Tannins
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Tannins
Tannins (or tannoids) are a class of astringent, polyphenolic biomolecules that bind to and precipitate proteins and various other organic compounds including amino acids and alkaloids. The term ''tannin'' (from Anglo-Norman ''tanner'', from Medieval Latin ''tannāre'', from ''tannum'', oak bark) refers to the use of oak and other bark in tanning animal hides into leather. By extension, the term ''tannin'' is widely applied to any large polyphenolic compound containing sufficient hydroxyls and other suitable groups (such as carboxyls) to form strong complexes with various macromolecules. The tannin compounds are widely distributed in many species of plants, where they play a role in protection from predation (acting as pesticides) and might help in regulating plant growth. The astringency from the tannins is what causes the dry and puckery feeling in the mouth following the consumption of unripened fruit, red wine or tea. Likewise, the destruction or modification of tann ...
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Tannin Heap
Tannins (or tannoids) are a class of astringent, polyphenolic biomolecules that bind to and precipitate proteins and various other organic compounds including amino acids and alkaloids. The term ''tannin'' (from Anglo-Norman ''tanner'', from Medieval Latin ''tannāre'', from ''tannum'', oak bark) refers to the use of oak and other bark in tanning animal hides into leather. By extension, the term ''tannin'' is widely applied to any large polyphenolic compound containing sufficient hydroxyls and other suitable groups (such as carboxyls) to form strong complexes with various macromolecules. The tannin compounds are widely distributed in many species of plants, where they play a role in protection from predation (acting as pesticides) and might help in regulating plant growth. The astringency from the tannins is what causes the dry and puckery feeling in the mouth following the consumption of unripened fruit, red wine or tea. Likewise, the destruction or modification of t ...
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Hydrolyzable Tannin
A hydrolyzable tannin or pyrogallol-type tannin is a type of tannin that, on heating with hydrochloric or sulfuric acids, yields gallic or ellagic acids. At the center of a hydrolyzable tannin molecule, there is a carbohydrate (usually D-glucose but also cyclitols like quinic or shikimic acids). The hydroxyl groups of the carbohydrate are partially or totally esterified with phenolic groups such as gallic acid in gallotannins or ellagic acid in ellagitannins. Hydrolysable tannins are mixtures of polygalloyl glucoses and/or poly-galloyl quinic acid derivatives containing in between 3 up to 12 gallic acid residues per molecule. Hydrolyzable tannins are hydrolyzed by weak acids or weak bases to produce carbohydrate and phenolic acids. Examples of gallotannins are the gallic acid esters of glucose in tannic acid (C76H52O46), found in the leaves and bark of many plant species. Hydrolysable tannins can be extracted from different vegetable plants, such as chestnut wood (''Castan ...
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Proanthocyanidin
Proanthocyanidins are a class of polyphenols found in many plants, such as cranberry, blueberry, and grape seeds. Chemically, they are oligomeric flavonoids. Many are oligomers of catechin and epicatechin and their gallic acid esters. More complex polyphenols, having the same polymeric building block, form the group of tannins. Proanthocyanidins were discovered in 1947 by Jacques Masquelier, who developed and patented techniques for the extraction of oligomeric proanthocyanidins from pine bark and grape seeds. Often associated with prevention of urinary tract infections (UTIs) by consuming cranberries, grape seeds or red wine, proanthocyanidins have not been conclusively shown as effective for preventing or treating UTIs. Distribution in plants Proanthocyanidins, including the lesser bioactive and bioavailable polymers (four or more catechins), represent a group of condensed flavan-3-ols, such as procyanidins, prodelphinidins and propelargonidins. They can be found in many plant ...
