Ethyl macadamiate

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Ethyl macadamiate
Ethyl oleate.png
Ethyl oleate, a major constituent of ethyl macadamiate
Names
Other names
Floramac 10
Identifiers
DrugBank
Properties
AppearanceClear, colorless liquid
Density 0.88 g/cm3
Melting point 10 °C (50 °F; 283 K)(congeals)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Ethyl macadamiate is the ester of ethyl alcohol and the fatty acids derived from Macadamia ternifolia seed oil. [1] Ethyl macadamiate is used in some cosmetic formulations. [1]

Ester chemical compounds consisting of a carbonyl adjacent to an ether linkage

In chemistry, an ester is a chemical compound derived from an acid in which at least one –OH (hydroxyl) group is replaced by an –O–alkyl (alkoxy) group. Usually, esters are derived from a carboxylic acid and an alcohol. Glycerides, which are fatty acid esters of glycerol, are important esters in biology, being one of the main classes of lipids, and making up the bulk of animal fats and vegetable oils. Esters with low molecular weight are commonly used as fragrances and found in essential oils and pheromones. Phosphoesters form the backbone of DNA molecules. Nitrate esters, such as nitroglycerin, are known for their explosive properties, while polyesters are important plastics, with monomers linked by ester moieties. Esters usually have a sweet smell and are considered high-quality solvents for a broad array of plastics, plasticizers, resins, and lacquers. They are also one of the largest classes of synthetic lubricants on the commercial market.

Fatty acid carboxylic acid with a long aliphatic chain, which is either saturated or unsaturated

In chemistry, particularly in biochemistry, a fatty acid is a carboxylic acid with a long aliphatic chain, which is either saturated or unsaturated. Most naturally occurring fatty acids have an unbranched chain of an even number of carbon atoms, from 4 to 28. Fatty acids are usually not found in organisms, but instead as three main classes of esters: triglycerides, phospholipids, and cholesterol esters. In any of these forms, fatty acids are both important dietary sources of fuel for animals and they are important structural components for cells.

<i>Macadamia ternifolia</i> Australasian tree species

Macadamia ternifolia is a tree in the flowering plant family Proteaceae, native to Queensland in Australia, and is listed as vulnerable under the EPBC Act.

Contents

Chemical structure

Ethyl macadamiate is a mixture of the ethyl esters of the free fatty acids produced by the complete saponification of macadamia oil. The primary constituents of ethyl macadamiate are ethyl oleate and ethyl palmitoleate.

Saponification is a process that involves conversion of fat or oil into soap and alcohol by the action of heat in the presence of aqueous alkali (e.g. NaOH). Soaps are salts of fatty acids whereas fatty acids are saturated monocarboxylic acids that have long carbon chains (at least 10) e.g. CH3(CH2)14COOH.

Macadamia oil non-volatile oil expressed from the nut meat of the macadamia

Macadamia oil is the non-volatile oil collected from the nut meat of the macadamia tree, a native Australian nut. It is used in food as a frying or salad oil, and in cosmetic formulations as an emollient or fragrance fixative.

Ethyl oleate chemical compound

Ethyl oleate is a fatty acid ester formed by the condensation of oleic acid and ethanol. It is a colorless to light yellow liquid. Ethyl oleate is produced by the body during ethanol intoxication.

Physical properties

Ethyl macadamiate is a clear, colorless liquid at room temperature, with a typical fatty ester odor. Ethyl macadamiate's melting (congealing) point is 10 °C (50 °F) and its specific gravity is 0.88. Ethyl macadamiate spreads very aggressively, and has a light, nongreasy dry skinfeel similar to that of some silicone derivatives, however, ethyl macadamiate is non-volatile.

Room temperature

Colloquially, room temperature is the range of air temperatures that most people prefer for indoor settings, which feel comfortable when wearing typical indoor clothing. Human comfort can extend beyond this range depending on humidity, air circulation and other factors. In certain fields, like science and engineering, and within a particular context, room temperature can mean different agreed-on ranges. In contrast, ambient temperature is the actual temperature of the air in any particular place, as measured by a thermometer. It may be very different from usual room temperature, for example an unheated room in winter.

