Grapefruit Mercaptan
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Grapefruit Mercaptan
Grapefruit mercaptan is the common name for a natural organic compound found in grapefruit. It is a monoterpenoid that contains a thiol (also known as a mercaptan) functional group. Structurally a hydroxy group of terpineol is replaced by the thiol in grapefruit mercaptan, so it also called thioterpineol. Volatile thiols typically have very strong, often unpleasant odors that can be detected by humans in very low concentrations. Grapefruit mercaptan has a very potent, but not unpleasant, odor, and it is the chemical constituent primarily responsible for the aroma of grapefruit. This characteristic aroma is a property of only the ''R'' enantiomer. Pure grapefruit mercaptan, or citrus-derived oils rich in grapefruit mercaptan, are sometimes used in perfumery and the flavor industry to impart citrus aromas and flavors. However, both industries actively seek substitutes for grapefruit mercaptans for use as a grapefruit flavorant, since its decomposition products are often highly dis ...
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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. Livin ...
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Perfumery
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". Per ...
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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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Flavors
Flavor or flavour is either the sensory perception of taste or smell, or a flavoring in food that produces such perception. Flavor or flavour may also refer to: Science * Flavors (programming language), an early object-oriented extension to Lisp * Flavour (particle physics), a quantum number of elementary particles related to their weak interactions *Flavor of Linux, another term for any particular Linux distribution; by extension, "flavor" can be applied to any program or other computer code that exists in more than one current variant at the same time Film and TV * ''Flavors'' (film), romantic comedy concerning Asian-Indian immigrants in America Music Artists and bands * Flavor Flav (born 1959), former rap/hip-hop promoter and current reality television actor * Flavour N'abania (born 1983), Nigerian singer-songwriter * Flavor (band), minor hit with "Sally Had A Party" in 1968 Albums * ''Flavours'' (album), 1975 album by The Guess Who * ''Flavors'' (album), by American R& ...
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Thiols
In organic chemistry, a thiol (; ), or thiol derivative, is any organosulfur compound of the form , where R represents an alkyl or other organic substituent. The functional group itself is referred to as either a thiol group or a sulfhydryl group, or a sulfanyl group. Thiols are the sulfur analogue of alcohols (that is, sulfur takes the place of oxygen in the hydroxyl () group of an alcohol), and the word is a blend of "''thio-''" with "alcohol". Many thiols have strong odors resembling that of garlic or rotten eggs. Thiols are used as odorants to assist in the detection of natural gas (which in pure form is odorless), and the "smell of natural gas" is due to the smell of the thiol used as the odorant. Thiols are sometimes referred to as mercaptans () or mercapto compounds, a term introduced in 1832 by William Christopher Zeise and is derived from the Latin ('capturing mercury')''Oxford American Dictionaries'' (Mac OS X Leopard). because the thiolate group () bonds very strongly ...
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Terpineol
Terpineol is any of four isomeric monoterpenoids. Terpenoids are terpene that are modified by the addition of a functional group, in this case, an alcohol. Terpineols have been isolated from a variety of sources such as cardamom, cajuput oil, pine oil, and petitgrain oil. Four isomers exist: α-, β-, γ-terpineol, and terpinen-4-ol. β- and γ-terpineol differ only by the location of the double bond. Terpineol is usually a mixture of these isomers with α-terpineol as the major constituent. : Terpineol has a pleasant odor similar to lilac and is a common ingredient in perfumes, cosmetics, and flavors. α-Terpineol is one of the two most abundant aroma constituents of lapsang souchong tea; the α-terpineol originates in the pine smoke used to dry the tea. (+)-α-terpineol is a chemical constituent of skullcap. Synthesis and biosynthesis Although it is naturally occurring, terpineol is commonly manufactured from alpha-pinene, which is hydrated in the presence of sulfuric a ...
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Nootkatone
Nootkatone is a natural organic compound, a sesquiterpenoid, and a ketone that is the most important and expensive aromatic of grapefruit, and which also occurs in other organisms. Previously, nootkatone was thought to be one of the main chemical components of the smell and flavour of grapefruits. In high purity, it usually is found as colorless crystals. Crude extractives are liquid, viscous, and yellow. Nootkatone typically is extracted from grapefruit through the chemical or biochemical oxidation of valencene. It is found in Alaska yellow cedar trees, as well as in vetiver grass. Mechanism of action As is true of other plant terpenoids, nootkatone activates α-adrenergic type 1 octopamine receptor (PaOA1) in susceptible arthropods, causing fatal spasms. Natural origin Nootkatone was 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 The Nuu-chah-nulth (; ...
