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Concept
Amphiphile
Summary
An amphiphile (from the Greek αμφις amphis, both, and φιλíα philia, love, friendship), or amphipath, is a chemical compound possessing both hydrophilic (water-loving, polar) and lipophilic (fat-loving) properties. Such a compound is called amphiphilic or amphipathic. Amphiphilic compounds include surfactants (these detergents are commonly called "soap" but are different from traditional soap in both composition and method of action for cleaning). The phospholipid amphiphiles are the major structural component of cell membranes.
Amphiphiles are the basis for a number of areas of research in chemistry and biochemistry, notably that of lipid polymorphism.
Organic compounds containing hydrophilic groups at both ends of the molecule are called bolaamphiphilic. The micelles they form in the aggregate are prolate.
The lipophilic group is typically a large hydrocarbon moiety, such as a long chain of the form CH3(CH2)n, with n > 4.
The hydrophilic group falls into one of the following categories:
charged groups
anionic. Examples, with the lipophilic part of the molecule represented by R, are:
carboxylates: RCO2−
sulfates: RSO4−
sulfonates: RSO3−
phosphates (the charged functional group in phospholipids)
cationic. Examples:
ammoniums: RNH3+
polar, uncharged groups. Examples are alcohols with large R groups, such as diacyl glycerol (DAG), and oligo ethylene glycol with long alkyl chains.
Often, amphiphilic species have several lipophilic parts, several hydrophilic parts, or several of both. Proteins and some block copolymers are such examples.
Amphiphilic compounds have lipophilic (typically hydrocarbon) structures and hydrophilic polar functional groups (either ionic or uncharged).
As a result of having both lipophilic and hydrophilic portions, some amphiphilic compounds may dissolve in water and to some extent in non-polar organic solvents.
When placed in an immiscible biphasic system consisting of aqueous and organic solvents, the amphiphilic compound will partition the two phases.
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