α-pyrone
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α-pyrone
2-Pyrone (α-pyrone or pyran-2-one) is an unsaturated cyclic chemical compound with the molecular formula C5H4O2. It is isomeric with 4-pyrone. 2-Pyrone is used in organic synthesis as a building block for more complex chemical structures because it may participate in a variety of cycloaddition reactions to form bicyclic lactones. For example, it readily undergoes Diels-Alder reactions with alkynes producing, upon loss of carbon dioxide, substituted benzenes. The Gogte Synthesis (1938) is a method for the alkylation of certain pyrones with acid chlorides. The parent 2-pyrone can be produced from decarboxylation of coumalic acid. Derivatives The most common natural products containing a 2-pyrone are the bufanolides and kavalactones. Oxovitisin A, a pyranoanthocyanin found in wine, also contains a 2-pyrone element. 6-Amyl-α-pyrone (6PP) is a derivative of 2-pyrone, found in animal foods and heated beef. Due to its good organoleptic properties with coconut aroma, it is used a ...
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6-Amyl-α-pyrone
6-Amyl-α-pyrone, also 6-pentyl-2-pyrone or 6PP, is an unsaturated lactone molecule. It contains two double bonds in the ring and a Pentyl group, pentyl substituent at carbon adjacent to the ring oxygen. It is a colorless liquid which possesses characteristic coconut aroma, produced biologically by ''Trichoderma'' species. It is found in animal foods, peach (''Prunus persica''), and heated beef. Reactivity Chemically, 6PP is converted into a linear ketone via ring opening and decarboxylation in presence of water, which subsequently undergoes solid base catalyzed aldol condensation reaction into C14/C15 hydrocarbon precursor. Upon heating in presence of Pd/C catalyst with formic acid, the double bonds of the 6PP get reduced to yield the flavoring compound δ-Decalactone, δ-decalactone. In presence of strong reducing agent like lithium aluminium hydride, the double bonds of the ring get saturated and transformed into 1,5-decanediol via sequential hydrogenation steps. References ...
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Pyrone
Pyrones or pyranones are a class of heterocyclic chemical compounds. They contain an unsaturated six-membered ring, which has one oxygen atom and a carbonyl functional group. There are two isomers, denoted as 2-pyrone and 4-pyrone. The 2-pyrone (or α-pyrone) structure is a lactone and is found in nature as part of the coumarin ring system. The 4-pyrone (or γ-pyrone) structure is an ether–ketone found in some natural chemical compounds such as chromone, maltol and kojic acid. See also * Furanone 2-Furanone is a heterocyclic organic compound. It is also known as γ-crotonolactone (GCL), as it is formally the lactone derived from γ-hydroxy isocrotonic acid. The chemical is colloquially called "butenolide", and is the parent structure for ..., which has one fewer carbon atom in the ring. * Pyridones, which contain a nitrogen in place of the oxygen that is part of the ring References {{heterocyclic-stub ...
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Kavalactone
Kavalactones are a class of lactone compounds found in kava roots and ''Alpinia zerumbet'' (shell ginger) and in several Gymnopilus, Phellinus and Inonotus fungi. Some kavalactones are bioactive. They are responsible for the psychoactive, analgesic, euphoric and sedative effects of kava. Bioactivity Kava extract interacts with many pharmaceuticals and herbal medications. In human volunteers, in vivo inhibition includes CYP1A2 and CYP2E1 through use of probe drugs to measure inhibition. Research Its anxiolytic and hepatotoxic properties have been investigated. The major kavalactones (except for desmethoxyyangonin, desmethoxyyangonin) potentiate GABAA receptor, GABAA receptors, which may underlie the anxiolytic and sedative properties of kava. Further, Reuptake inhibitor, inhibition of the reuptake of norepinephrine, norepinephrine and dopamine, binding to the CB1 receptor, CB1 receptor, inhibition of voltage-gated sodium channel, sodium and voltage-gated calcium channel, calciu ...
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Decarboxylation
Decarboxylation is a chemical reaction that removes a carboxyl group and releases carbon dioxide (CO2). Usually, decarboxylation refers to a reaction of carboxylic acids, removing a carbon atom from a carbon chain. The reverse process, which is the first chemical step in photosynthesis, is called carboxylation, the addition of CO2 to a compound. Enzymes that catalyze decarboxylations are called decarboxylases or, the more formal term, carboxy-lyases (Enzyme Commission number, EC number 4.1.1). In organic chemistry The term "decarboxylation" usually means replacement of a carboxyl group () with a hydrogen atom: : Decarboxylation is one of the oldest known organic reactions. It is one of the processes assumed to accompany pyrolysis and destructive distillation. Overall, decarboxylation depends upon stability of the carbanion synthon , although the anion may not be a true chemical intermediate. Typically, carboxylic acids decarboxylate slowly, but carboxylic acids with an α el ...
