Basic information
- CAS
548-54-9- Standard SMILES
O=C1N=c2ccccc2=C1c1cc(-c2c[nH]c3ccc(O)cc23)[nH]c1O- InChIKey
XAPNKXIRQFHCHN-AQTBWJFISA-N- Molecular formula
- C20H13N3O3
- Average molar mass
- 343.3 g/mol
- Monoisotopic mass
- 343.09569129
Overview
Violacein is a member of the class of hydroxyindoles resulting from the formal oxidative coupling between the 3-position of 1,3-dihydro-2H-indol-2-one and the 3-position of 1,3-dihydro-2H-pyrrol-2-one, which is substituted at the 5 position by a 5-hydroxy-1H-indol-3-yl group, where the newly-formed double bond has E configuration. It is a purple chromobacterial pigment that has antibacterial, antifungal, antiprotozoan, and anticancer properties. It has a role as an antibacterial agent, an antineoplastic agent, an antifungal agent, an apoptosis inducer and a bacterial metabolite. It is a member of pyrroles, a member of oxindoles, an olefinic compound and a member of hydroxyindoles. It is functionally related to a proviolacein.
Names & identifiers
- Preferred name
- Violacein
- IUPAC
- 3-[2-hydroxy-5-(5-hydroxy-1H-indol-3-yl)-1H-pyrrol-3-yl]indol-2-one
- English name
- violacein
- Molecular formula
- C20H13N3O3
- Molecular weight
- 343.34
Names & synonyms
Violacein548-54-9QJH0DSQ3SGUNII-QJH0DSQ3SGBRN 00499232-INDOLINONE, 3-(2-(5-HYDROXYINDOL-3-YL)-5-OXO-2-PYRROLIN-4-YLIDENE)-3-(2-(5-Hydroxyindol-3-yl)-5-oxo-2-pyrrolin-4-ylidene)-2-indolinone4-26-00-00715 (Beilstein Handbook Reference)(E)-3-(5-(5-Hydroxy-1H-indol-3-yl)-2-oxo-1,2-dihydro-3H-pyrrol-3-ylidene)indolin-2-one3-(5-(5-Hydroxy-1H-indol-3-yl)-2-oxo-1,2-dihydro-3H-pyrrol-3-ylidene)indolin-2-one(3E)-3-[5-(5-hydroxy-1H-indol-3-yl)-2-oxo-1,2-dihydro-3H-pyrrol-3-ylidene]-1,3-dihydro-2H-indol-2-one774154-34-6
Show more names
Violacein from Janthinobacterium lividumViolacein from Janthinobacterium lividumOxindole, 3-(2-(5-hydroxyindol-3-yl)-5-oxo-2-pyrrolin-4-ylidene)- (6ci)3-[2-(5-Hydroxy-1H-indol-3-yl)-5-oxo-2-pyrrolin-4-ylidene]-2-indolinone3-[2-(5-Hydroxy-1H-indol-3-yl)-5-oxo-2-pyrrolin-4-ylidene]-1,3-dihydro-2H-indol-2-one
Anorosin(3Z)-violaceinVIOLACEIN [MI]SCHEMBL151999orb1694342CHEMBL1652263SCHEMBL15263185SCHEMBL15263187
Properties
Computed structural properties
- XLogP
- 2.7
- Topological polar surface area
- 101 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 753
Physicochemical properties
- Melting point
- 350 °C · >350 °C (decomp)
- Boiling point
- 821.4 · 821.4±65.0 °C(Predicted)
- Density
- 1.549 · 1.549±0.06 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- 2 O: · H2O: insoluble
- form
- A solid
- pka
- 9.72 · 9.72±0.40(Predicted)
- color
- Brown to black
- Water Solubility
- 2 O: · H2O: insolubleacetone: solubleethanol: solublemethanol: soluble
- Cosmetics Ingredients Functions
- ANTIOXIDANTANTIMICROBIALCOLORANT
- 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/h1-9,21,24H,(H,22,26)(H,23,25)/b18-13-
- InChIKey
- XAPNKXIRQFHCHN-AQTBWJFISA-N
- SMILES
- N1C(=C\C(=C4/c5c(cccc5)NC/4=O)\C1=O)c2c3c([nH]c2)ccc(c3)O
- EWG's Food Scores
- 1 · 1
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Applications
DescriptionViolacein is a naturally occurring di-indole-pyrrole violet-blue colored pigment that possesses numerous biological functions such as antimicrobial, antiviral, anticancer, antiulcerogenic, anti-leishmanial, and enzyme modulation properties (Narsing et al. 2017). Violacein is biosynthesized by bacterial species such as Chromobacterium violaceum, Collimonas sp., Pseudoalteromonas sp., Pseudomonas aeruginosa, and Janthinobacterium sp. This natural pigment is used extensively in the cosmetic, food, pharmaceutical, and textile industries (Baiano 2014).
UsesViolacein is an intense violet pigment formed by the condensation of two tryptophan units, found in a number of bacteria, notably Chromobacterium violaceum. The regulation of pigment biosynthesis is the chromogenic basis for the use of C. violaceum CV26 for the detection of quorum sensing mediators. Violacein exhibits broad spectrum actvity against bacteria, protozoans (including malaria), viruses and mammalian cell lines. Violacein cell toxicity resembles TNF-α signal transduction.
UsesViolacein is tryptpphan-derived pigment produced by environmental bacterial. Violacein inhibits gram-positive pathogens by tearing off cytoplasmic cells as observed in Bacillus subtilis and Staphylococcus aureus cells using fluorescence microscopy.
UsesViolacein from Janthinobacterium lividum has been used:for cell culture assaysas a standard to determine the crude violacein concentration in ethanol extracts of D. violaceinigra str. NI28 culturesas a standard to identify violacein in the leaf samples of Nicotiana
General DescriptionViolacein from Janthinobacterium lividum is used as a colorant for natural and synthetic fabrics. It functions as a respiratory pigment and regulates tryptophan production. Violacein exhibits anti-protozoal activity.
Suppliers28 total
陕西缔都新材料有限公司81124267 17392282731 · [email protected]
武汉敬康恩生物医药科技有限公司13720134139 086-15871494362 13720134139 · [email protected]
Related reactions
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Compound notes
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