Aleksandrouli ( Georgian : ალექსანდროული ) is a Georgian red grape variety .
30-752: The grape is reputed to be one of the oldest and greatest of the Georgian varieties, but is also reported by the Geilweilerhof database as a selected seedling of Muscat of Alexandria . This may reflect two varieties, the Alexandrouli wine grape and the table grape Alexandriuli Muscat. Used in Georgia to produce a semi-sweet red wine known as Khvanchkara or as a medium bodied, semi-dry, chewy blend (with Mujuretuli ) having good acids and claimed to have aroma flavours reminiscent of pomegranates . The grape seems to prefer
60-420: A class of natural products consisting of compounds with the formula (C 5 H 8 ) n for n ≥ 2. Terpenes are major biosynthetic building blocks. Comprising more than 30,000 compounds, these unsaturated hydrocarbons are produced predominantly by plants , particularly conifers . In plants, terpenes and terpenoids are important mediators of ecological interactions , while some insects use some terpenes as
90-463: A form of defense. Other functions of terpenoids include cell growth modulation and plant elongation, light harvesting and photoprotection, and membrane permeability and fluidity control. Terpenes are classified by the number of carbons: monoterpenes (C 10 ), sesquiterpenes (C 15 ), diterpenes (C 20 ), as examples. The terpene alpha-pinene is a major component of the common solvent , turpentine . The one terpene that has major applications
120-472: A hot climate and is particularly sensitive to the cold during its flowering season. In the northern hemisphere it is ripe in August, and is a seeded grape. Wine made from Muscat of Alexandria has a distinctive taste of grapes, and was popular in the postwar era when tastes tended towards the sweet and uncomplicated. The vines are prolific producers but are very susceptible to powdery mildew and so are only grown in
150-469: A mixture of terpenes (e.g., pinene ), obtained from the distillation of pine tree resin , is used as an organic solvent and as a chemical feedstock (mainly for the production of other terpenoids). Rosin , another by-product of conifer tree resin, is widely used as an ingredient in a variety of industrial products, such as inks , varnishes and adhesives . Rosin is also used by violinists (and players of similar bowed instruments) to increase friction on
180-421: A natural mechanism of cloud seeding . The clouds reflect sunlight, allowing the forest temperature to regulate. Some insects use some terpenes as a form of defense. For example, termites of the subfamily Nasutitermitinae ward off predatory insects through the use of a specialized mechanism called a fontanellar gun , which ejects a resinous mixture of terpenes. The one terpene that has major applications
210-399: Is natural rubber (i.e., polyisoprene ). The possibility that other terpenes could be used as precursors to produce synthetic polymers has been investigated as an alternative to the use of petroleum-based feedstocks. However, few of these applications have been commercialized. Many other terpenes, however, have smaller scale commercial and industrial applications. For example, turpentine ,
240-411: Is natural rubber (i.e., polyisoprene ). The possibility that other terpenes could be used as precursors to produce synthetic polymers has been investigated. Many terpenes have been shown to have pharmacological effects. Terpenes are also components of some traditional medicines, such as aromatherapy , and as active ingredients of pesticides in agriculture. The term terpene was coined in 1866 by
270-576: Is a shortened form of "terpentine", an obsolete spelling of " turpentine ". Although sometimes used interchangeably with "terpenes", terpenoids (or isoprenoids ) are modified terpenes that contain additional functional groups , usually oxygen-containing. The terms terpenes and terpenoids are often used interchangeably, however. Furthermore, terpenes are produced from terpenoids and many terpenoids are produced from terpenes. Both have strong and often pleasant odors, which may protect their hosts or attract pollinators. The number of terpenes and terpenoids
300-842: Is a sweet wine widely produced in the Setúbal Peninsula region, just south of Lisbon , as well as in Favaios , Alijó and other areas of the Portuguese Douro , in northern Portugal. In Bolivia, the grape has been used since at least the 1700s to make " singani ," the distinctive wine brandy produced in the Cinti Valley and in the Central Valley of Tarija. C13- norisoprenoids , such as 3-Oxo-α-ionol, are present in Muscat leaves. Norisoprenoid Terpenes ( / ˈ t ɜːr p iː n / ) are
330-423: Is associated with di- and trisubstituted alkenes . Di- and trisubstituted alkenes resist polymerization (low ceiling temperatures ) but are susceptible to acid-induced carbocation formation. Terpenes may be classified by the number of isoprene units in the molecule; a prefix in the name indicates the number of isoprene pairs needed to assemble the molecule. Commonly, terpenes contain 2, 3, 4 or 6 isoprene units;