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Nature Publishing Group
Nature Portfolio (formerly known as Nature Publishing Group and Nature Research) is a division of the international scientific publishing company Springer Nature that publishes academic journals, magazines, online databases, and services in science and medicine. Nature Research's flagship publication is ''Nature'', a weekly multidisciplinary journal first published in 1869. It also publishes the ''Nature-''titled research journals, ''Nature Reviews'' journals (since 2000), society-owned academic journals, and a range of open access journals, including ''Scientific Reports'' and ''Nature Communications''. Springer Nature also publishes ''Scientific American'' in 16 languages, a magazine intended for the general public. In 2013, prior to the merger with Springer and the creation of Springer Nature, Nature Publishing Group's owner, Holtzbrinck Publishing Group, bought a controlling stake in Frontiers. Before Springer Nature was formed in 2015, Nature Research (as the Nature Publi ...
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Nature Chemical Biology
''Nature Chemical Biology'' is a monthly peer-reviewed scientific journal published by Nature Portfolio. It was established in June 2005 by founding Chief Editor Terry L. Sheppard as part of Nature Publishing Group. Sheppard was the Chief Editor of the journal 2004–2022. The current editor-in-chief is Russell Johnson. Aims and scope The publishing focus of ''Nature Chemical Biology'' is a forum for original research and commentary in chemical biology. Published topics encompass concepts and research methods in chemistry, biology, and related disciplines with the result of controlling biological systems at the molecular level. Authors (contributors) are chemical biologists, also chemists involved in interdisciplinary research between chemistry and biology, along with biologists who produce research results in understanding and controlling biological processes at the molecular level. Interdisciplinary research in chemistry and biology is emphasized. The journal's main focus ...
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Quorum Sensing
In biology, quorum sensing or quorum signaling (QS) is the process of cell-to-cell communication that allows bacteria to detect and respond to cell population density by gene regulation, typically as a means of acclimating to environmental disadvantages. Quorum sensing is a type of cellular signaling, and can be more specifically considered a type of paracrine signaling. However, it also contains traits of autocrine signaling: a cell produces both an autoinducer molecule and the receptor for the autoinducer. As one example, quorum sensing enables bacteria to restrict the expression of specific genes to the high cell densities at which the resulting phenotypes will be most beneficial, especially for phenotypes that would be ineffective at low cell densities and therefore too energetically costly to express. Many species of bacteria use quorum sensing to coordinate gene expression according to the density of their local population. In a similar fashion, some social insects use q ...
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Trichoderma
''Trichoderma'' is a genus of fungi in the family Hypocreaceae that is present in all soils, where they are the most prevalent culturable fungi. Many species in this genus can be characterized as opportunistic avirulent plant symbionts. This refers to the ability of several ''Trichoderma ''species to form mutualistic endophytic relationships with several plant species. ''Trichoderma'' species are also responsible for green mold disease in mushroom cultivation. The genomes of several ''Trichoderma'' species'' ''have been sequenced and are publicly available from the JGI. Taxonomy The genus was described by Christiaan Hendrik Persoon in 1794, but the taxonomy has remained difficult to resolve. For a long time, it was considered to consist of only one species, '' Trichoderma viride'', named for producing green mold. Subdivision In 1991, Bissett divided the genus into five sections, partly based on the aggregate species described by Rifai: *''Pachybasium'' (20 species) *''Lo ...
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Oxovitisin A
Oxovitisin A is an oxovitisin, a type of pyranoanthocyanin with a pyranone (2-pyrone) component. It is found in aged Port wines. It does not contain an oxonium ion component ( flavylium cation), as anthocyanins do. Therefore, it does not have an absorption maximum at 520 nm. Oxovitisins are stable yellowish Varieties of the color yellow may differ in hue, colorfulness, chroma (also called saturation, intensity, or colorfulness) or lightness (or value, tone, or brightness), or in two or three of these qualities. Variations in value are also called ... pigments with similar unique spectral features, displaying only a pronounced broad band around 370 nm in the UV−vis spectrum. It is an oxidative derivative of carboxypyranomalvidin-3-glucoside (vitisin A).Oxovitisins: A New Class of Neutral Pyranone-anthocyanin Derivatives in Red Wines. Jingren He, Joana Oliveira, Artur M. S. Silva, Nuno Mateus and Victor De Freitas, J. Agric. Food Chem., 2010, 58 (15), pages 8814–88 ...
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Bufanolide
Bufanolide is a C24 steroid and, indirectly, a parent structure of bufadienolide. Its derivatives was found in ''Bufo'' and ''Scilla'', as an aglycone of cardiac glycosides and is usually toxic Toxicity is the degree to which a chemical substance or a particular mixture of substances can damage an organism. Toxicity can refer to the effect on a whole organism, such as an animal, bacterium, or plant, as well as the effect on a subst .... References {{Cardiac glycosides Bufanolides ...
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Coumalic Acid
Coumalic acid is an organic compound with the molecular formula C6H4O4. Its melting point is around 210 °C. In laboratory coumalic acid may be obtained by self-condensation of malic acid 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 ( ... in fuming sulfuric acid: References {{Reflist 2-Pyrones Carboxylic acids ...
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