• Title/Summary/Keyword: Alpha Hydroxy Acid

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Synthesis of $(\pm)-\alpha-Hydroxy-\alpha$-(p-Chlorobiphenyl)Acetic Acid and its Resolution ($(\pm)-\alpha-Hydroxy-\alpha$-(p-Chlorobiphenyl)acetic acid 합성과 분할)

  • 권순경
    • YAKHAK HOEJI
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    • v.39 no.4
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    • pp.433-437
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    • 1995
  • Optically pure(-)-and (+)-$\alpha$-hydroxy-$\alpha$-(p-chlorobiphenyl)acetic acids were prepared. The racemate was synthesized through three steps. By condensation of p-cnorobiphenyl with diethyl ketomalonate in the presence of SnCl$_{4}$, diethyl $\alpha$-hydroxy-$\alpha$-(p-chlorobiphenyl)malonate (1) was formed and subsequently ($\pm$)-$\alpha$-hydroxy-$\alpha$-(p-chlorobiphenyl)acetic acid (3) was obtained through hydrolysis and decarboxylation. For the separation of the racemate the classical resolution method, derivatization of a racemate by reaction with an optically pure compound was employed. In this case the optically pure compound were [R]-(+)-$\alpha$-methylbenzylamine and [S]-(-)-$\alpha$-methylbenzylamine. Diastereomeric salts between acids and bases could be easily separated by crystallization in absolute ethanol.

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Triterpenes and Phenolic Constituents from Viscum album L. (상기생의 트라이테르펜 및 페놀성 성분)

  • 최상진;권학철;정애경;최상운;김경란;이선미;표석능;이강노
    • YAKHAK HOEJI
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    • v.45 no.6
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    • pp.591-598
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    • 2001
  • The photochemical study of Viscum album (Loranthaceae) led to the isolation of twelve compounds, lupeol (1), betulonic acid (2), betulinic acid (3), terminic acid (4), ursolic acid (5), $\beta$-sitosterol (6), $\alpha$- spinasterol (7), oleanolic acid (8) , 5-hydroxy-1- (4′-hydoxyphenyl) -7- (4"-hydroxyphenyl) -hepta-1- en-3-on (9), 2′-hydroxy -4′, 6′- dimethoxychalcone -4-O-glycoside (10) ,2′-hydroxy-4′, 6′-dimethoxychalcone -4-O- [apiosal(1longrightarrow12)]glucoside (11) and syringin (12). Their structures were established by chemical and spectroscopic methods. The cytotoxicity of the isolated compounds was evaluated by sulforhodamine B assay against five cultured human tumor cell lines.

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Isolation and Structural Elucidation of Related Impurities in Canrenone

  • Yang, Ya-Xi;Chen, Guo-Rong
    • Bulletin of the Korean Chemical Society
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    • v.30 no.10
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    • pp.2398-2402
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    • 2009
  • Ten steroidal compounds as impurities in canrenone were isolated from the enriched mother liquor by using various chromatographic methods. Their structures were elucidated by spectrometric analysis, among which three new compounds were characterized as 3-(3-oxo-7$\alpha$-(ethoxycarbonyl)methyl-17$\beta$-hydroxy-4-androsten-17$\alpha$-yl) propionic acid $\gamma$-lactone (1), 3-(3-oxo-7$\alpha$-ethoxy-17$\beta$-hydroxy-4-androsten-17$\alpha$-yl) propionic acid $\gamma$-lactone (2) and 3-(3-oxo- 5$\beta$-propionic acid-$\gamma$-lactone-6$\beta$,17$\beta$-hydroxy-4-androstan-17$\alpha$-yl) propionic acid $\gamma$-lactone (3).

Immunodulatory Activity of Triterpenes and Phenolic Compounds from Viscum Album L. (상기생의 트라이테르펜 및 페놀성 성분의 면역조절 작용)

  • 박대섭;최상진;김경란;이선미;이강노;표석능
    • Biomolecules & Therapeutics
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    • v.11 no.1
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    • pp.1-4
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    • 2003
  • Plants are known as important source in the search for new drugs. The twelve compounds from Viscum album (Loranthaceae), lupeol (1), betulonic acid (2), betulinic acid (3), terminic acid (4), ursolic acid (5), $\beta$-sitosterol (6), $\alpha$-spinasterol (7), oleanolic acid (8), 5-hydroxy-1-(4′-hydoxyphenyl)-7-(4"-hydroxyphenyl)-hepta-1-en-3-on (9), 2′-hydroxy-4′,6′-dimethoxychalcone-4-O-glucoside (10), 2′-hydroxy-4′,6′-dimethoxychalcone-4-O-[apiosyl(l$\longrightarrow$2)]glucoside (11) and syringin (12) were evaluated for their immunomodulatory properties. Compounds 6 and 11 induced the macrophage tumoricidal activity and the lymphocyte blastogenesis. In addition, these compounds stimulated the macrophages to induce the production of TNF-$\alpha$ and NO. These findings suggest that compounds 6 and 11 are modulating various elements of the host immune response.