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#1733202997323360-553: Is distributed in all three domains of life; archaea, bacteria and eukaryotes. The MVA pathway is universally distributed in archaea and non-photosynthetic eukaryotes, while the pathway is sparse in bacteria. In photosynthetic eukaryotes, some species possess the MVA pathway, while others have the MEP pathway or both MVA and MEP pathways. This is due to the acquisition of the MEP pathway by a common ancestor of Archaeplastida (algae + land plants) through
390-474: Is estimated at 55,000 chemical entities. The 1939 Nobel Prize in Chemistry was awarded to Leopold Ružička "for his work on polymethylenes and higher terpenes", "including the first chemical synthesis of male sex hormones ." Terpenes are major biosynthetic building blocks. Steroids , for example, are derivatives of the triterpene squalene . Terpenes and terpenoids are also the primary constituents of
420-430: Is isomerized to DMAPP by the enzyme isopentenyl pyrophosphate isomerase. IPP and DMAPP condense to give geranyl pyrophosphate , the precursor to monoterpenes and monoterpenoids. Geranyl pyrophosphate is also converted to farnesyl pyrophosphate and geranylgeranyl pyrophosphate , respectively C 15 and C 20 precursors to sesquiterpenes and diterpenes (as well as sesequiterpenoids and diterpenoids). Biosynthesis
450-632: Is made from the grape on the island of Pantelleria , and it is grown in Calabria and Sicily where it is known as Zibibbo . In Spain , the grape is the sixth most planted white grape variety with 10,318 hectares (25,496 acres) grown in 2015, mainly in Málaga , Alicante , Valencia , and the Canary Islands . It is an important grape in the Australian wine and South African wine industry. The vine thrives in
480-503: Is mediated by terpene synthase . The genomes of many plant species contain genes that encode terpenoid synthase enzymes imparting terpenes with their basic structure, and cytochrome P450s that modify this basic structure. Terpenes can be visualized as the result of linking isoprene (C 5 H 8 ) units "head to tail" to form chains and rings. A few terpenes are linked “tail to tail”, and larger branched terpenes may be linked “tail to mid”. Strictly speaking all monoterpenes have
510-597: Is one of the oldest genetically unmodified vines still in existence. The grape originated in North Africa , and the name is probably derived from its association with Ancient Egyptians who used the grape for wine making. It is also a table grape used for eating and raisins. Muscat of Alexandria is cultivated very heavily on the island of Lemnos in the North Eastern Aegean region of Greece , and reputedly Cleopatra drank muscat wine from there. In Italy wine
540-599: The bow hair, by ballet dancers on the soles of their shoes to maintain traction on the floor, by gymnasts to keep their grips while performing, and by baseball pitchers to improve their control of the baseball. Terpenes are widely used as fragrances and flavors in consumer products such as perfumes , cosmetics and cleaning products , as well as food and drink products. For example, the aroma and flavor of hops comes, in part, from sesquiterpenes (mainly α-humulene and β-caryophyllene ), which affect beer quality. Some form hydroperoxides that are valued as catalysts in
570-489: The endosymbiosis of ancestral cyanobacteria that possessed the MEP pathway. The MVA and MEP pathways were selectively lost in individual photosynthetic lineages. Also, the archaeal MVA pathway is not completely homologous to the eukaryotic MVA pathway. Instead, the eukaryotic MVA pathway is closer to the bacterial MVA pathway. The non-mevalonate pathway or the 2- C -methyl-D-erythritol 4-phosphate (MEP) pathway starts with pyruvate and glyceraldehyde 3-phosphate (G3P) as
600-655: The essential oils of many types of plants and flowers. In plants, terpenes and terpenoids are important mediators of ecological interactions . For example, they play a role in plant defense against herbivory , disease resistance , attraction of mutualists such as pollinators , as well as potentially plant- plant communication . They appear to play roles as antifeedants . Other functions of terpenoids include cell growth modulation and plant elongation, light harvesting and photoprotection, and membrane permeability and fluidity control. Higher amounts of terpenes are released by trees in warmer weather, where they may function as
630-544: The glycosides , which are linked to sugars. These are water-soluble solids. Conceptually derived from isoprenes , the structures and formulas of terpenes follow the biogenetic isoprene rule or the C 5 rule , as described in 1953 by Leopold Ružička and colleagues. The C 5 isoprene units are provided in the form of dimethylallyl pyrophosphate (DMAPP) and isopentenyl pyrophosphate (IPP). DMAPP and IPP are structural isomers to each other. This pair of building blocks are produced by two distinct metabolic pathways :
