Syringaldehyde
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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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Duff Reaction
The Duff reaction or hexamine aromatic formylation is a formylation reaction used in organic chemistry for the synthesis of benzaldehydes with hexamine as the formyl carbon source. It is named after James Cooper Duff, who was a chemist at the College of Technology, Birmingham, around 1920–1950. The electrophilic species in this electrophilic aromatic substitution reaction is the iminium ion CH2+NR2. The initial reaction product is an iminium which is hydrolyzed to the aldehyde. See mechanism below. The reaction requires strongly electron donating substituents on the aromatic ring such as in a phenol. Formylation occurs '' ortho'' to the electron donating substituent preferentially, unless the ''ortho'' positions are blocked, in which case the formylation occurs at the ''para'' position. Examples are the synthesis of 3,5-di-''tert''-butylsalicylaldehyde: and the synthesis of syringaldehyde: If both ''ortho'' positions are vacant then a diformylation is possible, as in the ...
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Whisky
Whisky or whiskey is a type of distilled alcoholic beverage made from fermented grain mash. Various grains (which may be malted) are used for different varieties, including barley, corn, rye, and wheat. Whisky is typically aged in wooden casks, which are typically made of charred white oak. Uncharred white oak casks previously used for the aging of sherry are also sometimes used. Whisky is a strictly regulated spirit worldwide with many classes and types. The typical unifying characteristics of the different classes and types are the fermentation of grains, distillation, and aging in wooden barrels. Etymology The word ''whisky'' (or ''whiskey'') is an anglicisation of the Classical Gaelic word (or ) meaning "water" (now written as in Modern Irish, and in Scottish Gaelic). This Gaelic word shares its ultimate origins with Germanic ''water'' and Slavic ''voda'' of the same meaning. Distilled alcohol was known in Latin as ("water of life"). This was translated into Old I ...
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Scolytus Multistriatus
''Scolytus multistriatus'', the European elm bark beetle or smaller European elm bark beetle, is a bark beetle species in the genus ''Scolytus''. In Europe, while ''S. multistriatus'' acts as vector of the Dutch elm disease, caused by the Ascomycota ''Ophiostoma ulmi'', it is much less effective than the large elm bark beetle, '' S. scolytus''. ''S. multistriatus'' uses vanillin and syringaldehyde as signals to find a host tree during oviposition.Vanillin and Syringaldehyde as Attractants for ''Scolytus multistriatus'' (Coleoptera: Scolytidae). Meyer H.J. and Norris D.M., Annals of the Entomological Society of America, 17 July 1967, Volume 60, Number 4, pages 858-859,abstract File:01a Scolytus multistriatus Imago 40fach.jpg, female file:01a Scolytus multistriatus Imago 40fach rechte Seite.jpg, female file:01a Scolytus multistriatus Imago 20fach.jpg, female file:01a Scolytus multistriatus Imago 20fach rechte Seite.jpg, female file:04 Scolytus multistriatus Fraßbild.jpg, ''Scoly ...
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Organic Compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The study of the properties, reactions, and syntheses of organic compounds comprise the discipline known as organic chemistry. For historical reasons, a few classes of carbon-containing compounds (e.g., carbonate salts and cyanide salts), along with a few other exceptions (e.g., carbon dioxide, hydrogen cyanide), are not classified as organic compounds and are considered inorganic. Other than those just named, little consensus exists among chemists on precisely which carbon-containing compounds are excluded, making any rigorous definition of an organic compound elusive. Although organic compounds make up only a small percentage of Earth's crust, they are of central importance because all known life is based on organic compounds. Living t ...
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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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Insect Pheromones
Insects (from Latin ') are pancrustacean Hexapoda, hexapod invertebrates of the class (biology), class Insecta. They are the largest group within the arthropod phylum. Insects have a chitinous exoskeleton, a three-part body (head, Thorax (insect anatomy), thorax and abdomen (insect anatomy), abdomen), three pairs of jointed Arthropod leg, legs, compound eyes and one pair of antenna (biology), antennae. Their blood is not totally contained in vessels; some circulates in an open cavity known as the haemocoel. Insects are the most diverse group of animals; they include more than a million described species and represent more than half of all known living organisms. The total number of Extant taxon, extant species is estimated at between six and ten million; In: potentially over 90% of the animal life forms on Earth are insects. Insects may be found in nearly all Natural environment, environments, although only a small number of species reside in the oceans, which are dominated by ...
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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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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 occurs in the outer seed coat of oil crops and is plentiful in some types of press cake leftover after vegetable oil extraction. Typical oil seed cake residues high in sinapine include ''Brassica juncea'' (1.22% by mass), and rapeseed (0.39-1.06% by mass). Isolation The typical protocol for extracting Sinapine from seed cakes entails defatting the cake with hexane via a Soxhlet apparatus followed by extraction with 70% methanol held at 75 °C. Metabolism Sinapine esterase is an enzyme whose two substrates are sinapine and H2O and whose two products are sinapic acid and choline. Sinapoylglucose—choline O-sinapoyltransferase is an enzyme whose two substrates are 1-''O''-sinapoyl-β-D-glucose and choline, whereas its two products ...
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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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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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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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