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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
One major factor in the manufacture of esters is the cost of the respective fatty acids versus fatty alcohols. In most cases we find that the lauric, myristic, palmitic, and stearic fatty acids are significantly cheaper than their counterpart alcohols. This is because the fatty alcohols are usually produced by the reduction of the acid group to an alcohol. Therefore, it is generally less expensive to produce an ester from a low-molecular-weight alcohol and a fatty acid than from a higher-molecular-weight fatty alcohol and a small acid.
Oils
Published in Heather A.E. Benson, Michael S. Roberts, Vânia Rodrigues Leite-Silva, Kenneth A. Walters, Cosmetic Formulation, 2019
Fabricio Almeida de Sousa, Vânia Rodrigues Leite-Silva
Fatty alcohols are oleochemicals derived from vegetable oils. These refined vegetable oils are first converted to a methyl ester or fatty acid, and the intermediate (methyl ester/fatty acid) then fractionated and hydrogenated to produce the fatty alcohol. In general, alcohols used in formulation are normal alcohols from natural fats and oils, having an even number of carbon atoms, and can be saturated or unsaturated.
Chemical Modulation of Topical and Transdermal Permeation
Published in Marc B. Brown, Adrian C. Williams, The Art and Science of Dermal Formulation Development, 2019
Marc B. Brown, Adrian C. Williams
Fatty alcohols (also termed “alkanols”) are typically applied in a co-solvent (for example, propylene glycol), at between 1 and 10%. As with the fatty acids (Section 3.2.2.5), some structure/activity relationships for fatty alcohol penetration enhancement have shown lower activities for branched alkanols compared to linear molecules. For saturated fatty alcohols, efficacy tends to increase up to ~C10 and then falls as chain length increases further. As with the fatty acids, enhancement efficacy generally increases with the inclusion of up to two unsaturated bonds into the alcohols, again likely due to the formation of free volume within the intercellular lipid bilayers as the fatty alcohol intercalates into their structure. Oleyl alcohol (cis-9-octadecen-1-ol) is an unsaturated fatty alcohol that functions as a non-ionic surfactant and which has been widely used as a chemical penetration enhancer.
Synthesis and anticancer properties of celastrol derivatives involved in the inhibition of VEGF
Published in Journal of Enzyme Inhibition and Medicinal Chemistry, 2023
Mingxia Song, Jiantao Wen, Yi Hua, Yangnv Zhu, Qishan Xia, Qiaoyue Guo, Yiqin Luo, Xianqing Deng, Yushan Huang
Based on these in vitro antiproliferative results, significant patterns of structure-activity relationships were not established. But some trends are still visible. Compounds 1–7 were substituted by fatty alcohols of different carbon chain lengths. The carbon chain length seems to affect the antiproliferative effect with two or three carbon as the optimum. When the hydroxyl group of compound 2 was replaced by bromine, it provided compound 8, which exhibited a weaker antiproliferative effect than celastrol. When the hydroxyl group of compounds 2 or 3 was replaced by a hydrophobic ester, methoxy, or phenoxy group, it provided the compounds 9, 10, and 11, respectively. The antiproliferative effects were also reduced when compared to compounds 2 or 3. The hydrophobicity and steric size were the possible influencing factors when defining compound 11 as the weakest one among them. Compounds 12–14 were designed to obtain derivatives with better anticancer activity due to the indole always improving the activity of the natural product. However, it doesn’t work in this study. Compounds 12, 13, and 14 exhibited activities similar to that of celastrol.
Bortezomib-loaded lipidic-nano drug delivery systems; formulation, therapeutic efficacy, and pharmacokinetics
Published in Journal of Microencapsulation, 2021
Mohammad Mahmoudian, Hadi Valizadeh, Raimar Löbenberg, Parvin Zakeri-Milani
The lipid matrix of these NPs is biocompatible and degradable, which is solid at room temperature and at body temperature. Various types of lipids are used to fabricate SLNs including (Manjunath et al. 2005, Doktorovova et al.2017):Triglycerides; glyceryl tristearate (Tristearin), glyceryl tripalmitate (Tripalmitin), glyceryl trilaurate (Trilaurin), glyceryl trimirystate (Trimyristin), etc.Waxes; cetyl palmitate, beeswax, etc.Partial glycerides; glyceryl monostearate, glyceryl monooleate, glyceryl palmitostearate, etc.Fatty alcohols; cetyl Alcohol, stearyl alcohol, etc.Fatty acids; palmitic acid, stearic acid, stearic acid, etc.
Sjögren-Larsson syndrome: a complex metabolic disease with a distinctive ocular phenotype
Published in Ophthalmic Genetics, 2019
Samiksha Fouzdar-Jain, Donny W Suh, William B Rizzo
In addition to aldehydes, fatty alcohols may also be implicated in the retinal phenotype. Long-chain alcohols (C16–C18) that cannot be oxidized to fatty acids in SLS accumulate in various cells and tissues, such as cultured fibroblasts, keratinocytes and plasma (95,96), and it is likely that they also accumulate in the SLS retina. Long-chain alcohols have a high partition coefficient for lipid bilayers where they can perturb the membrane lipid order (97,98). They can exist as free alcohols or be diverted into biosynthetic pathways resulting in accumulation of certain cell-specific lipids such as, for example, wax esters and alkyl-diacylglycerol as seen in cultured keratinocytes (96). In the skin of patients with SLS, ultrastructural evidence of lipid accumulation in the stratum corneum membranes is associated with a leaky epidermal water barrier and development of ichthyosis (11). If fatty alcohols or their lipid products also accumulate in the retina, they may disrupt membrane turnover or cellular functions, or contribute to the crystalline inclusions (Figure 5).