Sinapinic Acid
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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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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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Malate
Malic acid is an organic compound with the molecular formula . It is a dicarboxylic acid that is made by all living organisms, contributes to the sour taste of fruits, and is used as a food additive. Malic acid has two stereoisomeric forms (L- and D-enantiomers), though only the L-isomer exists naturally. The salts and esters of malic acid are known as malates. The malate anion is an intermediate in the citric acid cycle. Etymology The word 'malic' is derived from Latin ' mālum', meaning 'apple'. The related Latin word , meaning 'apple tree', is used as the name of the genus ''Malus'', which includes all apples and crabapples; and the origin of other taxonomic classifications such as Maloideae, Malinae, and Maleae. Biochemistry L-Malic acid is the naturally occurring form, whereas a mixture of L- and D-malic acid is produced synthetically. File:L-Äpfelsäure.svg, L-Malic acid File:D-Äpfelsäure.svg, D-Malic acid Malate plays an important role in biochemistry. In the C4 ...
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Sinapaldehyde
Sinapaldehyde is an organic compound with the formula HO(CH3O)2C6H2CH=CHCHO. It is a derivative of cinnamaldehyde, featuring one hydroxy group and two methoxy groups as substituents. It is an intermediate in the formation of sinapyl alcohol, a lignol that is a major precursor to lignin. Biosynthetic role In sweetgum (''Liquidambar styraciflua''), sinapaldehyde arises in two steps from coniferyl aldehyde beginning with hydroxylation mediated by coniferyl aldehyde 5-hydroxylase. The diphenol is then methylated at the 5-OH by the action of caffeate ''O''-methyltransferase. Sinapaldehyde is reduced to the alcohol by the action of dehydrogenase enzymes. In ''Arabidopsis thaliana'', the enzyme dihydroflavonol 4-reductase uses NADP+ to reduce sinapaldehyde to sinapyl alcohol. It is found in ''Senra incana'' (Hibisceae). It is a low molecular weight phenol that is susceptible to extraction from cork stoppers into wine.Polyphenolic Composition of ''Quercus suber'' Cork from Different ...
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Sinapyl Alcohol
Sinapyl alcohol is an organic compound structurally related to cinnamic acid. It is biosynthetized via the phenylpropanoid biochemical pathway, its immediate precursor being sinapaldehyde. This phytochemical is one of the monolignols, which are precursor to lignin or lignans. It is also a biosynthetic precursor to various stilbenoids and coumarins. See also *Sinapinic acid *Syringol *Syringaldehyde *Syringic acid *Acetosyringone *Sinapine *Canolol *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 ... References {{DEFAULTSORT:Sinapyl Alcohol Monolignols Ethers ...
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Acetosyringone
Acetosyringone is a phenolic natural product and a chemical compound related to acetophenone and 2,6-dimethoxyphenol. It was first described in relation to lignan/phenylpropanoid-type phytochemicals, with isolation from a variety of plant sources, in particular, in relation to wounding and other physiologic changes. Occurrence and biological role Historically, this substance has been best known for its involvement in plant-pathogen recognition, especially its role as a signal attracting and transforming unique, oncogenic bacteria in genus ''Agrobacterium''. The ''virA'' gene on the Ti plasmid of ''Agrobacterium tumefaciens'' and the Ri plasmid of ''Agrobacterium rhizogenes'' is used by these soil bacteria to infect plants, via its encoding for a receptor for acetosyringone and other phenolic phytochemicals exuded by plant wounds. This compound also allows higher transformation efficiency in plants, as shown in ''A. tumefaciens''-mediated transformation procedures, and so is of ...
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Syringic Acid
Syringic acid is a naturally occurring phenolic compound and dimethoxybenzene that is commonly found as a plant metabolite. Natural occurrence Syringic acid can be found in several plants including ''Ardisia elliptica'' and '' Schumannianthus dichotomus''. Synthesis Syringic acid can be prepared by selectively hydrolyzing ( demethylating) eudesmic acid with 20% sulfuric acid. Presence in food Syringic acid can be found in several fruits including olives, dates, spices, pumpkin, grapes, acai palm, honey, red wine, among others. Its presence in the ancient Egyptian drink shedeh could confirm it was made out of grape, as syringic acid is released by the breakdown of the compound malvidin, also found in red wine. It is also found in vinegar. Applications Various studies have found syringic acid to exhibit useful pharmaceutical properties such as anti-oxidant, anti-microbial, anti-inflammation, anti-cancer, and anti-diabetic. Syringic acid can be enzymatically polymerise ...
