choi SY, Yoon KH, Lee JI, Mitchell RJ (2015). "Violacein: Properties and Production of a Versatile Bacterial Pigment". BioMed Research International. 2015: 465056. doi:10.1155/2015/465056. PMC 4538413. PMID 26339614.
^ Andrighetti-Fröhner CR, Antonio RV, Creczynski-Pasa TB, Barardi CR, Simões CM (September 2003). "Cytotoxicity and potential antiviral evaluation of violacein produced by Chromobacterium violaceum". Memórias do Instituto Oswaldo Cruz. 98 (6): 843–848. doi:10.1590/s0074-02762003000600023. PMID 14595466.

[Duran-1] Durán N, Justo GZ, Durán M, Brocchi M, Cordi L, Tasic L, et al. (2016). "Advances in Chromobacterium violaceum and properties of violacein-Its main secondary metabolite: A review". Biotechnology Advances. 34 (5): 1030–1045. doi:10.1016/j.biotechadv.2016.06.003. hdl:11336/49517. PMID 27288924.

[Myeong-2] Myeong NR, Seong HJ, Kim HJ, Sul WJ (April 2016). "Complete genome sequence of antibiotic and anticancer agent violacein producing Massilia sp. strain NR 4-1". Journal of Biotechnology. 223: 36–37. doi:10.1016/j.jbiotec.2016.02.027. PMID 26916415.

[Choi-3] Choi SY, Yoon KH, Lee JI, Mitchell RJ (2015). "Violacein: Properties and Production of a Versatile Bacterial Pigment". BioMed Research International. 2015: 465056. doi:10.1155/2015/465056. PMC 4538413. PMID 26339614.

[4] Andrighetti-Fröhner CR, Antonio RV, Creczynski-Pasa TB, Barardi CR, Simões CM (September 2003). "Cytotoxicity and potential antiviral evaluation of violacein produced by Chromobacterium violaceum". Memórias do Instituto Oswaldo Cruz. 98 (6): 843–848. doi:10.1590/s0074-02762003000600023. PMID 14595466.

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