Geranylacetone
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Geranylacetone
Geranylacetone is an organic compound with the formula CH3C(O)(CH2)2CH=C(CH3)(CH2)2CH=C(CH3)2. A colorless oil, it is the product of coupling geranyl and acetonyl groups. It is a precursor to synthetic squalene. Synthesis and occurrence Geranylacetone can be produced by transesterification of ethyl acetoacetate with linalool: : The esterification of linalool can also be effected with ketene or isopropenyl methyl ether. The resulting linalyl ester undergoes Carroll rearrangement to give geranylacetone. Geranyl acetone is a precursor to isophytol, which is used in the manufacture of Vitamin E. Other derivatives of geranyl acetone are farnesol and nerolidol. Geranylacetone is a flavor component of many plants including rice, mango, and tomatoes. Together with other ketones, geranylacetone results from the degradation of vegetable matter by ozone. Biosynthesis It arises by the oxidation of certain carotenoids. Such reaction are catalyzed by carotenoid oxygenase __NOTOC__ Car ...
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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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Farnesol
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. Farnesol is produced from 5-carbon isoprene compounds in both plants and animals. Phosphate-activated derivatives of farnesol are the building blocks of possibly all acyclic sesquiterpenoids. These compounds are doubled to form 30-carbon squalene, which is the precursor for steroids in plants, animals, and fungi. Farnesol and its derivatives are important starting compounds for natural and artificial organic synthesis. Uses Farnesol is present in many essential oils such as citronella, neroli, cyclamen, lemon grass, tuberose, rose, musk, balsam, and tolu. It is used in perfumery to emphasize the odors of sweet, floral perfumes. It enhances perfume scent by acting as a co-solvent that regulates the volatility of the odorants. It is especially used in lilac perfume ...
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Carotenoid Oxygenase
__NOTOC__ Carotenoid oxygenases are a family of enzymes involved in the cleavage of carotenoids to produce, for example, retinol, commonly known as vitamin A. This family includes an enzyme known as RPE65 which is abundantly expressed in the retinal pigment epithelium where it catalyzed the formation of 11-cis-retinol from all-trans-retinyl esters. Carotenoids such as beta-carotene, lycopene, lutein and beta-cryptoxanthin are produced in plants and certain bacteria, algae and fungi, where they function as accessory photosynthetic pigments and as scavengers of oxygen radicals for photoprotection. They are also essential dietary nutrients in animals. Carotenoid oxygenases cleave a variety of carotenoids into a range of biologically important products, including apocarotenoids in plants that function as hormones, pigments, flavours, floral scents and defence compounds, and retinoids in animals that function as vitamins, chromophores for opsins and signalling molecules. Examples o ...
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Carotenoid
Carotenoids (), also called tetraterpenoids, are yellow, orange, and red organic compound, organic pigments that are produced by plants and algae, as well as several bacteria, and Fungus, fungi. Carotenoids give the characteristic color to pumpkins, carrots, parsnips, maize, corn, tomatoes, Domestic Canary, canaries, flamingos, salmon, lobster, shrimp, and daffodils. Carotenoids can be produced from Lipid, fats and other basic organic metabolic building blocks by all these organisms. It is also produced by Endosymbiont, endosymbiotic bacteria in Whitefly, whiteflies. Carotenoids from the diet are stored in the fatty tissues of animals, and exclusively Carnivore, carnivorous animals obtain the compounds from animal fat. In the human diet, Small intestine#Absorption, absorption of carotenoids is improved when consumed with fat in a meal. Cooking carotenoid-containing vegetables in oil and shredding the vegetable both increase carotenoid bioavailability. There are over 1,100 known c ...
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Ozone
Ozone (), or trioxygen, is an inorganic molecule with the chemical formula . It is a pale blue gas with a distinctively pungent smell. It is an allotrope of oxygen that is much less stable than the diatomic allotrope , breaking down in the lower atmosphere to (dioxygen). Ozone is formed from dioxygen by the action of ultraviolet (UV) light and electrical discharges within the Earth's atmosphere. It is present in very low concentrations throughout the latter, with its highest concentration high in the ozone layer of the stratosphere, which absorbs most of the Sun's ultraviolet (UV) radiation. Ozone's odour is reminiscent of chlorine, and detectable by many people at concentrations of as little as in air. Ozone's O3 structure was determined in 1865. The molecule was later proven to have a bent structure and to be weakly diamagnetic. In standard conditions, ozone is a pale blue gas that condenses at cryogenic temperatures to a dark blue liquid and finally a violet-black soli ...
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Tomato
The tomato is the edible berry of the plant ''Solanum lycopersicum'', commonly known as the tomato plant. The species originated in western South America, Mexico, and Central America. The Mexican Nahuatl word gave rise to the Spanish word , from which the English word ''tomato'' derived. Its domestication and use as a cultivated food may have originated with the indigenous peoples of Mexico. The Aztecs used tomatoes in their cooking at the time of the Spanish conquest of the Aztec Empire, and after the Spanish encountered the tomato for the first time after their contact with the Aztecs, they brought the plant to Europe, in a widespread transfer of plants known as the Columbian exchange. From there, the tomato was introduced to other parts of the European-colonized world during the 16th century. Tomatoes are a significant source of umami flavor. They are consumed in diverse ways: raw or cooked, and in many dishes, sauces, salads, and drinks. While tomatoes are fruits†...
