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Ambrein
Ambrein is a triterpene alcohol that is the chief constituent of ambergris, a secretion from the digestive system of the sperm whale, and has been suggested as the possible active component producing the supposed aphrodisiac effects of ambergris. Although ambrein itself is odorless, it serves as the biological precursor for a number of aromatic derivatives such as ambroxan and is thought to possess fixative properties for other odorants. It has been shown to act as an analgesic and it has been proven to increase sexual behavior in rats, providing some support for its traditional aphrodisiac use. Apart from its supposed aphrodisiac effects, ambrein has been shown to decrease spontaneous contractions of smooth muscles in rats, guinea pigs, and rabbits. It is able to reduce these contractions by serving as an antagonist and interfering with the Ca2+ ions from outside of the cell. Discovery In 1946, Ruzicka and Lardon "established that the fragrance of ambergris is based on the tr ...
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Ambrein Biosynthesis
Ambrein is a triterpene alcohol that is the chief constituent of ambergris, a secretion from the digestive system of the sperm whale, and has been suggested as the possible active component producing the supposed aphrodisiac effects of ambergris. Although ambrein itself is odorless, it serves as the biological precursor for a number of aromatic derivatives such as ambroxan and is thought to possess fixative properties for other odorants. It has been shown to act as an analgesic and it has been proven to increase sexual behavior in rats, providing some support for its traditional aphrodisiac use. Apart from its supposed aphrodisiac effects, ambrein has been shown to decrease spontaneous contractions of smooth muscles in rats, guinea pigs, and rabbits. It is able to reduce these contractions by serving as an antagonist and interfering with the Ca2+ ions from outside of the cell. Discovery In 1946, Leopold Ružička, Ruzicka and Lardon "established that the fragrance of ambergris is ...
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Ambergris
Ambergris ( or , la, ambra grisea, fro, ambre gris), ''ambergrease'', or grey amber is a solid, waxy, flammable substance of a dull grey or blackish colour produced in the digestive system of sperm whales. Freshly produced ambergris has a marine, fecal odor. It acquires a sweet, earthy scent as it ages, commonly likened to the fragrance of Isopropyl alcohol without the vaporous chemical astringency. Ambergris has been highly valued by perfume makers as a fixative that allows the scent to endure much longer, although it has been mostly replaced by synthetic ambroxide. Dogs are attracted to the smell of ambergris and are sometimes used by ambergris searchers. Etymology The word ''ambergris'' comes from the Old French "''ambre gris''" or "grey amber". The word "amber" comes from the same source, but it has been applied almost exclusively to fossilized tree resins from the Baltic region since the late 13th century in Europe. Furthermore, the word "amber" is derived from the Mid ...
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Ambroxan
Ambroxide, widely known by the brand name Ambroxan, is a naturally occurring terpenoid and one of the key constituents responsible for the odor of ambergris. It is an autoxidation product of ambrein. Ambroxide is used in perfumery for creating ambergris notes and as a fixative. Small amounts (< 0.01 ppm) are used as a in food.


Synthesis

Ambroxide is synthesized from , a component of the essential oil of . Sclareol is oxidatively degraded to a , which is
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Leopold Ružička
Leopold Ružička (; born Lavoslav Stjepan Ružička; 13 September 1887 – 26 September 1976) was a Croatian-Swiss scientist and joint winner of the 1939 Nobel Prize in Chemistry "for his work on polymethylenes and higher terpenes" "including the first chemical synthesis of male sex hormones." He worked most of his life in Switzerland, and received eight doctor ''honoris causa'' in science, medicine, and law; seven prizes and medals; and twenty-four honorary memberships in chemical, biochemical, and other scientific societies. Early life Ružička was born in Vukovar, Kingdom of Croatia-Slavonia, Lands of the Crown of Saint Stephen, Austro-Hungarian Empire (today in Croatia). His family of craftsmen and farmers was mostly of Croat origin, with a Czech great grandparent, Ružička, and a great grandmother and a great grandfather from Austria.Now available from He lost his father, Stjepan, at the age of four, and his mother, Amalija Sever, took him and his younger brother Stje ...
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Triterpene
Triterpenes are a class of chemical compounds composed of three terpene units with the molecular formula C30H48; they may also be thought of as consisting of six isoprene units. Animals, plants and fungi all produce triterpenes, including squalene, the precursor to all steroids. Structures Triterpenes exist in a great variety of structures. Nearly 200 different skeletons have been identified. These skeletons may be broadly divided according to the number of rings present. In general pentacyclic structures (5 rings) tend to dominate. Squalene is biosynthesized through the head-to-head condensation of two farnesyl pyrophosphate units. This coupling converts a pair of C15 components into a C30 product. Squalene serves as precursor for the formation of many triterpenoids, including bacterial hopanoids and eukaryotic sterols. Triterpenoids By definition triterpenoids are triterpenes that possess heteroatoms, usually oxygen. The terms ''triterpene'' and ''triterpenoid'' oft ...
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Triterpenes
Triterpenes are a class of chemical compounds composed of three terpene units with the molecular formula C30H48; they may also be thought of as consisting of six isoprene units. Animals, plants and fungi all produce triterpenes, including squalene, the precursor to all steroids. Structures Triterpenes exist in a great variety of structures. Nearly 200 different skeletons have been identified. These skeletons may be broadly divided according to the number of rings present. In general pentacyclic structures (5 rings) tend to dominate. Squalene is biosynthesized through the head-to-head condensation of two farnesyl pyrophosphate units. This coupling converts a pair of C15 components into a C30 product. Squalene serves as precursor for the formation of many triterpenoids, including bacterial hopanoids and eukaryotic sterols. Triterpenoids By definition triterpenoids are triterpenes that possess heteroatoms, usually oxygen. The terms ''triterpene'' and ''triterpenoid'' oft ...
