Fixative (perfumery)
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Fixative (perfumery)
A fixative is used to equalize the vapor pressures, and thus the volatilities, of the raw materials in a perfume oil, as well as to increase the tenacity. Fixatives can be resinoids ( benzoin, labdanum, myrrh, olibanum, storax, tolu balsam) or the molecules ambroxide, civetone and muscone, which were originally obtained from animals, but can and are now mostly synthesized because it is more economical, more consistent and more ethical (animals were either killed or are kept in captivity to collect the secretions from their perineal glands). Synthetic fixatives include substances of low volatility (diphenylmethane, dipropylene glycol (DPG), cyclopentadecanolide, ambroxide, benzyl salicylate) and virtually odorless solvents with very low vapor pressures (benzyl benzoate, diethyl phthalate, triethyl citrate Triethyl citrate is an ester of citric acid. It is a colorless, odorless liquid used as a food additive (E number E1505) to stabilize foams, especially as whipping aid for egg ...
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Vapor Pressure
Vapor pressure (or vapour pressure in English-speaking countries other than the US; see spelling differences) or equilibrium vapor pressure is defined as the pressure exerted by a vapor in thermodynamic equilibrium with its condensed phases (solid or liquid) at a given temperature in a closed system. The equilibrium vapor pressure is an indication of a liquid's evaporation rate. It relates to the tendency of particles to escape from the liquid (or a solid). A substance with a high vapor pressure at normal temperatures is often referred to as '' volatile''. The pressure exhibited by vapor present above a liquid surface is known as vapor pressure. As the temperature of a liquid increases, the kinetic energy of its molecules also increases. As the kinetic energy of the molecules increases, the number of molecules transitioning into a vapor also increases, thereby increasing the vapor pressure. The vapor pressure of any substance increases non-linearly with temperature according ...
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Muscone
Muscone is an organic compound that is the primary contributor to the odor of musk. The chemical structure of muscone was first elucidated by Leopold Ružička. It consists of a 15-membered ring ketone with one methyl substituent in the 3-position. It is an oily liquid that is found naturally as the (−)-enantiomer, (''R'')-3-methylcyclopentadecanone. Muscone has been synthesized as the pure (−)-enantiomer as well as the racemate. It is very slightly soluble in water and miscible with alcohol. Natural muscone is obtained from musk, a glandular secretion of the musk deer, which has been used in perfumery and medicine for thousands of years. Since obtaining natural musk requires killing the endangered animal, nearly all muscone used in perfumery today is synthetic. It has the characteristic smell of being "musky". One asymmetric synthesis of (−)-muscone begins with commercially available (+)-citronellal, and forms the 15-membered ring via ring-closing metathesis: A more rece ...
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Diethyl Phthalate
Diethyl phthalate (DEP) is a phthalate ester. It occurs as a colourless liquid without significant odour but has a bitter, disagreeable taste. It is more dense than water and insoluble in water; hence, it sinks in water. Synthesis and applications Diethyl phthalate is produced by the reaction of ethanol with phthalic anhydride, in the presence of a strong acid catalyst: It finds some use as a specialist plasticiser in PVC, it has also been used as a blender and fixative in perfume. Biodegradation Biodegradation by microorganisms Biodegradation of DEP in soil occurs by sequential hydrolysis of the two diethyl chains of the phthalate to produce monoethyl phthalate, followed by phthalic acid. This reaction occurs very slowly in an abiotic environment. Thus there exists an alternative pathway of biodegradation which includes transesterification or demethylation by microorganisms, if the soil is also contaminated with methanol, that would produce another three intermediate compoun ...
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Benzyl Benzoate
Benzyl benzoate is an organic compound which is used as a medication and insect repellent. As a medication it is used to treat scabies and lice. For scabies either permethrin or malathion is typically preferred. It is applied to the skin as a lotion. Typically two to three applications are needed. It is also present in Balsam of Peru, Tolu balsam, and in a number of flowers. Side effects may include irritation of the skin. It is not recommended in children. It is also used in other animals; however, it is considered toxic to cats. How it works is unclear. Benzyl benzoate was first studied medically in 1918. It is on the World Health Organization's List of Essential Medicines. Benzyl benzoate is sold under the brand name Scabanca among others and is available as a generic medication. It is not available for medical use in the United States. Uses Medical Benzyl benzoate is an effective and inexpensive topical treatment for human scabies. It has vasodilating and spasmoly ...
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Solvent
A solvent (s) (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for polar molecules and the most common solvent used by living things; all the ions and proteins in a cell are dissolved in water within the cell. The quantity of solute that can dissolve in a specific volume of solvent varies with temperature. Major uses of solvents are in paints, paint removers, inks, and dry cleaning. Specific uses for organic solvents are in dry cleaning (e.g. tetrachloroethylene); as paint thinners (toluene, turpentine); as nail polish removers and solvents of glue (acetone, methyl acetate, ethyl acetate); in spot removers (hexane, petrol ether); in detergents ( citrus terpenes); and in perfumes (ethanol). Solvents find various applications in chemical, pharmaceutical, oil, and gas industries, including in chemical syn ...