Specific gravity Relative density compared to water

Specific gravity is the ratio of the density of a substance to the density of a reference substance; equivalently, it is the ratio of the mass of a substance to the mass of a reference substance for the same given volume. Apparent specific gravity is the ratio of the weight of a volume of the substance to the weight of an equal volume of the reference substance. The reference substance for liquids is nearly always water at its densest ; for gases it is air at room temperature. Nonetheless, the temperature and pressure must be specified for both the sample and the reference. Pressure is nearly always 1 atm (101.325 kPa).

Silicone polymers that include any inert, synthetic compound made up of repeating units of siloxane, which is a chain of alternating silicon atoms and oxygen atoms, frequently combined with carbon and/or hydrogen

Silicones, also known as polysiloxanes, are polymers that include any synthetic compound made up of repeating units of siloxane, which is a chain of alternating silicon atoms and oxygen atoms, combined with carbon, hydrogen, and sometimes other elements. They are typically heat-resistant and either liquid or rubber-like, and are used in sealants, adhesives, lubricants, medicine, cooking utensils, and thermal and electrical insulation. Some common forms include silicone oil, silicone grease, silicone rubber, silicone resin, and silicone caulk.

Uses

Ethyl macadamiate is used in cosmetics, especially in skincare, haircare and suncare formulation. The dry skinfeel and high spread make ethyl macadamiate well suited for increasing sunscreen coverage. Ethyl macadamiate is an alternative to cyclomethicone and dimethicone as a skinfeel modifier where a botanical, nonvolatile and/or lipid-soluble substance is preferred.

Cosmetics substances used to enhance the appearance or odor of the human body

Cosmetics are substances or products used to enhance or alter the appearance of the face or fragrance and texture of the body. Many cosmetics are designed for use of applying to the face and body. They are generally mixtures of chemical compounds; some being derived from natural sources, and many synthetic or artificial. Cosmetics that are applied to the face to enhance ones appearance are often called make-up or makeup. Common make-up items include: lipstick, mascara, eye shadow, foundation, blush, and bronzer. Other common cosmetics include skin cleansers, body lotions, shampoo and conditioner, hairstyling products, perfume and cologne.

Related Research Articles

Wax class of chemical compounds that are plastic (malleable) near ambient temperatures.

Waxes are a diverse class of organic compounds that are lipophilic, malleable solids near ambient temperatures. They include higher alkanes and lipids, typically with melting points above about 40 °C (104 °F), melting to give low viscosity liquids. Waxes are insoluble in water but soluble in organic, nonpolar solvents. Natural waxes of different types are produced by plants and animals and occur in petroleum.

Drying oil oil that hardens to a tough, solid film after a period of exposure to air

A drying oil is an oil that hardens to a tough, solid film after a period of exposure to air. The oil hardens through a chemical reaction in which the components crosslink by the action of oxygen. Drying oils are a key component of oil paint and some varnishes. Some commonly used drying oils include linseed oil, tung oil, poppy seed oil, perilla oil, and walnut oil. Their use has declined over the past several decades, as they have been replaced by alkyd resins and other binders.

Valeric acid chemical compound

Valeric acid, or pentanoic acid, is a straight-chain alkyl carboxylic acid with the chemical formula CH
3(CH
2)
3COOH. Like other low-molecular-weight carboxylic acids, it has a very unpleasant odor. It is found naturally in the perennial flowering plant valerian, from which it gets its name. Its primary use is in the synthesis of its esters. Salts and esters of valeric acid are known as valerates or pentanoates. Volatile esters of valeric acid tend to have pleasant odors and are used in perfumes and cosmetics. Ethyl valerate and pentyl valerate are used as food additives because of their fruity flavors.

Mink oil is an oil used in medical and cosmetic products. It is obtained by the rendering of mink fat which has been removed from pelts destined for the fur industry.

Oleyl alcohol, octadecenol, or cis-9-octadecen-1-ol, is an unsaturated fatty alcohol with the molecular formula C18H36O or the condensed structural formula CH3(CH2)7-CH=CH-(CH2)8OH.