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Tanning (leather)
Tanning is the process of treating Skinning, skins and Hide (skin), hides of animals to produce leather. A tannery is the place where the skins are processed. Tanning hide into leather involves a process which permanently alters the protein structure of skin, making it more durable and less susceptible to decomposition and coloring. Before tanning, the skins are dehaired, degreased, desalted and soaked in water over a period of six hours to two days. Historically this process was considered a noxious or "odoriferous trade" and relegated to the outskirts of town. Historically, tanning used tannin, an acidic chemical compound from which the tanning process draws its name, derived from the bark of certain trees. An alternative method, developed in the 1800s, is chrome tanning, where chromium salts are used instead of natural tannins. History The English word for tanning is from medieval Latin , derivative of (oak bark), from French (tanbark), from old-Cornish (red oak). ...
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Astringency
An astringent (sometimes called adstringent) is a chemical that shrinks or constricts body tissues. The word derives from the Latin ''adstringere'', which means "to bind fast". Calamine lotion, witch hazel, and yerba mansa, a Californian plant, are astringents. Astringency, the dry, puckering or numbing mouthfeel caused by the tannins in unripe fruits, lets the fruit mature by deterring eating. Ripe fruits and fruit parts including blackthorn (sloe berries), ''Aronia'' chokeberry, chokecherry, bird cherry, rhubarb, quince and persimmon fruits (especially those which are unripe), banana skins (or unripe bananas), cashew fruits and acorns are astringent. Citrus fruits, like lemons, are somewhat astringent. Tannins, being a kind of polyphenol, bind salivary proteins and make them precipitate and aggregate, producing a rough, "sandpapery", or dry sensation in the mouth. The tannins in some teas, coffee, and red grape wines like Cabernet Sauvignon and Merlot produce mild astringenc ...
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Tannic Acid
Tannic acid is a specific form of tannin, a type of polyphenol. Its weak acidity ( pKa around 6) is due to the numerous phenol groups in the structure. The chemical formula for commercial tannic acid is often given as C76H52O46, which corresponds with decagalloyl glucose, but in fact it is a mixture of polygalloyl glucoses or polygalloyl quinic acid esters with the number of galloyl moieties per molecule ranging from 2 up to 12 depending on the plant source used to extract the tannic acid. Commercial tannic acid is usually extracted from any of the following plant parts: Tara pods (''Caesalpinia spinosa''), gallnuts from '' Rhus semialata'' or ''Quercus infectoria'' or Sicilian sumac leaves (''Rhus coriaria''). According to the definitions provided in external references such as international pharmacopoeia, Food Chemicals Codex and FAO-WHO tannic acid monograph only tannins obtained from the above-mentioned plants can be considered as tannic acid. Sometimes extracts from chestnu ...
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Astringent
An astringent (sometimes called adstringent) is a chemical that shrinks or constricts body tissues. The word derives from the Latin ''adstringere'', which means "to bind fast". Calamine lotion, witch hazel, and yerba mansa, a Californian plant, are astringents. Astringency, the dry, puckering or numbing mouthfeel caused by the tannins in unripe fruits, lets the fruit mature by deterring eating. Ripe fruits and fruit parts including blackthorn (sloe berries), ''Aronia'' chokeberry, chokecherry, bird cherry, rhubarb, quince and persimmon fruits (especially those which are unripe), banana skins (or unripe bananas), cashew fruits and acorns are astringent. Citrus fruits, like lemons, are somewhat astringent. Tannins, being a kind of polyphenol, bind salivary proteins and make them precipitate and aggregate, producing a rough, "sandpapery", or dry sensation in the mouth. The tannins in some teas, coffee, and red grape wines like Cabernet Sauvignon and Merlot produce mild as ...
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Precipitation (chemistry)
In an aqueous solution, precipitation is the process of transforming a dissolved chemical substance, substance into an insoluble solid from a Supersaturated solution, super-saturated solution. The solid formed is called the precipitate. In case of an inorganic chemical reaction leading to precipitation, the chemical reagent causing the solid to form is called the ''precipitant''. The clear liquid remaining above the precipitated or the centrifuged solid phase is also called the 'supernate' or 'supernatant'. The notion of precipitation can also be extended to other domains of chemistry (organic chemistry and biochemistry) and even be applied to the solid phases (''e.g.'', metallurgy and alloys) when solid impurities Segregation (materials science), segregate from a solid phase. Supersaturation The precipitation of a compound may occur when its concentration exceeds its solubility. This can be due to temperature changes, solvent evaporation, or by mixing solvents. Precipitatio ...