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Benzyl Salicylate
Benzyl salicylate is a salicylic acid benzyl ester, a chemical compound most frequently used in cosmetics as a fragrance additive or UV light absorber. It appears as an almost colorless liquid with a mild odor described as "very faint, sweet-floral, slightly balsamic" by some, while others smell nothing at all. There is debate whether the odour is caused solely by impurities or a genetic predisposition. It occurs naturally in a variety of plants and plant extracts and is widely used in blends of fragrance materials. There is some evidence that people may become sensitized to this material and as a result, there is a restriction standard concerning the use of this material in fragrances by the International Fragrance Association. It is used as a solvent for crystalline synthetic musks and as a component and fixative in floral perfumes such as carnation, jasmine, lilac, and wallflower.An Introduction to Perfumery by Curtis & Williams 2nd Edition, 2009, , See also *Oil of winterg ...
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Cyclopentadecanolide
Cyclopentadecanolide is a natural macrolide lactone and a synthetic musk. Natural occurrence Cyclopentadecanolide occurs in small quantities in angelica root essential oil and is responsible for its musklike odor. Production Cyclopentadecanolide is produced synthetically by ring expansion of cyclotetradecanone. Another synthesis route is the depolymerization of polyesters of 15-hydroxypentadecanoic acid. Uses Cyclopentadecanolide is used as a musklike perfume fixative in fine fragrances and as a flavoring agent 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 gustat .... It is a substitute for the extremely expensive animal musk. References {{reflist Flavors Lactones Perfume ingredients ...
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Dipropylene Glycol
Dipropylene glycol is a mixture of three isomeric chemical compounds, 4-oxa-2,6-heptandiol, 2-(2-hydroxy-propoxy)-propan-1-ol, and 2-(2-hydroxy-1-methyl-ethoxy)-propan-1-ol. It is a colorless, nearly odorless liquid with a high boiling point and low toxicity. Uses Dipropylene glycol finds many uses as a plasticizer, an intermediate in industrial chemical reactions, as a polymerization initiator or monomer, and as a solvent. Its low toxicity and solvent properties make it an ideal additive for perfume 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. Th ...s and skin and hair care products. It is also a common ingredient in commercial fog fluid, used in entertainment industry fog machines. References Cosmetics chemicals Monomers Plasticizers Diols Glycol ethers {{organic- ...
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Diphenylmethane
Diphenylmethane is an organic compound with the formula (C6H5)2CH2 (often abbreviated ). The compound consists of methane wherein two hydrogen atoms are replaced by two phenyl groups. It is a white solid. Diphenylmethane is a common skeleton in organic chemistry. The diphenylmethyl group is also known as ''benzhydryl''. Synthesis It is prepared by the Friedel–Crafts alkylation of benzyl chloride with benzene in the presence of a Lewis acid such as aluminium chloride: :C6H5CH2Cl + C6H6 → (C6H5)2CH2 + HCl Reactivity of the C-H bond The methylene group in diphenylmethane is mildly acidic with a p''K''a of 32.2, and so can be deprotonated with sodium amide. :(C6H5)2CH2 + NH2− → (C6H5)2CH− + NH3 The resulting carbanion can be alkylated. For example, treatment with ''n''-bromobutane produces 1,1-diphenylpentane in 92% yield. :(C6H5)2CH− + CH3CH2CH2CH2Br → (C6H5)2CHCH2CH2CH2CH3 + Br− Alkylation of various benzhydryl compounds has been demonstrated ...
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Civetone
Civetone is a macrocyclic ketone and the main odorous constituent of civet oil. It is a pheromone sourced from the African civet. It has a strong musky odor that becomes pleasant at extreme dilutions. Civetone is closely related to muscone, the principal odoriferous compound found in musk; the structure of both compounds was elucidated by Leopold Ružička. Today, civetone can be synthesized from precursor chemicals found in palm oil. Uses Civetone is used as a perfume fixative and flavor. In order to attract jaguars to camera traps, field biologists have used the cologne Calvin Klein's Obsession For Men. It is believed that the civetone in the cologne resembles a territorial marking.{{cite web, url=http://blogs.scientificamerican.com/thoughtful-animal/2013/10/10/youll-never-guess-how-biologists-lure-jaguars-to-camera-traps/, title=You'll Never Guess How Biologists Lure Jaguars To Camera Traps, work=Scientific American Blog Network See also * 5-Cyclohexadecenone 5-Cycloh ...
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Volatility (chemistry)
In chemistry, volatility is a material quality which describes how readily a substance vaporizes. At a given temperature and pressure, a substance with high volatility is more likely to exist as a vapour, while a substance with low volatility is more likely to be a liquid or solid. Volatility can also describe the tendency of a vapor to condense into a liquid or solid; less volatile substances will more readily condense from a vapor than highly volatile ones. Differences in volatility can be observed by comparing how fast substances within a group evaporate (or sublimate in the case of solids) when exposed to the atmosphere. A highly volatile substance such as rubbing alcohol (isopropyl alcohol) will quickly evaporate, while a substance with low volatility such as vegetable oil will remain condensed. In general, solids are much less volatile than liquids, but there are some exceptions. Solids that sublimate (change directly from solid to vapor) such as dry ice (solid carbon dioxi ...
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Ambroxide
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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