Tannin

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 (including as pesticides) and might help in regulating plant growth.[1] 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.[2] Likewise, the destruction or modification of tannins with time plays an important role when determining harvesting times.

Tannins have molecular weights ranging from 500 to over 3,000[3] (gallic acid esters) and up to 20,000 (proanthocyanidins).

Tannic acid
Tannic acid, a type of tannin
Tannin heap.jpeg
Tannin powder (mixture of compounds)
Bottle of tannic acid
A bottle of tannic acid solution in water

Structure and classes of tannins

There are three major classes of tannins: Shown below are the base unit or monomer of the tannin. Particularly in the flavone-derived tannins, the base shown must be (additionally) heavily hydroxylated and polymerized in order to give the high molecular weight polyphenol motif that characterizes tannins. Typically, tannin molecules require at least 12 hydroxyl groups and at least five phenyl groups to function as protein binders.[4]

Base Unit: Gallic acid
Gallic acid
Phloroglucinol structure
Phloroglucinol
Flavan-3-ol
Flavan-3-ol's scaffold
Class/Polymer: Hydrolyzable tannins Phlorotannins Condensed tannins and
Phlobatannins (C-ring
isomerized condensed tannins)[5]
Sources Plants Brown algae Plants (former), tree heartwood (latter)

Oligostilbenoids (oligo- or polystilbenes) are oligomeric forms of stilbenoids and constitute a class of tannins.[6]

Pseudo tannins

Pseudo tannins are low molecular weight compounds associated with other compounds. They do not change color during the Goldbeater's skin test, unlike hydrolysable and condensed tannins, and cannot be used as tanning compounds.[4] Some examples of pseudo tannins and their sources are:[7]

Pseudo tannin Source(s)
Gallic acid Rhubarb
Flavan-3-ols (Catechins) Tea, acacia, catechu, cocoa, guarana
Chlorogenic acid Nux-vomica, coffee, mate
Ipecacuanhic acid Carapichea ipecacuanha

History

Ellagic acid, gallic acid, and pyrogallic acid were first discovered by chemist Henri Braconnot in 1831.[8]:20 Julius Löwe was the first person to synthesize ellagic acid by heating gallic acid with arsenic acid or silver oxide.[8]:20 [9]

Maximilian Nierenstein studied natural phenols and tannins[10] found in different plant species. Working with Arthur George Perkin, he prepared ellagic acid from algarobilla and certain other fruits in 1905.[11] He suggested its formation from galloyl-glycine by Penicillium in 1915.[12] Tannase is an enzyme that Nierenstein used to produce m-digallic acid from gallotannins.[13] He proved the presence of catechin in cocoa beans in 1931.[14] He showed in 1945 that luteic acid, a molecule present in the myrobalanitannin, a tannin found in the fruit of Terminalia chebula, is an intermediary compound in the synthesis of ellagic acid.[15]

At these times, molecule formulas were determined through combustion analysis. The discovery in 1943 by Martin and Synge of paper chromatography provided for the first time the means of surveying the phenolic constituents of plants and for their separation and identification. There was an explosion of activity in this field after 1945, including prominent work by Edgar Charles Bate-Smith and Tony Swain at Cambridge University.[16]

In 1966, Edwin Haslam proposed a first comprehensive definition of plant polyphenols based on the earlier proposals of Bate-Smith, Swain and Theodore White, which includes specific structural characteristics common to all phenolics having a tanning property. It is referred to as the White–Bate-Smith–Swain–Haslam (WBSSH) definition.[17]

