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Thymol
Thymol (also known as 2-isopropyl-5-methylphenol, IPMP), , is a toxic monoterpenoid phenol derivative of ''p''-Cymene, isomeric with carvacrol. It occurs naturally in the oil of thyme, and it is extracted from ''Thymus vulgaris'' (common thyme), ajwain, and various other plants as a white crystalline substance of a pleasant aromatic odor and strong antiseptic properties. Thymol also provides the distinctive, strong flavor of the culinary herb thyme, also produced from ''T. vulgaris''. Thymol is only slightly soluble in water at neutral pH, but it is extremely soluble in alcohols and other organic solvents. It is also soluble in strongly alkaline aqueous solutions due to deprotonation of the phenol. Its dissociation constant ( p''K''a) is . Thymol absorbs maximum UV radiation at 274 nm. Chemical synthesis Thymol is produced by the alkylation of ''m''-cresol and propene: : A predicted method of biosynthesis of thymol in thyme and oregano begins with the cyclizati ...
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Thymol Biosynthesis
Thymol (also known as 2-isopropyl-5-methylphenol, IPMP), , is a toxic Monoterpene, monoterpenoid Phenols, phenol derivative of p-Cymene, ''p''-Cymene, isomeric with carvacrol. It occurs naturally in the oil of thyme, and it is Liquid–liquid extraction, extracted from ''Thymus vulgaris'' (common thyme), ajwain, and various other plants as a white crystalline substance of a pleasant Aromaticity, aromatic odor and strong antiseptic properties. Thymol also provides the distinctive, strong flavor of the Herb, culinary herb thyme, also produced from ''T. vulgaris''. Thymol is only slightly solubility, soluble in water at neutral pH, but it is extremely soluble in Alcohol (chemistry), alcohols and other organic solvents. It is also soluble in strongly alkaline aqueous solutions due to deprotonation of the phenol. Its dissociation constant (pKa, p''K''a) is . Thymol absorbs maximum ultraviolet, UV radiation at 274 nm. Chemical synthesis Thymol is produced by the alkylation of M ...
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Carvacrol
Carvacrol, or cymophenol, C6H3(CH3)(OH)C3H7, is a monoterpene, monoterpenoid phenol. It has a characteristic pungent, warm odor of oregano. Natural occurrence Carvacrol is present in the essential oil of ''Origanum vulgare'' (oregano), oil of thyme, oil obtained from Lepidium, pepperwort, and Monarda fistulosa, wild bergamot. The essential oil of thyme subspecies contains between 5% and 75% of carvacrol, while ''Satureja'' (savory) subspecies have a content between 1% and 45%. ''Origanum majorana'' (marjoram) and Dittany of Crete are rich in carvacrol, 50% and 60–80% respectively. It is also found in tequila and ''Lippia graveolens'' (Mexican oregano) in the verbena family. Sources * ''Coleus amboinicus'' * ''Lavandula multifida'' * ''Lepidium * ''Lippia graveolens'' * ''Monarda didyma'' * ''Monarda fistulosa'' * ''Nigella sativa'' * ''Origanum compactum'' * ''Origanum dictamnus'' * ''Origanum majorana'' * ''Origanum microphyllum'' * ''Origanum minutiflorum'' * ''Origanum o ...
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Thyme
Thyme () is a culinary herb consisting of the dried aerial parts of some members of the genus ''Thymus (plant), Thymus'' of flowering plants in the mint family Lamiaceae. Thymes are native to Eurasia and north Africa. Thymes have culinary, medicinal, and ornamental uses. The species most commonly cultivated and used for culinary purposes is ''Thymus vulgaris'', native to Southeast Europe. History Thymus serpyllum, Wild thyme grows in the Levant, where it might have been first cultivated. Ancient Egyptians used common thyme (''Thymus vulgaris'') for embalming. The Ancient Greece, ancient Greeks used it in their baths and burnt it as incense in their temples, believing it was a source of courage. The spread of thyme throughout Europe was thought to be due to the Ancient Rome, Romans, as they used it to purify their rooms and to "give an aromatic flavour to cheese and liqueurs". In the European Middle Ages, the herb was placed beneath pillows to aid sleep and ward off nightmares ...