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Animal Glandular Products
Animals are multicellular, eukaryotic organisms in the biological kingdom Animalia. With few exceptions, animals consume organic material, breathe oxygen, are able to move, can reproduce sexually, and go through an ontogenetic stage in which their body consists of a hollow sphere of cells, the blastula, during embryonic development. Over 1.5 million living animal species have been described—of which around 1 million are insects—but it has been estimated there are over 7 million animal species in total. Animals range in length from to . They have complex interactions with each other and their environments, forming intricate food webs. The scientific study of animals is known as zoology. Most living animal species are in Bilateria, a clade whose members have a bilaterally symmetric body plan. The Bilateria include the protostomes, containing animals such as nematodes, arthropods, flatworms, annelids and molluscs, and the deuterostomes, containing the echinoderms and ...
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Whale Products
Whales are a widely distributed and diverse group of fully aquatic placental marine mammals. As an informal and colloquial grouping, they correspond to large members of the infraorder Cetacea, i.e. all cetaceans apart from dolphins and porpoises. Dolphins and porpoises may be considered whales from a formal, cladistic perspective. Whales, dolphins and porpoises belong to the order Cetartiodactyla, which consists of even-toed ungulates. Their closest non-cetacean living relatives are the hippopotamuses, from which they and other cetaceans diverged about 54 million years ago. The two parvorders of whales, baleen whales (Mysticeti) and toothed whales (Odontoceti), are thought to have had their last common ancestor around 34 million years ago. Mysticetes include four extant (living) families: Balaenopteridae (the rorquals), Balaenidae (right whales), Cetotheriidae (the pygmy right whale), and Eschrichtiidae (the grey whale). Odontocetes include the Monodontidae (belugas and n ...
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Perfume Ingredients
Perfume (, ; french: parfum) is a mixture of fragrant essential oils or aroma compounds (fragrances), fixatives and solvents, usually in liquid form, used to give the human body, animals, food, objects, and living-spaces an agreeable scent. The 1939 Nobel Laureate for Chemistry, Leopold Ružička stated in 1945 that "right from the earliest days of scientific chemistry up to the present time, perfumes have substantially contributed to the development of organic chemistry as regards methods, systematic classification, and theory." Ancient texts and archaeological excavations show the use of perfumes in some of the earliest human civilizations. Modern perfumery began in the late 19th century with the commercial synthesis of aroma compounds such as vanillin or coumarin, which allowed for the composition of perfumes with smells previously unattainable solely from natural aromatics. History The word ''perfume'' derives from the Latin ''perfumare'', meaning "to smoke through" ...
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Squalene
Squalene is an organic compound. It is a triterpenoid with the formula C30H50. It is a colourless oil, although impure samples appear yellow. It was originally obtained from shark liver oil (hence its name, as ''Squalus'' is a genus of sharks). All plants and animals produce squalene as a biochemical intermediate to sterol biosynthesis. An estimated 12% of bodily squalene in humans is found in Sebaceous gland, sebum. Squalene has a role in topical skin lubrication and protection. Squalene is a precursor (chemistry), precursor for synthesis of all plant and animal sterols, including cholesterol and steroid hormones in the human body. Squalene is an important ingredient in some vaccine adjuvants: The Novartis and GlaxoSmithKline adjuvants are called MF59 and AS03, respectively. Role in steroid synthesis Squalene is the biochemical precursor to steroids. The squalene conversion begins with oxidation (via squalene monooxygenase) of one of its terminal double bonds, resulting in 2,3- ...
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Tetraprenyl-beta-curcumene Synthase
Tetraprenyl-β-curcumene synthase (EC 4.2.3.130, ''ytpB (gene)'') is an enzyme with systematic name ''all-trans''-heptaprenyl-diphosphate diphosphate-lyase (cyclizing, tetraprenyl-β-curcumene-forming). This enzyme catalyses the following chemical reaction : ''all-trans''-heptaprenyl diphosphate \rightleftharpoons tetraprenyl-β-curcumene + diphosphate This enzyme is isolated from '' Bacillus subtilis''. References External links * {{Portal bar, Biology, border=no EC 4.2.3 ...
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Squalene-hopene Cyclase
Squalene-hopene cyclase (SHC) () or ''hopan-22-ol hydro-lyase'' is an enzyme in the terpene cyclase/mutase family. It catalyzes the interconversion of squalene into a pentacyclic triterpenes, hopene and hopanol. This enzyme catalyses the following chemical reactions. : squalene \rightleftharpoons hop-22(29)-ene : squalene + H2O \rightleftharpoons hopan-22-ol SHC is important because its products, hopanoids, are very much like sterols in eukaryotes in that they condense lipid membranes and reduce permeability. In fact, SHC and sterol-producing enzymes ( oxidosqualene cyclase) are evolutionarily related to each other. Hopanoids are inferred to provide stability in the face of high temperatures and extreme acidity due to the rigid ring structure. Indeed, up-regulation of SHC occurs in certain bacteria in the presence of hot or acidic environments. SHC is found mostly in bacteria, but some eukaryotes, such as fungi and land plants, are also known to possess the enzyme. Introduct ...
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