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N-Phenylglycine
''N''-Phenylglycine is an organic compound with the formula C6H5NHCH2CO2H. This white solid achieved fame as the industrial precursor to indigo dye. It is a non-proteinogenic amino acid, non-proteinogenic alpha amino acid related to sarcosine, but with an ''N''-phenyl group in place of ''N''-methyl. Preparation It is prepared by the Strecker reaction involving the reaction of formaldehyde, hydrogen cyanide, and aniline. The resulting amino nitrile is hydrolyzed to give the carboxylic acid.Elmar Steingruber "Indigo and Indigo Colorants" Ullmann's Encyclopedia of Industrial Chemistry 2004, Wiley-VCH, Weinheim. See also * Phenylglycine, an isomer with the formula C6H5CH(NH2)CO2H. References [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Indigo Dye
Indigo dye is an organic compound with a distinctive blue color. Historically, indigo was a natural dye extracted from the leaves of some plants of the ''Indigofera'' genus, in particular ''Indigofera tinctoria''; dye-bearing ''Indigofera'' plants were commonly grown and used throughout the world, in Asia in particular, as an important crop, with the production of indigo dyestuff economically important due to the previous rarity of some blue dyestuffs historically. Most indigo dye produced today is synthetic, constituting several thousand tons each year. It is most commonly associated with the production of denim cloth and blue jeans, where its properties allow for effects such as stone washing and acid washing to be applied quickly. Uses The primary use for indigo is as a dye for cotton yarn, mainly used in the production of denim cloth suitable for blue jeans; on average, a pair of blue jeans requires just to of dye. Smaller quantities are used in the dyeing of wool and ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Phenylglycine
Phenylglycine is the organic compound with the formula C6H5CH(NH2)CO2H. It is a non-proteinogenic alpha amino acid related to alanine, but with a phenyl group in place of the methyl group. It is a white solid. The compound exhibits some biological activity. Preparation It is prepared from benzaldehyde by amino cyanation (Strecker synthesis). It can also be prepared from glyoxal and by reductive amination Reductive amination (also known as reductive alkylation) is a form of amination that involves the conversion of a carbonyl group to an amine via an intermediate imine. The carbonyl group is most commonly a ketone or an aldehyde. It is considered ... of phenylglyoxylic acid. Ester The ester methyl α‐phenylglycinate is used to convert carboxylic acids into homologated unsaturated ketones. These reactions proceed via cyclization of phenylglycinamides to oxazolones, which can be reductively cleaved with chromous reagents.{{cite encyclopedia , title=Methyl α‐Phenylgl ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
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 ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Non-proteinogenic Amino Acid
In biochemistry, non-coded or non-proteinogenic amino acids are distinct from the 22 proteinogenic amino acids (21 in eukaryotesplus formylmethionine in eukaryotes with prokaryote organelles like mitochondria) which are naturally encoded in the genome of organisms for the assembly of proteins. However, over 140 non-proteinogenic amino acids occur naturally in proteins and thousands more may occur in nature or be synthesized in the laboratory. Chemically synthesized amino acids can be called unnatural amino acids. Unnatural amino acids can be synthetically prepared from their native analogs via modifications such as amine alkylation, side chain substitution, structural bond extension cyclization, and isosteric replacements within the amino acid backbone. Many non-proteinogenic amino acids are important: * intermediates in biosynthesis, * in post-translational formation of proteins, * in a physiological role (e.g. components of bacterial cell walls, neurotransmitters and toxins), * n ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Sarcosine
Sarcosine, also known as ''N''-methylglycine, or monomethylglycine, is a monopeptide with the formula CH3N(H)CH2CO2H. It exists at neutral pH as the zwitterion CH3N+(H)2CH2CO2−, which can be obtained as a white, water-soluble powder. Like some amino acids, sarcosine converts to a cation at low pH and an anion at high pH, with the respective formulas CH3N+(H)2CH2CO2H and CH3N(H)CH2CO2−. Sarcosine is a close relative of glycine, with a secondary amine in place of the primary amine. Sarcosine is ubiquitous in biological materials. It is used in manufacturing biodegradable surfactants and toothpastes as well as in other applications. Sarcosine is sweet to the taste. Biochemistry Sarcosine is an intermediate and byproduct in glycine synthesis and degradation. Sarcosine is metabolized to glycine by the enzyme sarcosine dehydrogenase, while glycine-''N''-methyl transferase generates sarcosine from glycine. Sarcosine is an amino acid derivative that is naturally found in muscles ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Phenyl
In organic chemistry, the phenyl group, or phenyl ring, is a cyclic group of atoms with the formula C6 H5, and is often represented by the symbol Ph. Phenyl group is closely related to benzene and can be viewed as a benzene ring, minus a hydrogen, which may be replaced by some other element or compound to serve as a functional group. Phenyl group has six carbon atoms bonded together in a hexagonal planar ring, five of which are bonded to individual hydrogen atoms, with the remaining carbon bonded to a substituent. Phenyl groups are commonplace in organic chemistry. Although often depicted with alternating double and single bonds, phenyl group is chemically aromatic and has equal bond lengths between carbon atoms in the ring. Nomenclature Usually, a "phenyl group" is synonymous with C6H5− and is represented by the symbol Ph or, archaically, Φ. Benzene is sometimes denoted as PhH. Phenyl groups are generally attached to other atoms or groups. For example, triphenylmethane (Ph3 ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Methyl
