Although the first chemical synthesis was reported in 1914, unlike indigo, it has never been synthesized at commercial level. The main chemical constituent of the Tyrian dye was discovered by Paul Friedländer in 1909 to be 6,6′-dibromoindigo, derivative of indigo dye, which had been synthesized in 1903. Flavin-containing monooxygenase then couples two of these indole units to give the dye. The sequence begins with bromination of the benzo ring followed by conversion to 6-bromo indole. ĦBrIG can also be produced enzymatically in vitro from the amino acid tryptophan. The biosynthesis proceeds by the intermediacy of tyrindoxyl sulphate. It is produced by molluscs of the Muricidae species. The molecule consists of a pair of monobrominated indole rings linked by a carbon-carbon double bond. Presently, it is only a curiosity, although the related derivative indigo is of industrial significance. A deep purple solid, the compound is also known as Tyrian purple, a dye of historic significance. 6,6'-Dibromoindigo is an organic compound with the formula (BrC 6H 3C(O)CNH) 2.
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