Recently, there has been a tendency toward a gradual changing of raw materials in the detergent industry from petrochemicals to vegetable oils. Palm oil has been worthy of special attention because of satisfactory yields and suitable carbon distributions for various kinds of surfactants.
Alpha-sulfo-fatty acid methyl ester (MES), synthesized by the reaction of methyl ester and SO₃, has excellent detergency and make it possible to produce a more concentrated detergent, which is friendly to the environment. Ethoxylated fatty methyl ester (EFMe) is directly synthesized by the reaction of ethylene oxide and methyl ester, using a newly developed catalyst of Al-MgO composite.
The extraction of natural carotene from crude palm oil has been commercially successful. Applications of palm carotene include those of synthetic carotene as well as new pharmaceutical applications. Furthermore, new mild surfactants for hair and skin, made from oleochemical product, have been developed.
In this paper, new surfactants made from the methyl ester, the extraction of minor constituents from palm oil, and future trends in oleochemistry are discussed.

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Lysophosphatidylcholine (LPC) has been shown to have many physological functions such as the contraction of smooth muscle cells, secretion of a growth factor from endotherial cells and the chemoattraction of T-cells. Lysophospholipids derived from soy bean in this study was noted to enhance the production of glycosaminoglycan (GAG), particularly hyaluronic acid, in a confluent culture of normal human dermal fibroblasts in Dulbecco's modified Eagle medium containing 0.5% FCS.
The pretreatment of the lysophospholipids by phospholipase B resulted in less stimulation of GAG production. Glycerol, glycerophosphate, glycerophosphorylcholine and all fatty acids failed to stimulate GAG production. LPC from soy bean enhanced GAG production, but not those from egg yolk or bovine liver. LPCs bearing acyl-residues between any two carbons from 6 to 18, C_{12 : 0}-LPC, C_{14 : 1}-LPC and C_{18 : 3}-LPC significantly enhanced GAG production. The separate ad-dition of any LPC component in soy bean to the medium did not result in greater GAG production, but when all components were added together each at the same molar ratio as soy bean, GAG synthesis was stimulated.

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Naturally occurring lysophosphatidylcholine (LPC) has effect on many different cell proesses, such as monocyte chemotaxis, smooth muscle cell contraction, platelet activation and the secretion of growth factors from endothelial cells. In this study, examination was made of the effects of exogenous LPC on DNA synthesis in human dermal fibroblasts, NB1RGB. DNA synthesis was accelerated by C_{12 : 0}-, C_{14 : 1}- and C_{16 : 1}-LPC, all of which were previously shown to enhance the synthesis of glycosaminoglycan (GAG, mainly hyaluronic acid). C_{18 : 3}-L, PC possessing activity for GAG synthesis greatly repressed that of DNA. DNA synthesis enhanced by C_{12 : 0}-LPC failed to occur due to the presence together of staruosporine, genistein, islet-activating protein (IAP) and propranolol. Neither was there any GAG synthesis which had been enhanced by C_{12 : 0}-LPC and C_{18 : 3}-LPC, due to these inhibitors except for propranolol. Phosphatidylethanol had no effect either on DNA or GAG synthesis. Depressed DNA synthesis by C_{18 : 3}-LPC was not restored by IAP. The activation of adenylyl cyclase would thus appear unrelated to the depression of DNA synthesis.

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Certain lysophospholipids were previously shown to enhance hyaluronic acid production in confluent culture of normal human dermal fibroblasts. In the present study, hairless mice were given hypodermic injection of lysophospholipid derived from soy bean (Soy LPL) or lauloyl lysophosphatidylcholine (lauroly LPC). Hyaluronic acid production was noted to significantly increased at either 2800μg/mL Soy LPL or 13203080 μg/mL lauloyl LPC. These values were 10 times the effective concentration in vitro. Two weeks of prolonged administration of Soy LPL increased hyaluronic acid content in the skin, but the control level was resumed 4 weeks following injection. A living body would thus appear to naturally resist stimulation of lysophospholipid. After one hypodermic injection of 2200μg/mL lauloyl LPC, always noted to be an effective concentration, hyaluronic acid content in the skin was measured. At 24 h, this content had increased and at 48 h, the control level was noted. Lauloyl LPC would thus appear effective in early stages and its effect not to persist for a prolonged time. Abnormal skin appearance following hypodermic injection or prolonged lysophospholipid administratoin was not recognized. Lysophospholipids should thus prove effective as cutaneous moisturizing agants.