Occurrence

Tannins are distributed in species throughout the plant kingdom. They are commonly found in both gymnosperms as well as angiosperms. Mole studied the distribution of tannin in 180 families of dicotyledons and 44 families of monocotyledons (Cronquist). Most families of dicot contain tannin-free species (tested by their ability to precipitate proteins). The best known families of which all species tested contain tannin are: Aceraceae, Actinidiaceae, Anacardiaceae, Bixaceae, Burseraceae, Combretaceae, Dipterocarpaceae, Ericaceae, Grossulariaceae, Myricaceae for dicot and Najadaceae and Typhaceae in Monocot. To the family of the oak, Fagaceae, 73% of the species tested (N = 22) contain tannin. For those of acacias, Mimosaceae, only 39% of the species tested (N = 28) contain tannin, among Solanaceae rate drops to 6% and 4% for the Asteraceae. Some families like the Boraginaceae, Cucurbitaceae, Papaveraceae contain no tannin-rich species.[18]

The most abundant polyphenols are the condensed tannins, found in virtually all families of plants, and comprising up to 50% of the dry weight of leaves. Tannins of tropical woods tend to be of a cathetic nature rather than of the gallic type present in temperate woods.[19]

There may be a loss in the bio-availability of still other tannins in plants due to birds, pests, and other pathogens.[20]

Localization in plant organs

Tannins are found in leaf, bud, seed, root, and stem tissues. An example of the location of the tannins in stem tissue is that they are often found in the growth areas of trees, such as the secondary phloem and xylem and the layer between the cortex and epidermis. Tannins may help regulate the growth of these tissues.

Cellular localization

In all vascular plants studied so far, tannins are manufactured by a chloroplast-derived organelle, the tannosome.[21] Tannins are mainly physically located in the vacuoles or surface wax of plants. These storage sites keep tannins active against plant predators, but also keep some tannins from affecting plant metabolism while the plant tissue is alive; it is only after cell breakdown and death that the tannins are active in metabolic effects.

Tannins are classified as ergastic substances, i.e., non-protoplasm materials found in cells. Tannins, by definition, precipitate proteins. In this condition, they must be stored in organelles able to withstand the protein precipitation process. Idioblasts are isolated plant cells which differ from neighboring tissues and contain non-living substances. They have various functions such as storage of reserves, excretory materials, pigments, and minerals. They could contain oil, latex, gum, resin or pigments etc. They also can contain tannins. In Japanese persimmon (Diospyros kaki) fruits, tannin is accumulated in the vacuole of tannin cells, which are idioblasts of parenchyma cells in the flesh.[22]

Presence in soils

The convergent evolution of tannin-rich plant communities has occurred on nutrient-poor acidic soils throughout the world. Tannins were once believed to function as anti-herbivore defenses, but more and more ecologists now recognize them as important controllers of decomposition and nitrogen cycling processes. As concern grows about global warming, there is great interest to better understand the role of polyphenols as regulators of carbon cycling, in particular in northern boreal forests.[23]

Leaf litter and other decaying parts of kauri (Agathis australis), a tree species found in New Zealand, decompose much more slowly than those of most other species. Besides its acidity, the plant also bears substances such as waxes and phenols, most notably tannins, that are harmful to microorganisms.[24]

Presence in water and wood

The leaching of highly water soluble tannins from decaying vegetation and leaves along a stream may produce what is known as a blackwater river. Water flowing out of bogs has a characteristic brown color from dissolved peat tannins. The presence of tannins (or humic acid) in well water can make it smell bad or taste bitter, but this does not make it unsafe to drink.[25]

Tannins leaching from an unprepared driftwood decoration in an aquarium can cause pH lowering and coloring of the water to a tea-like tinge. A way to avoid this is to boil the wood in water several times, discarding the water each time. Using peat as an aquarium substrate can have the same effect. Many hours of boiling the driftwood may need to be followed by many weeks or months of constant soaking and many water changes before the water will stay clear. Adding baking soda to the water to raise its pH level will accelerate the process of leaching, as the more alkaline solution can draw out tannic acid from the wood faster than the pH-neutral water.[26]

