3,6-Dihydroxyindoxazene

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3,6-Dihydroxyindoxazene
Category Antibiotics
Catalog number BBF-01149
CAS 86004-57-1
Molecular Weight 151.12
Molecular Formula C7H5NO3
Purity >95%

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Description

It is produced by the strain of Chromobacterium violaceum BMF34-EG2. It has antibacterial effect against a number of gram-negative bacteria.

Specification

Synonyms Antibiotic Y-T0678H; Y-T0678H; 6-Hydroxy-3-oxo-1,2-benzisoxazolin; 6-Hydroxy-1,2-benzisoxazol-3(2H)-one; 6-Hydroxybenzo[d]isoxazol-3(2H)-one; 1,2-Benzoisoxazole-3,6-diol; Bactropone
IUPAC Name 6-hydroxy-1,2-benzoxazol-3-one
Canonical SMILES C1=CC2=C(C=C1O)ONC2=O
InChI InChI=1S/C7H5NO3/c9-4-1-2-5-6(3-4)11-8-7(5)10/h1-3,9H,(H,8,10)
InChI Key BSVWKKOEZYADMB-UHFFFAOYSA-N

Properties

Appearance Crystal
Antibiotic Activity Spectrum Gram-negative bacteria
Boiling Point 397.6 °C at 760 mmHg
Melting Point 248-250 °C
Density 1.503 g/cm3
Solubility Soluble in Methanol

Reference Reading

1. Chromobacterium violaceum: a review of pharmacological and industiral perspectives
N Durán, C F Menck Crit Rev Microbiol. 2001;27(3):201-22. doi: 10.1080/20014091096747.
Violet-pigmented bacteria, which have been described since the end of the 19th century, are occasionally the causative agent of septicemia and sometimes cause fatal infection in human and animals. Bacteria, producing violet colonies due to the production of a nondiffusible pigment violacein, were classified as a redefined genus Chromobacterium. Chromobacterium violaceum is gram-negative, and saprophyte from soil and water is normally considered nonpathogenic to human, but is an opportunistic pathogen of extreme virulence for human and animals. The biosynthesis and biological activities of violacein and the diverse effects of this pigment have been studied. Besides violacein, C. violaceum produces other antibiotics, such as aerocyanidin and aerocavin, which exhibit in vitro activity against both gram-negative and gram-positive bacteria. 3,6-Dihydroxyindoxazene and Y-TO678h exhibit a selective activity against gram-negative bacteria. Arphamenine A and B, and FR901228, that enhanced immunoresponse, and potentiators of beta-lactam antibiotics and chelators such as ferrioxamine exhibit important clinical potential applications. Lipopolysaccharides and polyhydroxyesters together with several enzymes appear as important metabolites with biotechnological applications. Many of these metabolites were already studied at the genome level.

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