{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,30]],"date-time":"2026-08-30T09:29:20Z","timestamp":1788082160152,"version":"build-2784847793"},"reference-count":44,"publisher":"MDPI AG","issue":"1","license":[{"start":{"date-parts":[[2024,12,30]],"date-time":"2024-12-30T00:00:00Z","timestamp":1735516800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Kwangdong Pharmaceutical Co., Ltd. (Seoul, Republic Korea)","award":["2023-1310-01"],"award-info":[{"award-number":["2023-1310-01"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Foods"],"abstract":"<jats:p>Commercial ascorbyl-6-O-esters (AEs) are composed of saturated fatty acids with relatively high melting points, resulting in limited solubility in lipophilic media. Therefore, a lipase-catalysed synthesis and purification method for ascorbyl-6-O-oleate (AO) was proposed in this study. The esterification synthesis (i.e., bonding of oleoyl group to ascorbic acid) rate was 19.7% using acetone as the reaction solvent. The transesterification synthesis (i.e., exchange of acyl group with oleic acid (OA) in ascorbyl-6-O-palmitate (AP)) rate increased to 73.8% (AP:OA = 1:3, molar ratio). The esterification product was purified sequentially by liquid\u2013liquid extraction using ethyl acetate and water, followed by hexane and acetonitrile, resulting in 94.8 area% AO confirmed by HPLC. When acetonitrile was replaced with 90% methanol, AO achieved 97.2 area%. Similarly, the transesterification product showed 94.3 area% AEs (AP:AO = 8.9:91.1) after recrystallisation and liquid\u2013liquid extraction. Finally, all purified AO revealed peaks corresponding to the hydroxyl groups at the C-2 and C-3 carbons (11.10 and 8.41 ppm, 1H-NMR), whereas OA selectively esterified at the C-6 carbon (13C-NMR). FT-IR confirmed the presence of the ester bond (1733 cm\u22121) and olefin structure (3006 cm\u22121) of OA, and LC-ESI-MS\/MS identified AO peaks at m\/z 439.3. DSC analysis showed broad endothermic curves at 23.1\u201346.7 \u00b0C when the purified AO samples were pre-cooled at \u221225 \u00b0C.<\/jats:p>","DOI":"10.3390\/foods14010070","type":"journal-article","created":{"date-parts":[[2025,1,1]],"date-time":"2025-01-01T13:37:51Z","timestamp":1735738671000},"page":"70","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["A Novel Eco-Friendly Process for the Synthesis and Purification of Ascorbyl-6-Oleates"],"prefix":"10.3390","volume":"14","author":[{"given":"Ha-Eun","family":"Ji","sequence":"first","affiliation":[{"name":"Department of Food Science and Technology, Chungnam National University, 99 Daehak-ro, Yuseong-gu, Daejeon 34134, Republic of Korea"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Se-Young","family":"Kim","sequence":"additional","affiliation":[{"name":"Department of Food Science and Technology, Chungnam National University, 99 Daehak-ro, Yuseong-gu, Daejeon 34134, Republic of Korea"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Heejin","family":"So","sequence":"additional","affiliation":[{"name":"Department of Human Nutrition, Food and Animal Sciences, University of Hawaii at Manoa, 1955 East-West Road, Honolulu, HI 96822, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Vivian","family":"Prayitno","sequence":"additional","affiliation":[{"name":"Department of Food Science and Technology, Chungnam National University, 99 Daehak-ro, Yuseong-gu, Daejeon 34134, Republic of Korea"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ki-Teak","family":"Lee","sequence":"additional","affiliation":[{"name":"Department of Food Science and Technology, Chungnam National University, 99 Daehak-ro, Yuseong-gu, Daejeon 34134, Republic of Korea"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0194-1457","authenticated-orcid":false,"given":"Jung-Ah","family":"Shin","sequence":"additional","affiliation":[{"name":"Department of Marine Bio Food Science, Gangneung-Wonju National University, 7 Jukheon-gil, Gangneung 25457, Gangwon-do, Republic of Korea"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2024,12,30]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1168","DOI":"10.1007\/s12010-017-2610-5","article-title":"Production of 6-O-l-Ascorbyl Palmitate by Immobilized Candida Antarctica Lipase B","volume":"184","author":"Yadav","year":"2018","journal-title":"Appl. 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