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Isopropenyl Compounds
In organic chemistry, 1-propenyl (or simply propenyl) has the formula CH=CHCH3 and 2-propenyl (isopropenyl) has the formula CH2=C-CH3. These groups are found in many compounds. Propenyl compounds are isomeric with allyl compounds, which have the formula CH2-CH=CH2. Chemicals with 1-propenyl groups * 2-chloropropylene *propenylbenzene (β-methylstyrene). Many phenylpropanoids and their derivatives feature derivatives of propenylbenzene: * Anethole * Asarone * Carpacin *Coniferyl alcohol *Isoeugenol *Isosafrole *Methyl isoeugenol *Pseudoisoeugenol Chemicals with 2-propenyl groups Several terpenes feature 2-propenyl substituents: *carvone *limonene See also * Propene * Functional group In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the re ... References {{organic-chem-stub Alken ...
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Organic Chemistry
Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms.Clayden, J.; Greeves, N. and Warren, S. (2012) ''Organic Chemistry''. Oxford University Press. pp. 1–15. . Study of structure determines their structural formula. Study of properties includes physical and chemical properties, and evaluation of chemical reactivity to understand their behavior. The study of organic reactions includes the chemical synthesis of natural products, drugs, and polymers, and study of individual organic molecules in the laboratory and via theoretical ( in silico) study. The range of chemicals studied in organic chemistry includes hydrocarbons (compounds containing only carbon and hydrogen) as well as compounds based on carbon, but also containing other elements, especially oxygen, nitrogen, sulfur, phosphorus (included in ...
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Isoeugenol
Isoeugenol is a phenylpropene, a propenyl-substituted guaiacol. A phenylpropanoid, it occurs in the essential oils of plants such as ylang-ylang (''Cananga odorata''), and is a component of wood smoke and liquid smoke. It can be synthesized from eugenol and has been used in the manufacture of vanillin. It may occur as either the cis ''(Z)'' or trans ''(E)'' isomer. Trans ''(E)'' isoeugenol is crystalline while cis ''(Z)'' isoeugenol is a liquid. Isoeugenol is one of several phenolic compounds responsible for the mold-inhibiting effect of smoke on meats and cheeses. Allergy Some individuals experience a hives-like reaction to long-term exposure to Isoeugenol, which is named as ''Fragrance'' in the ingredients of consumer products such as soaps, shampoos and detergents, bath tissue, and topical cosmetic applications. Sensitivity to isoeugenol (Fragrance) may be identified with a clinical patch test. See also * Pseudoisoeugenol * Methylisoeugenol * Desmethylisoeugenol Hydroxychavi ...
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Propene
Propylene, also known as propene, is an unsaturated organic compound with the chemical formula CH3CH=CH2. It has one double bond, and is the second simplest member of the alkene class of hydrocarbons. It is a colorless gas with a faint petroleum-like odor. Production Steam cracking The dominant technology for producing propylene is steam cracking. The same technology is applied to ethane to ethylene. These two conversions are the #2 and #1 processes in the chemical industry, as judged by their scale. In this process, propane undergoes dehydrogenation. The by-product is hydrogen: :CH3CH2CH3 → CH3CH=CH2 + H2 The yield of propene is about 85 m%. By-products are usually used as fuel for the propane dehydrogenation reaction. Steam cracking is one of the most energy-intensive industrial processes. The feedstock is naphtha or propane, especially in the Middle East, where there is an abundance of propane from oil/gas operations. Propene can be separated by fractional distilla ...