Softwoods, while in general much lower in tannins than hardwoods,[27] are usually not recommended for use in an aquarium[28] so using a hardwood with a very light color, indicating a low tannin content, can be an easy way to avoid tannins. Tannic acid is brown in color, so in general white woods have a low tannin content. Woods with a lot of yellow, red, or brown coloration to them (like cedar, redwood, red oak, etc.) tend to contain a lot of tannin.[29]

Tannin rich fresh water draining into Cox Bight from Freney Lagoon

Tannin-rich fresh water draining into Cox Bight from Freney Lagoon, Southwest Conservation Area, Tasmania, Australia

Bogwood Betta

Bog-wood (similar to, but not, driftwood) in an aquarium, turning the water a tea-like brown

Upper Tahquamenon falls Panoramic view

Upper Tahquamenon falls Panoramic view

Hebe River at Lobbs Bridge, Milabena

A tannin-rich stream produces a maroon colour near Milabena, Tasmania

Extraction

There is no single protocol for extracting tannins from all plant material. The procedures used for tannins are widely variable.[30] It may be that acetone in the extraction solvent increases the total yield by inhibiting interactions between tannins and proteins during extraction[30] or even by breaking hydrogen bonds between tannin-protein complexes.[31]

Tests for tannins

There are three groups of methods for the analysis of tannins: precipitation of proteins or alkaloids, reaction with phenolic rings, and depolymerization.[32]

Alkaloid precipitation

Alkaloids such as caffeine, cinchonine, quinine or strychnine, precipitates polyphenols and tannins. This property can be used in a quantitation method.[33]

Goldbeater's skin test

When goldbeater's skin or ox skin is dipped in HCl, rinsed in water, soaked in the tannin solution for 5 minutes, washed in water, and then treated with 1% FeSO4 solution, it gives a blue black color if tannin was present.

Ferric chloride test

Use of ferric chloride (FeCl3) tests for phenolics in general. Powdered plant leaves of the test plant (1.0 g) are weighed into a beaker and 10 ml of distilled water are added. The mixture is boiled for five minutes. Two drops of 5% FeCl3 are then added. Production of a greenish precipitate was an indication of the presence of tannins.[34] Alternatively, a portion of the water extract is diluted with distilled water in a ratio of 1:4 and few drops of 10% ferric chloride solution is added. A blue or green color indicates the presence of tannins (Evans, 1989).[35]

Other methods

The hide-powder method is used in tannin analysis for leather tannin and the Stiasny method for wood adhesives.[36][37] Statistical analysis reveals that there is no significant relationship between the results from the hide-powder and the Stiasny methods.[38][39]

Hide-powder method

400 mg of sample tannins are dissolved in 100 ml of distilled water. 3 g of slightly chromated hide-powder previously dried in vacuum for 24h over CaCl2 are added and the mixture stirred for 1 h at ambient temperature. The suspension is filtered without vacuum through a sintered glass filter. The weight gain of the hide-powder expressed as a percentage of the weight of the starting material is equated to the percentage of tannin in the sample.

Stiasny's method

100 mg of sample tannins are dissolved in 10 ml distilled water. 1 ml of 10M HCl and 2 ml of 37% formaldehyde are added and the mixture heated under reflux for 30 min. The reaction mixture is filtered while hot through a sintered glass filter. The precipitate is washed with hot water (5× 10 ml) and dried over CaCl2. The yield of tannin is expressed as a percentage of the weight of the starting material.

Reaction with phenolic rings

The bark tannins of Commiphora angolensis have been revealed by the usual color and precipitation reactions and by quantitative determination by the methods of Löwenthal-Procter and of Deijs[40] (formalin-hydrochloric acid method).[41]

