Disparlure Synthesis
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Disparlure Synthesis
''cis''-7,8-Epoxy-2-methyloctadecane (also known as disparlure) is a chemical compound with formula C19H38O. It is a sex pheromone found in moths, such as the spongy moth, and is used to attract a mate. It is also a harmful pesticide for many tree species. Occurrences Disparlure is produced by female moths, such as the spongy and nun moths. It is a sex pheromone, a chemical that is released by the moths in order to attract a male mate. Disparlure has two enantiomers, referred to by (+) and (-). The (+) enantiomer is typically used to attract the males by the females, while the (-) enantiomer tends to have the opposite effect. The (-) enantiomer inhibits attractions and turns the males away from females. Synthesis There are two main ways to synthesize disparlure. They are either using chiral pools, which are costly and time consuming, or asymmetric epoxidation, which is quick, easy, and cheap. Some studies have used asymmetric epoxidation, which involves processes such as constr ...
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Spongy Moth
''Lymantria dispar'', also known as the gypsy moth or the spongy moth, is a species of moth in the family Erebidae. ''Lymantria dispar'' is subdivided into several subspecies, with subspecies such as ''L. d. dispar'' and ''L. d. japonica'' being clearly identifiable without ambiguity. ''Lymantria dispar'' has been introduced to several continents and is now found in Europe, Africa, Asia, North America and South America. The polyphagous larvae live on a variety of deciduous and coniferous trees and can cause severe damage in years of mass reproduction. Due to these features, ''Lymantria dispar'' is listed among the world's 100 worst invasive alien species. Etymology The name “gypsy moth” does not have conclusive origins, however it has been in use since 1908. Moths of the subfamily Lymantriinae are commonly called tussock moths due to the tussock-like tufts of hair on the caterpillars.The Gypsy Moth: Research Toward Integrated Pest Management, United States Department of ...
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Nun Moth
The black arches or nun moth (''Lymantria monacha'')Carter, David. Butterflies and Moths, Dorling Kindersley, pg 271 is a small Palaearctic moth. It is considered a forest pest. Description The moths of ''Lymantria monacha'' have a wingspan of 40 to 50 mm. They have white forewings with black connected wavy arches which gives the moth its name. The light brown hindwings have white fringes having black spots. They also have a characteristic biscuit-coloured abdomen with a black band. Females are larger and have elongated wings. The eggs are oval, light brown or light red. Larvae are whitish grey to blackish, with grey hairs, red and blue warts, and a dark longitudinal dorsal line which is interrupted or broadened into spots in places. Pupa is golden glossy red-brown or dark brown, with reddish hairs dorsally and rather long anal point. Technical description and variation White forewing with black basal spots and four sharply angulate black transverse lines, the second of ...
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Pheromone
A pheromone () is a secreted or excreted chemical factor that triggers a social response in members of the same species. Pheromones are chemicals capable of acting like hormones outside the body of the secreting individual, to affect the behavior of the receiving individuals. There are ''alarm signal, alarm pheromones'', ''food trail pheromones'', ''sex pheromones'', and many others that affect behavior or physiology. Pheromones are used by many organisms, from basic unicellular prokaryotes to complex multicellular eukaryotes. Their use among insects has been particularly well documented. In addition, some vertebrates, plants and ciliates communicate by using pheromones. The ecological functions and evolution of pheromones are a major topic of research in the field of chemical ecology. Background The portmanteau word "pheromone" was coined by Peter Karlson and Martin Lüscher in 1959, based on the Greek φερω ''pheroo'' ('I carry') and ὁρμων ''hormon'' ('stimulating'). P ...
