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Capillin
Capillin is a naturally occurring organic compound with the chemical formula . The structure contains acetophenone and a polyyne (pentadiynyl) portion, conjugated together as an ynone. Chemical taxonomy Capillin is found in the essential oil of a number of ''Artemisia (genus), Artemisia'' species, including ''Artemisia monosperma'' and ''Artemisia dracunculus'' (tarragon). The substance was initially isolated from ''Artemisia capillaris'' in 1956. Applications Capillin is a biologically active substance. It has strong antifungal activity, and it is possibly antitumoral. Capillin exhibits cytotoxic activity and could cause apoptosis of certain human tumor cells. References

{{Reflist Aromatic ketones Alkyne derivatives ...
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Artemisia Dracunculus
Tarragon (''Artemisia dracunculus''), also known as estragon, is a species of perennial herbaceous plant, herb in the family Asteraceae. It is widespread in the wild across much of Eurasia and North America and is cultivated for culinary and medicinal purposes. One subspecies, ''Artemisia dracunculus'' var. ''sativa'', is cultivated to use the leaves as an aromatic culinary herb. In some other subspecies, the characteristic aroma is largely absent. The species is Polymorphism (biology), polymorphic. Informal names for distinguishing the variations include "French tarragon" (best for culinary use), "Russian tarragon," and "wild tarragon" (covers various states). Tarragon grows to tall, with slender branches. The leaves are lanceolate, long and broad, glossy green, with an Glossary of leaf morphology#Edge, entire margin. The flowers are produced in small capitulum (flower), capitula diameter, each capitulum containing up to 40 yellow or greenish-yellow florets. French tarragon, ...
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Organic Compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The study of the properties, reactions, and syntheses of organic compounds comprise the discipline known as organic chemistry. For historical reasons, a few classes of carbon-containing compounds (e.g., carbonate salts and cyanide salts), along with a few other exceptions (e.g., carbon dioxide, hydrogen cyanide), are not classified as organic compounds and are considered inorganic. Other than those just named, little consensus exists among chemists on precisely which carbon-containing compounds are excluded, making any rigorous definition of an organic compound elusive. Although organic compounds make up only a small percentage of Earth's crust, they are of central importance because all known life is based on organic compounds. Living t ...
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Acetophenone
Acetophenone is the organic compound with the formula C6H5C(O)CH3. It is the simplest aromatic ketone. This colorless, viscous liquid is a precursor to useful resins and fragrances. Production Acetophenone is formed as a byproduct of the cumene process, the industrial route for the synthesis of phenol and acetone. In the Hock rearrangement of isopropylbenzene hydroperoxide, migration of a methyl group rather than the phenyl group gives acetophenone and methanol as a result of an alternate rearrangement of the intermediate: :C6H5C(CH3)2O2H -> C6H5C(O)CH3 + CH3OH The cumene process is conducted on such a large scale that even the small amount of acetophenone by-product can be recovered in commercially useful quantities. Acetophenone is also generated from ethylbenzene hydroperoxide. Ethylbenzene hydroperoxide is primarily converted to 1-phenylethanol (α-methylbenzyl alcohol) in the process with a small amount of by-product acetophenone. Acetophenone is recovered or hydrogena ...
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Polyyne
In organic chemistry, a polyyne () is any organic compound with alternating single and triple bonds; that is, a series of consecutive alkynes, with ''n'' greater than 1. These compounds are also called polyacetylenes, especially in the natural products and chemical ecology literature, even though this nomenclature more properly refers to acetylene polymers composed of alternating single and double bonds with ''n'' greater than 1. They are also sometimes referred to as oligoynes, or carbinoids after "carbyne" , the hypothetical allotrope of carbon that would be the ultimate member of the series. In ''Avancés récentes en chimie des acétylènes – Recent advances in acetylene chemistry'' The synthesis of this substance has been claimed several times since the 1960s, but those reports have been disputed. Indeed, the substances identified as short chains of "carbyne" in many early organic synthesis attempts would be called polyynes today. The simplest polyyne is diacetylene o ...
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Ynone
In organic chemistry, an ynone is an organic compound containing a ketone () functional group and a triple bond. Many ynones are α,β-ynones, where the carbonyl and alkyne groups are conjugated. Capillin is a naturally occurring example. Some ynones are not conjugated. Synthesis of α,β-ynones One method for synthesizing ynones is the acyl substitution reaction of an alkynyldimethylaluminum with an acyl chloride. An alkynyldimethylaluminum compound is the reaction product of trimethylaluminum and a terminal alkyne. An alternative is the direct coupling of an acyl chloride with a terminal alkyne, using a copper-based nanocatalyst: Other methods utilize an oxidative cleavage of an aldehyde, followed by reaction with a hypervalent alkynyl iodide, using a gold catalyst. An alternative but longer synthetic method involves the reaction of an alkynyllithium compound with an aldehyde. The reaction produces a secondary alcohol that then can be oxidized via the Swern oxidation ...
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Essential Oil
An essential oil is a concentrated hydrophobic liquid containing volatile (easily evaporated at normal temperatures) chemical compounds from plants. Essential oils are also known as volatile oils, ethereal oils, aetheroleum, or simply as the oil of the plant from which they were extracted, such as oil of clove. An essential oil is essential in the sense that it contains the essence of the plant's fragrance—the characteristic fragrance of the plant from which it is derived. The term "essential" used here does ''not'' mean indispensable or usable by the human body, as with the terms essential amino acid or essential fatty acid, which are so called because they are nutritionally required by a living organism. Essential oils are generally extracted by distillation, often by using steam. Other processes include expression, solvent extraction, '' sfumatura'', absolute oil extraction, resin tapping, wax embedding, and cold pressing. They are used in perfumes, cosmetics, soaps, air ...