Omega-9 fatty acids are a family of unsaturated fatty acids which have in common a final carbon–carbon double bond in the omega−9 position; that is, the ninth bond from the methyl end of the fatty acid.

Jojoba esters are the hydrogenation or transesterification product of Jojoba oil. Jojoba Esters are commonly used in cosmetic formulations as an emollient, due to its remarkable similarity to the natural oils produced by the human skin, and its high oxidative stability. Fully hydrogenated jojoba esters are most often small beads used to exfoliate the skin.

Heptanoic acid, also called enanthic acid, is an organic compound composed of a seven-carbon chain terminating in a carboxylic acid. It is an oily liquid with an unpleasant, rancid odor. It contributes to the odor of some rancid oils. It is slightly soluble in water, but very soluble in ethanol and ether.

Acrylate polymers are a group of polymers noted for their transparency, resistance to breakage, and elasticity. They are also commonly known as acrylics or polyacrylates. Acrylate polymer is commonly used in cosmetics such as nail polish as an adhesive.

Hydrolyzed jojoba esters are the hydrolysate of jojoba esters derived by acid, enzyme or other method of hydrolysis. Hydrolyzed jojoba esters are commonly used in cosmetic formulations.

Ethylhexyl palmitate, or octyl palmitate, is the fatty acid ester derived from 2-ethylhexanol and palmitic acid. Ethylhexyl palmitate is commonly used in cosmetic formulations.

Orris oil oil obtained from the root of iris × germanica

Orris oil is an essential oil derived from irises, particularly Iris germanica. It is sometimes used as a flavoring agent and as an ingredient in perfume production. It can also have uses in body lotions.

Fatty acid ester class of chemical compounds

Fatty acid esters (FAEs) are a type of ester that result from the combination of a fatty acid with an alcohol. When the alcohol component is glycerol, the fatty acid esters produced can be monoglycerides, diglycerides, or triglycerides. Dietary fats are chemically triglycerides.

Omega-3 acid ethyl esters pharmaceutical product

Omega-3 acid ethyl esters are the omega-3 fatty acids eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) found in fish oil. Together with dietary changes, they are used to treat high blood triglycerides which may reduce the risk of pancreatitis. They are generally less preferred than statins and use is not recommended by NHS Scotland as the evidence does not support a decreased risk of heart disease. Omega-3 acid ethyl esters are taken by mouth.

Ethyl eicosapentaenoic acid chemical compound

Ethyl eicosapentaenoic acid is a derivative of the omega-3 fatty acid eicosapentaenoic acid (EPA) that is used in combination with changes in diet to lower triglyceride levels in adults with severe hypertriglyceridemia. This was the second class of fish oil-based drug to be approved for use as a drug and was approved by the FDA in 2012. These fish oil drugs are similar to fish oil dietary supplements but the ingredients are better controlled and have been tested in clinical trials.

Omega-7 fatty acids are a class of unsaturated fatty acids in which the site of unsaturation is seven carbon atoms from the end of the carbon chain. The two most common omega-7 fatty acids in nature are palmitoleic acid and vaccenic acid. They are widely used in cosmetics due to their moisturizing properties. Diets rich in omega-7 fatty acids have been shown to have beneficial health effects, such as increasing levels of HDL cholesterol and lowering levels of LDL cholesterol.

Sucrose esters class of chemical compounds

Sucrose esters or sucrose fatty acid esters are a group of surfactants chemically synthesized from esterification of sucrose and fatty acids. This group of substances is remarkable for the wide range of hydrophilic-lipophilic balance (HLB) that it covers. The polar sucrose moiety serves as a hydrophilic end of the molecule, while the long fatty acid chain serves as a lipophilic end of the molecule. Due to this amphipathic property, sucrose esters act as emulsifiers; i.e., they have the ability to bind both water and oil simultaneously. Depending on the HLB value, some can be used as water-in-oil emulsifiers, and some as oil-in-water emulsifiers. Sucrose esters are used in cosmetics, food preservatives, food additives, and other products. A class of sucrose esters with highly substituted hydroxyl groups, olestra, is also used as a fat replacer in food.

References

  1. 1 2 "Ethyl macadamiate". DrugBank.
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