Identification of Monomenthyl Succinate, Monomenthyl Glutarate, and Dimenthyl Glutarate in Nature by High Performance Liquid Chromatography-Tandem Mass Spectrometry
Menthol, menthone, and other natural compounds provide a cooling effect and a minty flavor and have found wide application in chewing gum and oral care products. Monomenthyl succinate, monomenthyl glutarate, and dimenthyl glutarate provide a cooling effect without the burning sensation associated wi...
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| Veröffentlicht in: | Journal of agricultural and food chemistry 2004-06, Vol.52 (11), p.3536-3541 |
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| container_title | Journal of agricultural and food chemistry |
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| creator | Hiserodt, Richard D Adedeji, Jide John, T. V Dewis, Mark L |
| description | Menthol, menthone, and other natural compounds provide a cooling effect and a minty flavor and have found wide application in chewing gum and oral care products. Monomenthyl succinate, monomenthyl glutarate, and dimenthyl glutarate provide a cooling effect without the burning sensation associated with menthol. Additionally, because they do not have a distinct flavor, they can be used in applications other than mint flavors. Because these menthyl esters have not been reported in nature, we undertook to identify a natural source for these cooling compounds. Using high performance liquid chromatography-tandem mass spectrometry, monomenthyl succinate was identified in Lycium barbarum and Mentha piperita, and monomenthyl glutarate and dimenthyl glutarate were identified in Litchi chinesis. The identifications were based on the correlation of mass spectrometric and chromatographic retention time data for the menthyl esters in the extracts with authentic standards which resulted in a 99.980% confidence in the identifications. Keywords: Lycium barbarum; Mentha piperita; Litchi chinesis; monomenthyl succinate; monomenthyl glutarate; dimenthyl glutarate; high performance liquid chromatography-tandem mass spectrometry (LC/MS/MS); Nature Identical (NI) |
| doi_str_mv | 10.1021/jf049798m |
| format | Article |
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The identifications were based on the correlation of mass spectrometric and chromatographic retention time data for the menthyl esters in the extracts with authentic standards which resulted in a 99.980% confidence in the identifications. Keywords: Lycium barbarum; Mentha piperita; Litchi chinesis; monomenthyl succinate; monomenthyl glutarate; dimenthyl glutarate; high performance liquid chromatography-tandem mass spectrometry (LC/MS/MS); Nature Identical (NI)</description><identifier>ISSN: 0021-8561</identifier><identifier>EISSN: 1520-5118</identifier><identifier>DOI: 10.1021/jf049798m</identifier><identifier>PMID: 15161227</identifier><identifier>CODEN: JAFCAU</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Aroma and flavouring agent industries ; Biological and medical sciences ; chemical constituents of plants ; Chromatography, High Pressure Liquid ; cooling compounds ; esters ; flavor compounds ; Flavoring Agents ; Food additives ; Food industries ; fruits (plant anatomy) ; Fundamental and applied biological sciences. Psychology ; General aspects ; Glutarates - analysis ; high performance liquid chromatography ; leaves ; Litchi - chemistry ; Litchi chinesis ; Lycium ; Lycium - chemistry ; Lycium barbarum ; Lycium chinesis ; Mass Spectrometry ; Mentha piperita ; Mentha piperita - chemistry ; Menthol - analogs & derivatives ; Menthol - analysis ; menthyl esters ; plant extracts ; Succinates - analysis</subject><ispartof>Journal of agricultural and food chemistry, 2004-06, Vol.52 (11), p.3536-3541</ispartof><rights>Copyright © 2004 American Chemical Society</rights><rights>2004 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a434t-50f9903561c5f6b187bb0d428a28b25f549bcdc121ec4a3f47ceab03ef5098633</citedby><cites>FETCH-LOGICAL-a434t-50f9903561c5f6b187bb0d428a28b25f549bcdc121ec4a3f47ceab03ef5098633</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jf049798m$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jf049798m$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>315,781,785,2766,27078,27926,27927,56740,56790</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=15779871$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15161227$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Hiserodt, Richard