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Hydroxycinnamic Acid
Hydroxycinnamic acids (hydroxycinnamates) are a class of aromatic acids or phenylpropanoids having a C6–C3 skeleton. These compounds are hydroxy derivatives of cinnamic acid. In the category of phytochemicals that can be found in food, there are : * α-Cyano-4-hydroxycinnamic acid * Caffeic acid – burdock, hawthorn, artichoke, pear, basil, thyme, oregano, apple * Cichoric acid * Cinnamic acid – aloe * Chlorogenic acid – echinacea, strawberries, pineapple, coffee, sunflower, blueberries * Diferulic acids * Coumaric acid * Ferulic acid (3-methoxy-4-hydroxycinnamic acid) – oats, rice, artichoke, orange, pineapple, apple, peanut * Sinapinic acid (3,5-dimethoxy-4-hydroxycinnamic acid or sinapic acid) Hydroxycinnamoyltartaric acids * Caftaric acid – grapes and wine, mainly the ''trans'' isomer * Coutaric acid Coutaric acid is a hydroxycinnamoyltartaric acid found in wine, pomace and grape. It is an ester formed from coumaric acid and tartaric acid Tartaric ac ...
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Aromatic Acid
Aromatic acids are a type of aromatic compound. Included in that class are substances containing an aromatic ring and an organic acid functional group. There are several categories of aromatic acids including: *Phenolic acids: substances containing an aromatic ring and an organic carboxylic acid function (C6-C1 skeleton). *Aromatic amino acids An aromatic amino acid is an amino acid that includes an aromatic ring. Among the 20 standard amino acids, the following are classically considered aromatic: phenylalanine, tryptophan and tyrosine. Although histidine contains an aromatic ring, ... References {{organic-chemistry-stub ...
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Diferulic Acids
Diferulic acids (also known as dehydrodiferulic acids) are organic compounds that have the general chemical formula C20H18O8, they are formed by dimerisation of ferulic acid. Curcumin and curcuminoids, though having a structure resembling diferulic acids', are not formed that way but through a condensation process. Just as ferulic acid is not the proper IUPAC name, the diferulic acids also tend to have trivial names that are more commonly used than the correct IUPAC name. Diferulic acids are found in plant cell walls, particularly those of grasses. Structures There are currently nine known structures for diferulic acids. They are usually named after the positions on each molecule that form the bond between them. Included in the group are 8,5'-DiFA (DC) (or decarboxylated form) and 8,8'-DiFA (THF) (or tetrahydrofuran form), which are not true diferulic acids, but probably have a similar biological function. The 8,5'-DiFA (DC) lost CO2 during its formation, the 8,8'-DiFA (THF) g ...
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Coutaric Acid
Coutaric acid is a hydroxycinnamoyltartaric acid found in wine, pomace and grape. It is an ester formed from coumaric acid and tartaric acid Tartaric acid is a white, crystalline organic acid that occurs naturally in many fruits, most notably in grapes, but also in bananas, tamarinds, and citrus. Its salt, potassium bitartrate, commonly known as cream of tartar, develops naturally .... References Hydroxycinnamic acid esters Vinylogous carboxylic acids {{aromatic-stub ...
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Trans Isomer
Trans- is a Latin prefix meaning "across", "beyond", or "on the other side of". Used alone, trans may refer to: Arts, entertainment, and media * Trans (festival), a former festival in Belfast, Northern Ireland, United Kingdom * ''Trans'' (film), a 1998 American film * Trans Corp, an Indonesian business unit of CT Corp in the fields of media, lifestyle, and entertainment ** Trans Media, a media subsidiary of Trans Corp *** Trans TV, an Indonesian television network *** Trans7, an Indonesian television network Literature * '' Trans: Gender and Race in an Age of Unsettled Identities'', a 2016 book by Rogers Brubaker * '' Trans: When Ideology Meets Reality'', a 2021 book by Helen Joyce Music * ''Trans'' (album), by Neil Young * ''Trans'' (Stockhausen), a 1971 orchestral composition Places * Trans, Mayenne, France, a commune * Trans, Switzerland, a village Science and technology * Trans effect in inorganic chemistry, the increased lability of ligands that are trans to certain o ...
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Caftaric Acid
Caftaric acid is a non-flavonoid phenolic compound. It is found in the juice of grapes (''Vitis vinifera'') and impacts the color of white wine. It is an esterified phenolic acid, composed of caffeic acid, a hydroxycinnamate produced by plants, and tartaric acid, the principal organic acid found in grape berries. As such, caftaric acid is found in all grape juices and wines. During alcoholic and malolactic fermentation, the ester can be enzymatically hydrolysed, releasing the two constituents. Caffeic acid is susceptible to chemical oxidation, and subsequent redox reactions involving caffeic acid can contribute to wine browning over time, and the straw-gold color that can develop in some white wines after bottling. Aside from wine, it is abundantly present in raisins. It also occurs in ''Cichorium intybus'' (common chicory) and is one of the bioactive components of ''Echinacea purpurea'' (Eastern purple coneflower). Caftaric acid has a good bioavailability when fed in rats. In ...
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Sinapinic Acid
Sinapinic acid, or sinapic acid (Sinapine - Origin: L. Sinapi, sinapis, mustard, Gr., cf. F. Sinapine.), is a small naturally occurring hydroxycinnamic acid. It is a member of the phenylpropanoid family. It is a commonly used matrix in MALDI mass spectrometry. It is a useful matrix for a wide variety of peptides and proteins. It serves well as a matrix for MALDI due to its ability to absorb laser radiation and to also donate protons (H+) to the analyte of interest. Sinapic acid can form dimers with itself (one structure) and ferulic acid (three different structures) in cereal cell walls and therefore may have a similar influence on cell-wall structure to that of the diferulic acids. Sinapine is an alkaloidal amine found in black mustard seeds. It is considered a choline ester of sinapinic acid. Natural occurrences Sinapinic acid can be found in wine and vinegar. Metabolism Sinapate 1-glucosyltransferase is an enzyme that uses UDP-glucose and sinapate to produce UDP and ...
