Synthesis and Characterization of a New Hydroquinone Derivative
A novel amphiphilic hydroquinone derivative having a C18 alkyl chain phosphate attached to the hydroquinone (HQ) moiety was chemically synthesized. The thermal stability, distribution between organic and aqueous phases, and in vitro skin permeability were evaluated. This HQ derivative was identified...
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| Veröffentlicht in: | Journal of oleo science 2015-09, Vol.64 (9), p.1033-1033 |
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| container_title | Journal of oleo science |
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| creator | Hisama, Masayoshi Matsuda, Sanae Arai, Junichi Masui, Katsunobu Yamamura, Haruo |
| description | A novel amphiphilic hydroquinone derivative having a C18 alkyl chain phosphate attached to the hydroquinone (HQ) moiety was chemically synthesized. The thermal stability, distribution between organic and aqueous phases, and in vitro skin permeability were evaluated. This HQ derivative was identified as disodium p-phenylene diisostearyl diphosphate (HQ-2P2IS) by UV, infrared, mass, and nuclear magnetic resonance spectroscopies. Product HQ-2P2IS was obtained in good yield (56%), and it exhibited satisfactory stability in neutral solution, comparable to that of HQ. Its skin permeability was also higher than that of HQ. HQ-2P2IS is susceptible to enzymatic hydrolysis by tissue phosphatase, which releases HQ in the skin tissues. Thus, these characteristics indicate that the novel hydroquinone derivative presented herein, i.e., HQ-2P2IS, may serve as an effective pro-hydroquinone for skin care applications. |
| format | Article |
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The thermal stability, distribution between organic and aqueous phases, and in vitro skin permeability were evaluated. This HQ derivative was identified as disodium p-phenylene diisostearyl diphosphate (HQ-2P2IS) by UV, infrared, mass, and nuclear magnetic resonance spectroscopies. Product HQ-2P2IS was obtained in good yield (56%), and it exhibited satisfactory stability in neutral solution, comparable to that of HQ. Its skin permeability was also higher than that of HQ. HQ-2P2IS is susceptible to enzymatic hydrolysis by tissue phosphatase, which releases HQ in the skin tissues. Thus, these characteristics indicate that the novel hydroquinone derivative presented herein, i.e., HQ-2P2IS, may serve as an effective pro-hydroquinone for skin care applications.</description><identifier>ISSN: 1345-8957</identifier><identifier>EISSN: 1347-3352</identifier><language>eng</language><publisher>Tokyo: Japan Science and Technology Agency</publisher><subject>Derivatives ; Diphosphates ; Hydrolysis ; Hydroquinone ; Infrared ; Magnetic permeability ; Phases ; Phosphates</subject><ispartof>Journal of oleo science, 2015-09, Vol.64 (9), p.1033-1033</ispartof><rights>Copyright Japan Science and Technology Agency 2015</rights><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784</link.rule.ids></links><search><creatorcontrib>Hisama, Masayoshi</creatorcontrib><creatorcontrib>Matsuda, Sanae</creatorcontrib><creatorcontrib>Arai, Junichi</creatorcontrib><creatorcontrib>Masui, Katsunobu</creatorcontrib><creatorcontrib>Yamamura, Haruo</creatorcontrib><title>Synthesis and Characterization of a New Hydroquinone Derivative</title><title>Journal of oleo science</title><description>A novel amphiphilic hydroquinone derivative having a C18 alkyl chain phosphate attached to the hydroquinone (HQ) moiety was chemically synthesized. The thermal stability, distribution between organic and aqueous phases, and in vitro skin permeability were evaluated. This HQ derivative was identified as disodium p-phenylene diisostearyl diphosphate (HQ-2P2IS) by UV, infrared, mass, and nuclear magnetic resonance spectroscopies. Product HQ-2P2IS was obtained in good yield (56%), and it exhibited satisfactory stability in neutral solution, comparable to that of HQ. Its skin permeability was also higher than that of HQ. HQ-2P2IS is susceptible to enzymatic hydrolysis by tissue phosphatase, which releases HQ in the skin tissues. Thus, these characteristics indicate that the novel hydroquinone derivative presented herein, i.e., HQ-2P2IS, may serve as an effective pro-hydroquinone for skin care applications.