D</creatorcontrib><creatorcontrib>Adedeji, Jide</creatorcontrib><creatorcontrib>John, T. V</creatorcontrib><creatorcontrib>Dewis, Mark L</creatorcontrib><title>Identification of Monomenthyl Succinate, Monomenthyl Glutarate, and Dimenthyl Glutarate in Nature by High Performance Liquid Chromatography-Tandem Mass Spectrometry</title><title>Journal of agricultural and food chemistry</title><addtitle>J. Agric. Food Chem</addtitle><description>Menthol, menthone, and other natural compounds provide a cooling effect and a minty flavor and have found wide application in chewing gum and oral care products. Monomenthyl succinate, monomenthyl glutarate, and dimenthyl glutarate provide a cooling effect without the burning sensation associated with menthol. Additionally, because they do not have a distinct flavor, they can be used in applications other than mint flavors. Because these menthyl esters have not been reported in nature, we undertook to identify a natural source for these cooling compounds. Using high performance liquid chromatography-tandem mass spectrometry, monomenthyl succinate was identified in Lycium barbarum and Mentha piperita, and monomenthyl glutarate and dimenthyl glutarate were identified in Litchi chinesis. The identifications were based on the correlation of mass spectrometric and chromatographic retention time data for the menthyl esters in the extracts with authentic standards which resulted in a 99.980% confidence in the identifications. Keywords: Lycium barbarum; Mentha piperita; Litchi chinesis; monomenthyl succinate; monomenthyl glutarate; dimenthyl glutarate; high performance liquid chromatography-tandem mass spectrometry (LC/MS/MS); Nature Identical (NI)</description><subject>Aroma and flavouring agent industries</subject><subject>Biological and medical sciences</subject><subject>chemical constituents of plants</subject><subject>Chromatography, High Pressure Liquid</subject><subject>cooling compounds</subject><subject>esters</subject><subject>flavor compounds</subject><subject>Flavoring Agents</subject><subject>Food additives</subject><subject>Food industries</subject><subject>fruits (plant anatomy)</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>General aspects</subject><subject>Glutarates - analysis</subject><subject>high performance liquid chromatography</subject><subject>leaves</subject><subject>Litchi - chemistry</subject><subject>Litchi chinesis</subject><subject>Lycium</subject><subject>Lycium - chemistry</subject><subject>Lycium barbarum</subject><subject>Lycium chinesis</subject><subject>Mass Spectrometry</subject><subject>Mentha piperita</subject><subject>Mentha piperita - chemistry</subject><subject>Menthol - analogs & derivatives</subject><subject>Menthol - analysis</subject><subject>menthyl esters</subject><subject>plant extracts</subject><subject>Succinates - analysis</subject><issn>0021-8561</issn><issn>1520-5118</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFks1uEzEURkeIiobCghcAb0BCYsA_43hmiRJIWyWlUtING-uOx04cZsap7ZHI-_CguCRqQSCxsnS_o2Ndf86yFwS_J5iSD1uDi0pUZfcoGxFOcc4JKR9nI5zCvORjcpo9DWGLMS65wE-yU8LJmFAqRtmPi0b30RqrIFrXI2fQwvWuS8PNvkXLQSnbQ9Tv_hjP2iGC_zWGvkFT-1eAbI-uIA5eo3qPzu16g661N8530CuN5vZ2sA2abLzrILq1h91mn6-STHdoASGg5U6rmFId_f5ZdmKgDfr58TzLbj5_Wk3O8_mX2cXk4zyHghUx59hUFWZpX8XNuCalqGvcFLQEWtaUG15UtWoUoUSrApgphNJQY6YNx1U5Zuwse3Pw7ry7HXSIsrNB6baFXrshSEEqXjJM_wsSwRmnxZ3x7QFU3oXgtZE7bzvwe0mwvOtO3neX2JdH6VB3unkgj2Ul4PURgKCgNT49pQ2_cSJ5BElcfuBsiPr7fQ7-mxwLJrhcXS_l1-nVbEHYpZwm_tWBN-AkrH1y3iwpJgzjqkifhj7cDCrIrRt8n2r4xwo_AZ5lyHk</recordid><startdate>20040602</startdate><enddate>20040602</enddate><creator>Hiserodt, Richard D</creator><creator>Adedeji, Jide</creator><creator>John, T. V</creator><creator>Dewis, Mark L</creator><general>American Chemical Society</general><scope>FBQ</scope><scope>BSCLL</scope><scope>IQODW</scope><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>7QR</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>20040602</creationdate><title>Identification of Monomenthyl Succinate, Monomenthyl Glutarate, and Dimenthyl Glutarate in Nature by High Performance Liquid Chromatography-Tandem Mass Spectrometry</title><author>Hiserodt, Richard D ; Adedeji, Jide ; John, T. V ; Dewis, Mark