Cyclotene
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Cyclotene
2-Hydroxy-3-methyl-2-cyclopenten-1-one is an organic compound related to 1,2-cyclopentanedione. It is the enol tautomer of the diketone 3-methylcyclopentane-1,2-dione. Being an enol, the compound is often called methylcyclopentenolone. It is a colorless solid. Synthesis and structure The compound is prepared by base-catalyzed condensation of 1‐hydroxyhexane‐2,5‐dione, a derivative of hydroxymethylfurfural. The structure has been confirmed by X-ray crystallography. Quantum calculations also indicate that the enol is strongly favored relative to the diketo tautomer. Furthermore, the enolization occurs at the methyl-substituted carbon. Use and occurrence It is one of many products from the pyrolysis of lignocellulose. It is used in flavors and perfumery for its maple- or caramel-like odor. It contributes to the flavor or odor of many foods including wines, coffee, paprika, and salmon. It is sometimes called maple lactone because it occurs in maple syrup (it is not, h ...
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Enol
In organic chemistry, alkenols (shortened to enols) are a type of reactive structure or intermediate in organic chemistry that is represented as an alkene ( olefin) with a hydroxyl group attached to one end of the alkene double bond (). The terms ''enol'' and ''alkenol'' are portmanteaus deriving from "-ene"/"alkene" and the "-ol" suffix indicating the hydroxyl group of alcohols, dropping the terminal "-e" of the first term. Generation of enols often involves removal of a hydrogen adjacent (α-) to the carbonyl group—i.e., deprotonation, its removal as a proton, . When this proton is not returned at the end of the stepwise process, the result is an anion termed an enolate (see images at right). The enolate structures shown are schematic; a more modern representation considers the molecular orbitals that are formed and occupied by electrons in the enolate. Similarly, generation of the enol often is accompanied by "trapping" or masking of the hydroxy group as an ether, such as ...
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Sigma Aldrich
Sigma-Aldrich (formally MilliporeSigma) is an American chemical, life science, and biotechnology company that is owned by the German chemical conglomerate Merck Group. Sigma-Aldrich was created in 1975 by the merger of Sigma Chemical Company and Aldrich Chemical Company. It grew through various acquisitions until it had over 9,600 employees and was listed on the Fortune 1000. The company is headquartered in St. Louis and has operations in approximately 40 countries. In 2015, the German chemical conglomerate Merck Group acquired Sigma-Aldrich for $17 billion. The company is currently a part of Merck's life science business and in combination with Merck's earlier acquired Millipore, operates as MilliporeSigma. History Sigma Chemical Company of St. Louis and Aldrich Chemical Company of Milwaukee were both American specialty chemical companies when they merged in August 1975. The company grew throughout the 1980s and 1990s, with significant expansion in facilities, acquisitions ...
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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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1,2-Cyclopentanedione
1,2-Cyclopentanedione is the organic compound with the formula (CH2)3(CO)2. It is one of two isomeric cyclopentanediones, the other being 1,3-cyclopentanedione. It was first prepared by base-induced condensation of di ethylglutarate with diethyloxalate, followed by hydrolysis of the resulting diketodiester followed by decarboxylation. The enol is predicted to be about 1-3 kcal/mol more stable than the diketo form. The enol structure has been confirmed by X-ray crystallography X-ray crystallography is the experimental science determining the atomic and molecular structure of a crystal, in which the crystalline structure causes a beam of incident X-rays to diffract into many specific directions. By measuring the angles .... Structurally related to 1,2-cyclopentanedione is 2-hydroxy-3-methyl-2-cyclopenten-1-one is a flavor additive, also called cyclotene. References {{DEFAULTSORT:Cyclopentanedione, 1, 2- Diketones Cyclic ketones ...
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Tautomer
Tautomers () are structural isomers (constitutional isomers) of chemical compounds that readily interconvert. The chemical reaction interconverting the two is called tautomerization. This conversion commonly results from the relocation of a hydrogen atom within the compound. The phenomenon of tautomerization is called tautomerism, also called desmotropism. Tautomerism is for example relevant to the behavior of amino acids and nucleic acids, two of the fundamental building blocks of life. Care should be taken not to confuse tautomers with depictions of "contributing structures" in chemical resonance. Tautomers are distinct chemical species that can be distinguished by their differing atomic connectivities, molecular geometries, and physicochemical and spectroscopic properties, whereas resonance forms are merely alternative Lewis structure (valence bond theory) depictions of a single chemical species, whose true structure is best described as the "average" of the idealized, hypothe ...