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Chiral Pool
The chiral pool is a "collection of abundant enantiopure building blocks provided by nature" used in synthesis. In other words, a chiral pool would be a large quantity of common organic enantiomers. Contributors to the chiral pool are amino acids, sugars, and terpenes. Their use improves the efficiency of total synthesis. Not only does the chiral pool contribute a premade carbon skeleton, their chirality is usually preserved in the remainder of the reaction sequence. This strategy is especially helpful if the desired molecule resembles cheap enantiopure natural products. Many times, suitable enantiopure starting materials cannot be identified. The alternative to the use of the chiral pool is asymmetric synthesis, whereby achiral precursors are employed or racemic intermediates are resolved. Examples The use of the chiral pool is illustrated by the synthesis of the anticancer drug paclitaxel (Taxol). The incorporation of the C10 precursor verbenone, a member of the chiral pool, ...
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Epoxidation
In organic chemistry, an epoxide is a cyclic ether () with a three-atom ring. This ring approximates an equilateral triangle, which makes it strained, and hence highly reactive, more so than other ethers. They are produced on a large scale for many applications. In general, low molecular weight epoxides are colourless and nonpolar, and often volatile. Nomenclature A compound containing the epoxide functional group can be called an epoxy, epoxide, oxirane, and ethoxyline. Simple epoxides are often referred to as oxides. Thus, the epoxide of ethylene (C2H4) is ethylene oxide (C2H4O). Many compounds have trivial names; for instance, ethylene oxide is called "oxirane". Some names emphasize the presence of the epoxide functional group, as in the compound ''1,2-epoxyheptane'', which can also be called ''1,2-heptene oxide''. A polymer formed from epoxide precursors is called an '' epoxy'', but such materials do not contain epoxide groups (or contain only a few residual epoxy gr ...
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Chromatography
In chemical analysis, chromatography is a laboratory technique for the separation of a mixture into its components. The mixture is dissolved in a fluid solvent (gas or liquid) called the ''mobile phase'', which carries it through a system (a column, a capillary tube, a plate, or a sheet) on which a material called the ''stationary phase'' is fixed. Because the different constituents of the mixture tend to have different affinities for the stationary phase and are retained for different lengths of time depending on their interactions with its surface sites, the constituents travel at different apparent velocities in the mobile fluid, causing them to separate. The separation is based on the differential partitioning between the mobile and the stationary phases. Subtle differences in a compound's partition coefficient result in differential retention on the stationary phase and thus affect the separation. Chromatography may be preparative or analytical. The purpose of preparativ ...
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Disparlure Synthesis
''cis''-7,8-Epoxy-2-methyloctadecane (also known as disparlure) is a chemical compound with formula C19H38O. It is a sex pheromone found in moths, such as the spongy moth, and is used to attract a mate. It is also a harmful pesticide for many tree species. Occurrences Disparlure is produced by female moths, such as the spongy and nun moths. It is a sex pheromone, a chemical that is released by the moths in order to attract a male mate. Disparlure has two enantiomers, referred to by (+) and (-). The (+) enantiomer is typically used to attract the males by the females, while the (-) enantiomer tends to have the opposite effect. The (-) enantiomer inhibits attractions and turns the males away from females. Synthesis There are two main ways to synthesize disparlure. They are either using chiral pools, which are costly and time consuming, or asymmetric epoxidation, which is quick, easy, and cheap. Some studies have used asymmetric epoxidation, which involves processes such as constr ...
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Epoxides
In organic chemistry, an epoxide is a cyclic ether () with a three-atom ring. This ring approximates an equilateral triangle, which makes it strained, and hence highly reactive, more so than other ethers. They are produced on a large scale for many applications. In general, low molecular weight epoxides are colourless and nonpolar, and often volatile. Nomenclature A compound containing the epoxide functional group can be called an epoxy, epoxide, oxirane, and ethoxyline. Simple epoxides are often referred to as oxides. Thus, the epoxide of ethylene (C2H4) is ethylene oxide (C2H4O). Many compounds have trivial names; for instance, ethylene oxide is called "oxirane". Some names emphasize the presence of the epoxide functional group, as in the compound ''1,2-epoxyheptane'', which can also be called ''1,2-heptene oxide''. A polymer formed from epoxide precursors is called an ''epoxy'', but such materials do not contain epoxide groups (or contain only a few residual epoxy grou ...
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