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Limonene
Limonene is a colorless liquid aliphatic hydrocarbon classified as a cyclic monoterpene, and is the major component in the oil of citrus fruit peels. The -isomer, occurring more commonly in nature as the fragrance of oranges, is a flavoring agent in food manufacturing. It is also used in chemical synthesis as a precursor to carvone and as a renewables-based solvent in cleaning products. The less common -isomer has a piny, turpentine-like odor, and is found in the edible parts of such plants as caraway, dill, and bergamot orange plants. Limonene takes its name from Italian ''limone'' ("lemon"). Limonene is a chiral molecule, and biological sources produce one enantiomer: the principal industrial source, citrus fruit, contains -limonene ((+)-limonene), which is the (''R'')-enantiomer. Racemic limonene is known as dipentene. -Limonene is obtained commercially from citrus fruits through two primary methods: centrifugal separation or steam distillation. Chemical reactions Limon ...
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Carvone
Carvone is a member of a family of chemicals called terpenoids. Carvone is found naturally in many essential oils, but is most abundant in the oils from seeds of caraway (''Carum carvi''), spearmint (''Mentha spicata''), and dill. Uses Both carvones are used in the food and flavor industry. ''R''-(−)-Carvone is also used for air freshening products and, like many essential oils, oils containing carvones are used in aromatherapy and alternative medicine. ''S''-(+)-Carvone has shown a suppressant effect against high-fat diet induced weight gain in mice. Food applications As the compound most responsible for the flavor of caraway, dill and spearmint, carvone has been used for millennia in food. Wrigley's Spearmint Gum and spearmint flavored Life Savers are major users of natural spearmint oil from ''Mentha spicata''. Caraway seed is extracted with alcohol to make the European drink Kümmel. Agriculture ''S''-(+)-Carvone is also used to prevent premature sprouting of potatoes ...
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Terpene
Terpenes () are a class of natural products consisting of compounds with the formula (C5H8)n for n > 1. Comprising more than 30,000 compounds, these unsaturated hydrocarbons are produced predominantly by plants, particularly conifers. Terpenes are further classified by the number of carbons: monoterpenes (C10), sesquiterpenes (C15), diterpenes (C20), as examples. The terpene alpha-pinene, is a major component of the common solvent, turpentine. History and terminology The term ''terpene'' was coined in 1866 by the German chemist August Kekulé to denote all hydrocarbons having the empirical formula C10H16, of which camphene was one. Previously, many hydrocarbons having the empirical formula C10H16 had been called "camphene", but many other hydrocarbons of the same composition had had different names. Kekulé coined the term "terpene" in order to reduce the confusion. The name "terpene" is a shortened form of "terpentine", an obsolete spelling of "turpentine". Although sometimes ...
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P-isopropenylphenol
4-Isopropenylphenol is an organic compound with the formula . The molecule consists of a 2-propenyl group (CH2=''C''-CH3) affixed to the 4 position of phenol. The compound is an intermediate in the production of bisphenol A (BPA), 2.7 Mkg/y of which are produced annually (2007). It is also generated by the recycling of ''o,p''-BPA, a byproduct of the production of the ''p,p''-isomer of BPA. Synthesis and reactions The high-temperature hydrolysis of BPA gives the title compound together with phenol: : The compound can also be produced by catalytic dehydrogenation of 4-isopropylphenol. 4-Isopropenylphenol undergoes ''O''-protonation by sulfuric acid, giving the carbocation A carbocation is an ion with a positively charged carbon atom. Among the simplest examples are the methenium , methanium and vinyl cations. Occasionally, carbocations that bear more than one positively charged carbon atom are also encountere ..., which undergoes a variety of dimerization reactions ...
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Pseudoisoeugenol
Pseudoisoeugenol is a naturally occurring phenylpropene and an isomer of eugenol. Natural occurrence and derivatives Pseudoisoeugenol naturally occurs in the essential oils of roots from plants within the genus ''Pimpinella''. In addition to its standard form, the compound also occurs in a variety of structural derivatives. Common derivatives include the compound with its side chain bearing an epoxide functional group and the aromatic ring being associated with one of many possible esters in the 2nd position. Common esters include angelic acid, 2-methylbutanoic acid, tiglic acid, and 2-methylpropionic acid esters. Hydrolysis of these esters, either ''in-vivo'' or by using strong acids, forms 2-methyl-5-methoxybenzofuran. Biosynthesis Biosynthesis of the compound is hypothesized to proceed via a NIH shift of anethole. See also *Isoeugenol Isoeugenol is a phenylpropene, a propenyl-substituted guaiacol. A phenylpropanoid, it occurs in the essential oils of plants such as ylang- ...
