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Variegatic Acid
Variegatic acid (3,3',4,4'-tetrahydroxypulvinic acid) is an orange pigment found in some mushrooms. It is responsible for the bluing reaction seen in many bolete mushrooms when they are injured. When mushroom tissue containing variegatic acid is exposed to air, the chemical is enzymatically oxidized to blue quinone methide anions, specifically chinonmethid anions. It is derived from xerocomic acid, which is preceded by atromentic acid and atromentin, and its genetic basis is unknown. In its oxidized form (due to the production of a second lactone ring) is variegatorubin, similar to xerocomorubin. It was first isolated from '' Suillus variegatus''. It has strong antioxidant properties, and a nonspecific inhibitory effect on cytochrome P450 enzymes. A total synthesis was reported in 2001 that uses a Suzuki cross coupling reaction. It was found antibiotically inactive against an array of bacteria and fungi using the disk diffusion assay at 50 μg. However, at similar concentrat ...
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Pigment
A pigment is a colored material that is completely or nearly insoluble in water. In contrast, dyes are typically soluble, at least at some stage in their use. Generally dyes are often organic compounds whereas pigments are often inorganic compounds. Pigments of prehistoric and historic value include ochre, charcoal, and lapis lazuli. Economic impact In 2006, around 7.4 million tons of inorganic, organic, and special pigments were marketed worldwide. Estimated at around US$14.86 billion in 2018 and will rise at over 4.9% CAGR from 2019 to 2026. The global demand for pigments was roughly US$20.5 billion in 2009. According to an April 2018 report by ''Bloomberg Businessweek'', the estimated value of the pigment industry globally is $30 billion. The value of titanium dioxide – used to enhance the white brightness of many products – was placed at $13.2 billion per year, while the color Ferrari red is valued at $300 million each year. Physical principles ...
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Suzuki Reaction
The Suzuki reaction is an organic reaction, classified as a cross-coupling reaction, where the coupling partners are a boronic acid and an organohalide and the catalyst is a palladium(0) complex. It was first published in 1979 by Akira Suzuki, and he shared the 2010 Nobel Prize in Chemistry with Richard F. Heck and Ei-ichi Negishi for their contribution to the discovery and development of palladium-catalyzed cross-couplings in organic synthesis. This reaction is also known as the Suzuki–Miyaura reaction or simply as the Suzuki coupling. It is widely used to synthesize poly olefins, styrenes, and substituted biphenyls. Several reviews have been published describing advancements and the development of the Suzuki reaction. The general scheme for the Suzuki reaction is shown below, where a carbon-carbon single bond is formed by coupling a halide (R1-X) with an organoboron species (R2-BY2) using a palladium catalyst and a base. Reaction mechanism The mechanism of the Suzuki r ...
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Polyphenols
Polyphenols () are a large family of naturally occurring organic compounds characterized by multiples of phenol units. They are abundant in plants and structurally diverse. Polyphenols include flavonoids, tannic acid, and ellagitannin, some of which have been used historically as dyes and for tanning garments. Etymology The name derives from the Ancient Greek word (''polus'', meaning "many, much") and the word phenol which refers to a chemical structure formed by attaching to an aromatic benzenoid (phenyl) ring to a hydroxyl (-OH) group as is found in alcohols (hence the ''-ol'' suffix). The term polyphenol has been in use at least since 1894. Definition The term polyphenol is not well-defined, but is generally agreed that they are natural products "having a polyphenol structure (i.e., several hydroxyl groups on aromatic rings)" including four principal classes: "phenolic acids, flavonoids, stilbenes, and lignans". *Flavonoids include flavones, flavonols, flavanols, f ...
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Biological Pigments
Biological pigments, also known simply as pigments or biochromes, are substances produced by living organisms that have a color resulting from selective color absorption. Biological pigments include plant pigments and flower pigments. Many biological structures, such as skin, eyes, feathers, fur and hair contain pigments such as melanin in specialized cells called chromatophores. In some species, pigments accrue over very long periods during an individual's lifespan. Pigment color differs from structural color in that it is the same for all viewing angles, whereas structural color is the result of selective reflection or iridescence, usually because of multilayer structures. For example, butterfly wings typically contain structural color, although many butterflies have cells that contain pigment as well. Biological pigments See conjugated systems for electron bond chemistry that causes these molecules to have pigment. * Heme/porphyrin-based: chlorophyll, bilirubin, hemocy ...
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Vulpinic Acid
Vulpinic acid is a natural product first found in and important in the symbiosis underlying the biology of lichens. It is a simple methyl ester derivative of its parent compound, pulvinic acid, and a close relative of pulvinone, both of which derive from aromatic amino acids such as phenylalanine via secondary metabolism. The roles of vulpinic acid are not fully established, but may include properties that make it an antifeedant for herbivores. The compound is relatively toxic to mammals. Chemical description Vulpinic acid was first isolated from lichens in 1925. As an isolated, purified substance, it is bright yellow in color. Vulpinic acid is derived biosynthetically by esterification from pulvinic acid; pulvinate itself derives from the aromatic amino acids phenylalanine and tyrosine, via dimerization and oxidative ring-cleavage of arylpyruvic acids, a process that also produces the related pulvinones. There have been several chemical syntheses reported for vulpinic acid. ...
