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6,6′-Dibromoindigo
6,6'-Dibromoindigo is an organic compound with the formula (BrC6H3C(O)CNH)2. A deep purple solid, the compound is also known as Tyrian purple, a dye of historic significance. Presently, it is only a curiosity, although the related derivative indigo is of industrial significance. The molecule consists of a pair of monobrominated indole rings linked by a carbon-carbon double bond. It is produced by molluscs of the ''Muricidae'' species. Biosynthesis The biosynthesis proceeds by the intermediacy of tyrindoxyl sulphate. 6BrIG can also produced enzymatically in vitro from the amino acid tryptophan. The sequence begins with bromination of the benzo ring followed by conversion to 6-bromoindole Indole is an aromatic heterocyclic organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other c .... Flavin-containing monooxygenase the ...
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Tyrian Purple
Tyrian purple ( grc, πορφύρα ''porphúra''; la, purpura), also known as Phoenician red, Phoenician purple, royal purple, imperial purple, or imperial dye, is a reddish-purple natural dye. The name Tyrian refers to Tyre, Lebanon. It is secreted by several species of predatory sea snails in the family Muricidae, rock snails originally known by the name 'Murex'. In ancient times, extracting this dye involved tens of thousands of snails and substantial labor, and as a result, the dye was highly valued. The colored compound is 6,6′-dibromoindigo. History Biological pigments were often difficult to acquire, and the details of their production were kept secret by the manufacturers. Tyrian purple is a pigment made from the mucus of several species of Murex snail. Production of Tyrian purple for use as a fabric dye began as early as 1200 BCE by the Phoenicians, and was continued by the Greeks and Romans until 1453 CE, with the fall of Constantinople. The pigment was expensiv ...
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Organic Compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The study of the properties, reactions, and syntheses of organic compounds comprise the discipline known as organic chemistry. For historical reasons, a few classes of carbon-containing compounds (e.g., carbonate salts and cyanide salts), along with a few other exceptions (e.g., carbon dioxide, hydrogen cyanide), are not classified as organic compounds and are considered inorganic. Other than those just named, little consensus exists among chemists on precisely which carbon-containing compounds are excluded, making any rigorous definition of an organic compound elusive. Although organic compounds make up only a small percentage of Earth's crust, they are of central importance because all known life is based on organic compounds. Living t ...
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Indigo Dye
Indigo dye is an organic compound with a distinctive blue color. Historically, indigo was a natural dye extracted from the leaves of some plants of the ''Indigofera'' genus, in particular ''Indigofera tinctoria''; dye-bearing ''Indigofera'' plants were commonly grown and used throughout the world, in Asia in particular, as an important crop, with the production of indigo dyestuff economically important due to the previous rarity of some blue dyestuffs historically. Most indigo dye produced today is synthetic, constituting several thousand tons each year. It is most commonly associated with the production of denim cloth and blue jeans, where its properties allow for effects such as stone washing and acid washing to be applied quickly. Uses The primary use for indigo is as a dye for cotton yarn, mainly used in the production of denim cloth suitable for blue jeans; on average, a pair of blue jeans requires just to of dye. Smaller quantities are used in the dyeing of wool and ...
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Indole
Indole is an aromatic heterocyclic organic compound with the formula C8 H7 N. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered pyrrole ring. Indole is widely distributed in the natural environment and can be produced by a variety of bacteria. As an intercellular signal molecule, indole regulates various aspects of bacterial physiology, including spore formation, plasmid stability, resistance to drugs, biofilm formation, and virulence. The amino acid tryptophan is an indole derivative and the precursor of the neurotransmitter serotonin. General properties and occurrence Indole is a solid at room temperature. It occurs naturally in human feces and has an intense fecal odor. At very low concentrations, however, it has a flowery smell, and is a constituent of many perfumes. It also occurs in coal tar. The corresponding substituent is called indolyl. Indole undergoes electrophilic substitution, mainly at position 3 (see diagra ...
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Mollusc
Mollusca is the second-largest phylum of invertebrate animals after the Arthropoda, the members of which are known as molluscs or mollusks (). Around 85,000  extant species of molluscs are recognized. The number of fossil species is estimated between 60,000 and 100,000 additional species. The proportion of undescribed species is very high. Many taxa remain poorly studied. Molluscs are the largest marine phylum, comprising about 23% of all the named marine organisms. Numerous molluscs also live in freshwater and terrestrial habitats. They are highly diverse, not just in size and anatomical structure, but also in behaviour and habitat. The phylum is typically divided into 7 or 8 taxonomic classes, of which two are entirely extinct. Cephalopod molluscs, such as squid, cuttlefish, and octopuses, are among the most neurologically advanced of all invertebrates—and either the giant squid or the colossal squid is the largest known invertebrate species. The gastropods ...
