{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,10]],"date-time":"2026-10-10T03:17:22Z","timestamp":1791602242617,"version":"4.3.4"},"reference-count":52,"publisher":"MDPI AG","issue":"7","license":[{"start":{"date-parts":[[2019,4,2]],"date-time":"2019-04-02T00:00:00Z","timestamp":1554163200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["21472235, 21464015"],"award-info":[{"award-number":["21472235, 21464015"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Xinjiang Tianshan Talents Program","award":["2018"],"award-info":[{"award-number":["2018"]}]},{"name":"Young Elite Scientist Sponsorship Program by CAST","award":["2017QNRC001"],"award-info":[{"award-number":["2017QNRC001"]}]},{"name":"Western Light program of CAS","award":["2017-XBQNXZ-B-001"],"award-info":[{"award-number":["2017-XBQNXZ-B-001"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The stability of gossypol was investigated by the spectroscopic method. Gossypol was dissolved in three different solvents (CHCl3, DMSO, and CH3OH) under different storage conditions (dark and with nitrogen protection, natural light and with nitrogen protection, ambient air conditions) for different time intervals (0 days, 3 days, 5 days, 7 days, 15 days, 30 days, and 45 days) at room temperature. Then, the stability of gossypol was investigated by 1H NMR, UV-vis, and HPLC-QTOF-MS spectrometry. Results showed that gossypol existed in aldehyde\u2013aldehyde form in chloroform within five days. Then, both aldehyde\u2013aldehyde and lactol\u2013lactol tautomeric forms existed and maintained a stable solution for 45 days. Gossypol dissolved in methanol mainly existed in aldehyde\u2013aldehyde form. Only a tiny amount of lactol\u2013lactol was found in freshly prepared methanol solution. Gossypol was found to only exist in lactol\u2013lactol form between 30\u201345 days. Gossypol existed in aldehyde\u2013aldehyde, lactol\u2013lactol, and ketol\u2013ketol forms in dimethyl sulfoxide, and there was a competitive relationship between aldehyde\u2013aldehyde and lactol\u2013lactol form during the 45 days. Among all the solvents and conditions studied, gossypol was found to be highly stable in chloroform. Under the tested conditions, the natural light and atmospheric oxygen had little effect on its stability. Although the spectroscopy data seemed to be changed over time in the three different solvents, it was actually due to the tautomeric transformation rather than molecular decomposition.<\/jats:p>","DOI":"10.3390\/molecules24071286","type":"journal-article","created":{"date-parts":[[2019,4,3]],"date-time":"2019-04-03T03:39:28Z","timestamp":1554262768000},"page":"1286","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":23,"title":["Investigating Stability and Tautomerization of Gossypol\u2014A Spectroscopy Study"],"prefix":"10.3390","volume":"24","author":[{"given":"Lulu","family":"Wang","sequence":"first","affiliation":[{"name":"Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, China"},{"name":"University of Chinese Academy of Sciences, Beijing 100049, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yanxia","family":"Liu","sequence":"additional","affiliation":[{"name":"Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, China"},{"name":"University of Chinese Academy of Sciences, Beijing 100049, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9457-1450","authenticated-orcid":false,"given":"Yagang","family":"Zhang","sequence":"additional","affiliation":[{"name":"Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, China"},{"name":"University of Chinese Academy of Sciences, Beijing 100049, China"},{"name":"Department of chemical and environmental engineering, Xinjiang Institute of Engineering, Urumqi 830026, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Akram","family":"Yasin","sequence":"additional","affiliation":[{"name":"Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Letao","family":"Zhang","sequence":"additional","affiliation":[{"name":"Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2019,4,2]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"84","DOI":"10.1002\/prac.18990600108","article-title":"Gossypol, ein Bestandtheil der Baumwollsamen","volume":"60","author":"Marchlewski","year":"1899","journal-title":"J. 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