• Polymer(Korea)
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• v.30 no.1
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• pp.35-44
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• 2006

Poly[1-(cholesteryloxycarbonyloxy)ethylene](PCOE) and poly[1-(cholesteryloxycarbonylheptanoyloxy)ethylene] (PCOSE) were prepared by reacting poly(vinyl alcohol) with cholesteryl chloroformate or 8-cholesteryloxycarbonylheptanoly] chloride (CH8C), and their thermal and optical properties were investigated. CH8C formed a monotropic cholesteric phase whereas PCOE and PCOSE exihibited enantiotropic cholesteric phases. Like in the case of CH8C, the optical pitch $(\lambda_m)$ of PCOSE decreased with increasing temperature. PCOE, contrast with PCOSE, did not display reflection colors, suggesting that the helical twisting power or the cholesteryl group highly depends on the length or the spacer joining the cholesteryl group to the main chain. The mesophase properties of PCOE and PCOSE were entirely different from those of poly $(cholesteryl-\omega-acryloyloxyalkanoates)$. The results indicate that the mode of chemical linkage of the side chain group with the main chain plays an important role in the formation, stabilization, and temperature dependence of $\lambda_m$ of the cholesteric mesophase.

• Archives of Pharmacal Research
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• v.6 no.2
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• pp.115-121
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• 1983

Cholesteryl p-[3-(2-chloroethyl_-3-nitrosoureido] phenylthioaccetate (2) was synthesized : an intermediate, p-[3(2-chloroethyl_-3-nitrosoureido] phenylthioacetic acid (1) is a congener of an antitumor chlorambucil which both the -CH$_{2}$CH$_{2}$-linkage and -N(CH$_{2}$CH$_{2}$Cl)$_{2}$ group of chlorambucil molecule is doubly modified into the respective -S-linkage and -NH-CO-NNO-CH$_{2}$CH$_{2}$CL group. The attackment of cholesterol moiety as a carrier group to p-[3-(2-chloroethyl-3nitrosoureido] phenylthioacetic acid was accomplished through the esterification of cholesterol with p-[3-(2-chloroethyl-3-nitrosoureido] phenylthioacetyl chloride which was obtained from the treatment of p-[3-(2-chloroethyl)-3-nitrosourei-do] phenylthioaceticacid with SOCL$_{2}$, p-[3-(2-chloroethyl)ureido]]-phenythioacetic acid was nitrosated with NaNO$_{2}$ IN 98-100% HCOOH to give exclusively p-[3-(2-chloroethyl_-3-nitrosoureido] phenylthioacetic acid. Antitumor evaluation of compounds, 1 and 2 on L 1210 leukemia did show significant activity (ED$_{40}$ : 1.14.mu./ml and 8.4.mu.g/ml, repectively). Further studies were subjected..

• Journal of the Korean Chemical Society
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• v.35 no.3
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• pp.249-252
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• 1991

Two new metabolites have been characterized from the methylene chloride extracts of Bezoar Bovis, a well known oriental drug : 8-octadecenoic methyl ester and cholesta-3,5-diene. Their structures were deduced from $^1$H-NMR and GC-mass spectra.

• Polymer(Korea)
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• v.31 no.1
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• pp.58-67
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• 2007

Fully cholesteryloxycarbonated and (8-cholesteryloxycarbonyl) heptanoated disaccharide derivatives were synthesized by reacting cellobiose, maltose, and lactose with cholesteryl chloroformate or 8- cholesteryloxycarbonylheptanoyl chloride, and their thermotropic liquid crystalline properties were investigated. All the cholesteryloxycarbonated derivatives (CH1DSs) formed enantiotropic cholesteric phases, whereas all the (8-cholesteryloxycarbonyl) heptanoated derivatives (CH8DSs) exhibited monotropic cholesteric phases with left-handed helicoidal structures whose optical pitches (${\lambda}m's$) decrease with increasing temperature. All the CH1DSs, contrast with the CH8DSs, did not display reflection colors over the full cholesteric range, suggesting that the helicoidal twisting power of the cholesteryl group highly depends on the length of the spacer joining the cholesteryl group to the disaccharide chain. The thermal stability and degree of order in the mesophase and the temperature dependence of the ${\lambda}m$ observed for EH8DSs were entirely different from those reported for the cholesterol-bearing dimers and triplet and the (8-cholesteryloxycarbonyl) heptanoated polysaccharide derivatives. The results were discussed in terms of the difference in the number of the mesogenic units per mole of repeating unit and the flexibility of the main chain.

