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China","doi-asserted-by":"publisher","award":["No. 32130083"],"award-info":[{"award-number":["No. 32130083"]}],"id":[{"id":"10.13039\/na","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,8,26]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Four stereoisomers of 4-acetoxy-2-hexyltetrahydrofuran and their sulfur analogues were synthesized. Odor evaluation showed that configuration governs properties: in the acetoxy series, (2R,4S) had the lowest thresholds (89 \u03bcg\/L in water, 9.1 \u03bcg\/L in air) with a peach-like sweet odor, while (2S,4R) had the highest (3.3 \u00d7 103 \u03bcg\/L, 7.7 \u00d7 102 \u03bcg\/L) with earthy notes; only (2R)-configured isomers exhibited the characteristic sweet peach note. In the acetylthio series, thresholds dropped dramatically: (2R,4S) showed the lowest (0.25 \u03bcg\/L in water, 3.6 ng\/L in air) with mushroom-celery odor, while (2S,4R) had a sulfurous, rotten-egg odor. The (2S,4S) and (2R,4R) isomers exhibited garlic-mushroom and plastic-metallic odors, respectively. Thus, sulfur substitution at the 4-position drastically lowers detection thresholds and shifts odor profiles from fruity toward sulfurous, mushroom-like notes.<\/jats:p>","DOI":"10.1021\/acs.jafc.6c06271","type":"journal-article","created":{"date-parts":[[2026,8,13]],"date-time":"2026-08-13T16:02:40Z","timestamp":1786636960000},"page":"26555-26566","source":"Crossref","is-referenced-by-count":0,"title":["Synthesis and Olfactory\nEvaluation of the Four Stereoisomers\nof 4-Acetoxy- and 4-Acetylthio-2-Hexyltetrahydrofuran"],"prefix":"10.1021","volume":"74","author":[{"given":"Fangyao","family":"Su","sequence":"first","affiliation":[{"name":"Key Laboratory of Geriatric Nutrition and Health (Beijing Technology and Business University) , , ,","place":["Beijing, China, 100048"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yiqing","family":"Jia","sequence":"additional","affiliation":[{"name":"Key Laboratory of Geriatric Nutrition and Health (Beijing Technology and Business University) , , ,","place":["Beijing, China, 100048"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Qingyuan","family":"Zhao","sequence":"additional","affiliation":[{"name":"Key Laboratory of Geriatric Nutrition and Health (Beijing Technology and Business University) , , ,","place":["Beijing, China, 100048"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xinyi","family":"Zhang","sequence":"additional","affiliation":[{"name":"Key Laboratory of Geriatric Nutrition and Health (Beijing Technology and Business University) , , ,","place":["Beijing, China, 100048"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yongguo","family":"Liu","sequence":"additional","affiliation":[{"name":"Key Laboratory of Geriatric Nutrition and Health (Beijing Technology and Business University) , , ,","place":["Beijing, China, 100048"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Baoguo","family":"Sun","sequence":"additional","affiliation":[{"name":"Key Laboratory of Geriatric Nutrition and Health (Beijing Technology and Business University) , , ,","place":["Beijing, China, 100048"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7117-6420","authenticated-orcid":true,"given":"Hongyu","family":"Tian","sequence":"additional","affiliation":[{"name":"Key Laboratory of Geriatric Nutrition and Health (Beijing Technology and Business University) , , ,","place":["Beijing, China, 100048"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sen","family":"Liang","sequence":"additional","affiliation":[{"name":"Key Laboratory of Geriatric Nutrition and Health (Beijing Technology and Business University) , , ,","place":["Beijing, China, 100048"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,8,13]]},"reference":[{"key":"2026090104471763700_cit1","article-title":"Structure\u2013Odor Relationships","volume-title":"Scent and Chemistry: The Molecular World of Odors","author":"Ohloff","year":"2022","edition":"2"},{"key":"2026090104471763700_cit2","doi-asserted-by":"publisher","first-page":"3018","DOI":"10.3390\/ijms20123018","article-title":"Is It Possible\nto Predict the Odor of a Molecule on the Basis of Its Structure?","volume":"20","author":"Genva","year":"2019","journal-title":"Int. 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