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Mango
A mango is an edible stone fruit produced by the tropical tree ''Mangifera indica''. It is believed to have originated in the region between northwestern Myanmar, Bangladesh, and northeastern India. ''M. indica'' has been cultivated in South and Southeast Asia since ancient times resulting in two types of modern mango cultivars: the "Indian type" and the "Southeast Asian type". Other species in the genus ''Mangifera'' also produce edible fruits that are also called "mangoes", the majority of which are found in the Malesian ecoregion. Worldwide, there are several hundred cultivars of mango. Depending on the cultivar, mango fruit varies in size, shape, sweetness, skin color, and flesh color which may be pale yellow, gold, green, or orange. Mango is the national fruit of India, Pakistan and the Philippines, while the mango tree is the national tree of Bangladesh. Etymology The English word ''mango'' (plural "mangoes" or "mangos") originated in the 16th century from the Por ...
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Rice
Rice is the seed of the grass species ''Oryza sativa'' (Asian rice) or less commonly ''Oryza glaberrima ''Oryza glaberrima'', commonly known as African rice, is one of the two domesticated rice species. It was first domesticated and grown in West Africa around 3,000 years ago. In agriculture, it has largely been replaced by higher-yielding Asian r ...'' (African rice). The name wild rice is usually used for species of the genera ''Zizania (genus), Zizania'' and ''Porteresia'', both wild and domesticated, although the term may also be used for primitive or uncultivated varieties of ''Oryza''. As a cereal, cereal grain, domesticated rice is the most widely consumed staple food for over half of the world's World population, human population,Abstract, "Rice feeds more than half the world's population." especially in Asia and Africa. It is the agricultural commodity with the third-highest worldwide production, after sugarcane and maize. Since sizable portions of sugarcane and ma ...
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Nerolidol
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 internal double bonds, 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 involve include nerolidyl diphosphate and the fragrance nerolidyl acetate. Synthesis and occurrence Nerolidol is produced commercially from geranylacetone by the addition of vinyl Grignard reagent. It is used as a source of farnesol, vitamin E, and vitamin K1. Significant sources of natural nerolidol is Cabreuva oil and the oil of ''Dalbergia parviflora''. It is also present in neroli, ginger, jasmine, lavender, tea tree, ''Cannabis sativa'', and lemon ...
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Vitamin E
Vitamin E is a group of eight fat soluble compounds that include four tocopherols and four tocotrienols. Vitamin E deficiency, which is rare and usually due to an underlying problem with digesting dietary fat rather than from a diet low in vitamin E, can cause Neurological disorder, nerve problems. Vitamin E is a fat-soluble antioxidant which may help protect cell membranes from reactive oxygen species. Worldwide, government organizations recommend adults consume in the range of 3 to 15 mg per day. As of 2016, consumption was below recommendations according to a worldwide summary of more than one hundred studies that reported a median dietary intake of 6.2 mg per day for alpha-tocopherol. Population studies suggested that people who consumed foods with more vitamin E, or who chose on their own to consume a vitamin E dietary supplement, had lower incidence of cardiovascular diseases, cancer, dementia, and other diseases. However, placebo-controlled clinical trials using ...
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Geranyl
Geraniol is a monoterpenoid and an alcohol. It is the primary component of citronella oil and is a primary component of rose oil, palmarosa oil. It is a colorless oil, although commercial samples can appear yellow. It has low solubility in water, but it is soluble in common organic solvents. The functional group derived from geraniol (in essence, geraniol lacking the terminal −OH) is called geranyl. Uses and occurrence In addition to rose oil, palmarosa oil, and citronella oil, it also occurs in small quantities in geranium, lemon, and many other essential oils. With a rose-like scent, it is commonly used in perfumes. It is used in flavors such as peach, raspberry, grapefruit, red apple, plum, lime, orange, lemon, watermelon, pineapple, and blueberry. Geraniol is produced by the scent glands of honeybees to mark nectar-bearing flowers and locate the entrances to their hives. It is also commonly used as an insect repellent, especially for mosquitoes. The scent of geraniol is ...
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Isophytol
Isophytol is a terpenoid alcohol that is used as a fragrance and as an intermediate in the production of vitamin E and K1. Occurrence Isophytol has been in found in two red algae species and more than 15 plant species. Concentrations found have been low. Synthesis It can be synthesized in six steps from pseudoionone and propargyl alcohol. Total synthesis begins with the combination of acetylene and acetone to produce 3-methyl-1-butyn-3-ol. Hydrogenation by palladium catalysis results in 3-methyl-1-buten-3-ol. Reaction with diketene or acetic acid ester creates the acetoacetate; thermal reaction leads to 2-methyl-2-hepten-6-one. The steps of adding acetylene and then isopropenyl methyl ether and hydrogenating the product are done twice (this involves an intermediate of pseudoionone); then acetylene is added to create dehydroisophytol. Hydrogenation results in isophytol. Uses Production industrially was estimated to be 35000 to 40000 tons in 2002, created by total synthesis, with ...
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