Synthesis of [2H8]-enterolactone and [2H10]-enterodiol
Enterolactone and enterodiol are the main mammalian metabolites of dietary butyrolactone type lignans. The study of biological properties and potential health effects of these compounds requires isotopically labelled compounds as standards for quantitative measurements. An expedient deutero‐labellin...
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| Veröffentlicht in: | Journal of labelled compounds & radiopharmaceuticals 2004-01, Vol.47 (1), p.25-30 |
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| container_title | Journal of labelled compounds & radiopharmaceuticals |
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| creator | Leppälä, Eija Wähälä, Kristiina |
| description | Enterolactone and enterodiol are the main mammalian metabolites of dietary butyrolactone type lignans. The study of biological properties and potential health effects of these compounds requires isotopically labelled compounds as standards for quantitative measurements. An expedient deutero‐labelling method for enterolactone is to use the D3PO4·BF3/D2O complex at room temperature which will exchange all eight aromatic hydrogens, even from inactivated meta positions, to form [2,4,5,6,2′,4′,5′,6′‐2H8]‐enterolactone in 74% yield and 99% isotopic purity. [2,4,5,6,9,9,2′,4′,5′,6′‐2H10]‐Enterodiol was prepared from [2,4,5,6,2′,4′,5′,6′‐2H8]‐enterolactone by reduction with LiAlD4 which introduces two more deuterium atoms into the molecule. Copyright © 2003 John Wiley & Sons, Ltd. |
| doi_str_mv | 10.1002/jlcr.793 |
| format | Article |
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The study of biological properties and potential health effects of these compounds requires isotopically labelled compounds as standards for quantitative measurements. An expedient deutero‐labelling method for enterolactone is to use the D3PO4·BF3/D2O complex at room temperature which will exchange all eight aromatic hydrogens, even from inactivated meta positions, to form [2,4,5,6,2′,4′,5′,6′‐2H8]‐enterolactone in 74% yield and 99% isotopic purity. [2,4,5,6,9,9,2′,4′,5′,6′‐2H10]‐Enterodiol was prepared from [2,4,5,6,2′,4′,5′,6′‐2H8]‐enterolactone by reduction with LiAlD4 which introduces two more deuterium atoms into the molecule. Copyright © 2003 John Wiley & Sons, Ltd.</description><identifier>ISSN: 0362-4803</identifier><identifier>EISSN: 1099-1344</identifier><identifier>DOI: 10.1002/jlcr.793</identifier><language>eng</language><publisher>Chichester, UK: John Wiley & Sons, Ltd</publisher><subject>Chemistry ; deuterium ; enterodiol ; enterolactone ; Exact sciences and technology ; labelling ; lignan ; metabolite ; Noncondensed benzenic compounds ; Organic chemistry ; phytoestrogen ; Preparations and properties</subject><ispartof>Journal of labelled compounds & radiopharmaceuticals, 2004-01, Vol.47 (1), p.25-30</ispartof><rights>Copyright © 2003 John Wiley & Sons, Ltd.</rights><rights>2005 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3313-af6e96755a13c70b2d869059e06f645b76b9643b4a3bd8188c15ff5f11ddf7753</citedby><cites>FETCH-LOGICAL-c3313-af6e96755a13c70b2d869059e06f645b76b9643b4a3bd8188c15ff5f11ddf7753</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fjlcr.793$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fjlcr.793$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,4010,27900,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=15848904$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Leppälä, Eija</creatorcontrib><creatorcontrib>Wähälä, Kristiina</creatorcontrib><title>Synthesis of [2H8]-enterolactone and [2H10]-enterodiol</title><title>Journal of labelled compounds & radiopharmaceuticals</title><addtitle>J Label Compd Radiopharm</addtitle><description>Enterolactone and enterodiol are the main mammalian metabolites of dietary butyrolactone type lignans. The study of biological properties and potential health effects of these compounds requires isotopically labelled compounds as standards for quantitative measurements. An expedient deutero‐labelling method for enterolactone is to use the D3PO4·BF3/D2O complex at room temperature which will exchange all eight aromatic hydrogens, even from inactivated meta positions, to form [2,4,5,6,2′,4′,5′,6′‐2H8]‐enterolactone in 74% yield and 99% isotopic purity. [2,4,5,6,9,9,2′,4′,5′,6′‐2H10]‐Enterodiol was prepared from [2,4,5,6,2′,4′,5′,6′‐2H8]‐enterolactone by reduction with LiAlD4 which introduces two more deuterium atoms into the molecule. Copyright © 2003 John Wiley & Sons, Ltd.