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Syringol
Syringol is the organic compound with the formula HO(CH3O)2C6H3. The molecule is a phenol, with methoxy groups in the flanking (2 and 6) positions. It is the symmetrically dimethylated derivative of pyrogallol. It is a colorless solid, although typical samples are brown owing to air-oxidized impurities. Together with guaiacol, syringol and its derivatives are produced by the pyrolysis of lignin. Specifically, syringol is derived from the thermal decomposition of the sinapyl alcohol component. As such, syringol is an important component of wood smoke. Syringyl/guaiacyl ratio Lignin, comprising a major fraction of biomass, is sometimes classified according to the syringyl component. Pyrolysis of lignin derived from sinapyl alcohol affords syringol. The conversion involves replacement of the propenyl alcohol substituent of the sinapyl alcohol by hydrogen. A high syringyl (or S) content is indicative of lignin from angiosperms. In contrast, pyrolysis of lignin from gymnosperms gi ...
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Syringaldehyde
Syringaldehyde is an organic compound that occurs in trace amounts widely in nature. Some species of insects use syringaldehyde in their chemical communication systems. ''Scolytus multistriatus'' uses it as a signal to find a host tree during oviposition. Because it contains many functional groups, it can be classified in many ways - aromatic, aldehyde, phenol. It is a colorless solid (impure samples appear yellowish) that is soluble in alcohol and polar organic solvents. Its refractive index is 1.53. Natural sources Syringaldehyde can be found naturally in the wood of spruce and maple trees. Syringaldehyde is also formed in oak barrels and extracted into whisky, which it gives spicy, smoky, hot and smoldering wood aromas. Preparation This compound may be prepared from syringol by the Duff reaction: : See also *Phenolic content in wine *Syringol *Syringic acid *Acetosyringone *Sinapyl alcohol *Sinapinic acid *Sinapaldehyde *Sinapine *Canolol Canolol is a phenolic comp ...
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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. Origin of the phenolic compounds The natural phenols are not evenly distributed within the fruit. Phenolic acids are largely present in the pulp, anthocyanins and stilbenoids in the skin, and other phenols (catechins, proanthocyanidins and flavonols) in ...
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Canola Oil
Close-up of canola blooms Canola flower Rapeseed oil is one of the oldest known vegetable oils. There are both edible and industrial forms produced from rapeseed, the seed of several cultivars of the plant family Brassicaceae. Historically, it was eaten in limited quantities due to high levels of erucic acid, which is damaging to the cardiac muscle of animals and imparts a bitter taste, and glucosinolates, which made it less nutritious in animal feed. Rapeseed oil can contain up to 54% erucic acid. Canola oil is a food-grade version derived from rapeseed cultivars bred for low erucic acid content. Also known as low erucic acid rapeseed (LEAR) oil, it has been generally recognized as safe by the United States Food and Drug Administration. Canola oil is limited by government regulation to a maximum of 2% erucic acid by weight in the US and the EU, with special regulations for infant food. These low levels of erucic acid do not cause harm in humans. In commerce, non-food variet ...
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Canolol
Canolol is a phenolic compound found in crude canola oil. It is produced by decarboxylation of sinapic acid during canola seed roasting.Isolation and Identification of a Potent Radical Scavenger (Canolol) from Roasted High Erucic Mustard Seed Oil from Nepal and Its Formation during Roasting. Kshitij Shrestha, Christian V Stevens, Bruno De Meulenaer, J. Agric. Food Chem., 2012, 60 (30), pp 7506–7512, See also *Phenolic content in wine *Syringaldehyde *Syringol *Syringic acid *Acetosyringone *Sinapyl alcohol *Sinapaldehyde *Sinapinic acid *Sinapine Sinapine is an alkaloidal amine found in some seeds, particularly oil seeds of plants in the family Brassicaceae. It is the choline ester of sinapic acid. Sinapine was discovered by Etienne Ossian Henry in 1825. Occurrence Sinapine typically ... References O-methylated natural phenols Vinyl compounds Vegetable oils {{phenol-stub ...
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