Reduction of cis- and trans-1,2-epithio-p-menth-8-ene: preparation of new fragrant terpenoid thiols
The synthesis of 2‐mercapto‐p‐menth‐8‐ene (3) and 1‐mercapto‐p‐menth‐8‐ene (4) are described, starting, respectively, from thioepoxydation of (+)‐trans‐limonene 1,2‐epoxide (1a) and (+)‐cis‐limonene 1,2‐epoxide (1b) via hydride reduction of episulphides 2a and 2b. Structural determination of these s...
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| Veröffentlicht in: | Flavour and fragrance journal 2003-01, Vol.18 (1), p.52-56 |
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| container_title | Flavour and fragrance journal |
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| creator | Candela, Karine Fellous, Roland Joulain, Daniel Faure, Robert |
| description | The synthesis of 2‐mercapto‐p‐menth‐8‐ene (3) and 1‐mercapto‐p‐menth‐8‐ene (4) are described, starting, respectively, from thioepoxydation of (+)‐trans‐limonene 1,2‐epoxide (1a) and (+)‐cis‐limonene 1,2‐epoxide (1b) via hydride reduction of episulphides 2a and 2b. Structural determination of these sulphur‐containing terpenoids was achieved by one‐ and two‐dimensional NMR spectroscopy. The odours of these two new monoterpene thiols were described, respectively, as reminescent of grapefruit juice and as being typically alliaceous. Copyright © 2002 John Wiley & Sons, Ltd. |
| doi_str_mv | 10.1002/ffj.1153 |
| format | Article |
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Structural determination of these sulphur‐containing terpenoids was achieved by one‐ and two‐dimensional NMR spectroscopy. The odours of these two new monoterpene thiols were described, respectively, as reminescent of grapefruit juice and as being typically alliaceous. Copyright © 2002 John Wiley & Sons, Ltd.</description><identifier>ISSN: 0882-5734</identifier><identifier>EISSN: 1099-1026</identifier><identifier>DOI: 10.1002/ffj.1153</identifier><identifier>CODEN: FFJOED</identifier><language>eng</language><publisher>Chichester, UK: John Wiley & Sons, Ltd</publisher><subject>2D-NMR ; Alicyclic compounds, terpenoids, prostaglandins, steroids ; Aroma and flavouring agent industries ; Biological and medical sciences ; Chemistry ; Exact sciences and technology ; Food industries ; Fundamental and applied biological sciences. 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J</addtitle><description>The synthesis of 2‐mercapto‐p‐menth‐8‐ene (3) and 1‐mercapto‐p‐menth‐8‐ene (4) are described, starting, respectively, from thioepoxydation of (+)‐trans‐limonene 1,2‐epoxide (1a) and (+)‐cis‐limonene 1,2‐epoxide (1b) via hydride reduction of episulphides 2a and 2b. Structural determination of these sulphur‐containing terpenoids was achieved by one‐ and two‐dimensional NMR spectroscopy. The odours of these two new monoterpene thiols were described, respectively, as reminescent of grapefruit juice and as being typically alliaceous. Copyright © 2002 John Wiley & Sons, Ltd.</description><subject>2D-NMR</subject><subject>Alicyclic compounds, terpenoids, prostaglandins, steroids</subject><subject>Aroma and flavouring agent industries</subject><subject>Biological and medical sciences</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Food industries</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>monoterpenoid episulphides</subject><subject>monoterpenoid thiols</subject><subject>odorous compounds</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>reduction</subject><subject>Terpenoids</subject><subject>thioepoxydation</subject><issn>0882-5734</issn><issn>1099-1026</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><recordid>eNp1kM1O3DAURi3USp1SpD5CNkVd1HD9G4cdGnWggIoEI7G0nMw1mGacYGdEefsazZSuurqb8x3pHkI-MzhiAPzY-8cjxpTYIzMGTUMZcP2OzMAYTlUt5AfyMedHABA1wIx0N7jadFMYYjX4qguZVi6uqim5mCn7ximOYXoIAx3pGuP0QA3FiCfVmHB0yf0dRnyufHL3ZTZVE6YR4xCKpiz7_Im8967PeLC7-2S5-L6cn9Or67Mf89Mr2kluBFWi9bxtnWmUYChNIwyTBqXQSivjEdq2NkrXWkhZQO6wdmzlnOfAwXixTw632jENTxvMk12H3GHfu4jDJltmtG4EyAJ-3YJdGnJO6O2YwtqlF8vAvka0JaJ9jVjQLzuny53ry4uxNPrHS6mlMlA4uuWeQ48v__XZxeJi593xIU_4-4136ZfVtaiVvft5Zs_ny9tLzm7shfgD3HmN0A</recordid><startdate>200301</startdate><enddate>200301</enddate><creator>Candela, Karine</creator><creator>Fellous, Roland</creator><creator>Joulain, Daniel</creator><creator>Faure, Robert</creator><general>John