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Preferred IUPAC name Spiro[4.5]decane | |
Identifiers | |
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CompTox Dashboard (EPA) | |
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Properties | |
C10H18 | |
Molar mass | 138.25 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Spirodecane is a chemical compound. It features a cyclohexane ring bound directly to a cyclopentane ring. [1] Different spirodecane sesquiterpenes have been produced in cultured mycelia by the fungus Cordyceps ophioglossoides. [2]
Azaspirodecane is an analogue in which the cyclohexane group has been replaced with a piperidine.
Cyclohexane is a cycloalkane with the molecular formula C6H12. Cyclohexane is non-polar. Cyclohexane is a colourless, flammable liquid with a distinctive detergent-like odor, reminiscent of cleaning products. Cyclohexane is mainly used for the industrial production of adipic acid and caprolactam, which are precursors to nylon.
Ophiocordyceps sinensis, known colloquially as caterpillar fungus, is an entomopathogenic fungus in the family Ophiocordycipitaceae. It is mainly found in the meadows above 3,500 metres (11,500 ft) on the Tibetan Plateau in Tibet and the Himalayan regions of Bhutan, India, and Nepal. It parasitizes larvae of ghost moths and produces a fruiting body which is valued in traditional Chinese medicine as an aphrodisiac. Caterpillar fungus contains the compound cordycepin, an adenosine derivative. However, the fruiting bodies harvested in nature usually contain high amounts of arsenic and other heavy metals, so they are potentially toxic and sales have been strictly regulated by China's State Administration for Market Regulation since 2016.
Cordyceps is a genus of ascomycete fungi that includes over 260 species worldwide, many of which are parasitic. Diverse variants of cordyceps have had more than 1,500 years of use in Chinese medicine. Most Cordyceps species are endoparasitoids, parasitic mainly on insects and other arthropods ; a few are parasitic on other fungi.
Bilobalide is a biologically active terpenic trilactone present in Ginkgo biloba.
Cyclohexane conformations are any of several three-dimensional shapes adopted by molecules of cyclohexane. Because many compounds feature structurally similar six-membered rings, the structure and dynamics of cyclohexane are important prototypes of a wide range of compounds.
Sesquiterpene lactones (SLs) are a class of sesquiterpenoids that contain a lactone ring. They are most often found in plants of the family Asteraceae. Other plant families with SLs are Umbelliferae and Magnoliaceae (magnolias). A collection of colorless, lipophilic solids, SLs are a rich source of drugs. They can be allergenic and toxic in grazing livestock causing severe neurological problems in horses. Some are also found in corals of the order Alcyonacea.
Atropisomers are stereoisomers arising because of hindered rotation about a single bond, where energy differences due to steric strain or other contributors create a barrier to rotation that is high enough to allow for isolation of individual rotamers. They occur naturally and are of occasional importance in pharmaceutical design. When the substituents are achiral, these conformers are enantiomers (atropoenantiomers), showing axial chirality; otherwise they are diastereomers (atropodiastereomers).
In organic chemistry, a ring flip is the interconversion of cyclic conformers that have equivalent ring shapes that results in the exchange of nonequivalent substituent positions. The overall process generally takes place over several steps, involving coupled rotations about several of the molecule's single bonds, in conjunction with minor deformations of bond angles. Most commonly, the term is used to refer to the interconversion of the two chair conformers of cyclohexane derivatives, which is specifically referred to as a chair flip, although other cycloalkanes and inorganic rings undergo similar processes.
Parthenolide is a sesquiterpene lactone of the germacranolide class which occurs naturally in the plant feverfew, after which it is named, and in the closely related tansy. It is found in highest concentration in the flowers and fruit. Parthenolide's molecular structure depiction is often incorrect regarding the stereochemistry of the epoxide, although X-ray single crystal structures are available.