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Hydroxymethylfurfural
Hydroxymethylfurfural (HMF), also 5-(hydroxymethyl)furfural, is an organic compound formed by the dehydration of reducing sugars. It is a white low-melting solid (although commercial samples are often yellow) which is highly soluble in both water and organic solvents. The molecule consists of a furan ring, containing both aldehyde and alcohol functional groups. HMF can form in sugar-containing food, particularly as a result of heating or cooking. Its formation has been the topic of significant study as HMF was regarded as being potentially carcinogenic to humans. However, so far in vivo genotoxicity was negative. No relevance for humans concerning carcinogenic and genotoxic effects can be derived. HMF is classified as a food improvement agent and is primarily being used in the food industry in form of a food additive as a biomarker as well as a flavoring agent for food products. It is also produced industrially on a modest scale as a carbon-neutral feedstock for the production o ...
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X-ray Crystallography
X-ray crystallography is the experimental science determining the atomic and molecular structure of a crystal, in which the crystalline structure causes a beam of incident X-rays to diffract into many specific directions. By measuring the angles and intensities of these diffracted beams, a crystallographer can produce a three-dimensional picture of the density of electrons within the crystal. From this electron density, the mean positions of the atoms in the crystal can be determined, as well as their chemical bonds, their crystallographic disorder, and various other information. Since many materials can form crystals—such as salts, metals, minerals, semiconductors, as well as various inorganic, organic, and biological molecules—X-ray crystallography has been fundamental in the development of many scientific fields. In its first decades of use, this method determined the size of atoms, the lengths and types of chemical bonds, and the atomic-scale differences among various mat ...
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Pyrolysis
The pyrolysis (or devolatilization) process is the thermal decomposition of materials at elevated temperatures, often in an inert atmosphere. It involves a change of chemical composition. The word is coined from the Greek-derived elements ''pyro'' "fire", "heat", "fever" and '' lysis'' "separating". Pyrolysis is most commonly used in the treatment of organic materials. It is one of the processes involved in charring wood.''Burning of wood''
, InnoFireWood's website. Accessed on 2010-02-06.
In general, pyrolysis of organic substances produces volatile products and leaves , a carbon-rich solid residue. Extreme pyrolysis, which leaves mostly

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Lignocellulose
Lignocellulose refers to plant dry matter (biomass), so called lignocellulosic biomass. It is the most abundantly available raw material on the Earth for the production of biofuels. It is composed of two kinds of carbohydrate polymers, cellulose and hemicellulose, and an aromatic-rich polymer called lignin. Any biomass rich in cellulose, hemicelluloses, and lignin are commonly referred to as lignocellulosic biomass. Each component has a distinct chemical behavior. Being a composite of three very different components makes the processing of lignocellulose challenging. The evolved resistance to degradation or even separation is referred to as recalcitrance. Overcoming this recalcitrance to produce useful, high value products requires a combination of heat, chemicals, enzymes, and microorganisms. These carbohydrate-containing polymers contain different sugar monomers (six and five carbon sugars) and they are covalently bound to lignin. Lignocellulosic biomass can be broadly classified ...
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Maple Sugar
Maple sugar is a traditional sweetener in Canada and the northeastern United States, prepared from the sap of the maple tree ("maple sap"). Sources Three species of maple trees in the genus '' Acer'' are predominantly used to produce maple sugar: the sugar maple (''A. saccharum''), the black maple (''A. nigrum''), and the red maple (''A. rubrum''), because of the high sugar content (roughly two to five percent) in the sap of these species. The black maple is included as a subspecies or variety in a more broadly viewed concept of ''A. saccharum'', the sugar maple, by some botanists. Of these, the red maple has a shorter season because it buds earlier than sugar and black maples, which alters the flavor of the sap. A few other species of maple are also sometimes used as sources of sap for producing maple sugar, including the box elder (or Manitoba maple, ''A. negundo''), the silver maple (''A. saccharinum''), and the bigleaf maple (''A. macrophyllum''). Similar sugars may al ...
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Caramel
Caramel ( or ) is an orange-brown confectionery product made by heating a range of sugars. It can be used as a flavoring in puddings and desserts, as a filling in bonbons, or as a topping for ice cream and custard. The process of caramelization consists of heating sugar slowly to around . As the sugar heats, the molecules break down and re-form into compounds with a characteristic colour and flavour. A variety of candies, desserts, toppings, and confections are made with caramel: brittles, nougats, pralines, flan, crème brûlée, crème caramel, and caramel apples. Ice creams sometimes are flavored with or contain swirls of caramel. Etymology The English word comes from French ''caramel'', borrowed from Spanish ''caramelo'' (18th century), itself possibly from Portuguese ''caramelo''. Most likely that comes from Late Latin ''calamellus'' 'sugar cane', a diminutive of ''calamus'' 'reed, cane', itself from Greek κάλαμος. Less likely, it comes from a Medieval Latin ' ...
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