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IUPAC name 2,2-Dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylic acid | |
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3D model (JSmol) | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.022.788 |
PubChem CID | |
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CompTox Dashboard (EPA) | |
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Properties | |
C10H16O2 | |
Molar mass | 168.236 g·mol−1 |
Melting point | 17 °C (63 °F; 290 K)(1R,3R) or (+)-trans |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Chrysanthemic acid is an organic compound that is related to a variety of natural and synthetic insecticides. It is related to the pyrethrin I and II, as well as the pyrethroids. One of the four stereoisomers, (1R,3R)- or (+)-trans-chrysanthemic acid (pictured), is the acid part of the ester pyrethrin I, which occurs naturally in the seed cases of Chrysanthemum cinerariaefolium. Many synthetic pyrethroids, for example the allethrins, are esters of all four stereoisomers. [1] Staudinger and Ružička named chrysanthemic acid in 1924. [2]
Chrysanthemic acid is derived from its pyrophosphate ester, which in turn is produced naturally from two molecules of dimethylallyl diphosphate. [3]
Chrysanthemic acid is produced industrially in a cyclopropanation reaction of a diene as a mixture of cis- and trans isomers, followed by hydrolysis of the ester: [4]
Many pyrethroids are accessible by re-esterification of chrysanthemic acid ethylester.
Salvinorin A is the main active psychotropic molecule in Salvia divinorum. Salvinorin A is considered a dissociative hallucinogen.
Menthol is an organic compound, more specifically a monoterpenoid, made synthetically or obtained from the oils of corn mint, peppermint, or other mints. It is a waxy, clear or white crystalline substance, which is solid at room temperature and melts slightly above.
The pyrethrins are a class of organic compounds normally derived from Chrysanthemum cinerariifolium that have potent insecticidal activity by targeting the nervous systems of insects. Pyrethrin naturally occurs in chrysanthemum flowers and is often considered an organic insecticide when it is not combined with piperonyl butoxide or other synthetic adjuvants. Their insecticidal and insect-repellent properties have been known and used for thousands of years.
A pyrethroid is an organic compound similar to the natural pyrethrins, which are produced by the flowers of pyrethrums. Pyrethroids are used as commercial and household insecticides.
Permethrin is a medication and an insecticide. As a medication, it is used to treat scabies and lice. It is applied to the skin as a cream or lotion. As an insecticide, it can be sprayed onto clothing or mosquito nets to kill the insects that touch them.
Hermann Staudinger was a German organic chemist who demonstrated the existence of macromolecules, which he characterized as polymers. For this work he received the 1953 Nobel Prize in Chemistry.
The allethrins are a group of related synthetic compounds used in insecticides. They are classified as pyrethroids, i.e. synthetic versions of pyrethrin, a chemical with insecticidal properties found naturally in Chrysanthemum flowers. They were first synthesized in the United States by Milton S. Schechter in 1949. Allethrin was the first pyrethroid.
Deltamethrin is a pyrethroid ester insecticide. Deltamethrin plays a key role in controlling malaria vectors, and is used in the manufacture of long-lasting insecticidal mosquito nets; however, resistance of mosquitos and bed bugs to deltamethrin has seen a widespread increase.
p-Coumaric acid is a hydroxycinnamic acid, an organic compound that is a hydroxy derivative of cinnamic acid. There are three isomers of coumaric acid—o-coumaric acid, m-coumaric acid, and p-coumaric acid—that differ by the position of the hydroxy substitution of the phenyl group. p-Coumaric acid is the most abundant isomer of the three in nature. p-Coumaric acid exists in two forms trans-p-coumaric acid and cis-p-coumaric acid.
Squalene synthase (SQS) or farnesyl-diphosphate:farnesyl-diphosphate farnesyl transferase is an enzyme localized to the membrane of the endoplasmic reticulum. SQS participates in the isoprenoid biosynthetic pathway, catalyzing a two-step reaction in which two identical molecules of farnesyl pyrophosphate (FPP) are converted into squalene, with the consumption of NADPH. Catalysis by SQS is the first committed step in sterol synthesis, since the squalene produced is converted exclusively into various sterols, such as cholesterol, via a complex, multi-step pathway. SQS belongs to squalene/phytoene synthase family of proteins.
Cyhalothrin is the ISO common name for an organic compound that, in specific isomeric forms, is used as a pesticide. It is a pyrethroid, a class of synthetic insecticides that mimic the structure and properties of the naturally occurring insecticide pyrethrin which is present in the flowers of Chrysanthemum cinerariifolium. Pyrethroids such as cyhalothrin are often preferred as an active ingredient in agricultural insecticides because they are more cost-effective and longer acting than natural pyrethrins. λ-and γ-cyhalothrin are now used to control insects and spider mites in crops including cotton, cereals, potatoes and vegetables.
In enzymology, a copalyl diphosphate synthase is an enzyme that catalyzes the chemical reaction
In enzymology, a (carboxyethyl)arginine beta-lactam-synthase is an enzyme that catalyzes the chemical reaction
In enzymology, an abietadiene synthase is an enzyme that catalyzes the chemical reaction
In enzymology, a chrysanthemyl diphosphate synthase is an enzyme involved in the biosynthesis of terpenoids. This enzyme is also known as CPPase. It catalyzes the chemical reaction shown below :
In enzymology, a geranyltranstransferase is an enzyme that catalyzes the chemical reaction
Juvabione, historically known as the paper factor, is the methyl ester of todomatuic acid, both of which are sesquiterpenes (C15) found in the wood of true firs of the genus Abies. They occur naturally as part of a mixture of sesquiterpenes based upon the bisabolane scaffold. Sesquiterpenes of this family are known as insect juvenile hormone analogues (IJHA) because of their ability to mimic juvenile activity in order to stifle insect reproduction and growth. These compounds play important roles in conifers as the second line of defense against insect induced trauma and fungal pathogens.
Pyrethrin II is an organic compound that is a potent insecticide. It is one of the two pyrethrins, the other being pyrethrin I. Thousands of tons this mixture are produced annually from chrysanthemum plants, which are cultivated in warm climates. Whereas pyrethrin I is a derivative of (+)-trans-chrysanthemic acid, in pyrethrin II one methyl group is oxidized to a carboxymethyl group, the resulting core being called pyrethric acid. Knowledge of their chemical structures opened the way for the production of synthetic analogues, which are called pyrethroids. In terms of their biosynthesis, pyrethrins are classified as terpenoids, being derived from dimethylallyl pyrophosphate.
Pyrethrin I is one of the two pyrethrins, natural organic compounds with potent insecticidal activity. It is an ester of (+)-trans-chrysanthemic acid with (S)-(Z)-pyrethrolone.
Jasmolone is an irregular monoterpene. Irregular monoterpenes are derived from two isoprene C5 units, but do not follow the usual head-to-tail coupling mechanism. Jasmolins are found in pyrethrum flowers. They can specifically be found in the flower heads of Chrysanthemum cinerariaefolium. Jasmolins act as an insecticide for the flower. It is found in the cytoplasm of plants.