SYNERGISTIC SKIN PROPERTY INTERACTIONS BETWEEN ALPHA HYDROXY ACID AND SKIN MOISTURIZER IN A HAND DISHWASHING DETERGENT

  • Brumbaugh, E.H.;Sigler, M.L.;Casterton, P.L.;Dornoff, M.
    • Proceedings of the SCSK Conference
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    • 2003.09a
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    • pp.491-497
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    • 2003
  • The use of both an Alpha Hydroxy Acid, Citric Acid, and a Skin Moisturizer, Glycereth-26, formulated into a hand dishwashing detergent have been shown to be synergistic in their effects on certain skin health parameters. Each ingredient was evaluated alone and together in a hand dishwashing detergent via a 9-week use test. Panelists washed dishes using the sponge method commonly used in Asian markets and a 1:7 dilution of the concentrated dish detergent. Panelist's hands were evaluated initially and at 3-week intervals for nine weeks. After nine weeks panelist's hands showed significant improvements in Moisture Absorption and Transepidermal Water Loss (TEWL). A synergistic effect on TEWL was found between the AHA and the Moisturizer. These effects, showing an improvement in the condition of the panelist's skin are impressive, particularly since they were observed from a dishwashing product that is highly diluted and at near neutral pH during the washing process.

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SYNERGISTIC SKIN PROPERTY INTERACTIONS BETWEEN ALPHA HYDROXY ACID AND SKIN MOISTURIZER IN A HAND DISHWASHING DETERGENT

  • Brumbaugh, E.H.;Sigler, M.L.;Casterton, P.L.;Dornoff, J.M.
    • Proceedings of the SCSK Conference
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    • 2003.09b
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    • pp.417-423
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    • 2003
  • The use of both an Alpha Hydroxy Acid, Citric Acid, and a Skin Moisturizer, Glycereth-26, formulated into a hand dishwashing detergent have been shown to be synergistic in their effects on certain skin health parameters. Each ingredient was evaluated alone and together in a hand dishwashing detergent via a 9-week use test. Panelists washed dishes using the sponge method commonly used in Asian markets and a 1:7 dilution of the concentrated dish detergent. Panelist's hands were evaluated initially and at 3-week intervals for nine weeks. After nine weeks panelist's hands showed significant improvements in Moisture Absorption and Transepidermal Water Loss (TEWL). A synergistic effect on TEWL was found between the AHA and the Moisturizer. These effects, showing an improvement in the condition of the panelist's skin are impressive, particularly since they were observed from a dishwashing product that is highly diluted and at near neutral pH during the washing process.

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Sulphamic Acid: an Efficient Catalyst for the Synthesis of α-HydroxyPhosphonates Using Ultrasound Irradiation (술팜산: 초음파 조사를 이용한 α-히드록시 인산염 합성의 효과적인 촉매)

  • Sadaphal, Sandip A.;Sonar, Swapnil S.;Pokalwar, Rajkumar U.;Shitole, Nanasaheb V.;Shingare, Murlidhar S.
    • Journal of the Korean Chemical Society
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    • v.53 no.5
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    • pp.536-541
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    • 2009
  • Sulphamic acid has been exploited as a cost-effective catalyst and green alternative for conventional acidic materials to synthesize $\alpha$-hydroxy phosphonates under solvent-free condition. The reaction carried out using ultrasound irradiation with better yields and shorter reaction time.

Synthesis of α-Ketobutyrolactones and γ-Hydroxy-α-Keto Acids

  • Kang, Han-Young;Ji, Yu-Mi;Yu, Yeon-Kwon;Yu, Ji-Yeon;Lee, Young-Hoon;Lee, Sang-Joon
    • Bulletin of the Korean Chemical Society
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    • v.24 no.12
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    • pp.1819-1826
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    • 2003
  • In connection with the studies for developing new enzymes that could be useful in organic synthesis, practical preparation of racemic and enantiopure forms of ${\gamma}$-hydroxy-${\alpha}$-keto acids has been successfully achieved. For racemic form of ${\gamma}$-hydroxy-${\alpha}$-keto acids, indium-mediated allylation of aldehydes with 2-(bromomethyl)acrylic acid has been employed as a key step. Oxidative cleavage of the thus formed 2-methylenebutyrolactones provided the desired ${\alpha}$-ketobutyrolactones. Enzymatic resolution of the ${\gamma}$-hydroxy-${\alpha}$-methylene esters provided the desired${\gamma}$-hydroxy-${\alpha}$-methylene acids which were successfully converted to ${\gamma}$-hydroxy-${\alpha}$-ketobutyrolactones in optically pure forms.