violacein

Base Information

• Chemical Name: violacein
• CAS No.: 548-54-9
• Molecular Formula: C20H13 N3 O3
• Molecular Weight: 343.342
• Hs Code.: 2933990090
• UNII: QJH0DSQ3SG
• DSSTox Substance ID: DTXSID001028415
• Nikkaji Number: J6.448C
• Wikipedia: Violacein
• Wikidata: Q4013798,Q27225295,Q105324051,Q104402213
• Metabolomics Workbench ID: 103388
• ChEMBL ID: CHEMBL1652263
• Mol file: 548-54-9.mol

Synonyms:2-Indolinone,3-[2-(5-hydroxyindol-3-yl)-5-oxo-2-pyrrolin-4-ylidene]- (7CI,8CI);2H-Indol-2-one,3-[1,2-dihydro-5-(5-hydroxy-1H-indol-3-yl)-2-oxo-3H-pyrrol-3-ylidene]-1,3-dihydro-,(E)-; Oxindole, 3-[2-(5-hydroxyindol-3-yl)-5-oxo-2-pyrrolin-4-ylidene]- (6CI);Violacein

Chemical Property of violacein

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 821.4°Cat760mmHg
• Flash Point: 450.6°C
• PSA: 101.20000
• Density: 1.549g/cm³
• LogP: 3.11110
• Storage Temp.: 2-8°C
• Solubility.: H2O: insoluble
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 343.09569129
• Heavy Atom Count: 26
• Complexity: 753

Purity/Quality:

98%,99%, ^*data from raw suppliers

Violacein ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C(=O)N=C2C=C1)C3=C(NC(=C3)C4=CNC5=C4C=C(C=C5)O)O
• Description: Violacein 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).
• Uses: Violacein 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. Violacein 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. Violacein 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

Technology Process of violacein

There total 15 articles about violacein which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 82.0%

3-[5-(6-Benzyloxy-1,3a-dihydrocyclohepta[b]pyrrol-3-yl)-2-oxo-1,2-dihydropyrrol-3-ylidene]-1,3-dihydroindol-2-one (348128-39-2) → violacein (548-54-9)

Guidance literature:

With cyclohexa-1,4-diene; palladium on activated charcoal; In ethanol; for 1h;

DOI:10.1055/s-2001-12776

Reference yield: 2.5%

L-5-HTP (4350-09-8,4298-20-8) → Oxyviolacein (132185-16-1) + violacein (548-54-9) + Deoxyviolacein (5839-61-2)

Guidance literature:

fermentation in nutrient broth medium;

Reference yield:

5-benzyloxy-1H-indole (1215-59-4) → violacein (548-54-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 85 percent / aq. HCl / 4 h / Heating

2.1: 85 percent / DMAP / tetrahydrofuran / 0 - 20 °C

3.1: LiHMDS / tetrahydrofuran / 1 h / -78 °C

3.2: tetrahydrofuran / -78 - 20 °C

3.3: 24 percent / SiO₂ / 0.33 h / 180 - 210 °C

4.1: 82 percent / cyclohexa-1,4-diene / 10 percent Pd/C / ethanol / 1 h

With hydrogenchloride; dmap; cyclohexa-1,4-diene; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; ethanol;

DOI:10.1055/s-2001-12776

upstream raw materials:

3-[(E)-5-(5-methoxy-indol-3-yl)-2-oxo-1,2-dihydro-pyrrol-3-ylidene]-indolin-2-one

L-Tryptophan

L-5-HTP

3-[5-(6-Benzyloxy-1,3a-dihydrocyclohepta[b]pyrrol-3-yl)-2-oxo-1,2-dihydropyrrol-3-ylidene]-1,3-dihydroindol-2-one

Downstream raw materials:

Acetic acid 1-acetyl-3-{5-oxo-4-[2-oxo-1,2-dihydro-indol-(3E)-ylidene]-4,5-dihydro-1H-pyrrol-2-yl}-1H-indol-5-yl ester

tetramethylviolacein

3-[(E)-5-(5-methoxy-indol-3-yl)-2-oxo-1,2-dihydro-pyrrol-3-ylidene]-indolin-2-one

Refernces

• 1、 Petersen, Mette T.,Nielsen, Thomas E.. "Tandem ring-closing metathesis/isomerization reactions for the total synthesis of violacein". . p. 1986 - 1989. Retrieved 2013/06/05.
• 2、 Hoshino, Tsutomu,Ogasawara, Nagahiro. "Biosynthesis of Violacein: Evidence for the Intermediacy of 5-Hydroxy-L-tryptophan and the Structure of a New Pigment, Oxyviolacein, Produced by the Metabolism of 5-Hydroxytryptophan". . p. 2339 - 2346. Retrieved 2007/10/02.