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Ajwain
Ajwain or ajowan (''Trachyspermum ammi'') () —also known as ajowancaraway, thymol seeds, bishop's weed, or carom—is an annual herb in the family Apiaceae. Both the leaves and the seed‑like fruit (often mistakenly called seeds) of the plant are consumed by humans. The name " bishop's weed" also is a common name for other plants. The "seed" (i.e., the fruit) is often confused with lovage seed. Description Ajwain's small, oval, seed-like fruits are pale brown schizocarps, which resemble the seeds of other plants in the family Apiaceae such as caraway, cumin and fennel. They have a bitter and pungent taste, with a flavor similar to anise and oregano. They smell like thyme because they also contain thymol, but they are more aromatic and less subtle in taste, as well as being somewhat bitter and pungent. Even a small number of fruits tend to dominate the flavor of a dish. Vernacular Names Trachyspermum ammi, commonly known as Ajwain, is known by different names across I ...
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Monoterpene
Monoterpenes are a class of terpenes that consist of two isoprene units and have the molecular formula C10H16. Monoterpenes may be linear (acyclic) or contain rings (monocyclic and bicyclic). Modified terpenes, such as those containing oxygen functionality or missing a methyl group, are called monoterpenoids. Monoterpenes and monoterpenoids are diverse. They have relevance to the pharmaceutical, cosmetic, agricultural, and food industries. Biosynthesis Monoterpenes are derived biosynthetically from units of isopentenyl pyrophosphate, which is formed from acetyl-CoA via the intermediacy of mevalonic acid in the HMG-CoA reductase pathway. An alternative, unrelated biosynthesis pathway of IPP is known in some bacterial groups and the plastids of plants, the so-called MEP-(2-methyl-D-erythritol-4-phosphate) pathway, which is initiated from C5 sugars. In both pathways, IPP is isomerized to DMAPP by the enzyme isopentenyl pyrophosphate isomerase. Geranyl pyrophosphate is the precu ...
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M-Cresol
''meta''-Cresol, also 3-methylphenol, is an organic compound with the formula CH3C6H4(OH). It is a colourless, viscous liquid that is used as an intermediate in the production of other chemicals. It is a derivative of phenol and is an isomer of ''p''-cresol and ''o''-cresol. Production Together with many other compounds, ''m''-cresol is traditionally extracted from coal tar, the volatile materials obtained in the production of coke from (bituminous) coal. This residue contains a few percent by weight of phenol and isomeric cresols. In the cymene–cresol process, toluene is alkylated with propylene to give isomers of cymene, which can be oxidatively dealkylated analogous to the cumene process. Another method, involves carbonylation of a mixture of methallyl chloride and acetylene in the presence of nickel carbonyl. Applications ''m''-Cresol is a precursor to numerous compounds. Important applications include: * pesticides such as fenitrothion and fenthion * synthe ...
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Cytochrome P450
Cytochromes P450 (P450s or CYPs) are a Protein superfamily, superfamily of enzymes containing heme as a cofactor (biochemistry), cofactor that mostly, but not exclusively, function as monooxygenases. However, they are not omnipresent; for example, they have not been found in ''Escherichia coli''. In mammals, these enzymes oxidize steroids, fatty acids, xenobiotics, and participate in many biosyntheses. By hydroxylation, CYP450 enzymes convert xenobiotics into hydrophilic derivatives, which are more readily excreted. P450s are, in general, the terminal oxidase enzymes in electron transfer chains, broadly categorized as P450-containing systems. The term "P450" is derived from the spectrophotometry, spectrophotometric peak at the wavelength of the absorption spectroscopy, absorption maximum of the enzyme (450 nanometre, nm) when it is in the redox, reduced state and complexed with carbon monoxide. Most P450s require a protein partner to deliver one or more electrons to reduc ...
