Fat Solubility
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Lipophilicity (from
Greek Greek may refer to: Anything of, from, or related to Greece, a country in Southern Europe: *Greeks, an ethnic group *Greek language, a branch of the Indo-European language family **Proto-Greek language, the assumed last common ancestor of all kno ...
λίπος "fat" and φίλος "friendly") is the ability of a
chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...
to dissolve in
fat In nutrition science, nutrition, biology, and chemistry, fat usually means any ester of fatty acids, or a mixture of such chemical compound, compounds, most commonly those that occur in living beings or in food. The term often refers specif ...
s, oils,
lipid Lipids are a broad group of organic compounds which include fats, waxes, sterols, fat-soluble vitamins (such as vitamins A, D, E and K), monoglycerides, diglycerides, phospholipids, and others. The functions of lipids include storing ...
s, and
non-polar solvent A solvent (from the Latin language, Latin ''wikt:solvo#Latin, solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a Solution (chemistry), solution. A solvent is usually a liquid but can also be a solid, a gas ...
s such as
hexane Hexane () or ''n''-hexane is an organic compound, a straight-chain alkane with six carbon atoms and the molecular formula C6H14. Hexane is a colorless liquid, odorless when pure, and with a boiling point of approximately . It is widely used as ...
or
toluene Toluene (), also known as toluol (), is a substituted aromatic hydrocarbon with the chemical formula , often abbreviated as , where Ph stands for the phenyl group. It is a colorless, water Water is an inorganic compound with the c ...
. Such compounds are called lipophilic (translated as "fat-loving" or "fat-liking"). Such non-polar solvents are themselves lipophilic, and the adage "like dissolves like" generally holds true. Thus lipophilic substances tend to dissolve in other lipophilic substances, whereas
hydrophilic A hydrophile is a molecule or other molecular entity that is attracted to water molecules and tends to be dissolved by water.Liddell, H.G. & Scott, R. (1940). ''A Greek-English Lexicon'' Oxford: Clarendon Press. In contrast, hydrophobes are n ...
("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 London dispersion forces (LDF, also known as dispersion forces, London forces, instantaneous dipole–induced dipole forces, fluctuating induced dipole bonds or loosely as van der Waals forces) are a type of intermolecular force acting between at ...
, as the terms are often used interchangeably. However, the terms "lipophilic" and "
hydrophobic In chemistry, hydrophobicity is the chemical property of a molecule (called a hydrophobe) that is seemingly repelled from a mass of water. In contrast, hydrophiles are attracted to water. Hydrophobic molecules tend to be nonpolar and, thu ...
" are not synonymous, as can be seen with
silicone In Organosilicon chemistry, organosilicon and polymer chemistry, a silicone or polysiloxane is a polymer composed of repeating units of siloxane (, where R = Organyl group, organic group). They are typically colorless oils or elastomer, rubber ...
s and
fluorocarbons Fluorocarbons are chemical compounds with carbon-fluorine bonds. Compounds that contain many C-F bonds often have distinctive properties, e.g., enhanced stability, volatility, and hydrophobicity. Several fluorocarbons and their derivatives are ...
, which are hydrophobic but not lipophilic. __TOC__


Surfactants

Hydrocarbon In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and Hydrophobe, hydrophobic; their odor is usually fain ...
-based
surfactants Surfactants are chemical compounds that decrease the surface tension or interfacial tension between two liquids, a liquid and a gas, or a liquid and a solid. The word ''surfactant'' is a blend of "surface-active agent", coined in 1950. As t ...
are compounds that are
amphiphilic In chemistry, an amphiphile (), or amphipath, is a chemical compound possessing both hydrophilic (''water-loving'', polar) and lipophilic (''fat-loving'', nonpolar) properties. Such a compound is called amphiphilic or amphipathic. Amphiphilic c ...
(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 (physics), tension is what allows objects with a higher density than water such as razor blades and insects (e.g. Ge ...
) 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 Phospholipids are a class of lipids whose molecule has a hydrophilic "head" containing a phosphate group and two hydrophobic "tails" derived from fatty acids, joined by an alcohol residue (usually a glycerol molecule). Marine phospholipids typi ...
, molecules which have a highly water interactive, ionic
phosphate Phosphates are the naturally occurring form of the element phosphorus. In chemistry, a phosphate is an anion, salt, functional group or ester derived from a phosphoric acid. It most commonly means orthophosphate, a derivative of orthop ...
head groups attached to two long alkyl tails. By contrast,
fluorosurfactant Per- and polyfluoroalkyl substances (also PFAS, PFASs, and informally referred to as "forever chemicals") are a group of synthetic Organofluorine chemistry, organofluorine chemical compounds that have multiple fluorine atoms attached to an alkyl ...
s are not amphiphilic or detergents because fluorocarbons are not lipophilic.
Oxybenzone Oxybenzone or benzophenone-3 or BP-3 (trade names Milestab 9, Eusolex 4360, Escalol 567, KAHSCREEN BZ-3) is an organic compound belonging to the class of aromatic ketones known as benzophenones. It takes the form of pale-yellow crystals that are ...
, a common cosmetic ingredient often used in sunscreens, penetrates the skin particularly well 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.


See also

*
Ionic partition diagram Similar to Pourbaix diagrams for the speciation of redox species as a function of the redox potential and the pH, ionic partition diagrams indicate in which phase an acid or a base is predominantly present in a biphasic system as a function of ...
*
ITIES In electrochemistry, ITIES (interface between two immiscible electrolyte solutions) is an electrochemical interface that is either polarisable or polarised. An ITIES is polarisable if one can change the Galvani potential difference, or in other wo ...
*
Lipophilic bacteria Lipophilic bacteria (''fat-loving bacteria'') are bacteria that may proliferate in lipids. Types They include lipophilic corynebacteria. ''Cutibacterium acnes'' is a type of lipophilic bacteria, releasing fatty acids and worsening comedones in acn ...
*
Lipophobicity Lipophobicity, also sometimes called lipophobia (from the Greek λιποφοβία from λίπος ''lipos'' "fat" and φόβος ''phobos'' "fear"), is a chemical property of chemical compounds which means " fat rejection", literally "fear of fa ...
* Microemulsion


References

{{Chemical solutions Chemical properties