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Citronellol
Citronellol, or dihydrogeraniol, is a natural acyclic monoterpenoid. Both enantiomers occur in nature. (+)-Citronellol, which is found in citronella oils, including ''Cymbopogon nardus'' (50%), is the more common isomer. (−)-Citronellol is widespread, but particularly abundant in the oils of rose (18–55%) and ''Pelargonium'' geraniums. Preparation Several million kilograms of citronellol are produced annually. It is mainly obtained by hydrogenation of geraniol or nerol over copper chromite catalyst. Homogeneous catalysts are used for the production of enantiomers. Citronellene is also a precursor. Uses Citronellol is used in perfumes and as a fragrance in cleaning products. In many applications, one of the enantiomers is preferred. It is a component of citronella oil, an insect repellant. Citronellol is used as a raw material for the production of rose oxide. It is also a precursor to many commercial and potential fragrances such as citronellol acetate, citronellyl ...
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Rhodinol
Rhodinol is the chemical compound 3,7-dimethyloct-7-en-1-ol. As the (3S) isomer it is CAS 6812-78-8, and as the racemate it is CAS 141-25-3. In the field of perfumery materials, the term may refer to L-citronellol, to mixtures comprising mostly L- or racemic citronellol and geraniol, or to mixtures comprising mostly racemic 3,7-dimethyloct-7-en-1-ol and racemic citronellol. Two example synthetic Rhodinol products are Rhodinol 70, a racemic mixture comprising 40-60% 3,7-dimethyloct-7-en-1-ol and 40-60% citronellol, and Sigma-Aldrich Rhodinol, which consists of L-citronellol and geraniol. Rhodinol is also provided in perfumery in natural grades as materials extracted from geranium or citronella, comprising principally citronellol and geraniol. Rhodinol products are used in cosmetics and perfumery to impart flowery odors, particularly but not limited to being a component of rosy odor. 3,7-Dimethyloct-7-en-1-ol does not appear substantively in nature.
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Citronella Oil
Citronella oil Citronella oil is an essential oil obtained from the leaves and stems of different species of ''Cymbopogon'' (lemongrass). The oil is used extensively as a source of perfumery chemicals such as citronellal, citronellol, and geraniol. These chemicals find extensive use in soap, candles and incense, perfumery, cosmetic, and flavouring industries throughout the world. Citronella oil is also a plant-based insect repellent and has been registered for this use in the United States since 1948. The United States Environmental Protection Agency considers oil of citronella as a biopesticide with a non-toxic mode of action. Citronella oil has strong antifungal properties. Types Citronella oil is classified in trade into two chemotypes:Chang, Yu Shyun, 2007, ''8 Map species from Malaysia for ICS,'' Forest Research Institute Malaysia, Workshop on NFP, 28–29 May 2007, Nanchang, PR China Ceylon type * CAS: 89998-15-2 * CAS: 8000-29-1 * EINECS: 289-753-6 * FEMA: 2308 * Co ...
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Monoterpenes
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 precursor ...
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Geraniol
Geraniol is a monoterpenoid and an alcohol. It is the primary component of citronella oil and is a primary component of rose oil, palmarosa oil. It is a colorless oil, although commercial samples can appear yellow. It has low solubility in water, but it is soluble in common organic solvents. The functional group derived from geraniol (in essence, geraniol lacking the terminal −OH) is called geranyl. Uses and occurrence In addition to rose oil, palmarosa oil, and citronella oil, it also occurs in small quantities in geranium, lemon, and many other essential oils. With a rose-like scent, it is commonly used in perfumes. It is used in flavors such as peach, raspberry, grapefruit, red apple, plum, lime, orange, lemon, watermelon, pineapple, and blueberry. Geraniol is produced by the scent glands of honeybees to mark nectar-bearing flowers and locate the entrances to their hives. It is also commonly used as an insect repellent, especially for mosquitoes. The scen ...
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Pelargonium Graveolens
''Pelargonium graveolens'' is a ''Pelargonium'' species native to the Cape Provinces and the Northern Provinces of South Africa, Zimbabwe and Mozambique. Etymology ''Pelargonium'' comes from the Greek πελαργός ''pelargos'' which means stork. Another name for pelargoniums is stork's-bills due to the shape of their fruit. The specific epithet ''graveolens'' refers to the strong-smelling leaves. Description ''Pelargonium graveolens'' is an erect, multi-branched shrub, that grows up to 1.5 m and has a spread of 1 m. The leaves are deeply incised, velvety and soft to the touch (due to glandular hairs). The flowers vary from pale pink to almost white and the plant flowers from August to January. The leaves may be strongly rose-scented, although the leaf shape and scent vary. Some plants are very strongly scented and others have little or no scent. Some leaves are deeply incised and others less so, being slightly lobed like '' P. capitatum''. Common names and syn ...
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Geraniol
Geraniol is a monoterpenoid and an alcohol. It is the primary component of citronella oil and is a primary component of rose oil, palmarosa oil. It is a colorless oil, although commercial samples can appear yellow. It has low solubility in water, but it is soluble in common organic solvents. The functional group derived from geraniol (in essence, geraniol lacking the terminal −OH) is called geranyl. Uses and occurrence In addition to rose oil, palmarosa oil, and citronella oil, it also occurs in small quantities in geranium, lemon, and many other essential oils. With a rose-like scent, it is commonly used in perfumes. It is used in flavors such as peach, raspberry, grapefruit, red apple, plum, lime, orange, lemon, watermelon, pineapple, and blueberry. Geraniol is produced by the scent glands of honeybees to mark nectar-bearing flowers and locate the entrances to their hives. It is also commonly used as an insect repellent, especially for mosquitoes. The scen ...
