Lipophilicity (from Greek λίπος "fat" and φίλος "friendly"), refers to the ability of a chemical compound to dissolve in fats, oils, lipids, and

non-polar 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 p ...

s such as hexane or toluene. Such non-polar solvents are themselves lipophilic (translated as "fat-loving" or "fat-liking"), and the axiom that "like dissolves like" generally holds true. Thus lipophilic substances tend to dissolve in other lipophilic substances, but hydrophilic ("water-loving") substances tend to dissolve in water and other hydrophilic substances. Lipophilicity, hydrophobicity, and non-polarity may describe the same tendency towards participation in the London dispersion force, as the terms are often used interchangeably. However, the terms "lipophilic" and " hydrophobic" are not synonymous, as can be seen with

silicone A silicone or polysiloxane is a polymer made up of siloxane (−R2Si−O−SiR2−, where R = organic group). They are typically colorless oils or rubber-like substances. Silicones are used in sealants, adhesives, lubricants, medicine, cooking ...

s and fluorocarbons, which are hydrophobic but not lipophilic. __TOC__

Surfactants

Hydrocarbon-based surfactants are compounds that are amphiphilic (or amphipathic), having a hydrophilic, water interactive "end", referred to as their "head group", and a lipophilic "end", usually a long chain hydrocarbon fragment, referred to as their "tail". They congregate at low energy surfaces, including the air-water interface (lowering

surface tension Surface tension is the tendency of liquid surfaces at rest to shrink into the minimum surface area possible. Surface tension is what allows objects with a higher density than water such as razor blades and insects (e.g. water striders) to f ...

) and the surfaces of the water-immiscible droplets found in oil/water

emulsions An emulsion is a mixture of two or more liquids that are normally immiscible (unmixable or unblendable) owing to liquid-liquid phase separation. Emulsions are part of a more general class of two-phase systems of matter called colloids. Althoug ...

(lowering interfacial tension). At these surfaces they naturally orient themselves with their head groups in water and their tails either sticking up and largely out of water (as at the air-water interface) or dissolved in the water-immiscible phase that the water is in contact with (e.g. as the emulsified oil droplet). In both these configurations the head groups strongly interact with water while the tails avoid all contact with water. Surfactant molecules also aggregate in water as micelles with their head groups sticking out and their tails bunched together. Micelles draw oily substances into their hydrophobic cores, explaining the basic action of soaps and detergents used for personal cleanliness and for laundering clothes. Micelles are also biologically important for the transport of fatty substances in the small intestine surface in the first step that leads to the absorption of the components of fats (largely fatty acids and 2-monoglycerides). Cell membranes are bilayer structures principally formed from phospholipids, molecules which have a highly water interactive, ionic phosphate head groups attached to two long alkyl tails. By contrast, fluorosurfactants are not amphiphilic or detergents because fluorocarbons are not lipophilic. Oxybenzone, a common cosmetic ingredient often used in sunscreens, is particularly penetrative because it is not very lipophilic. Anywhere from 0.4% to 8.7% of oxybenzone can be absorbed after one topical sunscreen application, as measured in urine excretions.H. Gonzalez, H., Farbrot, A., Larko. O., and Wennberg, A. M. (2006), Percutaneous absorption of the sunscreen benzophenone-3 after repeated whole-body applications, with and without ultraviolet irradiation. British Journal of Dermatology, 154:337-340.

References

{{Chemical solutions Chemical properties

Surfactants

See also

References