Wiley & Sons, Ltd</general><general>Wiley</general><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QR</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>200301</creationdate><title>Reduction of cis- and trans-1,2-epithio-p-menth-8-ene: preparation of new fragrant terpenoid thiols</title><author>Candela, Karine ; Fellous, Roland ; Joulain, Daniel ; Faure, Robert</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4283-53bf2bba89531e48938148e4365658fe0bb785676344f2b2ae7a1daaf20208f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>2D-NMR</topic><topic>Alicyclic compounds, terpenoids, prostaglandins, steroids</topic><topic>Aroma and flavouring agent industries</topic><topic>Biological and medical sciences</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Food industries</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>monoterpenoid episulphides</topic><topic>monoterpenoid thiols</topic><topic>odorous compounds</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>reduction</topic><topic>Terpenoids</topic><topic>thioepoxydation</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Candela, Karine</creatorcontrib><creatorcontrib>Fellous, Roland</creatorcontrib><creatorcontrib>Joulain, Daniel</creatorcontrib><creatorcontrib>Faure, Robert</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>Chemoreception Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Flavour and fragrance journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Candela, Karine</au><au>Fellous, Roland</au><au>Joulain, Daniel</au><au>Faure, Robert</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Reduction of cis- and trans-1,2-epithio-p-menth-8-ene: preparation of new fragrant terpenoid thiols</atitle><jtitle>Flavour and fragrance journal</jtitle><addtitle>Flavour Fragr. J</addtitle><date>2003-01</date><risdate>2003</risdate><volume>18</volume><issue>1</issue><spage>52</spage><epage>56</epage><pages>52-56</pages><issn>0882-5734</issn><eissn>1099-1026</eissn><coden>FFJOED</coden><abstract>The synthesis of 2‐mercapto‐p‐menth‐8‐ene (3) and 1‐mercapto‐p‐menth‐8‐ene (4) are described, starting, respectively, from thioepoxydation of (+)‐trans‐limonene 1,2‐epoxide (1a) and (+)‐cis‐limonene 1,2‐epoxide (1b) via hydride reduction of episulphides 2a and 2b. Structural determination of these sulphur‐containing terpenoids was achieved by one‐ and two‐dimensional NMR spectroscopy. The odours of these two new monoterpene thiols were described, respectively, as reminescent of grapefruit juice and as being typically alliaceous. Copyright © 2002 John Wiley & Sons, Ltd.</abstract><cop>Chichester, UK</cop><pub>John Wiley & Sons, Ltd</pub><doi>10.1002/ffj.1153</doi><tpages>5</tpages></addata></record> |
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| ispartof | Flavour and fragrance journal, 2003-01, Vol.18 (1), p.52-56 |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | 2D-NMR Alicyclic compounds, terpenoids, prostaglandins, steroids Aroma and flavouring agent industries Biological and medical sciences Chemistry Exact sciences and technology Food industries Fundamental and applied biological sciences. Psychology monoterpenoid episulphides monoterpenoid thiols odorous compounds Organic chemistry Preparations and properties reduction Terpenoids thioepoxydation |
| title | Reduction of cis- and trans-1,2-epithio-p-menth-8-ene: preparation of new fragrant terpenoid thiols |
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