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Terpenoid
The terpenoids, also known as isoprenoids, are a class of naturally occurring organic chemicals derived from the 5-carbon compound isoprene and its derivatives called terpenes, diterpenes, etc. While sometimes used interchangeably with "terpenes", terpenoids contain additional functional groups, usually containing oxygen. When combined with the hydrocarbon terpenes, terpenoids comprise about 80,000 compounds. They are the largest class of plant secondary metabolites, representing about 60% of known natural products. Many terpenoids have substantial pharmacological bioactivity and are therefore of interest to medicinal chemists. Plant terpenoids are used for their aromatic qualities and play a role in traditional herbal remedies. Terpenoids contribute to the scent of eucalyptus, the flavors of cinnamon, cloves, and ginger, the yellow color in sunflowers, and the red color in tomatoes. Well-known terpenoids include citral, menthol, camphor, salvinorin A in the plant ''Salvia d ...
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Rose
A rose is either a woody perennial flowering plant of the genus ''Rosa'' (), in the family Rosaceae (), or the flower it bears. There are over three hundred species and tens of thousands of cultivars. They form a group of plants that can be erect shrubs, climbing, or trailing, with stems that are often armed with sharp prickles. Their flowers vary in size and shape and are usually large and showy, in colours ranging from white through yellows and reds. Most species are native to Asia, with smaller numbers native to Europe, North America, and northwestern Africa. Species, cultivars and hybrids are all widely grown for their beauty and often are fragrant. Roses have acquired cultural significance in many societies. Rose plants range in size from compact, miniature roses, to climbers that can reach seven meters in height. Different species hybridize easily, and this has been used in the development of the wide range of garden roses. Etymology The name ''rose'' comes from ...
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Pelargonium
''Pelargonium'' () is a genus of flowering plants that includes about 280 species of perennials, succulents, and shrubs, commonly called geraniums, pelargoniums, or storksbills. ''Geranium'' is also the botanical name and common name of a separate genus of related plants, also known as cranesbills. Both genera belong to the family Geraniaceae. Carl Linnaeus originally included all the species in one genus, ''Geranium'', and they were later separated into two genera by Charles Louis L'Héritier de Brutelle in 1789. While ''Geranium'' species are mostly temperate herbaceous plants, dying down in winter, ''Pelargonium'' species are evergreen perennials indigenous to warm temperate and tropical regions of the world, with many species in southern Africa. They are drought and heat tolerant, but can tolerate only minor frosts. Some species are extremely popular garden plants, grown as houseplants and bedding plants in temperate regions. They have a long flowering period, with flow ...
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Rose Oxide
A rose is either a woody perennial flowering plant of the genus ''Rosa'' (), in the family Rosaceae (), or the flower it bears. There are over three hundred species and tens of thousands of cultivars. They form a group of plants that can be erect shrubs, climbing, or trailing, with stems that are often armed with sharp prickles. Their flowers vary in size and shape and are usually large and showy, in colours ranging from white through yellows and reds. Most species are native to Asia, with smaller numbers native to Europe, North America, and northwestern Africa. Species, cultivars and hybrids are all widely grown for their beauty and often are fragrant. Roses have acquired cultural significance in many societies. Rose plants range in size from compact, miniature roses, to climbers that can reach seven meters in height. Different species hybridize easily, and this has been used in the development of the wide range of garden roses. Etymology The name ''rose'' comes from La ...
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Hydrogenation
Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to reduce or saturate organic compounds. Hydrogenation typically constitutes the addition of pairs of hydrogen atoms to a molecule, often an alkene. Catalysts are required for the reaction to be usable; non-catalytic hydrogenation takes place only at very high temperatures. Hydrogenation reduces double and triple bonds in hydrocarbons. Process Hydrogenation has three components, the unsaturated substrate, the hydrogen (or hydrogen source) and, invariably, a catalyst. The reduction reaction is carried out at different temperatures and pressures depending upon the substrate and the activity of the catalyst. Related or competing reactions The same catalysts and conditions that are used for hydrogenation reactions can also lead to isomerization of the alkenes f ...
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Nerol
Nerol is a monoterpenoid alcohol found in many essential oils such as lemongrass and hops. It was originally isolated from neroli oil, hence its name. This colourless liquid is used in perfumery. Like geraniol, nerol has a sweet rose odor but it is considered to be fresher.Karl-Georg Fahlbusch, Franz-Josef Hammerschmidt, Johannes Panten, Wilhelm Pickenhagen, Dietmar Schatkowski, Kurt Bauer, Dorothea Garbe, Horst Surburg "Flavors and Fragrances" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2002. Esters and related derivatives of nerol are referred to as neryl, e.g., neryl acetate. Isomeric with nerol is geraniol, which is ''trans''- or ''E''-isomer. Nerol readily loses water to form a set of C10 compounds called dipentene. Nerol can be synthesized by pyrolysis of beta-pinene, which also affords myrcene. Hydrochlorination of myrcene gives a series of isomeric chlorides. See also *Citral * Citronellol *Geraniol *Linalool Linalool () refers to two ...
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