</description><subject>Chemistry</subject><subject>deuterium</subject><subject>enterodiol</subject><subject>enterolactone</subject><subject>Exact sciences and technology</subject><subject>labelling</subject><subject>lignan</subject><subject>metabolite</subject><subject>Noncondensed benzenic compounds</subject><subject>Organic chemistry</subject><subject>phytoestrogen</subject><subject>Preparations and properties</subject><issn>0362-4803</issn><issn>1099-1344</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><recordid>eNp1z11LwzAYBeAgCs4p-BN2I3iTmTTfl67ophTFLyaIhDRNsLO2Iyno_r0tnXrl1QvveThwADjGaIoRSs5WlQ1TocgOGGGkFMSE0l0wQoQnkEpE9sFBjCuEuozSEeAPm7p9c7GMk8ZPXpKFfIWubl1oKmPbpnYTUxf9H6OfoCib6hDseVNFd7S9Y_B0efGYLmB2O79KzzNoCcEEGs-d4oIxg4kVKE8KyRViyiHuOWW54LnilOTUkLyQWEqLmffMY1wUXghGxuB06LWhiTE4r9eh_DBhozHS_V7d79Xd3o6eDHRtojWVD6a2ZfzzTFKpEO0cHNxnWbnNv336Okvvh96tL2Prvn69Ce-aCyKYXt7M9fOSzmaZutMp-QYkQXF6</recordid><startdate>200401</startdate><enddate>200401</enddate><creator>Leppälä, Eija</creator><creator>Wähälä, Kristiina</creator><general>John Wiley & Sons, Ltd</general><general>Wiley</general><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>200401</creationdate><title>Synthesis of [2H8]-enterolactone and [2H10]-enterodiol</title><author>Leppälä, Eija ; Wähälä, Kristiina</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3313-af6e96755a13c70b2d869059e06f645b76b9643b4a3bd8188c15ff5f11ddf7753</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Chemistry</topic><topic>deuterium</topic><topic>enterodiol</topic><topic>enterolactone</topic><topic>Exact sciences and technology</topic><topic>labelling</topic><topic>lignan</topic><topic>metabolite</topic><topic>Noncondensed benzenic compounds</topic><topic>Organic chemistry</topic><topic>phytoestrogen</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Leppälä, Eija</creatorcontrib><creatorcontrib>Wähälä, Kristiina</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><jtitle>Journal of labelled compounds & radiopharmaceuticals</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Leppälä, Eija</au><au>Wähälä, Kristiina</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of [2H8]-enterolactone and [2H10]-enterodiol</atitle><jtitle>Journal of labelled compounds & radiopharmaceuticals</jtitle><addtitle>J Label Compd Radiopharm</addtitle><date>2004-01</date><risdate>2004</risdate><volume>47</volume><issue>1</issue><spage>25</spage><epage>30</epage><pages>25-30</pages><issn>0362-4803</issn><eissn>1099-1344</eissn><abstract>Enterolactone and enterodiol are the main mammalian metabolites of dietary butyrolactone type lignans. The study of biological properties and potential health effects of these compounds requires isotopically labelled compounds as standards for quantitative measurements. An expedient deutero‐labelling method for enterolactone is to use the D3PO4·BF3/D2O complex at room temperature which will exchange all eight aromatic hydrogens, even from inactivated meta positions, to form [2,4,5,6,2′,4′,5′,6′‐2H8]‐enterolactone in 74% yield and 99% isotopic purity. [2,4,5,6,9,9,2′,4′,5′,6′‐2H10]‐Enterodiol was prepared from [2,4,5,6,2′,4′,5′,6′‐2H8]‐enterolactone by reduction with LiAlD4 which introduces two more deuterium atoms into the molecule. Copyright © 2003 John Wiley & Sons, Ltd.</abstract><cop>Chichester, UK</cop><pub>John Wiley & Sons, Ltd</pub><doi>10.1002/jlcr.793</doi><tpages>6</tpages></addata></record> |
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| identifier | ISSN: 0362-4803 |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Chemistry deuterium enterodiol enterolactone Exact sciences and technology labelling lignan metabolite Noncondensed benzenic compounds Organic chemistry phytoestrogen Preparations and properties |
| title | Synthesis of [2H8]-enterolactone and [2H10]-enterodiol |
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