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Biosynthesis
Biosynthesis is a multi-step, enzyme-catalyzed process where substrates are converted into more complex products in living organisms. In biosynthesis, simple compounds are modified, converted into other compounds, or joined to form macromolecules. This process often consists of metabolic pathways. Some of these biosynthetic pathways are located within a single cellular organelle, while others involve enzymes that are located within multiple cellular organelles. Examples of these biosynthetic pathways include the production of lipid membrane components and nucleotides. Biosynthesis is usually synonymous with anabolism. The prerequisite elements for biosynthesis include: precursor compounds, chemical energy (e.g. ATP), and catalytic enzymes which may require coenzymes (e.g.NADH, NADPH). These elements create monomers, the building blocks for macromolecules. Some important biological macromolecules include: proteins, which are composed of amino acid monomers joined via peptide bon ...
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Amino Acid
Amino acids are organic compounds that contain both amino and carboxylic acid functional groups. Although hundreds of amino acids exist in nature, by far the most important are the alpha-amino acids, which comprise proteins. Only 22 alpha amino acids appear in the genetic code. Amino acids can be classified according to the locations of the core structural functional groups, as Alpha and beta carbon, alpha- , beta- , gamma- or delta- amino acids; other categories relate to Chemical polarity, polarity, ionization, and side chain group type (aliphatic, Open-chain compound, acyclic, aromatic, containing hydroxyl or sulfur, etc.). In the form of proteins, amino acid '' residues'' form the second-largest component (water being the largest) of human muscles and other tissues. Beyond their role as residues in proteins, amino acids participate in a number of processes such as neurotransmitter transport and biosynthesis. It is thought that they played a key role in enabling life ...
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Tryptophan
Tryptophan (symbol Trp or W) is an α-amino acid that is used in the biosynthesis of proteins. Tryptophan contains an α-amino group, an α- carboxylic acid group, and a side chain indole, making it a polar molecule with a non-polar aromatic beta carbon substituent. It is essential in humans, meaning that the body cannot synthesize it and it must be obtained from the diet. Tryptophan is also a precursor to the neurotransmitter serotonin, the hormone melatonin, and vitamin B3. It is encoded by the codon UGG. Like other amino acids, tryptophan is a zwitterion at physiological pH where the amino group is protonated (–; pKa = 9.39) and the carboxylic acid is deprotonated ( –COO−; pKa = 2.38). Humans and many animals cannot synthesize tryptophan: they need to obtain it through their diet, making it an essential amino acid. Function Amino acids, including tryptophan, are used as building blocks in protein biosynthesis, and proteins are required to sustain life. Man ...
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Paul Friedländer (chemist)
Paul Friedländer (29 August 1857 in Königsberg – 4 September 1923 in Darmstadt) was a German chemist best known for his research on derivates of indigo (for example thioindigo) and isolation of Tyrian purple from ''Murex brandaris''. Life and work Paul Friedländer was born as son of Ludwig Friedländer in Königsberg in 1857. The chemist Carl Gräbe was a regular guest of his father; thus after finishing the gymnasium, Friedländer studied chemistry in Königsberg in the laboratories of Gräbe. Later he studied at the Strasbourg and Munich where he assisted Adolf von Baeyer. He received his PhD for the work with Baeyer and completed his habilitation in 1883. He left the well-equipped laboratories of Baeyer in Munich in 1884 to work in the small company K. Oehler in Offenbach. In 1888, he became professor at the University of Karlsruhe. During a visit at his parents in Königsberg, he got engaged and married Martha Kobligk; they had three daughters. Although he liked stayi ...
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Indigo Structure Dyes
Indigo is a deep color close to the color wheel blue (a primary color in the RGB color space), as well as to some variants of ultramarine, based on the ancient dye of the same name. The word "indigo" comes from the Latin word ''indicum'', meaning "Indian", as the dye was originally exported to Europe from India. It is traditionally regarded as a color in the visible spectrum, as well as one of the seven colors of the rainbow: the color between blue and violet; however, sources differ as to its actual position in the electromagnetic spectrum. The first known recorded use of indigo as a color name in English was in 1289. History ''Indigofera tinctoria'' and related species were cultivated in East Asia, Egypt, India, Bangladesh and Peru in antiquity. The earliest direct evidence for the use of indigo dates to around 4000 BC and comes from Huaca Prieta, in contemporary Peru. Pliny the Elder mentions India as the source of the dye after which it was named. It was imported f ...
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