Colorimetric methods have existed such as the Neubauer-Löwenthal method which uses potassium permanganate as an oxidizing agent and indigo sulfate as an indicator, originally proposed by Löwenthal in 1877.[42] The difficulty is that the establishing of a titer for tannin is not always convenient since it is extremely difficult to obtain the pure tannin. Neubauer proposed to remove this difficulty by establishing the titer not with regard to the tannin but with regard to crystallised oxalic acid, whereby he found that 83 g oxalic acid correspond to 41.20 g tannin. Löwenthal's method has been criticized. For instance, the amount of indigo used is not sufficient to retard noticeably the oxidation of the non-tannins substances. The results obtained by this method are therefore only comparative.[43][44] A modified method, proposed in 1903 for the quantification of tannins in wine, Feldmann's method, is making use of calcium hypochlorite, instead of potassium permanganate, and indigo sulfate.[45]

Food items with tannins

Accessory fruits

Strawberries contain both hydrolyzable and condensed tannins.[46]

Berries

Strawberries in white bowl
Strawberries in a bowl

Most berries, such as cranberries,[47] and blueberries,[48] contain both hydrolyzable and condensed tannins.

Nuts

Nuts that can be consumed raw, such as hazelnuts, walnuts, and pecans, contain high amounts of tannins. Almonds have a lower content. Tannin concentration in the crude extract of these nuts did not directly translate to the same relationships for the condensed fraction.[49]

Herbs and spices

Cloves, tarragon, cumin, thyme, vanilla, and cinnamon all contain tannins.

Legumes

Most legumes contain tannins. Red-colored beans contain the most tannins, and white-colored beans have the least. Peanuts without shells have a very low tannin content. Chickpeas (garbanzo beans) have a smaller amount of tannins.[50]

Chocolate

Chocolate liquor contains about 6% tannins.[51]

Drinks with tannins

Principal human dietary sources of tannins are tea and coffee.[52] Most wines aged in charred oak barrels possess tannins absorbed from the wood.[53] Soils high in clay also contribute to tannins in wine grapes.[54] This concentration gives wine its signature astringency.[55]

Coffee pulp has been found to contain low to trace amounts of tannins.[56]

Fruit juices

Although citrus fruits do not themselves contain tannins, orange-colored juices often contain food dyes with tannins. Apple juice, grape juices and berry juices are all high in tannins. Sometimes tannins are even added to juices and ciders to create a more astringent feel to the taste.[57]

Beer

In addition to the alpha acids extracted from hops to provide bitterness in beer, condensed tannins are also present. These originate both from the malt and hops. Especially in Germany, trained brewmasters consider the presence of tannins as a flaw. In some styles, the presence of this astringency is acceptable or even desired, as, for example, in a Flanders red ale.[58]

In lager type beers, the tannins can form a precipitate with specific haze-forming proteins in the beer resulting in turbidity at low temperature. This chill haze can be prevented by removing part of the tannins or part of the haze-forming proteins. Tannins are removed using PVPP, haze-forming proteins by using silica or tannic acid.[59]

Properties for animal nutrition

Tannins have traditionally been considered antinutritional, but it is now known that their beneficial or antinutritional properties depend upon their chemical structure and dosage. The new technologies used to analyze molecular and chemical structures have shown that a division into condensed and hydrolyzable tannins is too simplistic.[60] Recent studies have demonstrated that products containing chestnut tannins included at low dosages (0.15–0.2%) in the diet of chickens may be beneficial.[61]

Some studies suggest that chestnut tannins have positive effects on silage quality in the round bale silages, in particular reducing NPNs (non protein nitrogen) in the lowest wilting level.[62]

Improved fermentability of soya meal nitrogen in the rumen may occur.[63] Studies conducted in 2002 on in vitro ammonia release and dry matter degradation of soybean meal comparing three different types of tannins (quebracho, acacia and chestnut) demonstrated that chestnut tannins are more efficient in protecting soybean meal from in vitro degradation by rumen bacteria.[64]

Condensed tannins inhibit herbivore digestion by binding to consumed plant proteins and making them more difficult for animals to digest, and by interfering with protein absorption and digestive enzymes (for more on that topic, see plant defense against herbivory). Many tannin-consuming animals secrete a tannin-binding protein (mucin) in their saliva. Tannin-binding capacity of salivary mucin is directly related to its proline content. Salivary proline-rich proteins (PRPs) are sometimes used to inactivate tannins. One reason is that they inactivate tannins to a greater extent than do dietary proteins resulting in reduced fecal nitrogen losses. PRPs additionally contain non-specific nitrogen and non-essential amino acids making them more convenient than valuable dietary protein.

