2-hydroxycinnamate
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2-hydroxycinnamate
''o''-Coumaric acid is a hydroxycinnamic acid, an organic compound that is a hydroxy derivative of cinnamic acid. There are three isomers of coumaric acids — ''o''-coumaric acid, ''m''-coumaric acid, and ''p''-coumaric acid — that differ by the position of the hydroxy substitution of the phenyl group. Natural occurrence ''o''-Coumaric acid can be found in vinegar Vinegar is an aqueous solution of acetic acid and trace compounds that may include flavorings. Vinegar typically contains 5–8% acetic acid by volume. Usually, the acetic acid is produced by a double fermentation, converting simple sugars to et .... 2-Coumarate reductase is an enzyme that produces 2-coumarate from 3-(2-hydroxyphenyl)propanoate and NAD+. This enzyme participates in phenylalanine metabolism. References External links ''o''-Coumaric acid at www.phenol-explorer.eu Hydroxycinnamic acids Vinylogous carboxylic acids {{aromatic-stub ...
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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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Hydroxyl
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 groups. Both the negatively charged anion , called hydroxide, and the neutral radical , known as the hydroxyl radical, consist of an unbonded hydroxy group. According to IUPAC definitions, the term ''hydroxyl'' refers to the hydroxyl radical () only, while the functional group is called a ''hydroxy group''. Properties Water, alcohols, carboxylic acids, and many other hydroxy-containing compounds can be readily deprotonated due to a large difference between the electronegativity of oxygen (3.5) and that of hydrogen (2.1). Hydroxy-containing compounds engage in intermolecular hydrogen bonding increasing the electrostatic attraction between molecules and thus to higher boiling and melting points than found for compounds that lack this f ...
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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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Isomer
In chemistry, isomers are molecules or polyatomic ions with identical molecular formulae – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism is existence or possibility of isomers. Isomers do not necessarily share similar chemical or physical properties. Two main forms of isomerism are structural or constitutional isomerism, in which ''bonds'' between the atoms differ; and stereoisomerism or spatial isomerism, in which the bonds are the same but the ''relative positions'' of the atoms differ. Isomeric relationships form a hierarchy. Two chemicals might be the same constitutional isomer, but upon deeper analysis be stereoisomers of each other. Two molecules that are the same stereoisomer as each other might be in different conformational forms or be different isotopologues. The depth of analysis depends on the field of study or the chemical and physical properties of interest. The English word "isomer" () is a back-for ...
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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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Vinegar
Vinegar is an aqueous solution of acetic acid and trace compounds that may include flavorings. Vinegar typically contains 5–8% acetic acid by volume. Usually, the acetic acid is produced by a double fermentation, converting simple sugars to ethanol using yeast, and ethanol to acetic acid by acetic acid bacteria. Many types of vinegar are available, depending on source materials. It is now mainly used in the culinary arts as a flavorful, acidic cooking ingredient, or in pickling. Various types are used as condiments or garnishes, including balsamic vinegar and malt vinegar. As the most easily manufactured mild acid, it has a wide variety of industrial and domestic uses, including use as a household cleaner. Etymology The word "vinegar" arrived in Middle English from Old French (''vyn egre''; sour wine), which in turn derives from Latin: ''vinum'' (wine) + ''acer'' (sour). Chemistry The conversion of ethanol (CH3CH2OH) and oxygen (O2) to acetic acid (CH3COOH) takes plac ...
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2-Coumarate Reductase
In enzymology, a 2-coumarate reductase or melilotate dehydrogenase () is an enzyme that catalyzes the chemical reaction :3-(2-hydroxyphenyl)propanoate + NAD+ \rightleftharpoons 2-coumarate + NADH + H+ Thus, the two substrates of this enzyme are 3-(2-hydroxyphenyl)propanoate and NAD+, whereas its 3 products are 2-coumarate, NADH, and H+. This enzyme belongs to the family of oxidoreductases, specifically those acting on the CH-CH group of donor with NAD+ or NADP+ as acceptor. The systematic name of this enzyme class is 3-(2-hydroxyphenyl)propanoate:NAD+ oxidoreductase. This enzyme participates in phenylalanine metabolism Phenylalanine (symbol Phe or F) is an essential α-amino acid with the formula . It can be viewed as a benzyl group substituted for the methyl group of alanine, or a phenyl group in place of a terminal hydrogen of alanine. This essential amino ac .... References * EC 1.3.1 NADH-dependent enzymes Enzymes of unknown structure Hydroxycinnamic ...
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NAD+
Nicotinamide adenine dinucleotide (NAD) is a coenzyme central to metabolism. Found in all living cells, NAD is called a dinucleotide because it consists of two nucleotides joined through their phosphate groups. One nucleotide contains an adenine nucleobase and the other nicotinamide. NAD exists in two forms: an oxidized and reduced form, abbreviated as NAD and NADH (H for hydrogen), respectively. In metabolism, nicotinamide adenine dinucleotide is involved in redox reactions, carrying electrons from one reaction to another. The cofactor is, therefore, found in two forms in cells: NAD is an oxidizing agent – it accepts electrons from other molecules and becomes reduced. This reaction, also with H+, forms NADH, which can then be used as a reducing agent to donate electrons. These electron transfer reactions are the main function of NAD. However, it is also used in other cellular processes, most notably as a substrate of enzymes in adding or removing chemical groups to ...
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Hydroxycinnamic Acids
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 – grapes and wine, both ''trans'' and ''cis'' isomers * Fertaric acid Fertaric acid is a hydroxycinnamic acid found in wine and grapes. It is an ester formed ...
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