In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula . In formulas, the group is often abbreviated as Me. This hydrocarbon group occurs in many organic compounds. It is a very stable group in most molecules. While the methyl group is usually part of a larger molecule, bounded to the rest of the molecule by a single covalent bond (), it can be found on its own in any of three forms: methanide anion (), methylium cation () or methyl radical (). The anion has eight valence electrons, the radical seven and the cation six. All three forms are highly reactive and rarely observed. Methyl cation, anion, and radical Methyl cation The methylium cation () exists in the gas phase, but is otherwise not encountered. Some compounds are considered to be sources of the cation, and this simplification is used pervasively in organic chemistry. For example, protonation of methanol gives an elect ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Strecker Reaction
The Strecker amino acid synthesis, also known simply as the Strecker synthesis, is a method for the synthesis of amino acids by the reaction of an aldehyde with ammonia in the presence of potassium cyanide. The condensation reaction yields an α-aminonitrile, which is subsequently hydrolyzed to give the desired amino acid. The method is used commercially for the production of racemic methionine from methional. While usage of ammonium salts gives unsubstituted amino acids, primary and secondary amines also give substituted amino acids. Likewise, the usage of ketones, instead of aldehydes, gives α,α-disubstituted amino acids. Reaction mechanism In the first part of the reaction, the carbonyl group, carbonyl oxygen of an aldehyde is protonated, followed by a nucleophilic addition, nucleophilic attack of ammonia to the carbonyl carbon. After subsequent proton exchange, water is cleaved from the iminium ion intermediate. A cyanide ion then attacks the iminium carbon yielding an am ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Formaldehyde
Formaldehyde ( , ) (systematic name methanal) is a naturally occurring organic compound with the formula and structure . The pure compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde (refer to section Forms below), hence it is stored as an aqueous solution (formalin), which is also used to store animal specimens. It is the simplest of the aldehydes (). The common name of this substance comes from its similarity and relation to formic acid. Formaldehyde is an important precursor to many other materials and chemical compounds. In 1996, the installed capacity for the production of formaldehyde was estimated at 8.7 million tons per year. It is mainly used in the production of industrial resins, e.g., for particle board and coatings. Forms Formaldehyde is more complicated than many simple carbon compounds in that it adopts several diverse forms. These compounds can often be used interchangeably and can be interconverted. *Molecular formald ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Hydrogen Cyanide
Hydrogen cyanide, sometimes called prussic acid, is a chemical compound with the formula HCN and structure . It is a colorless, extremely poisonous, and flammable liquid that boils slightly above room temperature, at . HCN is produced on an industrial scale and is a highly valued precursor to many chemical compounds ranging from polymers to pharmaceuticals. Large-scale applications are for the production of potassium cyanide and adiponitrile, used in mining and plastics, respectively. It is more toxic than solid cyanide compounds due to its volatile nature. Structure and general properties Hydrogen cyanide is a linear molecule, with a triple bond between carbon and nitrogen. The tautomer of HCN is HNC, hydrogen isocyanide. Hydrogen cyanide is weakly acidic with a p''K''a of 9.2. It partially ionizes in water solution to give the cyanide anion, CN−. A solution of hydrogen cyanide in water, represented as HCN, is called ''hydrocyanic acid''. The salts of the cyanide ani ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Aniline
Aniline is an organic compound with the formula C6 H5 NH2. Consisting of a phenyl group attached to an amino group, aniline is the simplest aromatic amine In organic chemistry, an aromatic amine is an organic compound consisting of an aromatic ring attached to an amine. It is a broad class of compounds that encompasses aniline Aniline is an organic compound with the formula C6 H5 NH2. Consi .... It is an industrially significant Commodity chemicals, commodity chemical, as well as a versatile starting material for fine chemical synthesis. Its main use is in the manufacture of precursors to polyurethane, dyes, and other industrial chemicals. Like most volatile amines, it has the odor of rotten fish. It Combustion, ignites readily, burning with a smoky flame characteristic of aromatic compounds. It is toxic to humans. Relative to benzene, it is electron-rich. It thus participates more rapidly in electrophilic aromatic substitution reactions. Likewise, it is also prone ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Indigo Synthesis V
Indigo is a deep color close to the color wheel blue (a primary color in the RGB color space), as well as to some variants of ultramarine, based on the ancient dye of the same name. The word "indigo" comes from the Latin word ''indicum'', meaning "Indian", as the dye was originally exported to Europe from India. It is traditionally regarded as a color in the visible spectrum, as well as one of the seven colors of the rainbow: the color between blue and violet; however, sources differ as to its actual position in the electromagnetic spectrum. The first known recorded use of indigo as a color name in English was in 1289. History ''Indigofera tinctoria'' and related species were cultivated in East Asia, Egypt, India, Bangladesh and Peru in antiquity. The earliest direct evidence for the use of indigo dates to around 4000 BC and comes from Huaca Prieta, in contemporary Peru. Pliny the Elder mentions India as the source of the dye after which it was named. It was imported f ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
