(E)-cinnamate
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(E)-cinnamate
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. The ''cis''-isomer is called allocinnamic acid. 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; and its more volatile ethyl ester, et ...
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Benzoic Acid
Benzoic acid () is a white (or colorless) solid organic compound with the formula , whose structure consists of a benzene ring () with a carboxyl () substituent. The benzoyl group is often abbreviated "Bz" (not to be confused with "Bn," which is used for benzyl), thus benzoic acid is also denoted as BzOH, since the benzoyl group has the formula –. It is the simplest aromatic carboxylic acid. The name is derived from gum benzoin, which was for a long time its only source. Benzoic acid occurs naturally in many plants and serves as an intermediate in the biosynthesis of many secondary metabolites. Salts of benzoic acid are used as food preservatives. Benzoic acid is an important precursor for the industrial synthesis of many other organic substances. The salts and esters of benzoic acid are known as benzoates (). History Benzoic acid was discovered in the sixteenth century. The dry distillation of gum benzoin was first described by Nostradamus (1556), and then by ...
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Catechin
Catechin is a flavan-3-ol, a type of secondary metabolite providing antioxidant roles in plants. It belongs to the subgroup of polyphenols called flavonoids. The name of the catechin chemical family derives from ''catechu'', which is the tannic juice or boiled extract of ''Mimosa catechu'' (''Acacia catechu'' L.f.). Chemistry Catechin possesses two benzene rings (called the A and B rings) and a dihydropyran heterocycle (the C ring) with a hydroxyl group on carbon 3. The A ring is similar to a resorcinol moiety while the B ring is similar to a catechol moiety. There are two chirality (chemistry), chiral centers on the molecule on carbons 2 and 3. Therefore, it has four diastereoisomers. Two of the isomers are in trans configuration, ''trans'' configuration and are called ''catechin'' and the other two are in cis configuration, ''cis'' configuration and are called ''epicatechin''. The most common catechin isomer is (+)-catechin. The other stereoisomer is (−)-catechin or ''en ...
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Acetyl Chloride
Acetyl chloride () is an acyl chloride derived from acetic acid (). It belongs to the class of organic compounds called acid halides. It is a colorless, corrosive, volatile liquid. Its formula is commonly abbreviated to AcCl. Synthesis On an industrial scale, the reaction of acetic anhydride with hydrogen chloride produces a mixture of acetyl chloride and acetic acid: : Laboratory routes Acetyl chloride was first prepared in 1852 by French chemist Charles Gerhardt by treating potassium acetate with phosphoryl chloride. Acetyl chloride is produced in the laboratory by the reaction of acetic acid with chlorodehydrating agents such as phosphorus trichloride (), phosphorus pentachloride (), sulfuryl chloride (), phosgene, or thionyl chloride (). However, these methods usually give acetyl chloride contaminated by phosphorus or sulfur impurities, which may interfere with the organic reactions. Other methods When heated, a mixture of dichloroacetyl chloride and acetic aci ...
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Cinnamaldehyde
Cinnamaldehyde is an organic compound with the formula or . Occurring naturally as predominantly the ''trans'' (''E'') isomer, it gives cinnamon its flavor and odor. It is a phenylpropanoid that is naturally synthesized by the shikimate pathway. This pale yellow, viscous liquid occurs in the bark of cinnamon trees and other species of the genus '' Cinnamomum''. It is an essential oil. The bark of cinnamon tree contains high concentrations of cinnamaldehyde. Structure and synthesis Cinnamaldehyde was isolated from cinnamon essential oil in 1834 by Jean-Baptiste Dumas and Eugène-Melchior Péligot and synthesized in the laboratory by the Italian chemist Luigi Chiozza in 1854. The natural product is '' trans''-cinnamaldehyde. The molecule consists of a benzene ring attached to an unsaturated aldehyde. Cinnamaldehyde is an α,β-unsaturated carbonyl compound. Its color is due to the π → π* transition: increased conjugation in comparison with acrolein shifts this band towa ...
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Honey
Honey is a sweet and viscous substance made by several species of bees, the best-known of which are honey bees. Honey is made and stored to nourish bee colonies. Bees produce honey by gathering and then refining the sugary secretions of plants (primarily floral nectar) or the secretions of other insects, like the honeydew of aphids. This refinement takes place both within individual bees, through regurgitation and enzymatic activity, and during storage in the hive, through water evaporation that concentrates the honey's sugars until it is thick and viscous. Honey bees stockpile honey in the hive. Within the hive is a structure made from wax called honeycomb. The honeycomb is made up of hundreds or thousands of hexagonal cells, into which the bees regurgitate honey for storage. Other honey-producing species of bee store the substance in different structures, such as the pots made of wax and resin used by the stingless bee. Honey for human consumption is collected ...
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Shea Butter
Shea butter ( , , or ; ) is a fat (triglyceride; mainly oleic acid and stearic acid) extracted from the nut of the African shea tree ('' Vitellaria paradoxa''). It is ivory in color when raw and commonly dyed yellow with borututu root or palm oil. It is widely used in cosmetics as a moisturizer or lotion. It is edible and is used in food preparation in some African countries. It is occasionally mixed with other oils as a substitute for cocoa butter, although the taste is noticeably different. The English word "shea" comes from , the tree's name in Bambara. It is known by many local names, such as in the Dagbani language, in the Wali language, in Twi, or in Hausa, in the Igbo language, in the Yoruba language, and in the Wolof language of Senegal. It is also known as Moo-yaa in the Acholi language. History The common name is () in the Bambara language of Mali. This is the origin of the English word, one pronunciation of which rhymes with "tea" , although t ...