Histatins, another type of salivary proteins, also precipitate tannins from solution, thus preventing alimentary adsorption.[65]

Tannin market

Tannin in Plastic container.jpeg
Tannin in a plastic container

Tannin production began at the beginning of the 19th century with the industrial revolution, to produce tanning material for the need for more leather. Before that time, processes used plant material and were long (up to six months).

There was a collapse in the vegetable tannin market in the 1950s–1960s, due to the appearance of synthetic tannins, which were invented in response to a scarcity of vegetable tannins during World War II. At that time, many small tannin industry sites closed.[66] Vegetable tannins are estimated to be used for the production of 10–20% of the global leather production.

The cost of the final product depends on the method used to extract the tannins, in particular the use of solvents, alkali and other chemicals used (for instance glycerin). For large quantities, the most cost-effective method is hot water extraction.

Tannic acid is used worldwide as clarifying agent in alcoholic drinks and as aroma ingredient in both alcoholic and soft drinks or juices. Tannins from different botanical origins also find extensive uses in the wine industry.

Uses

Tannins are an important ingredient in the process of tanning leather. Tanbark from oak, mimosa, chestnut and quebracho tree has traditionally been the primary source of tannery tannin, though inorganic tanning agents are also in use today and account for 90% of the world's leather production.[67]

Tannins produce different colors with ferric chloride (either blue, blue black, or green to greenish-black) according to the type of tannin. Iron gall ink is produced by treating a solution of tannins with iron(II) sulfate.[68]

Tannin is a component in a type of industrial particleboard adhesive developed jointly by the Tanzania Industrial Research and Development Organization and Forintek Labs Canada.[69] Pinus radiata tannins has been investigated for the production of wood adhesives.[70]

Condensed tannins, e.g., quebracho tannin, and Hydrolyzable tannins, e.g., chestnut tannin, appear to be able to substitute a high proportion of synthetic phenol in phenol-formaldehyde resins for wood particleboard.

Tannins can be used for production of anti-corrosive primer, sold under brand-name "Nox Primer" for treatment of rusted steel surfaces prior to painting, rust converter to transform oxidized steel into a smooth sealed surface and rust inhibitor.

The use of resins made of tannins has been investigated to remove mercury and methylmercury from solution.[71] Immobilized tannins have been tested to recover uranium from seawater.[72]

See also

References

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External links

Albumin tannate

Albumin tannate (also known as Tannin albuminate) is an antidiarrheal.

Arecatannin

Arecatannins are a class of condensed tannins in the sub-class procyanidins contained in the seeds of Areca catechu also called betel nut. The arecatannin-type natural products from Ceylonese cassia bark and Areca seed are examples polyphenols by both current definitions, and fit the distinct definition of a polymeric phenol as well.

Blackwater river

A blackwater river is a type of river with a slow-moving channel flowing through forested swamps or wetlands. As vegetation decays, tannins leach into the water, making a transparent, acidic water that is darkly stained, resembling tea. Most major blackwater rivers are in the Amazon Basin and the Southern United States. The term is used in fluvial studies, geology, geography, ecology, and biology. Not all dark rivers are blackwater in that technical sense. Some rivers in temperate regions, which drain or flow through areas of dark black loam, are simply black due to the color of the soil; these rivers are black mud rivers. There are also black mud estuaries.

