Amphiphilic Silicones to Extract Botanical Actives

Oct 1, 2010 | Contact Author | By: Anthony J. O'Lenick, Jr., Siltech LLC, and Kevin O'Lenick, SurfaTech Corp.
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Title: Amphiphilic Silicones to Extract Botanical Actives
extractionx menstruumx siliconex group oppositesx partition coefficientx
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Keywords: extraction | menstruum | silicone | group opposites | partition coefficient

Abstract: Silicone-based compounds enable chemists to extract the desired fractions of materials from plants as well as impart cosmetic aesthetics. Here the authors discuss how to extract actives using amphiphilic silicones that have different partition coefficients, which are obtained by altering the ratio of oil-, water- and fluoro-soluble groups on the silicone molecule.

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AJ O'Lenick, Jr., and K O'Lenick, Amphiphilic silicones to extract botanical actives, Cosm & Toil 125(10) 42-47 (Oct 2010)

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Liquid-liquid extraction, also known as solvent extraction or partitioning, is a method used to separate compounds based on their relative partitioning in two different immiscible liquids. It is the extraction of a substance from one liquid phase into another liquid phase; in other words, it is the separation of a substance from a mixture by preferentially dissolving that substance in a suitable solvent. By this process, a soluble compound is separated from an insoluble matrix.

The present article deals with the ability to extract actives from botanical compounds or other mixtures in amphiphilic silicone compounds having different partition coefficients, which are obtained by altering the ratio of oil-soluble, water-soluble and fluoro-soluble groups on the silicone molecule. The ratio of the various groups determines the ability of the molecule to partition in different phases as well as what will be extracted into each phase.

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Table 1. Group opposites

Table 1. Group opposites

Silicone oil is neither oil-soluble nor water-soluble. Silicone oil is in fact hydrophobic (water-hating) and oleophobic (oil-hating); however, defining a phase by its incompatibilities is not technically appealing—silicone oil is thus siliphilic or silicone-loving.

Table 2. Mutually insoluble groups

Table 2. Mutually insoluble groups

There are four types of groups that are mutually insoluble.

Figure 1. Glucoraphanin structure

Figure 1. Glucoraphanin structure

One constituent in broccoli sprouts of particular interest is sulforaphane, a break down product of glucosinolate glucoraphanin.

Figure 2. Dried and crushed broccoli extracted using each menstruum material

Figure 2. Dried and crushed broccoli extracted using each menstruum material

Dried and crushed broccoli was extracted using each menstruum material: a) Oil-soluble silicone, cetyl dimethicone; b) water-soluble silicone, PEG- 8 dimethicone; c) silicone-soluble, dimethyl fluid; and d) fluoro-soluble silicone perfluorononyl ethyl dimethicone.

Expression of Partition Coefficients

 In biochemical applications, partition coefficients are often expressed in terms of an octanol/water coefficient or Ko/w—i.e., the ratio at equilibrium of the concentration of a nonionized organic compound in an organic solvent (e.g., octanol) versus the concentration of the compound in water. Ko/w has been correlated with oleophilicity, the affinity of a compound to an oleophilic environment; compounds having a Ko/w value > 1 are oleophilic while those < 1 are hydrophilic. Ko/w thus provides an important predictive measure of the ability of a compound to pass through the skin’s acid mantle and permeate the oleophilic membranes of cells in the epidermis and dermis.

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