Sesquiterpenes

chemical compound

Farnesol is a natural 15-carbon organic compound which is an acyclic sesquiterpene alcohol. Under standard conditions, it is a colorless liquid. It is hydrophobic, and thus insoluble in water, but miscible with oils. As the pyrophosphate ester, farnesol is a precursor to many terpenes and terpenoids. It is a constitutional isomer of Nerolidol.

The ionones, from greek ἴον ion "violet", are a series of closely related chemical substances that are part of a group of compounds known as rose ketones, which also includes damascones and damascenones. Ionones are aroma compounds found in a variety of essential oils, including rose oil. β-Ionone is a significant contributor to the aroma of roses, despite its relatively low concentration, and is an important fragrance chemical used in perfumery. The ionones are derived from the degradation of carotenoids.

Artesunate is a medication used to treat malaria. The intravenous form is preferred to quinine for severe malaria. Often it is used as part of combination therapy, such as artesunate plus mefloquine. It is not used for the prevention of malaria. Artesunate can be given by injection into a vein, injection into a muscle, by mouth, and by rectum.

Caryophyllene (), more formally (−)-β-caryophyllene (BCP), is a natural bicyclic sesquiterpene that occurs widely in nature. Caryophyllene is notable for having a cyclobutane ring, as well as a trans-double bond in a 9-membered ring, both rarities in nature.

thumb|right|Big Sagebrush ([[Artemisia tridentata) contains sesquiterpene lactones which are sesquiterpenoids (built from three isoprene units) and contain a lactone ring, hence the name. These compounds are found in many other plants and can cause allergic reactions and toxicity if consumed in excess, particularly in grazing livestock.]] thumb|Phallus indusiatus, in [[Cooktown, Queensland, Australia, which produces two unique sesquiterpenes]] Sesquiterpenes are a class of terpenes that consist of three isoprene units and often have the molecular formula C15H24. Like monoterpenes, sesquiterpen

Artemether is a medication used for the treatment of malaria. The injectable form is specifically used for severe malaria rather than quinine. In adults, it may not be as effective as artesunate. It is given by injection in a muscle. It is also available by mouth in combination with lumefantrine, known as artemether/lumefantrine.

chemical compound

Bisabolol, or more formally α-(−)-bisabolol or also known as levomenol, is a natural monocyclic sesquiterpene alcohol. It is a colorless viscous oil that is the primary constituent of the essential oil from German chamomile (Matricaria recutita) and Myoporum crassifolium. High concentrations of bisabolol can also be found in certain medicinal cannabis cultivars. It is poorly soluble in water and glycerine, but soluble in ethanol. The enantiomer, α-(+)-bisabolol, is also found naturally but is rare. Synthetic bisabolol is usually a racemic mixture of the two, α-(±)-bisabolol. It is the terpenoi

Humulene, also known as α-humulene or α-caryophyllene, is a naturally occurring monocyclic sesquiterpene (C15H24), containing an 11-membered ring and consisting of 3 isoprene units containing three nonconjugated C=C double bonds, two of them being triply substituted and one being doubly substituted. It was first found in the essential oils of Humulus lupulus (hops), from which it derives its name. Humulene is an isomer of β-caryophyllene, and the two are often found together as a mixture in many aromatic plants.

Guaiazulene, also azulon or 1,4-dimethyl-7-isopropylazulene, is a dark blue crystalline hydrocarbon. A derivative of azulene, guaiazulene is a bicyclic sesquiterpene that is a constituent of some essential oils, mainly oil of guaiac and chamomile oil, which also serve as its commercial sources. Various soft corals also contain guaiazulene as a principal pigment. Its low melting point makes guaiazulene difficult to handle, in contrast to the crystalline nature of the parent azulene. The electronic structure (and colors) of guaiazulene and azulene are very similar.

The term farnesene refers to a set of six closely related chemical compounds which all are sesquiterpenes. α-Farnesene and β-farnesene are isomers, differing by the location of one double bond. α-Farnesene is 3,7,11-trimethyl-1,3,6,10-dodecatetraene and β-farnesene is 7,11-dimethyl-3-methylene-1,6,10-dodecatriene. The alpha form can exist as four stereoisomers that differ about the geometry of two of its three internal double bonds (the stereoisomers of the third internal double bond are identical). The beta isomer exists as two stereoisomers about the geometry of its central double bond.

