{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,14]],"date-time":"2026-09-14T18:21:12Z","timestamp":1789410072918,"version":"build-2803163510"},"reference-count":14,"publisher":"Wiley","issue":"6","license":[{"start":{"date-parts":[[1990,6,1]],"date-time":"1990-06-01T00:00:00Z","timestamp":644198400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Lipids"],"published-print":{"date-parts":[[1990,6]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Diacylglycerols have been separated as their (<jats:italic>S<\/jats:italic>)\u2010(+)\u2010or (<jats:italic>R<\/jats:italic>)\u2010(\u2212)\u20101\u2010(1\u2010naphthyl)ethyl urethanes by high performance liquid chromatography (HPLC) on a column of silica gel with 0.5% 2\u2010propanol in hexane as the mobile phase. The elution order of components derivatized with the (<jats:italic>S<\/jats:italic>)\u2010form of the reagent was 1,3\u2010, followed by 1,2\u2010, and finally 2,3\u2010diacyl\u2010<jats:italic>sn<\/jats:italic>\u2010glycerols. The elution order of 1,2\u2010 and 2,3\u2010diastereomers was reversed when the (<jats:italic>R<\/jats:italic>)\u2010form of 1\u2010(1\u2010naphthyl)ethyl isocyanate was used for derivatization. Single\u2010acid 1,2\u2010 and 2,3\u2010diastereomers were separated to the baseline with a resolution factor from 5.2\u20135.7, and the resolution factor between 1,3\u2010 and 1,2\u2010 or 2,3\u2010diacyl\u2010<jats:italic>sn<\/jats:italic>\u2010glycerol derivatives was more than 23. Molecular species of single\u2010acid diacylglycerol derivatives were separated in the sequence 18\u22361&lt;18\u22360&lt;18\u22362&lt;16.0.<\/jats:p><jats:p>In order to assess this methodology as part of a procedure for the stereospecific analysis of triacyl\u2010<jats:italic>sn<\/jats:italic>\u2010glycerols, we prepared diacyl\u2010<jats:italic>rac<\/jats:italic>\u2010glycerols from maize oil, evening primrose oil and egg yolk triacylglycerols by partial hydrolysis with ethyl magnesium bromide. The 1,3\u2010, 1,2\u2010 and 2,3\u2010diacyl\u2010<jats:italic>sn<\/jats:italic>\u2010glycerols as (<jats:italic>S<\/jats:italic>)\u2010(+)\u20101\u2010(1\u2010naphthyl)ethyl urethanes were isolated and their fatty acid compositions were determined. Although this only permitted an indirect determination of the compositions of positions<jats:italic>sn<\/jats:italic>\u20101,\u20102 and\u20103, it was sufficient to indicate the potential of the methodology because results comparable to those published earlier were achieved.<\/jats:p>","DOI":"10.1007\/bf02544346","type":"journal-article","created":{"date-parts":[[2007,2,7]],"date-time":"2007-02-07T20:45:02Z","timestamp":1170881102000},"page":"349-353","source":"Crossref","is-referenced-by-count":92,"title":["Chromatographic resolution of chiral diacylglycerol derivatives: Potential in the stereospecific analysis of triacyl\u2010<i>sn<\/i>\u2010glycerols"],"prefix":"10.1002","volume":"25","author":[{"given":"Paivi","family":"Laakso","sequence":"first","affiliation":[{"name":"Hannah Research Institute Ayr Scotland KA6 5HL"},{"name":"Dept. of Chemistry and Biochemistry, Laboratory of Food Chemistry University of Turku Turku 20500 Finland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"William W.","family":"Christie","sequence":"additional","affiliation":[{"name":"Hannah Research Institute Ayr Scotland KA6 5HL"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[1990,6]]},"reference":[{"key":"e_1_2_2_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00431a004"},{"key":"e_1_2_2_3_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9673(01)93547-2"},{"key":"e_1_2_2_4_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF02537287"},{"key":"e_1_2_2_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/0021-9673(87)80023-7"},{"key":"e_1_2_2_6_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF02540133"},{"key":"e_1_2_2_7_1","doi-asserted-by":"publisher","DOI":"10.1016\/0005-2760(69)90211-2"},{"key":"e_1_2_2_8_1","volume-title":"Gas Chromatography and Lipids","author":"Christie W.W.","year":"1989"},{"key":"e_1_2_2_9_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0378-4347(00)84110-9"},{"key":"e_1_2_2_10_1","first-page":"197","volume-title":"Handbook of Lipid Research","author":"Breckenridge W.C.","year":"1978"},{"key":"e_1_2_2_11_1","first-page":"313","volume-title":"Analysis of Oils and Fats","author":"Christie W.W.","year":"1986"},{"key":"e_1_2_2_12_1","first-page":"336","volume-title":"Proceedings, 15th Scandinavian Symposium on Lipids","author":"Kuksis A.","year":"1989"},{"key":"e_1_2_2_13_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-2275(20)39585-7"},{"key":"e_1_2_2_14_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF02537340"},{"key":"e_1_2_2_15_1","doi-asserted-by":"publisher","DOI":"10.1016\/0005-2760(70)90094-9"}],"container-title":["Lipids"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/aocs.onlinelibrary.wiley.com\/doi\/pdf\/10.1007\/BF02544346","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,19]],"date-time":"2025-10-19T10:58:18Z","timestamp":1760871498000},"score":1,"resource":{"primary":{"URL":"https:\/\/aocs.onlinelibrary.wiley.com\/doi\/10.1007\/BF02544346"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[1990,6]]},"references-count":14,"journal-issue":{"issue":"6","published-print":{"date-parts":[[1990,6]]}},"alternative-id":["10.1007\/BF02544346"],"URL":"https:\/\/doi.org\/10.1007\/bf02544346","archive":["Portico"],"relation":{},"ISSN":["0024-4201","1558-9307"],"issn-type":[{"value":"0024-4201","type":"print"},{"value":"1558-9307","type":"electronic"}],"subject":[],"published":{"date-parts":[[1990,6]]}}}