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#1733202997323660-532: The mevalonate (MVA) pathway and the non-mevalonate (MEP) pathway . These two pathways are mutually exclusive in most organisms, except for some bacteria and land plants. In general, most archaea and eukaryotes use the MVA pathway, while bacteria mostly have the MEP pathway. IPP and DMAPP are final products of both MVA and MEP pathways and the relative abundance of these two isoprene units is enzymatically regulated in host organisms. This pathway conjugates three molecules of acetyl CoA . The mevalonate (MVA) pathway
690-451: The German chemist August Kekulé to denote all hydrocarbons having the empirical formula C 10 H 16 , of which camphene was one. Previously, many hydrocarbons having the empirical formula C 10 H 16 had been called "camphene", but many other hydrocarbons of the same composition had had different names. Kekulé coined the term "terpene" in order to reduce the confusion. The name "terpene"
720-451: The carbon source. C 5 IPP and C 5 DMAPP are the end-products in either pathway and are the precursors of terpenoids with various carbon numbers (typically C 5 to C 40 ), side chains of (bacterio) chlorophylls , hemes and quinones . Synthesis of all higher terpenoids proceeds via formation of geranyl pyrophosphate (GPP), farnesyl pyrophosphate (FPP), and geranylgeranyl pyrophosphate (GGPP). In both MVA and MEP pathways, IPP
750-627: The most arid regions. Production was mainly in California, Australia and South Africa, but the wine styles originated in southern Europe and northern Africa, Turkey and the Levant. Much was used in the production of sherry and port as well as brandy, either distilled as brandy spirit or for base wine. As demand for these wines declined from the 1960s, gordo blanco was used to create still and sparkling wines using European-sounding labels like "Riesling", "Moselle" and "Champagne" and "Liebfrauwein" (until such use
780-1235: The production of polymers. Many terpenes have been shown to have pharmacological effects, although most studies are from laboratory research, and clinical research in humans is preliminary. Terpenes are also components of some traditional medicines, such as aromatherapy . Reflecting their defensive role in plants, terpenes are used as active ingredients of pesticides in agriculture. Terpenes are colorless, although impure samples are often yellow. Boiling points scale with molecular size: terpenes, sesquiterpenes, and diterpenes respectively at 110, 160, and 220 °C. Being highly non-polar, they are insoluble in water. Being hydrocarbons, they are highly flammable and have low specific gravity (float on water). They are tactilely light oils considerably less viscous than familiar vegetable oils like corn oil (28 cP ), with viscosity ranging from 1 cP (à la water) to 6 cP. Terpenes are local irritants and can cause gastrointestinal disturbances if ingested. Terpenoids (mono-, sesqui-, di-, etc.) have similar physical properties but tend to be more polar and hence slightly more soluble in water and somewhat less volatile than their terpene analogues. Highly polar derivatives of terpenoids are
810-630: The same chemical formula C 10 H 16 . Similarly all sesquiterpenes and diterpenes have formulas of C 15 H 24 and C 20 H 32 respectively. The structural diversity of mono-, sesqui-, and diterpenes is a consequence of isomerism. Terpenes and terpenoids are usually chiral . Chiral compounds can exist as non-superposable mirror images, which exhibit distinct physical properties such as odor or toxicity. Most terpenes and terpenoids feature C=C groups, i.e. they exhibit unsaturation. Since they carry no functional groups aside from their unsaturation, terpenes are structurally distinctive. The unsaturation
840-564: The tetraterpenes (8 isoprene units) form a separate class of compounds called carotenoids; the others are rare. While terpenes and terpenoids occur widely, their extraction from natural sources is often problematic. Consequently, they are produced by chemical synthesis, usually from petrochemicals . In one route, acetone and acetylene are condensed to give 2-Methylbut-3-yn-2-ol , which is extended with acetoacetic ester to give geranyl alcohol . Others are prepared from those terpenes and terpenoids that are readily isolated in quantity, say from
870-462: The wetter western half of Georgia. Alexandrouli is also known under the synonyms Aleksandroouly, Aleksandrouli, Aleksandrouli Shavi, Alexandreouli, Alexandroouli, Alexandrouli, Kabistona, and Kabistoni. Muscat of Alexandria Muscat of Alexandria is a white wine grape that is a member of the Muscat family of Vitis vinifera . It is considered an "ancient vine", and wine experts believe it
900-462: Was banned by law and trade agreements) which bore only a stylistic resemblance to their inspiration. In Málaga the grape is often blended with Pedro Ximénez to create a strong wine that varies in color from gold to dark black. In Australia, the grape is used principally to increase the alcohol content in both white and red wines in a cool season, in wines sold as "Moscato", and in cheap bladder pack wines. In Portugal , Vinho Moscatel (Moscatel Wine)
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