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Ultraviolet
Ultraviolet radiation, also known as simply UV, is electromagnetic radiation of wavelengths of 10–400 nanometers, shorter than that of visible light, but longer than X-rays. UV radiation is present in sunlight and constitutes about 10% of the total electromagnetic radiation output from the Sun. It is also produced by electric arcs, Cherenkov radiation, and specialized lights, such as mercury-vapor lamps, tanning lamps, and black lights. The photons of ultraviolet have greater energy than those of visible light, from about 3.1 to 12  electron volts, around the minimum energy required to ionize atoms. Although long-wavelength ultraviolet is not considered an ionizing radiation because its photons lack sufficient energy, it can induce chemical reactions and cause many substances to glow or fluoresce. Many practical applications, including chemical and biological effects, are derived from the way that UV radiation can interact with organic molecules. The ...
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Alkylation
Alkylation is a chemical reaction that entails transfer of an alkyl group. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effecting alkylation. Alkyl groups can also be removed in a process known as dealkylation. Alkylating agents are often classified according to their nucleophilic or electrophilic character. In oil refining contexts, alkylation refers to a particular alkylation of isobutane with alkene, olefins. For upgrading of petroleum, alkylation produces a premium blending stock for gasoline. In medicine, alkylation of DNA is used in chemotherapy to damage the DNA of cancer cells. Alkylation is accomplished with the class of drugs called alkylating antineoplastic agents. Nucleophilic alkylating agents Nucleophilic alkylating agents deliver the equivalent of an alkyl anion (carbanion). The formal "alkyl anion" attacks an electrophile, forming a new covalent bond ...
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Propene
Propylene, also known as propene, is an unsaturated organic compound with the chemical formula . 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. Propylene is a product of combustion from forest fires, cigarette smoke, and motor vehicle and aircraft exhaust. It was discovered in 1850 by A. W. von Hoffmann's student Captain (later Major General) John Williams Reynolds as the only gaseous product of thermal decomposition of amyl alcohol to react with chlorine and bromine. Production Steam cracking The dominant technology for producing propylene is steam cracking, using propane as the feedstock. Cracking propane yields a mixture of ethylene, propylene, methane, hydrogen gas, and other related compounds. The yield of propylene is about 15%. The other principal feedstock is naphtha, especially in the Middle East and Asia. Propylene can be separated by fractional distilla ...
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Royal Society Of Chemistry
The Royal Society of Chemistry (RSC) is a learned society and professional association in the United Kingdom with the goal of "advancing the chemistry, chemical sciences". It was formed in 1980 from the amalgamation of the Chemical Society, the Royal Institute of Chemistry, the Faraday Society, and the Society for Analytical Chemistry with a new Royal Charter and the dual role of learned society and professional body. At its inception, the Society had a combined membership of 49,000 in the world. The headquarters of the Society are at Burlington House, Piccadilly, London. It also has offices in Thomas Graham House in Cambridge (named after Thomas Graham (chemist), Thomas Graham, the first president of the Chemical Society) where ''RSC Publishing'' is based. The Society has offices in the United States, on the campuses of The University of Pennsylvania and Drexel University, at the University City Science Center in Philadelphia, Pennsylvania, in both Beijing and Shanghai, People' ...
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Dienol
Dienestrol (, ) (brand names Dienoestrol, Denestrolin, Dienol and many others), also known as dienoestrol (), is a synthetic nonsteroidal estrogen medication of the stilbestrol group which is or was used to treat menopausal symptoms in the United States and Europe. It has been studied for use by rectal administration in the treatment of prostate cancer in men as well. The medication was introduced in the U.S. in 1947 by Schering as Synestrol and in France in 1948 as Cycladiene. Dienestrol is a close analogue of diethylstilbestrol. It has approximately 223% and 404% of the affinity of estradiol at the ERα and ERβ, respectively. Dienestrol diacetate (brand names Faragynol, Gynocyrol, others) also exists and has been used medically. Isomers Dienestrol structure.svg, Dienestrol (unspecified) - CA 84-17-3E,E-Dienestrol structure.svg, ''E'',''E''-Dienestrol - CA13029-44-2Z,Z-Dienestrol structure.svg, ''Z'',''Z''-Dienestrol - CA 35495-11-5 See also * Benzestrol * Hexestrol Hexes ...
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