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Artemisia (genus)
''Artemisia'' () is a large, diverse genus of plants with between 200 and 400 species belonging to the daisy family Asteraceae. Common names for various species in the genus include mugwort, wormwood, and sagebrush. ''Artemisia'' comprises hardy herbaceous plants and shrubs, which are known for the powerful chemical constituents in their essential oils. ''Artemisia'' species grow in temperate climates of both hemispheres, usually in dry or semiarid habitats. Notable species include '' A. vulgaris'' (common mugwort), '' A. tridentata'' (big sagebrush), '' A. annua'' (sagewort), '' A. absinthium'' (wormwood), ''A. dracunculus'' (tarragon), and '' A. abrotanum'' (southernwood). The leaves of many species are covered with white hairs. Most species have strong aromas and bitter tastes from terpenoids and sesquiterpene lactones, which discourage herbivory, and may have had a selective advantage. The small flowers are wind-pollinated. ''Artemisia'' species are used ...
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Artemisia Monosperma
''Artemisia monosperma'' is a species of flowering plant in the wormwood genus ''Artemisia'', family Asteraceae, native to Libya, Egypt, the Levant, and the Arabian Peninsula. It plays an important role in ecological succession Ecological succession is the process of change in the species structure of an ecological community over time. The time scale can be decades (for example, after a wildfire) or more or less. Bacteria allows for the cycling of nutrients such as ca ... by stabilizing sand dunes. References monosperma Flora of Libya Flora of Egypt Flora of Sinai Flora of Palestine (region) Flora of Lebanon Flora of Syria Flora of the Arabian Peninsula Plants described in 1813 {{Anthemideae-stub ...
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Artemisia Capillaris
''Artemisia capillaris'', ( zh, 茵陈蒿 yīn chén hāo), is a species of flowering plant in the wormwood genus ''Artemisia'', family Asteraceae. Artemisia capillaris is biennial or perennial herb, 30-80(100) cm tall with vertical, woody rootstock and usually a single to few, slender, erect, pale purplish or reddish brown, glabrous stems. Leaves are silky hairy, basal ones shortly petiolate, middle stem leaves almost sessile. Synflorescence is a narrow to wide panicle with many capitula composed of 8 to 12 yellow florets. Oblong-ovate, brown achenes are minuscule ca. 0.8 mm.http://www.efloras.org/florataxon.aspx?flora_id=2&taxon_id=200023185 It is native to Pakistan, the western Himalayas, Assam, all of China, Mongolia, the Korean Peninsula, Irkutsk Oblast and Primorsky Krai in Russia, the Ryukyus, and Japan, and has been widely introduced to Afghanistan, India, Nepal, Southeast Asia, all of Malesia, and Taiwan. It is used in traditional Chinese medicine Traditional Chi ...
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Antifungal
An antifungal medication, also known as an antimycotic medication, is a pharmaceutical fungicide or fungistatic used to treat and prevent mycosis such as athlete's foot, ringworm, candidiasis (thrush), serious systemic infections such as cryptococcal meningitis, and others. Such drugs are usually yes obtained by a doctor's prescription, but a few are available over the counter (OTC). Types of antifungal There are two types of antifungals: local and systemic. Local antifungals are usually administered topically or vaginally, depending on the condition being treated. Systemic antifungals are administered orally or intravenously. Of the clinically employed azole antifungals, only a handful are used systemically. These include ketoconazole, itraconazole, fluconazole, fosfluconazole, voriconazole, posaconazole, and isavuconazole. Examples of non-azole systemic antifungals include griseofulvin and terbinafine. Classes Polyenes A polyene is a molecule with multiple conjugated do ...
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Apoptosis
Apoptosis (from grc, ἀπόπτωσις, apóptōsis, 'falling off') is a form of programmed cell death that occurs in multicellular organisms. Biochemical events lead to characteristic cell changes (morphology) and death. These changes include blebbing, cell shrinkage, nuclear fragmentation, chromatin condensation, DNA fragmentation, and mRNA decay. The average adult human loses between 50 and 70 billion cells each day due to apoptosis. For an average human child between eight and fourteen years old, approximately twenty to thirty billion cells die per day. In contrast to necrosis, which is a form of traumatic cell death that results from acute cellular injury, apoptosis is a highly regulated and controlled process that confers advantages during an organism's life cycle. For example, the separation of fingers and toes in a developing human embryo occurs because cells between the digits undergo apoptosis. Unlike necrosis, apoptosis produces cell fragments called apoptotic ...
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Aromatic Ketones
In chemistry, aromaticity is a chemical property of cyclic ( ring-shaped), ''typically'' planar (flat) molecular structures with pi bonds in resonance (those containing delocalized electrons) that gives increased stability compared to saturated compounds having single bonds, and other geometric or connective non-cyclic arrangements with the same set of atoms. Aromatic rings are very stable and do not break apart easily. Organic compounds that are not aromatic are classified as aliphatic compounds—they might be cyclic, but only aromatic rings have enhanced stability. The term ''aromaticity'' with this meaning is historically related to the concept of having an aroma, but is a distinct property from that meaning. Since the most common aromatic compounds are derivatives of benzene (an aromatic hydrocarbon common in petroleum and its distillates), the word ''aromatic'' occasionally refers informally to benzene derivatives, and so it was first defined. Nevertheless, many non-ben ...
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