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New automatic washing machines for home use with different load capacities were studied. Variation in liquor ratio on detergency was investigated using artificially soiled test cloths (JIS C 9606, Testfabrics type A-A and WFK type 10D). The effect of lowering this ratio on amount of detergent was examined so as to determine optimal conditions for soil removal.
Detergency decreased with reduction in the liquor ratio for large automatic washing machines as also noted for standard. Detergency decreased with increase in standard loading capacity. The amount of detergent to maintain 38.6% detergency was determined as following based on soil removal with standard automatic washing machines,
y=4.56x+13.8
where y is amount of detergent and x, clothing weight. This equation gave values greater than those determined from the adsorbed amount of LAS on cloth, a factor known to lessen detergency.

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The decoloration of Orange II catalyzed by horseradish peroxidase (HRP) was examined in the presence of glucose and glucose oxidase (GOD). Hydrogen peroxide (H₂O₂) formed during enzymatic reaction of glucose with GOD was continuously consumed as a substrate in the enzymatic cycle of HRP. In the HRP-catalyzed decoloration of Orange II coupled with the glucose-GOD system, the rate of decoloration Orange II was less than that in the HRP-catalyzed decoloration of Orange II with H₂O₂. The different initial concentrations of H₂O₂ may have been the reason for this, in that the H₂O₂ increased with reaction time in the enzymatic reaction of glucose with GOD. In coupling enzymatic reactions, the rate of decoloration Orange II was dependent on pH and concentrations of glucose and GOD. This rate showed a broad maximum at pH 8.5-9.0. And increased with glucose and GOD concentrations. The decololation rate of Orange II under optimum conditions was sufficient to inhibit the transfer of Orange II.

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Membrane extrusion vesicles of egg yolk lecithin were prepared and their diameters and lamellarity were determined from dynamic light scattering measurement and the fluorescent probe method, respectively. The fluorescent probe lipid used was dimyristoylphosphatidylethanolamine 4-nitrobenz-2-oxa-1, 3-diazole (NBD-DMPE). The mean radius of the vesicles sharply decreased with the number of extrusions and became ca. 60 nm at more than ten cycles of extrusion through a 0.1 mm pore-size membrane filter. For a unilamellar vesicle with 60 nm radius and bilayer thickness of 3 nm, the external lipid fraction should be 0.53. The experimentally obtained value was 0.52±0.03 at a molar ratio of NBD-DMPE in total lipid less than 0.3%. At higher NBD-DMPE (0.3%1.0%), the external marker lipid fraction was 0.550.61 immediately following preparation and subsequently decreased slowly to ca. 0.5. It thus follows that 1) vesicles after ten cycles of extrusion are unilamellar, 2) NBD-DMPE becomes distributed in the outer layer of the lecithin bilayer during extrusion, and 3) flip-flop motion of NBD-DMPE occurs after extrusion, leading to even distribution of the marker lipid in the vesicles.

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Lauryl-imino-diacetate (LIDA) is an amphoteric surfactant useful as a base for human body detergents. Owing to its stable dibasic acid moiety, application is possible over a wide pH range.
In this study, assessment was made of the cytotoxicity of LIDA and other surfactants by NR, WST-1, leakage in LDH and hemolysis. All those methods are alternatives to animal experiments such as the Draize test. Membrane fluidity change of human epidermal keratinocytes by surfactants was detected by polarized light measurement of probe molecules in the cell membrane.
LIDA and lauryl-imino-dipropionate (LIDP) showed low cytotoxicity in all cases. Membrane fluidity scarcely changed for LIDA and LIDP, whereas for lauryl-amino-acetate (LAA) and lauryl-amino-propionate (LAP), change was quite clear. The change in fluidity by LAA and LAP may have been related to the induction of cytotoxicity.

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Glycosylation reactions of methyl 2, 3, 4, 6-tetra-O-benzyl-D-glucopyranosylsulfoxide with various alcohols under high pressure in toluene using O-mesityrenesulfonylhydroxylamine as the activator gave the corresponding glucosides each in good yield and selectivity.

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The solubilization of alkylparabens with non-ionic surfactants was examined by equilibrium dialysis. The R value (Total amount of paraben/Free amount of paraben) increased linearly with the molar concentration of surfactant (C). Futhermore, the relationship between the slopes of the R vs. C lines and HLBs of the surfactants was represented by a linear function.

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