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Ferulic Acid
Ferulic acid is a hydroxycinnamic acid, an organic compound with the formula (CH3O)HOC6H3CH=CHCO2H. The name is derived from the genus ''Ferula'', referring to the giant fennel (''Ferula communis''). Classified as a phenolic phytochemical, ferulic acid is an amber colored solid. Esters of ferulic acid are found in plant cell walls, covalently bonded to hemicellulose such as arabinoxylans. Occurrence in nature As a building block of lignocelluloses, such as pectin and lignin, ferulic acid is ubiquitous in the plant kingdom, including a number of vegetable sources. It occurs in particularly high concentrations in popcorn and bamboo shoots. It is a major metabolite of chlorogenic acids in humans along with caffeic and isoferulic acid, and is absorbed in the small intestine, whereas other metabolites such as dihydroferulic acid, feruloylglycine and dihydroferulic acid sulfate are produced from chlorogenic acid in the large intestine by the action of gut flora. In cereals, f ...
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Coumaric Acid
Coumaric acid is a phenolic derivative of cinnamic acid having a hydroxy group In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy ... as substituent at one of the aromatic positions: * ''o''-Coumaric acid * ''m''-Coumaric acid * ''p''-Coumaric acid {{Chemistry index ...
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Chlorogenic Acid
Chlorogenic acid (CGA) is the ester of caffeic acid and (−)-quinic acid, functioning as an intermediate in lignin biosynthesis. The term "chlorogenic acids" refers to a related polyphenol family of esters, including hydroxycinnamic acids (caffeic acid, ferulic acid and ''p''-coumaric acid) with quinic acid. Despite the "chloro" of the name, chlorogenic acids contain no chlorine. Instead, the name comes from the Greek χλωρός (khloros, light green) and -γένος (ghenos, a suffix meaning "giving rise to"), pertaining to the green color produced when chlorogenic acids are oxidized. Structural properties Structurally, chlorogenic acid is the ester formed between caffeic acid and the 3-hydroxyl of L-quinic acid. Isomers of chlorogenic acid include the caffeoyl ester at other hydroxyl sites on the quinic acid ring: 4-''O''-caffeoylquinic acid (cryptochlorogenic acid or 4-CQA) and 5-''O''-caffeoylquinic acid (neochlorogenic acid or 5-CQA). The epimer at position 1 has not ...
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Phenylpropanoid
The phenylpropanoids are a diverse family of organic compounds that are synthesized by plants from the amino acids phenylalanine and tyrosine. Their name is derived from the six-carbon, aromatic phenyl group and the three-carbon propene tail of coumaric acid, which is the central intermediate in phenylpropanoid biosynthesis. From 4-coumaroyl-CoA emanates the biosynthesis of myriad natural products including lignols (precursors to lignin and lignocellulose), flavonoids, isoflavonoids, coumarins, aurones, stilbenes, catechin, and phenylpropanoids. The coumaroyl component is produced from cinnamic acid. Phenylpropanoids are found throughout the plant kingdom, where they serve as essential components of a number of structural polymers, provide protection from ultraviolet light, defend against herbivores and pathogens, and also mediate plant-pollinator interactions as floral pigments and scent compounds. Hydroxycinnamic acids Phenylalanine is first converted to cinnamic aci ...
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Cinnamic Acid
Cinnamic acid is an organic compound with the formula C6H5-CH=CH- COOH. It is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents. Classified as an unsaturated carboxylic acid, it occurs naturally in a number of plants. It exists as both a ''cis'' and a ''trans'' isomer, although the latter is more common. Occurrence and production Biosynthesis Cinnamic acid is a central intermediate in the biosynthesis of a myriad of natural products including lignols (precursors to lignin and lignocellulose), flavonoids, isoflavonoids, coumarins, aurones, stilbenes, catechin, and phenylpropanoids. Its biosynthesis involves the action of the enzyme phenylalanine ammonia-lyase (PAL) on phenylalanine. Natural occurrence It is obtained from oil of cinnamon, or from balsams such as storax. It is also found in shea butter. Cinnamic acid has a honey-like odor; it and its more volatile ethyl ester (ethyl cinnamate) are flavor components ...
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Cichoric Acid
Chicoric acid (also known as cichoric acid) is a hydroxycinnamic acid, an organic compound of the phenylpropanoid class and occurs in a variety of plant species. It is a derivative of both caffeic acid and tartaric acid. As a suitable marker for the distinction of ''Echinacea'' species, it is often assayed using RP-HPLC and Thin layer chromatography (TLC) methods. Sources Chicoric acid has first been isolated from ''Cichorium intybus'' (chicory) but also occurs in significant amounts in ''Echinacea'', in particular ''E. purpurea'', dandelion leaves, basil, lemon balm, and aquatic plants, including algae and seagrasses. Biological functions Chicoric acid has been shown to stimulate phagocytosis in both ''in vitro'' and ''in vivo'' studies, to inhibit the function of hyaluronidase (an enzyme that breaks down hyaluronic acid in the human body), to protect collagen from damage due to free radicals, and to inhibit the function of HIV-1 integrase. See also * Caftaric acid Caf ...
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