L</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a434t-50f9903561c5f6b187bb0d428a28b25f549bcdc121ec4a3f47ceab03ef5098633</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Aroma and flavouring agent industries</topic><topic>Biological and medical sciences</topic><topic>chemical constituents of plants</topic><topic>Chromatography, High Pressure Liquid</topic><topic>cooling compounds</topic><topic>esters</topic><topic>flavor compounds</topic><topic>Flavoring Agents</topic><topic>Food additives</topic><topic>Food industries</topic><topic>fruits (plant anatomy)</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>General aspects</topic><topic>Glutarates - analysis</topic><topic>high performance liquid chromatography</topic><topic>leaves</topic><topic>Litchi - chemistry</topic><topic>Litchi chinesis</topic><topic>Lycium</topic><topic>Lycium - chemistry</topic><topic>Lycium barbarum</topic><topic>Lycium chinesis</topic><topic>Mass Spectrometry</topic><topic>Mentha piperita</topic><topic>Mentha piperita - chemistry</topic><topic>Menthol - analogs & derivatives</topic><topic>Menthol - analysis</topic><topic>menthyl esters</topic><topic>plant extracts</topic><topic>Succinates - analysis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hiserodt, Richard D</creatorcontrib><creatorcontrib>Adedeji, Jide</creatorcontrib><creatorcontrib>John, T. 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V</au><au>Dewis, Mark L</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Identification of Monomenthyl Succinate, Monomenthyl Glutarate, and Dimenthyl Glutarate in Nature by High Performance Liquid Chromatography-Tandem Mass Spectrometry</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>2004-06-02</date><risdate>2004</risdate><volume>52</volume><issue>11</issue><spage>3536</spage><epage>3541</epage><pages>3536-3541</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><coden>JAFCAU</coden><abstract>Menthol, menthone, and other natural compounds provide a cooling effect and a minty flavor and have found wide application in chewing gum and oral care products. Monomenthyl succinate, monomenthyl glutarate, and dimenthyl glutarate provide a cooling effect without the burning sensation associated with menthol. Additionally, because they do not have a distinct flavor, they can be used in applications other than mint flavors. Because these menthyl esters have not been reported in nature, we undertook to identify a natural source for these cooling compounds. Using high performance liquid chromatography-tandem mass spectrometry, monomenthyl succinate was identified in Lycium barbarum and Mentha piperita, and monomenthyl glutarate and dimenthyl glutarate were identified in Litchi chinesis. The identifications were based on the correlation of mass spectrometric and chromatographic retention time data for the menthyl esters in the extracts with authentic standards which resulted in a 99.980% confidence in the identifications. Keywords: Lycium barbarum; Mentha piperita; Litchi chinesis; monomenthyl succinate; monomenthyl glutarate; dimenthyl glutarate; high performance liquid chromatography-tandem mass spectrometry (LC/MS/MS); Nature Identical (NI)</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>15161227</pmid><doi>10.1021/jf049798m</doi><tpages>6</tpages></addata></record> |
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| ispartof | Journal of agricultural and food chemistry, 2004-06, Vol.52 (11), p.3536-3541 |
| issn | 0021-8561 1520-5118 |
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| source | MEDLINE; ACS Publications |
| subjects | Aroma and flavouring agent industries Biological and medical sciences chemical constituents of plants Chromatography, High Pressure Liquid cooling compounds esters flavor compounds Flavoring Agents Food additives Food industries fruits (plant anatomy) Fundamental and applied biological sciences. Psychology General aspects Glutarates - analysis high performance liquid chromatography leaves Litchi - chemistry Litchi chinesis Lycium Lycium - chemistry Lycium barbarum Lycium chinesis Mass Spectrometry Mentha piperita Mentha piperita - chemistry Menthol - analogs & derivatives Menthol - analysis menthyl esters plant extracts Succinates - analysis |
| title | Identification of Monomenthyl Succinate, Monomenthyl Glutarate, and Dimenthyl Glutarate in Nature by High Performance Liquid Chromatography-Tandem Mass Spectrometry |
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