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Flavorant
A flavoring (or flavouring), also known as flavor (or flavour) or flavorant, is a food additive used to improve the taste or smell of food. It changes the perceptual impression of food as determined primarily by the chemoreceptors of the gustatory and olfactory systems. Along with additives, other components like sugars determine the taste of food. A flavoring is defined as a substance that gives another substance taste, altering the characteristics of the solute, causing it to become sweet, sour, tangy, etc. Although the term, in common language, denotes the combined chemical sensations of taste and smell, the same term is used in the fragrance and flavors industry to refer to edible chemicals and extracts that alter the flavor of food and food products through the sense of smell. Owing to the high cost, or unavailability of natural flavor extracts, most commercial flavorings are "nature-identical", which means that they are the chemical equivalent of natural flavors ...
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Chirality (chemistry)
In chemistry, a molecule or ion is called chiral () if it cannot be superposed on its mirror image by any combination of rotations, translations, and some conformational changes. This geometric property is called chirality (). The terms are derived from Ancient Greek χείρ (''cheir'') 'hand'; which is the canonical example of an object with this property. A chiral molecule or ion exists in two stereoisomers that are mirror images of each other, called enantiomers; they are often distinguished as either "right-handed" or "left-handed" by their absolute configuration or some other criterion. The two enantiomers have the same chemical properties, except when reacting with other chiral compounds. They also have the same physical properties, except that they often have opposite optical activities. A homogeneous mixture of the two enantiomers in equal parts is said to be racemic, and it usually differs chemically and physically from the pure enantiomers. Chiral molecule ...
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Grapefruit
The grapefruit (''Citrus'' × ''paradisi'') is a subtropical citrus tree known for its relatively large, sour to semi-sweet, somewhat bitter fruit. The interior flesh is segmented and varies in color from pale yellow to dark pink. Grapefruit is a citrus hybrid originating in Barbados. It is an accidental cross between the sweet orange (''C. sinensis'') and the pomelo or shaddock (''C. maxima''), both of which were introduced from Asia in the 17th century. It has also been called the '' forbidden fruit''. In the past it was referred to as the ''pomelo'', but that term is now mostly used as the common name for ''Citrus maxima''. In 2019, world production of grapefruits (combined with pomelos) was 9.3 million tonnes, of which 53% was in China. Other significant producers include Vietnam, United States and Mexico. Description The evergreen grapefruit trees usually grow to around tall, although they may reach . The leaves are long (up to ), thin, glossy, and dark green. They p ...
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Unpleasant Odor
An odor (American English) or odour (Commonwealth English; see spelling differences) is caused by one or more volatilized chemical compounds that are generally found in low concentrations that humans and animals can perceive via their sense of smell. An odor is also called a "smell" or a "scent", which can refer to either a pleasant or an unpleasant odor. While "odor" and "smell" can refer to pleasant and unpleasant odors, the terms "scent", "aroma", and "fragrance" are usually reserved for pleasant-smelling odors and are frequently used in the food and cosmetic industry to describe floral scents or to refer to perfumes. Physiology of smell Sense of smell The perception of odors, or sense of smell, is mediated by the olfactory nerve. The olfactory receptor (OR) cells are neurons present in the olfactory epithelium, which is a small patch of tissue at the back of the nasal cavity. There are millions of olfactory receptor neurons that act as sensory signaling cells. E ...
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Terpineol
Terpineol is any of four isomeric monoterpenoids. Terpenoids are terpene that are modified by the addition of a functional group, in this case, an alcohol. Terpineols have been isolated from a variety of sources such as cardamom, cajuput oil, pine oil, and petitgrain oil. Four isomers exist: α-, β-, γ-terpineol, and terpinen-4-ol. β- and γ-terpineol differ only by the location of the double bond. Terpineol is usually a mixture of these isomers with α-terpineol as the major constituent. : Terpineol has a pleasant odor similar to lilac and is a common ingredient in perfumes, cosmetics, and flavors. α-Terpineol is one of the two most abundant aroma constituents of lapsang souchong tea; the α-terpineol originates in the pine smoke used to dry the tea. (+)-α-terpineol is a chemical constituent of skullcap. Synthesis and biosynthesis Although it is naturally occurring, terpineol is commonly manufactured from alpha-pinene, which is hydrated in the presence of sulfuric a ...
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