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Methyl Isoeugenol
Methyl isoeugenol (isomethyleugenol) is a phenylpropanoid, the methyl ether of isoeugenol, found in certain essential oils. It can occur as both (''E'')- and (''Z'')-isomers. See also * Methyl eugenol Methyl eugenol (allylveratrol) is a natural chemical compound classified as a phenylpropene, a type of phenylpropanoid. It is the methyl ether of eugenol and is important to insect behavior and pollination. It is found in various essential oils. ... References O-methylated phenylpropanoids Phenylpropenes {{Organic-compound-stub ...
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Isosafrole
Isosafrole is an organic compound that is used in the fragrance industry. Structurally, the molecule is related to phenylpropene, a type of aromatic organic chemical. Its fragrance is reminiscent of anise or licorice. It is found in small amounts in various essential oils, but is most commonly obtained by isomerizing the plant oil safrole. It exists as two geometric isomers, ''cis''-isosafrole and ''trans''-isosafrole. Isosafrole is a precursor to the important fragrance piperonal.Karl-Georg Fahlbusch, Franz-Josef Hammerschmidt, Johannes Panten, Wilhelm Pickenhagen, Dietmar Schatkowski, Kurt Bauer, Dorothea Garbe and Horst Surburg "Flavors and Fragrances" in ''Ullmann's Encyclopedia of Industrial Chemistry'', Wiley-VCH, Weinheim, 2003. It can also be converted via the intermediate compound MDP2P into the psychoactive drug MDMA 3,4-Methylenedioxymethamphetamine (MDMA), commonly seen in Tablet (pharmacy), tablet form (ecstasy) and crystal form (molly or mandy), i ...
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Coniferyl Alcohol
Coniferyl alcohol is an organic compound with the formula HO(CH3O)C6H3CH=CHCH2OH. A colourless or white solid, it is one of the monolignols, produced via the phenylpropanoid biochemical pathway. When copolymerized with related aromatic compounds, coniferyl alcohol forms lignin or lignans. Coniferin is a glucoside of coniferyl alcohol. Coniferyl alcohol is an intermediate in biosynthesis of eugenol and of stilbenoids and coumarin. Gum benzoin contains significant amount of coniferyl alcohol and its esters. It is found in both gymnosperm and angiosperm plants. Sinapyl alcohol and paracoumaryl alcohol, the other two lignin monomers, are found in angiosperm plants and grasses. Occurrence Coniferyl alcohol is produced from coniferyl aldehyde by the action of dehydrogenase enzymes. It is a queen retinue pheromone (QRP), a type of honey bee pheromone found in the mandibular glands. In ''Forsythia intermedia'' a dirigent protein was found to direct the stereoselective biosynthesis of (+ ...
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Isomer
In chemistry, isomers are molecules or polyatomic ions with identical molecular formulae – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism is existence or possibility of isomers. Isomers do not necessarily share similar chemical or physical properties. Two main forms of isomerism are structural or constitutional isomerism, in which ''bonds'' between the atoms differ; and stereoisomerism or spatial isomerism, in which the bonds are the same but the ''relative positions'' of the atoms differ. Isomeric relationships form a hierarchy. Two chemicals might be the same constitutional isomer, but upon deeper analysis be stereoisomers of each other. Two molecules that are the same stereoisomer as each other might be in different conformational forms or be different isotopologues. The depth of analysis depends on the field of study or the chemical and physical properties of interest. The English word "isomer" () is a back-form ...
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