Nootkatone is an organic compound, a sesquiterpenoid, which means that it is a C15 derivative that also contains an oxygen-containing functional group (a ketone). It is the most valuable aroma compound of grapefruit. Nootkatone was originally isolated from the wood of the Alaskan yellow cedar, Cupressus nootkatensis. The species name, nootkatensis, is derived from the language of the Nuu-Chah-Nulth people of Canada (formerly referred to as the Nootka people).

Nerolidol, also known as peruviol and penetrol, is a naturally occurring sesquiterpene alcohol. A colorless liquid, it is found in the essential oils of many types of plants and flowers. There are four isomers of nerolidol', which differ in the geometry about the central double bond and configuration of the hydroxyl-bearing carbon, but most applications use such a mixture. The aroma of nerolidol is woody and reminiscent of fresh bark. It is used as a flavoring agent and in perfumery as well as in non-cosmetic products such as detergents and cleansers. Nerolidyl derivatives include nerolidyl di

Cedrol is a sesquiterpene alcohol found in the essential oil of conifers (cedar oil), especially in the genera Cupressus (cypress) and Juniperus (juniper). It has also been identified in Origanum onites, a plant related to oregano. Its main uses are in the chemistry of aroma compounds. It makes up about 19% of cedarwood oil Texas and 15.8% of cedarwood oil Virginia.

Vetivazulene is an azulene derivate obtained from vetiver oil. It is a bicyclic sesquiterpene and an isomer of guaiazulene.

chemical compound

Zingiberene is a monocyclic sesquiterpene that is the predominant constituent of the oil of ginger (Zingiber officinale), from which it gets its name. It can contribute up to 30% of the essential oils in ginger rhizomes. This is the compound that gives ginger its distinct flavoring.

Longifolene is a common sesquiterpene. It is an oily liquid hydrocarbon found primarily in the high-boiling fraction of certain pine resins. The name is derived from that of a pine species from which the compound was isolated. It is a tricyclic chiral molecule. The enantiomer commonly found in pines and other higher plants exhibits a positive optical rotation of +42.73°. The other enantiomer (optical rotation −42.73°) is found in small amounts in certain fungi and liverworts. ==Occurrence== Terpentine obtained from Pinus longifolia (obsolete name for Pinus roxburghii Sarg.) contains as much as

thumb|The Phyla dulcis plant, which naturally produces hernandulcin. Hernandulcin is an intensely sweet chemical compound gained from the chiefly Mexican and South American plant Lippia dulcis.

Cadalene or cadalin (4-isopropyl-1,6-dimethylnaphthalene) is a polycyclic aromatic hydrocarbon with a chemical formula C15H18 and a cadinane skeleton. It is derived from generic sesquiterpenes, and ubiquitous in essential oils of many higher plants.

Valencene is a sesquiterpene that is an aroma component of citrus fruit and citrus-derived odorants. It is obtained inexpensively from Valencia oranges. Valencene is biosynthesized from farnesyl pyrophosphate (FPP) by the CVS enzyme.

Cubebol is a natural sesquiterpene alcohol first identified in cubeb oil. It is also found in basil. It was patented as a cooling agent in 2001 by Firmenich, an international flavor company. The taste of cubebol is cooling and refreshing. The patent describes application of cubebol as a refreshing agent in various products, ranging from chewing gum to sorbets, drinks, toothpaste, and gelatin-based confectioneries.

Artemotil (INN; also known as β-arteether), is a fast acting blood schizonticide specifically indicated for the treatment of chloroquine-resistant Plasmodium falciparum malaria and cerebral malaria cases. It is a semi-synthetic derivative of artemisinin, a natural product of the Chinese plant Artemisia annua. It is currently only used as a second line drug in severe cases of malaria.

