Recent applications of phospholipids are summarized. Except for lecithin, the only phospholipid that is manufactured is phosphatidylcholine (a variety of glycerophospholipid).
During past ten years, phospholipid has been studied on (1) Physiological activity of phospholipids (2) Raw material for producing liposomes (3) Complexes of phospholipids and other materials and (4) Chemical modification by phospholipids. Many new products applied phospholipids have been developed.
Phospholipids are new raw materials. Phospholipid applications will be made more progress on practical use as components of physiological membranes, elements of complex formation and substances for chemical modification.

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The effect of length of hydrophobic chains of a glycolipid catalyst was studied on hydrolyses of amino acid esters from those having hydrophilic to those having hydrophobic natures. The glycolipid was allowed to interact with phosphatidyl cholin, added as reaction field, to exhibit increased or decreased hydrolyzing activities, depending on the chain length of the glycolipid. The glycolipid was found to show different, ability to recognize substrates in accordance with the chain length, also. The influence of surrounding lipids on an enzymatic model catalyst will be discussed.

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Electrolysis of aliphatic, aromatic, and α, β-unsaturated methyl ketones in an anhydrous alcohol containing sodium or lithium bromide using an undivided cell equipped with carbon rods as the anode and the cathode brought about electrochemical Haloform reaction to give the corresponding carboxylates in good to excellent yields. The reaction was found to be mediated with bromonium ion, generated by anodic oxidation of bromide ion. Absence of bromoform in the product mixtures of this reaction may be attributed to ready reduction of bromoform to highly volatile compounds, which may provide high simplicity of reaction procedure.
Facile and efficient introduction of carboalkoxyl groups to aromatic rings and olefinic bonds was accomplished in two steps through initial Friedel-Crafts acetylation followed by the present electrochemical method.

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A method was developed for measurement of free ricinoleic acid and 12-hydroxystearic acid in castor oil and hydrogenated castor oil by LC/MS. The interface employed was atmospheric pressure chemical ionization (APCI), which showed a high sensitivity for the fatty acids through Selected Ion Monitoring (SIM) of their respective quasi-molecular ions, m/z 297 and 299. The detection limit was ing, with S/N ratio of 23. In the range of 4100ng linear relationships were observed between peak area and the injected amount of each hydroxy fatty acid with correlation coefficients of 0.999 or above. The method showed a satisfactory reproducibility with a coefficient variation of 6.6% or less, and a recovery rate of 89.7104.2% for the added standards. Results coincided well with amounts calculated from acid value. The minor free fatty acids, linoleic acid and oleic acid were also detected in castor oil. The method developed proved simple, fast and excellently suited to measurement of trace amounts of free fatty acids in the presence of glycerides consisting of the same acids.

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New fluoroalkylated oligomers with carbon-carbon bonds and containing trimethylammonium units were prepared under very mild conditions by reactions of fluoroalkanoyl peroxides as key materials with 2-acryloxyethyltrimethylammonium chloride. The oligomers were soluble in water, methanol, ethanol and dimethyl sulfoxide. Fluoroalkanoyl peroxides were also used to prepare fluoroalkylated co-oligomers containing trimethylammonium units by co-oligomerization with co-monomers such as trimethylvinylsilane, methyl methacrylate, ethyl methacrylate and butyl methacrylate. The co-oilgomers were soluble, as well, in not only polar solvents such as water, methanol and ethanol but non-polar aromatic solvents, such as benzene and toluene. Fluoroalkylated oligomers containing trimethylammonium units could reduce the surface tension of water to 10 mN/m, and were applicable to new cationic oligosurfactants as well as the usual low molecular fluorinated surfactants, even though they were high molecular fluoroalkylated compounds. The fluorinated oligomers were inactive toward HIV-1 (human immunodeficiency virus type 1) replication in MT-4 cells. However, they possessed antibacterial activity toward Staphylococcus aureus.

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Novel anionic surfactants containing azobenzene unit with fluorocarbon chain at the end of hydrophobic moiety have been synthesized. The compounds, 4-perfluoroalkylanilines, were prepared by the reaction of perfluoroalkyl iodides and aniline in the presence of copper bronze. Hydroxyazobenzene derivatives having fluorocarbon chain were obtained through the diazotization and followed by the azo-coupling reactions with phenol. In order to obtain a stable sulfate-type anionic surfactant, the intermediate, 2- [4- [4- (perfluoroalkyl) phenylazo] phenoxy] bromoethane, was derived to introduce a spacer chain by use of 1, 2-dibromoethane. Finally, four amphiphiles were synthesized by the reaction of sodium sulfate with the bromide derivatives. These products were characterized by 1H-NMR, IR, and Mass spectra.

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Aqueous solutions of several transition metal salts were solubilized in AOT reversed micelles in octane. They were shown to promote the hydrolysis of oil-soluble alanine decyl ester. When copper (II) acetate was used, the initial reaction rate was dependent not only on the initial substrate concentration but on the metal concentration as well. High concentrations of the metal salt and substrate resulted in large initial rates. However, the reactions were decelerated when conversion was twice the ratio of metal salt to initial substrate content. Similar behavior of the reaction rate was observed for other metal salts. The reaction mechanism is discussed in terms of the formation of several intermediate complexes and their relative stabilities.

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It is found that isomerization of glyceryl monopentadecanoate occures in ethanol without catalyst. The isomerization has been assessed by using various semi-empirical orbital calculations (i.e., CNDO/2, INDO, MINDO/3, MNDO, AM1 and PM3). Among these calculation methods, those based on the Neglect of Diatomic Differential Overlap (NDDO) approximations have been compared with the experimental results. As a result, the calculated values of the equilibrium composition of 1-monoglyceride and 2-monoglyceride by PM3 are in good agreement with the experimental values in the ethanol solutions.

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A considerable amount of a new monophosphate, magnesium 1, 2-epithioglycerol-3-phosphate was found to exist in Pleurotus salmoneostramineus L. Vass., an edible pink-colored mushroom. The structure of this unique substance is described.

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