Blackwater rivers are lower in nutrients than whitewater rivers and have ionic concentrations higher than rainwater. The unique conditions lead to flora and fauna that differ from both whitewater and clearwater rivers. The classification of Amazonian rivers into black, clear, and whitewater was first proposed by Alfred Russel Wallace in 1853 based on water colour, but the types were more clearly defined by chemistry and physics by Harald Sioli (de) from the 1950s to the 1980s. Although many Amazonian rivers fall clearly into one of these categories, others show a mix of characteristics and may vary depending on season and flood levels.

Condensed tannin

Condensed tannins (proanthocyanidins, polyflavonoid tannins, catechol-type tannins, pyrocatecollic type tannins, non-hydrolyzable tannins or flavolans) are polymers formed by the condensation of flavans. They do not contain sugar residues.They are called proanthocyanidins as they yield anthocyanidins when depolymerized under oxidative conditions. Different types of condensed tannins exist, such as the procyanidins, propelargonidins, prodelphinidins, profisetinidins, proteracacinidins, proguibourtinidins or prorobinetidins. All of the above are formed from flavan-3-ols, but flavan-3,4-diols, called (leucoanthocyanidin) also form condensed tannin oligomers, e.g. leuco-fisetinidin form profisetinidin, and flavan-4-ols form condensed tannins, e.g. 3',4',5,7-flavan-4-ol form proluteolinidin (luteoforolor). One particular type of condensed tannin, found in grape, are procyanidins, which are polymers of 2 to 50 (or more) Catechin units joined by carbon-carbon bonds. These are not susceptible to being cleaved by hydrolysis.

While many hydrolyzable tannins and most condensed tannins are water-soluble, several tannins are also highly octanol-soluble. Some large condensed tannins are insoluble. Differences in solubilities are likely to affect their biological functions.

Flavono-ellagitannin

The Flavono-ellagitannins or complex tannins are a class of tannins formed from the complexation of an ellagitannin with a flavonoid. Flavono-ellagitannins can be found in Quercus mongolica var. grosseserrata.

Gallotannin

A gallotannin is any of a class of molecules belonging to the hydrolysable tannins. Gallotannins are polymers formed when gallic acid, a polyphenol monomer, esterifies and binds with the hydroxyl group of a polyol carbohydrate such as glucose.

Gamaret

Gamaret is a variety of red wine grape. It was created by André Jaquinet at Station Fédérale de Recherches en Production Végétale de Changins in 1970 by crossing Gamay and Reichensteiner. Gamaret was developed for cultivation in French Switzerland, and is a full sibling of Garanoir, which was intended for the German part of the country.Total Swiss plantations of the variety in 2009 stood at 380 hectares (940 acres).Gamaret has good resistance to rot and ripens early. It gives dark purple wine with aromas of blackberries and spices and subtle tannin.

Hydrolysable 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 (Castanea sativa), oak wood (Quercus robur, Quercus petraea and Quercus alba), tara pods (Caesalpinia spinosa), gallnuts (Quercus infectoria and Rhus semialata), myrobalan (Terminalia chebula), sumac (Rhus coriaria) and Aleppo gallnuts (Andricus kollari).

Leather

Leather is a natural durable and flexible material created by tanning animal rawhides and skins. The most common raw material is cattle hide. It can be produced at manufacturing scales ranging from artisan to modern industrial scale.

Leather is used to make a variety of articles, including footwear, automobile seats, clothing, bags, book bindings, fashion accessories, and furniture. It is produced in a wide variety of types and styles and decorated by a wide range of techniques. The earliest record of leather artifacts dates back to 2200 BC.

List of Acacia species used for tannin production

This is a list of Acacia species (sensu lato) that are used for the production of tannins.

Phenolic content in tea

The phenolic content in tea refers to the phenols and polyphenols, natural plant compounds which are found in tea. These chemical compounds affect the flavor and mouthfeel and are speculated to provide potential health benefits. Polyphenols in tea include catechins, theaflavins, tannins, and flavonoids.