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Pulvinone
Pulvinone, an organic compound belonging to the esters, lactones, alcohols and butenolides classes, is a yellow crystalline solid. Although the pulvinone is not a natural product, several naturally occurring hydroxylated derivatives are known. These hydroxylated pulvinones are produced by fungal species, such as the in Europe common Larch Bolete (''Boletus elegans'', also known as ''Suillus grevillei''), or by moulds such as ''Aspergillus terreus''. History Fungi (such as boleti), moulds and lichens produce a wide range of pigments made up of one (monomer) or several (oligomers) units of pulvinic acid. In 1831, in the course of a study of the constituents of lichens (''Cetraria Vulpina''), the French chemist and pharmacist Antoine Bebert discovered a compound named ''vulpinic acid'', the first known naturally occurring methyl ester of pulvinic acid. More details about the structure of this pigment were disclosed in 1860 by the German chemists Franz Möller and Adolph Strecker.'' ...
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Pulvinic Acid
Pulvinic acids are natural chemical pigments found in some lichens, derived biosynthetically from the aromatic amino acids phenylalanine and tyrosine, via dimerization and oxidative ring-cleavage of aryl pyruvic acids, a process that also produces the related pulvinones. Hydroxypulvinic acid pigments (pulvinic acid type family of pigments) have been found in ''Boletus'' (e.g. '' Boletus erythropus''), '' Boletinus'', ''Chalciporus'', ''Gyrodon'', ''Leccinum'', '' Pulveroboletus'', ''Suillus'' (e.g. ''Suillus luteus'', ''Suillus bovinus'', and ''Suillus grevillei''), ''Paxillus'' (e.g. ''Paxillus involutus''), ''Serpula'' (e.g. '' Serpula lacrymans''), '' Xerocomus'' (e.g. '' Xerocomus chrysenteron''), ''Hygrophoropsis'' (e.g. ''Hygrophoropsis aurantiaca''), '' Retiboletus'' (e.g. '' Retiboletus nigerrimus''), '' Pulveroboletus'' (e.g. '' Pulveroboletus auriflammeus''), and are generally characteristic of Boletales. In addition to pulvinone, derivatives and related pigments ...
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Boletales
The Boletales are an order of Agaricomycetes containing over 1300 species with a diverse array of fruiting body types. The boletes are the best known members of this group, and until recently, the Boletales were thought to only contain boletes. The Boletales are now known to contain distinct groups of agarics, puffballs, and other fruiting-body types. Taxonomy The order Boletales originally was created to describe boletes, but based on micromorphological and molecular phylogenetic characteristics, a large number of nonbolete species have recently been reclassified to belong to this group, as well. The order also includes some gilled mushrooms, in the families Gomphidiaceae, Serpulaceae, Tapinellaceae, Hygrophoropsidaceae, and Paxillaceae, which often have the same flesh texture as the boletes, spore-bearing tissue which is also easily separable from the cap, and similar microscopic characteristics of spores and cystidia. Taxonomic studies using secondary metabolites and later ...
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Saprobic
Saprotrophic nutrition or lysotrophic nutrition is a process of chemoheterotrophic extracellular digestion involved in the processing of decayed (dead or waste) organic matter. It occurs in saprotrophs, and is most often associated with fungi (for example ''Mucor'') and soil bacteria. Saprotrophic microscopic fungi are sometimes called saprobes; saprotrophic plants or bacterial flora are called saprophytes ( sapro- 'rotten material' + -phyte 'plant'), although it is now believed that all plants previously thought to be saprotrophic are in fact parasites of microscopic fungi or other plants. The process is most often facilitated through the active transport of such materials through endocytosis within the internal mycelium and its constituent hyphae. states the purpose of saprotrophs and their internal nutrition, as well as the main two types of fungi that are most often referred to, as well as describes, visually, the process of saprotrophic nutrition through a diagram of hyph ...
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Fenton Chemistry
Fenton's reagent is a solution of hydrogen peroxide (H2O2) with ferrous iron (typically iron(II) sulfate, FeSO4) as a catalyst that is used to oxidize contaminants or waste waters as part of an advanced oxidation process. Fenton's reagent can be used to destroy organic compounds such as trichloroethylene (TCE) and tetrachloroethylene (perchloroethylene, PCE). It was developed in the 1890s by Henry John Horstman Fenton as an analytical reagent. Overview Iron(II) is oxidized by hydrogen peroxide to iron(III), forming a hydroxyl radical and a hydroxide ion in the process. Iron(III) is then reduced back to iron(II) by another molecule of hydrogen peroxide, forming a hydroperoxyl radical and a proton. The net effect is a disproportionation of hydrogen peroxide to create two different oxygen-radical species, with water (H+ + OH−) as a byproduct. The free radicals generated by this process then engage in secondary reactions. For example, the hydroxyl is a powerful, no ...
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Total Synthesis
Total synthesis is the complete chemical synthesis of a complex molecule, often a natural product, from simple, commercially-available precursors. It usually refers to a process not involving the aid of biological processes, which distinguishes it from semisynthesis. Syntheses may sometimes conclude at a precursor with further known synthetic pathways to a target molecule, in which case it is known as a formal synthesis. Total synthesis target molecules can be natural products, medicinally-important active ingredients, known intermediates, or molecules of theoretical interest. Total synthesis targets can also be organometallic or inorganic, though these are rarely encountered. Total synthesis projects often require a wide diversity of reactions and reagents, and subsequently requires broad chemical knowledge and training to be successful. Often, the aim is to discover a new route of synthesis for a target molecule for which there already exist known routes. Sometimes, however, no ...
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