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Storax
Storax (; , ''stúrax''), often commercially sold as styrax, is a natural fragrant resin isolated from the wounded bark of ''Liquidambar orientalis'' Mill. (Asia Minor) and ''Liquidambar styraciflua'' L. (Eastern US, Mexico, Central America) (Altingiaceae). It is distinct from Benzoin resin, benzoin (also called "storax"), a similar resin obtained from the Styracaceae plant family. Composition Purified storax contains circa 33–50% storesin, an Alcohol (chemistry), alcoholic resin, both free and as cinnamic esters. It contains 5–15% cinnamic acid, 5–15% cinnamyl cinnamate, circa 10% phenylpropyl cinnamate; small amounts of ethyl cinnamate, benzyl cinnamate, and styrene. Some may contain traces of vanillin. Some sources report a resin containing triterpenic acids (oleanolic acid, oleanolic and 3-epioleanolic acids). Uses Storax has a pleasant, floral/lilac, leathery, balsamic smell. Storax and its derivatives (Resinoid (perfumery), resinoid, essential oil, Absolute (perfumer ...
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Balsam
Balsam is the resinous exudate (or sap) which forms on certain kinds of trees and shrubs. Balsam (from Latin ''balsamum'' "gum of the balsam tree," ultimately from a Semitic source such as ) owes its name to the biblical Balm of Gilead. Chemistry Balsam is a solution of plant-specific resins in plant-specific solvents (essential oils). Such resins can include resin acids, esters, or alcohols. The exudate is a mobile to highly viscous liquid often containing crystallized resin particles. Over time, and as a result of other influences, the exudate loses its liquidizing components or gets chemically converted into a solid material (i.e. by autoxidation). Balsams often contain benzoic or cinnamic acid or their esters. Plant resins are sometimes classified according to other plant constituents in the mixture, for example as: * pure resins ( guaiac, hashish), * gum-resins (containing gums/polysaccharides), * oleo-gum-resins (a mixture of gums, resins and essential oils), * ...
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Cinnamon
Cinnamon is a spice obtained from the inner bark of several tree species from the genus ''Cinnamomum''. Cinnamon is used mainly as an aromatic condiment and flavouring additive in a wide variety of cuisines, sweet and savoury dishes, biscuits, breakfast cereals, Snack, snack foods, bagels, teas, hot chocolate and traditional foods. The aroma and flavour of cinnamon derive from its essential oil and principal component, cinnamaldehyde, as well as numerous other constituents, including eugenol. Cinnamon is the name for several species of trees and the commercial spice products that some of them produce. All are members of the genus ''Cinnamomum'' in the family Lauraceae. Only a few ''Cinnamomum'' species are grown commercially for spice. ''Cinnamomum verum'' (alternatively ''C. zeylanicum''), known as "Ceylon cinnamon" after its origins in Sri Lanka (formerly Ceylon), is considered to be "true cinnamon", but most cinnamon in international commerce is derived from four other speci ...
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Phenylalanine
Phenylalanine (symbol Phe or F) is an essential α-amino acid with the chemical formula, formula . It can be viewed as a benzyl group substituent, substituted for the methyl group of alanine, or a phenyl group in place of a terminal hydrogen of alanine. This essential amino acid is classified as neutral, and chemical polarity, nonpolar because of the inert and hydrophobic nature of the benzyl side chain. The chirality (chemistry)#Naming conventions, L-isomer is used to biochemically form proteins coded for by DNA. Phenylalanine is a precursor for tyrosine, the monoamine neurotransmitters dopamine, norepinephrine (noradrenaline), and epinephrine (adrenaline), and the biological pigment melanin. It is Genetic code, encoded by the messenger RNA codons UUU and UUC. Phenylalanine is found naturally in the milk of mammals. It is used in the manufacture of food and drink products and sold as a nutritional supplement as it is a direct precursor to the neuromodulation, neuromodulator phe ...
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Phenylalanine Ammonia-lyase
The enzyme phenylalanine ammonia lyase (EC 4.3.1.24) catalysis, catalyzes the conversion of L-phenylalanine to ammonia and cinnamic acid, ''trans''-cinnamic acid.: :L-phenylalanine = ''trans''-cinnamate + NH3 Phenylalanine ammonia lyase (PAL) is the first and committed step in the Phenylpropanoids metabolism, phenyl propanoid pathway and is therefore involved in the biosynthesis of the polyphenol compounds such as flavonoids, phenylpropanoids, and lignin in plants. Phenylalanine ammonia lyase is found widely in plants, as well as some bacteria, yeast, and fungi, with isoenzymes existing within many different species. It has a molecular mass in the range of 270–330 kilodalton, kDa. The activity of PAL is induced dramatically in response to various stimuli such as tissue wounding, pathogenic attack, light, low temperatures, and plant hormone, hormones. PAL has recently been studied for possible therapeutic benefits in humans afflicted with phenylketonuria. It has also been ...
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