Analytical and Sensory Characterization of the Stereoisomers of 3‑Mercaptocycloalkanones and 3‑Mercaptocycloalkanols
3-Mercaptocycloalkanones and 3-mercaptocycloalkanols (chain lengths C5–C7) were obtained by addition of thioacetic acid to the respective 2-cycloalken-1-ones and subsequent enzyme-mediated hydrolysis and reduction with LiAlH4, respectively. The stereoisomers were separated via capillary gas chromato...
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Veröffentlicht in: | Journal of agricultural and food chemistry 2020-07, Vol.68 (27), p.7184-7193 |
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creator | Wakabayashi, Motoko Wakabayashi, Hidehiko Riegel, Anja Devenie Eisenreich, Wolfgang Engel, Karl-Heinz |
description | 3-Mercaptocycloalkanones and 3-mercaptocycloalkanols (chain lengths C5–C7) were obtained by addition of thioacetic acid to the respective 2-cycloalken-1-ones and subsequent enzyme-mediated hydrolysis and reduction with LiAlH4, respectively. The stereoisomers were separated via capillary gas chromatography using chiral stationary phases. Their configurations were determined based on 1H NMR data and enzyme-catalyzed kinetic resolutions. Odor thresholds and odor qualities were assessed by capillary gas chromatography/olfactometry. Compared to the analogous acyclic 4-mercapto-2-alkanones and 4-mercapto-2-alkanols, the cyclic polyfunctional thiols lacked fruity, tropical notes; the perceived odor properties ranged from cooked, roasted vegetables and meat types to onion-related notes. The odor thresholds of the enantiomers of the 3-mercaptocycloalkanones were mainly impacted by their ring size rather than their configuration. For the 3-mercaptocycloalkanols, the (S)-configuration at the stereogenic center bearing the thiol group and the relative configuration of the second asymmetric center with the hydroxyl group were of importance for low odor thresholds. |
doi_str_mv | 10.1021/acs.jafc.0c03113 |
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The stereoisomers were separated via capillary gas chromatography using chiral stationary phases. Their configurations were determined based on 1H NMR data and enzyme-catalyzed kinetic resolutions. Odor thresholds and odor qualities were assessed by capillary gas chromatography/olfactometry. Compared to the analogous acyclic 4-mercapto-2-alkanones and 4-mercapto-2-alkanols, the cyclic polyfunctional thiols lacked fruity, tropical notes; the perceived odor properties ranged from cooked, roasted vegetables and meat types to onion-related notes. The odor thresholds of the enantiomers of the 3-mercaptocycloalkanones were mainly impacted by their ring size rather than their configuration. 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Agric. Food Chem</addtitle><description>3-Mercaptocycloalkanones and 3-mercaptocycloalkanols (chain lengths C5–C7) were obtained by addition of thioacetic acid to the respective 2-cycloalken-1-ones and subsequent enzyme-mediated hydrolysis and reduction with LiAlH4, respectively. The stereoisomers were separated via capillary gas chromatography using chiral stationary phases. Their configurations were determined based on 1H NMR data and enzyme-catalyzed kinetic resolutions. Odor thresholds and odor qualities were assessed by capillary gas chromatography/olfactometry. Compared to the analogous acyclic 4-mercapto-2-alkanones and 4-mercapto-2-alkanols, the cyclic polyfunctional thiols lacked fruity, tropical notes; the perceived odor properties ranged from cooked, roasted vegetables and meat types to onion-related notes. The odor thresholds of the enantiomers of the 3-mercaptocycloalkanones were mainly impacted by their ring size rather than their configuration. For the 3-mercaptocycloalkanols, the (S)-configuration at the stereogenic center bearing the thiol group and the relative configuration of the second asymmetric center with the hydroxyl group were of importance for low odor thresholds.</description><subject>Adult</subject><subject>Chemistry and Biology of Aroma and Taste</subject><subject>Cycloparaffins - chemistry</subject><subject>Cycloparaffins - metabolism</subject><subject>Female</subject><subject>Gas Chromatography-Mass Spectrometry</subject><subject>Humans</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Male</subject><subject>Middle Aged</subject><subject>Molecular Structure</subject><subject>Odorants - analysis</subject><subject>Olfactometry</subject><subject>Smell</subject><subject>Stereoisomerism</subject><subject>Sulfhydryl Compounds - chemistry</subject><subject>Sulfhydryl Compounds - metabolism</subject><subject>Volatile Organic Compounds - chemistry</subject><subject>Volatile Organic Compounds - metabolism</subject><issn>0021-8561</issn><issn>1520-5118</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp1kD1PwzAQhi0EoqWwM6GMDKSc4zgfY1XxJRUxFObo4l7UFCcudioRJv4Cf5FfQtIWNpbz6fy87_Awds5hzCHg16jceIWFGoMCwbk4YEMuA_Al58khG0LH-ImM-ICdOLcCgETGcMwGIpAiFYkYsvdJjbptSoXaw3rhzal2xrbedIkWVUO2_MCmNLVnCq9ZkjfvTmRKZyqyrj-K78-vR7IK141RrdIG9SvWpia37fvnW7tTdlSgdnS2f0fs5fbmeXrvz57uHqaTmY9CRI0fIYGgIJb9SDkH7DYqkjwQHCOOocxlrgjjJAC5gCKMYxEVwKVKMI-SVIzY5a53bc3bhlyTVaVTpDXWZDYuC0Iu0jQUEHYo7FBljXOWimxtywptm3HIet9Z5zvrfWd7313kYt--ySta_AV-BXfA1Q7YRs3Gdrrd_30_6vGPwg</recordid><startdate>20200708</startdate><enddate>20200708</enddate><creator>Wakabayashi, Motoko</creator><creator>Wakabayashi, Hidehiko</creator><creator>Riegel, Anja Devenie</creator><creator>Eisenreich, Wolfgang</creator><creator>Engel, Karl-Heinz</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-8932-5175</orcidid></search><sort><creationdate>20200708</creationdate><title>Analytical and Sensory Characterization of the Stereoisomers of 3‑Mercaptocycloalkanones and 3‑Mercaptocycloalkanols</title><author>Wakabayashi, Motoko ; Wakabayashi, Hidehiko ; Riegel, Anja Devenie ; Eisenreich, Wolfgang ; Engel, Karl-Heinz</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a336t-6ae03e2753e279110a53eef8b231a61a45b5bcea78205d0f47736f015c8ab6893</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Adult</topic><topic>Chemistry and Biology of Aroma and Taste</topic><topic>Cycloparaffins - chemistry</topic><topic>Cycloparaffins - metabolism</topic><topic>Female</topic><topic>Gas Chromatography-Mass Spectrometry</topic><topic>Humans</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Male</topic><topic>Middle Aged</topic><topic>Molecular Structure</topic><topic>Odorants - analysis</topic><topic>Olfactometry</topic><topic>Smell</topic><topic>Stereoisomerism</topic><topic>Sulfhydryl Compounds - chemistry</topic><topic>Sulfhydryl Compounds - metabolism</topic><topic>Volatile Organic Compounds - chemistry</topic><topic>Volatile Organic Compounds - metabolism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wakabayashi, Motoko</creatorcontrib><creatorcontrib>Wakabayashi, Hidehiko</creatorcontrib><creatorcontrib>Riegel, Anja Devenie</creatorcontrib><creatorcontrib>Eisenreich, Wolfgang</creatorcontrib><creatorcontrib>Engel, Karl-Heinz</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of agricultural and food chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wakabayashi, Motoko</au><au>Wakabayashi, Hidehiko</au><au>Riegel, Anja Devenie</au><au>Eisenreich, Wolfgang</au><au>Engel, Karl-Heinz</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Analytical and Sensory Characterization of the Stereoisomers of 3‑Mercaptocycloalkanones and 3‑Mercaptocycloalkanols</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>2020-07-08</date><risdate>2020</risdate><volume>68</volume><issue>27</issue><spage>7184</spage><epage>7193</epage><pages>7184-7193</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><abstract>3-Mercaptocycloalkanones and 3-mercaptocycloalkanols (chain lengths C5–C7) were obtained by addition of thioacetic acid to the respective 2-cycloalken-1-ones and subsequent enzyme-mediated hydrolysis and reduction with LiAlH4, respectively. The stereoisomers were separated via capillary gas chromatography using chiral stationary phases. Their configurations were determined based on 1H NMR data and enzyme-catalyzed kinetic resolutions. Odor thresholds and odor qualities were assessed by capillary gas chromatography/olfactometry. Compared to the analogous acyclic 4-mercapto-2-alkanones and 4-mercapto-2-alkanols, the cyclic polyfunctional thiols lacked fruity, tropical notes; the perceived odor properties ranged from cooked, roasted vegetables and meat types to onion-related notes. The odor thresholds of the enantiomers of the 3-mercaptocycloalkanones were mainly impacted by their ring size rather than their configuration. For the 3-mercaptocycloalkanols, the (S)-configuration at the stereogenic center bearing the thiol group and the relative configuration of the second asymmetric center with the hydroxyl group were of importance for low odor thresholds.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>32539383</pmid><doi>10.1021/acs.jafc.0c03113</doi><tpages>10</tpages><orcidid>https://orcid.org/0000-0001-8932-5175</orcidid></addata></record> |
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subjects | Adult Chemistry and Biology of Aroma and Taste Cycloparaffins - chemistry Cycloparaffins - metabolism Female Gas Chromatography-Mass Spectrometry Humans Magnetic Resonance Spectroscopy Male Middle Aged Molecular Structure Odorants - analysis Olfactometry Smell Stereoisomerism Sulfhydryl Compounds - chemistry Sulfhydryl Compounds - metabolism Volatile Organic Compounds - chemistry Volatile Organic Compounds - metabolism |
title | Analytical and Sensory Characterization of the Stereoisomers of 3‑Mercaptocycloalkanones and 3‑Mercaptocycloalkanols |
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