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Pesticides
Pesticides are substances that are meant to control pests. This includes herbicide, insecticide, nematicide, molluscicide, piscicide, avicide, rodenticide, bactericide, insect repellent, animal repellent, microbicide, fungicide, and lampricide. The most common of these are herbicides which account for approximately 80% of all pesticide use. Most pesticides are intended to serve as plant protection products (also known as crop protection products), which in general, protect plants from weeds, fungi, or insects. As an example, the fungus ''Alternaria solani'' is used to combat the aquatic weed ''Salvinia''. In general, a pesticide is a chemical (such as carbamate) or biological agent (such as a virus, bacterium, or fungus) that deters, incapacitates, kills, or otherwise discourages pests. Target pests can include insects, plant pathogens, weeds, molluscs, birds, mammals, fish, nematodes (roundworms), and microbes that destroy property, cause nuisance, or spread disease, or ar ...
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Flavan-3-ol
Flavan-3-ols (sometimes referred to as flavanols) are a subgroup of flavonoids. They are derivatives of flavans that possess a 2-phenyl-3,4-dihydro-2''H''-chromen-3-ol skeleton. Flavan-3-ols are structurally diverse and include a range of compounds, such as catechin, epicatechin gallate, epigallocatechin, epigallocatechin gallate, proanthocyanidins, theaflavins, thearubigins. They are found in most plants and have a role in plant defense. Chemical structure The single-molecule (monomer) catechin, or isomer epicatechin (see diagram), adds four hydroxyls to flavan-3-ol, making building blocks for concatenated polymers (proanthocyanidins) and higher order polymers (anthocyanidins). Flavan-3-ols possess two chiral carbons, meaning four diastereoisomers occur for each of them. They are distinguished from the yellow, ketone-containing flavonoids such as quercitin and rutin, which are called flavonols. Early use of the term bioflavonoid was imprecisely applied to include the flava ...
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Phloroglucinol
Phloroglucinol is an organic compound with the formula C6H3(OH)3. It is a colorless solid. It is used in the synthesis of pharmaceuticals and explosives. Phloroglucinol is one of three isomeric benzenetriols. The other two isomers are hydroxyquinol (1,2,4-benzenetriol) and pyrogallol (1,2,3-benzenetriol). Phloroglucinol, and its benzenetriol isomers, are still defined as "phenols" according to the IUPAC official nomenclature rules of chemical compounds. Many such monophenolics are often termed "polyphenols" by the cosmetic and parapharmaceutical industries, which does not match the scientifically accepted definition. Synthesis and occurrence In 1855, phloroglucinol was first prepared from phloretin by the Austrian chemist Heinrich Hlasiwetz (1825–1875). A modern synthesis of involves hydrolysis of benzene-1,3,5-triamine and its derivatives. Representative is the following route from trinitrobenzene. : The synthesis is noteworthy because ordinary aniline derivatives are unre ...
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Phloroglucinol Structure
Phloroglucinol is an organic compound with the formula C6H3(OH)3. It is a colorless solid. It is used in the synthesis of pharmaceuticals and explosives. Phloroglucinol is one of three isomeric benzenetriols. The other two isomers are hydroxyquinol (1,2,4-benzenetriol) and pyrogallol (1,2,3-benzenetriol). Phloroglucinol, and its benzenetriol isomers, are still defined as "phenols" according to the IUPAC official nomenclature rules of chemical compounds. Many such monophenolics are often termed "polyphenols" by the cosmetic and parapharmaceutical industries, which does not match the scientifically accepted definition. Synthesis and occurrence In 1855, phloroglucinol was first prepared from phloretin by the Austrian chemist Heinrich Hlasiwetz (1825–1875). A modern synthesis of involves hydrolysis of benzene-1,3,5-triamine and its derivatives. Representative is the following route from trinitrobenzene. : The synthesis is noteworthy because ordinary aniline derivatives are un ...
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