Patchoulol or patchouli alcohol (C15H26O) is a sesquiterpene alcohol found in patchouli (Pogostemon cablin). Patchouli oil is an important material in perfumery. The (−)-optical isomer is one of the organic compounds responsible for the typical patchouli scent. Patchoulol is obtained industrially from patchouli leaf fermentation.

chemical compound

Aristolochene is a bicyclic sesquiterpene produced by certain fungi, most notably the cheese mold Penicillium roqueforti. It is biosynthesized from farnesyl pyrophosphate by the enzyme aristolochene synthase and serves as the parent hydrocarbon for a variety of fungal toxins.

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. none|600px

Copaene, or more precisely, α-copaene, is the common (or trivial) chemical name of an oily liquid hydrocarbon that is found in a number of essential oil-producing plants. The name is derived from that of the resin-producing tropical copaiba tree, Copaifera langsdorffii, from which the compound was first isolated in 1914. Its structure, including the chirality, was determined in 1963. The double-bond isomer with an exocyclic-methylene group, β-copaene, was first reported in 1967.

Germacrenes are a group of five naturally occurring volatile organic hydrocarbons of the sesquiterpene and cycloalkene class. Germacrenes are typically produced in a number of plant species for their antimicrobial and insecticidal properties, though they also play a role as insect pheromones. Two prominent molecules are germacrene A and germacrene D.

Gyrinal is an organic chemical compound  - an unsaturated ketoaldehyde - with the formula C14H18O3, obtained from the whirligig beetle (the water boatman, Gyrinus natator). It is a powerful antiseptic and fish and mammal toxin, and thus used as a defensive compound. Typically the beetles contain approx. 80 microgram of the compound. The LD50 of the compound is approx. 45 mg/kg in mice.

Cadinenes are a group of isomeric hydrocarbons that occur in a wide variety of essential oil-producing plants. The name is derived from that of the Cade juniper (Juniperus oxycedrus L.), the wood of which yields an oil from which cadinene isomers were first isolated.

Isocomene is a sesquiterpene first isolated from the perennial herb southern goldenbush (Isocoma wrightii), from which it derives its name. Its unusual structure consisting of three fused cyclopentane rings was first described by Zalkow et al. in 1977. The first total synthesis of isocomene was published by M.C. Pirrung in 1979. The key steps are a photocatalyzed intramolecular [2 + 2] cycloaddition reaction followed by a rearrangement reaction which forms three contiguous chiral centers.

Petasin is a natural chemical compound found in plants of the genus Petasites. Chemically, it is classified as a sesquiterpene and is the ester of petasol and angelic acid.

chemical compound

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 bi

chemical compound

Elemenes are a group of closely related natural chemical compounds found in a variety of plants. The elemenes, which include α-, β-, γ-, and δ-elemene, are structural isomers of each other and are classified as sesquiterpenes. The elemenes contribute to the floral aromas of some plants, and are used as pheromones by some insects.

Selinenes are a group of closely related isomeric chemical compounds that are classified as sesquiterpenes. The four selinenes have the formula C15H24. Selinenes have been isolated from a variety of plant sources. α-Selinene and β-selinene are the most common and are two of the principal components of the oil from celery seeds. Celery seed oil consists of a 60% and 20% of limonene and selinene, respectively.

Cedrene is a sesquiterpene found in the essential oil of cedar. The two isomers present in the oil are (−)-α-cedrene and (+)-β-cedrene, which differ in the position of a double bond.

Thujopsene is a natural chemical compound, classified as a sesquiterpene, with the molecular formula C15H24.

Irofulven or 6-hydroxymethylacylfulvene (also known as HMAF and MGI-114) is an experimental cancer drug. It belongs to the family of drugs called alkylating agents.

Norpatchoulenol is a tricyclic terpenoid found in commercial patchouli extract in small quantities, and thought to contribute significantly to the aroma of patchouli oil.

Amorpha-4,11-diene is a precursor to artemisinin.

Polygodial a is chemical compound found in dorrigo pepper, mountain pepper, horopito, canelo, paracress, water-pepper, and Dendrodoris limbata.

Guaiol or champacol is an organic compound, a sesquiterpenoid alcohol found in several plants, especially in the oil of guaiacum and cypress pine. It is a crystalline solid that melts at 92 °C. Guaiol is one of many terpenes found in Cannabis and it has been associated with decreasing anxiolytic activity.