Polyphenols found in green tea include but are not limited to epigallocatechin gallate (EGCG), epigallocatechin, epicatechin gallate, and epicatechin; flavanols such as kaempferol, quercetin, and myricitin are also found in green tea.

Phenolic content in wine

The phenolic content in wine refers to the phenolic compounds—natural phenol and polyphenols—in wine, which include a large group of several hundred chemical compounds that affect the taste, color and mouthfeel of wine. These compounds include phenolic acids, stilbenoids, flavonols, dihydroflavonols, anthocyanins, flavanol monomers (catechins) and flavanol polymers (proanthocyanidins). This large group of natural phenols can be broadly separated into two categories, flavonoids and non-flavonoids. Flavonoids include the anthocyanins and tannins which contribute to the color and mouthfeel of the wine. The non-flavonoids include the stilbenoids such as resveratrol and phenolic acids such as benzoic, caffeic and cinnamic acids.

Procyanidin

Procyanidins are members of the proanthocyanidin (or condensed tannins) class of flavonoids. They are oligomeric compounds, formed from catechin and epicatechin molecules. They yield cyanidin when depolymerized under oxidative conditions.

Quebracho tree

Quebracho is a common name in Spanish to describe very hard (density 0.9–1.3) wood tree species. The etymology of the name derived from quiebrahacha, or quebrar hacha, meaning "axe-breaker".

Roburin A

Roburin A is a tannin found in oak wood (Quercus robur and Quercus petraea or Quercus alba) or oak cork (Quercus suber).

It is a dimeric compound, composed of two vescalagin subunits probably linked through an ether bond between the diphenoyl group (hexahydroxydiphenic acid or HHDP) of one subunit and the triphenoyl moiety (nonahydroxytriphenic acid) of the other one.

Tanbark

Tanbark is the bark of certain species of tree. It is traditionally used for tanning hides into leather.The words "tannin", "tanning", "tan," and "tawny" are derived from the Medieval Latin tannare, "to convert into leather."

Bark mills are horse- or oxen-driven or water-powered edge mills and were used in earlier times to shred the tanbark to derive tannins for the leather industry. A "barker" was a person who stripped bark from trees to supply bark mills.

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 sourced from the above-mentioned plants can be considered as tannic acid. Sometimes extracts from chestnut or oak wood are also described as tannic acid but this is an incorrect use of the term. It is a yellow to light brown amorphous powder; 2850 grams dissolves in one litre of water (1.7 moles per liter).

While tannic acid is a specific type of tannin (plant polyphenol), the two terms are sometimes (incorrectly) used interchangeably. The long-standing misuse of the terms, and its inclusion in scholarly articles has compounded the confusion. This is particularly widespread in relation to green tea and black tea, both of which contain tannin but not tannic acid.Tannic acid is not an appropriate standard for any type of tannin analysis because of its poorly defined composition.

Tannin (monster)

Tannin (Hebrew: תנין‎; Arabic: التنين‎ Tinnin) or Tunannu (Ugaritic: 𐎚𐎐𐎐 tnn, vocalized tu-un-na-nu) was a sea monster in Canaanite, Phoenician, and Hebrew mythology used as a symbol of chaos and evil.

Tanning (leather)

Tanning is the process of treating skins and 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 also possibly coloring it.

Before tanning, the skins are unhaired, degreased, desalted and soaked in water over a period of 6 hours to 2 days. Historically this process was considered a noxious or "odoriferous trade" and relegated to the outskirts of town.

Traditionally, tanning used tannin, an acidic chemical compound from which the tanning process draws its name (tannin is in turn named after an old German word for oak or fir trees, from which the compound was derived). The use of a chromium (III) solution was adopted by tanners in the Industrial Revolution.

Types of natural tannins
Hydrolysable tannins
Condensed tannins
Phlorotannins
Flavono-ellagitannins
(complex tannins)
Other Miscellaneous
Lumber/
timber
Engineered
wood
Fuelwood
Fibers
Derivatives
By-products
Historical
See also

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