• Journal of the Society of Cosmetic Scientists of Korea
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• v.40 no.2
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• pp.141-153
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• 2014

This study is about the development of cholesteric liquid crystals (CLCs), which are highly applicable to cosmetics formulation. The CLCs made from non-animal origin were chosen not only because they are free of animal viruses but also because they give a sense of security to the cosmetic consumers. Three kinds of new cholesteric derivatives (CI, CC, CN) were synthesized using non-animal cholesterol [NAB cholesterol (ARCH LONZA)], which was originally made by fermentation process. To develop high applicability to cosmetics formulation, we attempted to find out the optimum compositions in which CLCs can maintain their color over a wide range of temperature. The CLCs in 41 different compositions were prepared by the combinations of three cholesteric derivatives and a visual evaluation method was employed to determine the range of temperature at which the CLCs display their color. The 205 UV-VIS spectral data obtained from 41 CLCs at various temperatures were simultaneously analyzed to investigate the critical factors affecting the characteristics of the CLCs. Results showed that A4, A5, A6 and A7 were the best compositions to cosmetics formulation. A6 composition had a great moisturizing effect by the artificial skin test ($AmoReSkin^{TM}$).

• Polymer(Korea)
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• v.28 no.1
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• pp.92-102
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• 2004

(6-Cholesteryloxycarbonylpentoxypropyl)celluloses (CHPCs) with degree of esterification (DE) ranging from 2.25 to 2.91 were synthesized by reacting hydroxypropyl cellulose with 6-cholesteryloxycarbonylpentanoyl chloride. The acrylic esters of CHPCs (CHPCEs) and their photocrosslinked films with liquidcrystalline order were also synthesized. The thermotropic properties of mesophase for both uncrosslinked and crosslinked samples and the swelling behavior of the crosslinked samples in acetone were investigated. The hydroxypropyl cellulose exhibited an enantiotropic cholesteric phas, while all the uncrosslinked cholesterylbearing samples exhibited a monotropic cholesteric phases; the 6-cholesteryloxycarbonylpentanoyl chloride also showed a monotropic smectic phase. The hydroxypropyl cellulose formed a right-handed helix whose optical pitch (λ$\sub$m/) increases with temperature, whereas all the uncrosslinked derivatives farmed left-handed helices whose λ$\sub$m/'s decreased with temperature. The thermal stability of the mesophase and the magnitude of λ$\sub$m/ at the same temperature for both CHPCs and CHPCEs decreased with increasing DE. All the crosslinked samples, in constrast with CHPCEs, did not display reflection colors but exhibited an anisotropic swelling characteristic of crosslinked gel retaining liquid-crystalline order.

• Polymer(Korea)
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• v.30 no.4
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• pp.338-349
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• 2006

Fully or nearly fully(8-cholesteryloxycarbonyl)heptanoated polysaccharide derivatives were synthesized by reacting cellulose, amylose, chitosan, chitin, alginic acid, pullulan or amylopectin with (8-cholesteryloxycarbonyl)heptanoyl chloride (CH8C), and their thermotropic liquid crystalline behaviors were investigated. Like in the case of CH8C, all the polysaccharide derivatives formed monotropic cholesteric phases with left-handed helicoidal structures whose optical pitches $({\lambda_m}'s)$ decrease with increasing temperature. Amylopectin derivative also formed a monotropic cholesteric phase with lefthanded helicoidal structures but, in contrast with the other derivatives, did not display reflection colors over the full cholesteric range, suggesting that the helicoidal twisting power of the cholesteryl group highly depends on the branched structure in amylopectin. The thermal stability and degree of order in the mesophase, the magnitude of ${\lambda}_m$ at the same temperature, and the temperature dependence of the ${\lambda}_m$ observed for polysaccharide derivatives were entirely different from those reported for the polymers in which the cholesteryl groups are attached to flexible or semiflexible backbones through flexible spacers. The results were discussed in terms of the difference in the chemical structures of the main and side chains and flexibility of the main chain.