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Emollient Esters and Oils
Published in Randy Schueller, Perry Romanowski, Conditioning Agents for Hair and Skin, 2020
John Carson, Kevin F. Gallagher
Ethyl esters are also well known compounds, but again, not as cosmetic ingredients. Ethyl oleate is used as a topical pharmaceutical agent, to enhance the skin penetration of lipophilic active ingredients. A pharmaceutical monograph exists describing the use of ethyl oleate for this purpose. Perhaps the enhanced skin penetration conferred by the unsaturated oleate is the reason the isopropyl esters of unsaturated acids (i.e., isopropyl linoleate) perform poorly in Goldemberg's subjective feel tests. They may penetrate into the skin and not remain at or near the surface to produce a subjective effect.
Materials for Nanoemulsions and Their Influence on the Biofate
Published in Vladimir Torchilin, Handbook of Materials for Nanomedicine, 2020
The oil phase is an important constituent in nanoemulsion formulation, and until now the oils that have been utilized in this phase are numerous: soybean (Chen et al., 2018a), safflower (Musa et al., 2013), cottonseed (Fofaria et al., 2016), castor (Araújo et al., 2011; Katzer et al., 2014), sesame (Sandhu et al., 2015), coconut, peanut (Morsia et al., 2017; palm kernel (Tanaka et al., 2017), flaxseed (Deshpande, 2014; Ganta et al., 2014), corn oil (Liu et al., 2015), olive oil (Sala-Vila et al., 2007), linseed (Sugasini and Lokesh, 2017), fish oil (Zhong et al., 2018), etc. Most of these oils are the re-esterified fractions of vegetable oils and depending upon their chain length are categorized as LCT (C13-C24), MCT (C6-C12). The trend of using MCT, a mixture of MCT:LCT and an addition of olive oil, fish oil instead of LCT alone is well described in the nutrient section of this chapter and in the previous edition of this chapter (Rozentur et al., 2010). In addition, MCTs are re-esterified with glycerol and are moderately more soluble in water than LCTs. In addition to oils from vegetable sources, fatty acids/alcohols (e.g., oleic acid, linoleic acid, myristic acid, lauryl, capryl alcohol, etc.) and glycerides/fatty acid esters (e.g., caprylic acid, triacetin, ethyl oleate, isopropyl myristate) are also reported in the literature (Akhtar et al., 2016; Carbonea et al., 2015; Li et al., 2014; Ammar et al., 2010; Yen et al., 2018; Nazari-Vanani et al., 2017; Tayel et al., 2013; Zao et al., 2013; Shen et al., 2011). The selection of oils for parenteral nanoemulsions is based on the oil’s level of nutrition and plasma clearance, while in drug delivery, as a rule of thumb, it is based on the oil’s ability to dissolve the active molecules. These indications along with their GRAS status by the FDA will gain attention for commercial use (Tables 9.1 and 9.2). Moreover, LCTs always require to be digested prior to absorption in order to convert them into mono- or di- glycerides. Therefore, mixed glycerides are often the choice of oil in drug delivery (firstly, to increase the solubility of poorly soluble drugs and secondly mixed glycerides are similar to lipid digestion products and thus are easily absorbed) (Salva et al., 2017; Ako-Adounvo et al., 2014). Accordingly, all ophthalmic nanoemulsions currently available on the market are composed of castor oil (Kompella et al., 2010; Salva et al., 2017), whereas parenteral nanoemulsions are mostly of intralipid composition (Table 9.2). Out of 36 FDA-approved lipid-based products for oral delivery, 8 were devoid of oils, and only later the incorporation of oils (LCT, MCT) and mixed glycerides became popular (Salva et al., 2017). Although all oils are well suited for skin delivery, only a handful of commercial formulations are available as shown in Table 9.2 (Pawar and Babu, 2014).
Cecropia pachystachya Trécul: identification, isolation of secondary metabolites, in silico study of toxicological evaluation and interaction with the enzymes 5-LOX and α-1-antitrypsin
Published in Journal of Toxicology and Environmental Health, Part A, 2022
Penina Sousa Mourão, Rafael de Oliveira Gomes, Clara Andrezza Crisóstomo Bezerra Costa, Orlando Francisco da Silva Moura, Herbert Gonzaga Sousa, George Roberto Lemos Martins Júnior, Danniel Cabral Leão Ferreira, Antônio Luiz Martins Maia Filho, Johnnatan Duarte de Freitas, Mahendra Rai, Francisco Das Chagas Alves Lima, Antonio Euzébio Gourlart Santana, Mariana Helena Chaves, Wellington Dos Santos Alves, Valdiléia Teixeira Uchôa
Ethyl 9-octadecenoate and ethyl octadecanoate were also identified in crude extracts (hexane, MeOH and MeOH:H2O) of the leaves of Lecythis pisonis Cambessedes, known as “sapucaia” or “cumbuca-de-macaco” (Barreto et al. 2020), and ethyl 9-octadecenoate in the acetone, chloroform and methanol extracts of Indoneesiella echioides (L) Nees (Elaiyaraja and Chandramohan 2016). The ethyl 9-octadecenoate, also termed ethyl oleate and ethyl (Z)-octadec-9-enoate, is widely used in commerce as a plasticizer, lubricant, biological additive, hydraulic fluid (Neta et al. 2012), as vehicles for progesterone administration (Elaiyaraja and Chandramohan 2016) and in cooking as an emulsifier, and may be isolated through the esterification reaction of oleic acid with ethanol using a triacylglycerol lipase isolated from the enzyme Candida antarctica B (Neta et al. 2012). Ethyl octadeca-9,12-dienoate and ethyl 9-octadecenoate possess antimicrobial activity (Adeoye-Isijola et al. 2018). Evidence thus indicated that these compounds were previously characterized in other plant extracts with the exception of ethyl octadecanoate in which no study of biological activity in vivo and/or in vitro was reported.