Sesquiterpenes are a class of terpenes that consist of three isoprene units and often have the molecular formula C15H24. Like monoterpenes, sesquiterpenes may be cyclic or contain rings, including many combinations. Biochemical modifications such as oxidation or rearrangement produce the related sesquiterpenoids. It is estimated (2006) that 3000 sesquiterpenes have been identified.
Helenalin, or (-)-4-Hydroxy-4a,8-dimethyl-3,3a,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione, is a toxic sesquiterpene lactone which can be found in several plants such as Arnica montana and Arnica chamissonis Helenalin is responsible for the toxicity of the Arnica spp. Although toxic, helenalin possesses some in vitro anti-inflammatory and anti-neoplastic effects. Helenalin can inhibit certain enzymes, such as 5-lipoxygenase and leukotriene C4 synthase. For this reason the compound or its derivatives may have potential medical applications.
Cypenamine, or cypenamine hydrochloride (USAN), also known as 2-phenylcyclopentylamine, is a psychostimulant drug which was developed by a group at the William S. Merrell Chemical Company in the 1940s. It is currently known only in scientific research and has never been developed for market use. Cypenamine is currently legal throughout the entire world, and though its chemical structure has a vague similarity to certain controlled stimulants like fencamfamine, it is likely that it is too distant for it to be considered an illicit analogue under the United States Federal Analogue Act of the Controlled Substances Act.
The Parikh–Doering oxidation is an oxidation reaction that transforms primary and secondary alcohols into aldehydes and ketones, respectively. The procedure uses dimethyl sulfoxide (DMSO) as the oxidant and the solvent, activated by the sulfur trioxide pyridine complex (SO3•C5H5N) in the presence of triethylamine or diisopropylethylamine as base. Dichloromethane is frequently used as a cosolvent for the reaction.
Capsidiol is a terpenoid compound that accumulates in tobacco Nicotiana tabacum and chili pepper Capsicum annuum in response to fungal infection. Capsidiol is categorized under the broad term of phytoalexin, a class of low molecular weight plant secondary metabolites that are produced during infection. Phytoalexins are also characterized as a part of a two pronged response to infection which involves a short term response consisting of production of free radicals near the site of infection and a long term response involving the production of hormones and an increase in enzymes to biosynthesize phytoalexins such as capsidiol.
Absinthin is a naturally produced triterpene lactone from the plant Artemisia absinthium (Wormwood). It constitutes one of the most bitter chemical agents responsible for absinthe's distinct taste. The compound shows biological activity and has shown promise as an anti-inflammatory agent, and should not be confused with thujone, a neurotoxin also found in Artemisia absinthium.
Juvabione, historically known as the paper factor, is the methyl ester of todomatuic acid. Both 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.
Gonane (cyclopentanoperhydrophenanthrene) is a chemical compound with formula C
17H
28, whose structure consists of four hydrocarbon rings fused together: three cyclohexane units and one cyclopentane. It can also be viewed as the result of fusing a cyclopentane molecule with a fully hydrogenated molecule of phenanthrene, hence the more descriptive name "perhydrocyclopenta[a]phenanthrene". The non-systematic version of the above name is "cyclopentanoperhydrophenanthrene".
Tolypocladium is a genus of fungi within the family Ophiocordycipitaceae. It includes species that are parasites of other fungi, insect pathogens, rotifer pathogens and soil inhabiting species with uncertain ecological roles.
Tolypocladium ophioglossoides, also known by two of its better known synonyms Elaphocordyceps ophioglossoides and Cordyceps ophioglossoides and commonly known as the goldenthread cordyceps, is a species of fungus in the family Ophiocordycipitaceae. It is parasitic on fruit bodies of the truffle-like Elaphomyces. The species is considered inedible, but is valued in traditional Chinese medicine.
Cordyceps militaris, commonly known as the caterpillar fungus, is a species of fungus in the family Cordycipitaceae, and the type species of the genus Cordyceps, which consists of hundreds of species. The species was originally described by Carl Linnaeus in 1753 as Clavaria militaris. Cordyceps militaris parasitizes insects and is used in traditional Chinese medicine and modern pharmaceuticals.