Botrydial is secondary metabolite secreted by the fungus Botrytis cinerea which is phytotoxic. Chemically it is a sesquiterpene. Botrydial was first isolated and described in 1974. B. cinerea is the causal agent of gray mold disease and is known to attack a wide range of plants (over 200 species) producing leaf-spot diseases and mildews on lettuces and tomatoes as well as rotting berries. For this reason, botrydial, as well as other B. cinerea originated sesquiterpene metabolites, represent an economically important disease for ornamental and agriculturally important crops. From all the metabo

Bisabolenes are a group of closely related natural chemical compounds which are classified as sesquiterpenes. Bisabolenes are produced from farnesyl pyrophosphate (FPP) and are present in the essential oils of bisabol, and of a wide variety of other plants including cubeb, lemon, and oregano. Various derivates also function as pheromones in different insects, such as stink bugs and fruit flies. Bisabolenes are produced by several fungi, though their biological role in that group of organisms remains unclear.

β-Santalol is an organic compound that is classified as a sesquiterpene. It comprises about 20% of the oil of sandalwood, the major component being α-santalol. In 2002, about 60 tons of sandalwood oil were produced by steam distillation of the heartwood of Santalum album. It is used in perfumery as a fixative, modifier and dominant (central accord).

α-Cadinol or 10α-hydroxy-4-cadinene is an organic compound, a sesquiterpenoid alcohol.

Carotol was first isolated by scientists Asahina and Tsukamoto in 1925. It is one of the primary components found in carrot seed oil comprising approximately 40% of this essential oil. This sesquiterpene alcohol is thought to be formed in carrot seeds (Daucus carota L., Umbelliferae) during the vegetation period. Additionally, studies have shown that carotol may be involved in allelopathic interactions expressing activity as an antifungal, herbicidal and insecticidal agent.

chemical compound

δ-Cadinol is an organic compound, a sesquiterpenoid alcohol produced by many plants as well as some animals and microorganisms. It is a white crystalline solid, soluble in isopropyl ether and ethanol. It is an epimer of α-cadinol.

α-Santalol ('''alpha-santalol') is an organic compound that is classified as a sesquiterpene. It comprises about 55% of the oil of sandalwood, another less abundant component being β-santalol. As of 2002, about 60 tons of sandalwood oil are produced annually by steam distillation of the heartwood of Santalum album''. It is a valued component for perfumes.

Mutisianthol is a sesquiterpene compound found in Mutisia homoeantha. It was first isolated by Bohlmann et al. in 1979.

Curzerene is a volatile, aromatic terpenoid found in many herbs and spices, such as Curcuma zeodaria. It is a bioactive isolate of Caribbean corals and is also found in myrrh. More specifically it has been found to make up a significant portion - 12.97% - of the smoke produced from burning Commiphora myrrha oleo gum resin. It is also a major component of myrrh oil, which has been shown in vitro to possess anti-inflammatory properties at sub-toxic by inhibiting the production of the inflammatory cytokine IL-6 by human gingival fibroblasts. Anecdotal evidence exists to support the anti-inflammat

Curdione is a chemical compound isolated from Curcuma wenyujin. Its molecular weight is 236.35 g/mol.

Guaienes are a series of closely related natural chemical compounds that have been isolated from a variety of plant sources. The guaienes are sesquiterpenes with the molecular formula C15H24. α-Guaiene is the most common and was first isolated from guaiac wood oil from Bulnesia sarmientoi. The guaienes are used in the fragrance and flavoring industries to impart earthy, spicy aromas and tastes.

Curzerenone is an antimicrobial isolate of Lindera pulcherrima.

Capnellene is a naturally occurring tricyclic hydrocarbon derived from Capnella imbricata, a species of soft coral found in Indonesia. Since the 1970s, capnellene has been targeted for synthesis by numerous investigators due to its stereochemistry, functionality, and the interesting geometry of the carbon skeleton. Many alcohol derivatives of capnellene have demonstrated potential as a chemotherapeutic agent with antibacterial, anti-inflammatory and anti-tumor properties.