WordNet

having an affinity for lipids (同)lipotropic
soluble in fats; "fat-soluble vitamin A"
(botany) either of the two parts of a bilabiate corolla or calyx
either the outer margin or the inner margin of the aperture of a gastropods shell
either of two fleshy folds of tissue that surround the mouth and play a role in speaking
the quantity of a particular substance that can dissolve in a particular solvent (yielding a saturated solution)
the quality of being soluble and easily dissolved in liquid
an oily organic compound insoluble in water but soluble in organic solvents; essential structural component of living cells (along with proteins and carbohydrates) (同)lipide, lipoid

PrepTutorEJDIC

〈C〉『くちびる』,口もと / 《複数形で》(発音器官としての)くちびる,口 / 〈U〉《俗》生意気な言葉 / 〈C〉(容器などの)口,へり,縁;(峡谷・火山などの)口 / 〈C〉(植物の)唇弁(しんべん)
溶解性;溶解度
脂質,あぶら

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/03/17 23:25:47」(JST)

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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 solvents such as hexane or toluene. These non-polar solvents are themselves lipophilic (translated as "fat-loving" or "fat-liking"^[1]^[2]) — the axiom that like dissolves like generally holds true. Thus lipophilic substances tend to dissolve in other lipophilic substances, while hydrophilic (water-loving) substances tend to dissolve in water and other hydrophilic substances.

Lipophilicity, hydrophobicity, and non-polarity can 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 silicones and fluorocarbons, which are hydrophobic but not lipophilic.

Chemical bonding[edit]

Lipophilic substances interact within themselves and with other substances through the London dispersion force. They have little to no capacity to form hydrogen bonds. When a molecule of a lipophilic substance is enveloped by water, surrounding water molecules enter into an 'ice-like' structure over the greater part of its molecular surface, the thermodynamically unfavourable event that drives oily substances out of water. Being 'driven out of water' is the quality of a substance referred to as hydrophobic (water-avoiding or water-fearing). Thus lipophilic substances tend to be water insoluble. They invariably have large o/w (octanol/water) partition coefficients.

Surfactants[edit]

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) and the surfaces of the water-immiscible droplets found in o/w emulsions (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.

References[edit]

^ Compendium of Chemical Terminology, lipophilic, accessed 15 Jan 2007.
^ Alyn William Johnson (1999). Invitation to Organic Chemistry. Jones & Bartlett Learning. p. 283. ISBN 978-0-7637-0432-2.

UpToDate Contents

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English Journal

Influence of particle size on lipid digestion and β-carotene bioaccessibility in emulsions and nanoemulsions.

Salvia-Trujillo L, Qian C, Martín-Belloso O, McClements DJ.SourceDepartment of Food Technology, University of Lleida, Lleida 25198, Spain.
Food chemistry.Food Chem.2013 Nov 15;141(2):1472-80. doi: 10.1016/j.foodchem.2013.03.050. Epub 2013 Mar 23.
The interest in incorporating carotenoids, such as β-carotene, into foods and beverages is growing due to their potential health benefits. However, the poor water-solubility and low bioavailability of carotenoids is currently a challenge to their incorporation into many foods. The aim of this work
PMID 23790941

Active drug encapsulation and release kinetics from hydrogel-in-liposome nanoparticles.

Wang Y, Tu S, Pinchuk AN, Xiong MP.SourcePharmaceutical Sciences Division, School of Pharmacy, University of Wisconsin-Madison, 777 Highland Avenue, Madison, WI 53705-2222, USA.
Journal of colloid and interface science.J Colloid Interface Sci.2013 Sep 15;406:247-55. doi: 10.1016/j.jcis.2013.05.081. Epub 2013 Jun 13.
Herein, we demonstrate for the first time the use of hydrogel-in-liposome nanoparticles (lipogels) as a promising drug delivery vehicle for the active encapsulation of the anticancer drug 17-DMAPG, a geldanamycin (GA) derivative. This model drug was chosen due to its improved aqueous solubility (4.6
PMID 23809875

Biorelevant solubility of poorly soluble drugs: Rivaroxaban, furosemide, papaverine and niflumic acid.

Takács-Novák K, Szőke V, Völgyi G, Horváth P, Ambrus R, Szabó-Révész P.SourceDepartment of Pharmaceutical Chemistry, Semmelweis University, H-1092 Hőgyes Endre street 9, Budapest, Hungary. Electronic address: novak.krisztina@pharma.semmelweis-univ.hu.
Journal of pharmaceutical and biomedical analysis.J Pharm Biomed Anal.2013 Sep;83:279-85. doi: 10.1016/j.jpba.2013.05.011. Epub 2013 May 18.
In this work the biorelevant solubility of four drugs representing different acid-base property, wide range of lipohilicity and low aqueous solubility was studied. The equilibrium solubility of rivaroxaban (non-ionizable), furosemide (acid), papaverine (base) and niflumic acid (ampholyte) was determ
PMID 23770783

Japanese Journal

Formulation and in Vitro Characterization of a Novel Solid Lipid-Based Drug Delivery System

Ma Hongxing,Chu Mingjuan,Itagaki Kiyoshi,Xin Ping,Zhou Xuegang,Zhang Dawei,Wang Youzhi,Fu Jia,Sun Shiqin
Chemical and Pharmaceutical Bulletin 62(12), 1173-1179, 2014
… Thus the main purpose of our study was to develop a promising solid lipid-based drug delivery system (S-SEDDS) for OA. … Finally, the solubility of the OA-loaded S-SEDDS was compared with that of OA powder in the dissolution assay. …
NAID 130004712911

Aqueous Gel Formation from Sodium Salts of Cellobiose Lipids

Imura Tomohiro,Yamamoto Shuhei,Yamashita Chikako,Taira Toshiaki,Minamikawa Hiroyuki,Morita Tomotake,Kitamoto Dai
Journal of Oleo Science 63(10), 1005-1010, 2014
… In this study, the sodium salts of CLs (CLNa) were prepared to improve aqueous solubility of the CLs, and their surface and gelation properties in aqueous solutions were examined by surface tension, rheology, and freeze-fracture transmission electron microscopy (FF-TEM) measurements. …
NAID 130004690908

Development of Highly Stable Nifedipine Solid–Lipid Nanoparticles

Barman Ranjan Kumar,Iwao Yasunori,Funakoshi Yuka,Ranneh Abdul-Hackam,Noguchi Shuji,Wahed Mir Imam Ibne,Itai Shigeru
Chemical and Pharmaceutical Bulletin 62(5), 399-406, 2014
… To improve the solubility of the drug nifedipine (NI), highly stabilized solid–lipid nanoparticles (SLNs) of nifedipine (NI-SLNs) were prepared by high pressure homogenization using two phospholipids, followed by lyophilization with individual sugar moieties (four monosaccharides and four disaccharides). …
NAID 130004053796