</description><subject>Derivatives</subject><subject>Diphosphates</subject><subject>Hydrolysis</subject><subject>Hydroquinone</subject><subject>Infrared</subject><subject>Magnetic permeability</subject><subject>Phases</subject><subject>Phosphates</subject><issn>1345-8957</issn><issn>1347-3352</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNpdjl1LwzAYhYMoOKf_IeCNN4Ukb96mvRKpHxPGduHuS5oP1lGT2bST-evt1CuvzuHwcHjOyIyDVBkAivOfjllRorokVyntGJt2VDNy_3YMw9alNlEdLK22utdmcH37pYc2Bho91XTlPuniaPv4MbYhBkcfJ-AwAQd3TS687pK7-cs52Tw_bapFtly_vFYPy2yfc5EBSl8a7cF6JhtfKuul4daqXKFgBjxIraVoGONoGCs8cODSKY1KNAYUzMnd7-3-JOHSUL-3ybiu08HFMdW8YEzmokAxobf_0F0c-zDJ1VwhykIBQ_gGaT5TQQ</recordid><startdate>20150901</startdate><enddate>20150901</enddate><creator>Hisama, Masayoshi</creator><creator>Matsuda, Sanae</creator><creator>Arai, Junichi</creator><creator>Masui, Katsunobu</creator><creator>Yamamura, Haruo</creator><general>Japan Science and Technology Agency</general><scope>8FD</scope><scope>F28</scope><scope>FR3</scope></search><sort><creationdate>20150901</creationdate><title>Synthesis and Characterization of a New Hydroquinone Derivative</title><author>Hisama, Masayoshi ; Matsuda, Sanae ; Arai, Junichi ; Masui, Katsunobu ; Yamamura, Haruo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-p612-354f9caf3df04bf97df4c1dd767520c3f34aa42b0015c008f31314e7a572bc373</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Derivatives</topic><topic>Diphosphates</topic><topic>Hydrolysis</topic><topic>Hydroquinone</topic><topic>Infrared</topic><topic>Magnetic permeability</topic><topic>Phases</topic><topic>Phosphates</topic><toplevel>online_resources</toplevel><creatorcontrib>Hisama, Masayoshi</creatorcontrib><creatorcontrib>Matsuda, Sanae</creatorcontrib><creatorcontrib>Arai, Junichi</creatorcontrib><creatorcontrib>Masui, Katsunobu</creatorcontrib><creatorcontrib>Yamamura, Haruo</creatorcontrib><collection>Technology Research Database</collection><collection>ANTE: Abstracts in New Technology & Engineering</collection><collection>Engineering Research Database</collection><jtitle>Journal of oleo science</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hisama, Masayoshi</au><au>Matsuda, Sanae</au><au>Arai, Junichi</au><au>Masui, Katsunobu</au><au>Yamamura, Haruo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Characterization of a New Hydroquinone Derivative</atitle><jtitle>Journal of oleo science</jtitle><date>2015-09-01</date><risdate>2015</risdate><volume>64</volume><issue>9</issue><spage>1033</spage><epage>1033</epage><pages>1033-1033</pages><issn>1345-8957</issn><eissn>1347-3352</eissn><abstract>A novel amphiphilic hydroquinone derivative having a C18 alkyl chain phosphate attached to the hydroquinone (HQ) moiety was chemically synthesized. The thermal stability, distribution between organic and aqueous phases, and in vitro skin permeability were evaluated. This HQ derivative was identified as disodium p-phenylene diisostearyl diphosphate (HQ-2P2IS) by UV, infrared, mass, and nuclear magnetic resonance spectroscopies. Product HQ-2P2IS was obtained in good yield (56%), and it exhibited satisfactory stability in neutral solution, comparable to that of HQ. Its skin permeability was also higher than that of HQ. HQ-2P2IS is susceptible to enzymatic hydrolysis by tissue phosphatase, which releases HQ in the skin tissues. Thus, these characteristics indicate that the novel hydroquinone derivative presented herein, i.e., HQ-2P2IS, may serve as an effective pro-hydroquinone for skin care applications.</abstract><cop>Tokyo</cop><pub>Japan Science and Technology Agency</pub><tpages>1</tpages></addata></record> |
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| subjects | Derivatives Diphosphates Hydrolysis Hydroquinone Infrared Magnetic permeability Phases Phosphates |
| title | Synthesis and Characterization of a New Hydroquinone Derivative |
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