{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,18]],"date-time":"2026-08-18T17:30:06Z","timestamp":1787074206671,"version":"build-2736575974"},"reference-count":43,"publisher":"American Chemical Society (ACS)","issue":"32","license":[{"start":{"date-parts":[[2026,8,1]],"date-time":"2026-08-01T00:00:00Z","timestamp":1785542400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/100012352","name":"Universit? degli Studi di Milano","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100012352","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100009882","name":"Regione Lombardia","doi-asserted-by":"publisher","award":["6154644"],"award-info":[{"award-number":["6154644"]}],"id":[{"id":"10.13039\/501100009882","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,8,18]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Serinol (2-amino-1,3-propanediol) is a key aminodiol used on a multiton industrial scale for the synthesis of iopamidol, a widely employed iodinated contrast agent in computed tomography (CT). Despite its small size and structural simplicity, serinol synthesis and purification remain costly and hazardous. Its isolation from process waste streams typically relies on energy-intensive techniques such as high-vacuum distillation or adsorption\u2013desorption on ion exchange resins, followed by evaporation of large water volumes. Crystallization of serinol offers a more sustainable and potentially scalable alternative. However, systematic crystallographic studies aimed at understanding its solid-state behavior remain scarce. In this work, we report a structural investigation of serinol in its free base form and four of its salts: hemioxalate, hydrochloride, stearate, and adamantane-1-carboxylate. The high density of polar protic functional groups in serinol promotes rich supramolecular architectures, governed by extensive and directional hydrogen-bonding networks. The combined spectroscopic and crystallographic analysis supports the formation of ammonium salts and highlights the structural factors governing their solid-state organization and supramolecular assembly. These insights into the solid-state structure of serinol derivatives lay the groundwork for the rational design of crystallization-based purification of serinol in industrial settings.<\/jats:p>","DOI":"10.1021\/acsomega.6c06041","type":"journal-article","created":{"date-parts":[[2026,8,4]],"date-time":"2026-08-04T14:05:36Z","timestamp":1785852336000},"page":"48681-48691","source":"Crossref","is-referenced-by-count":0,"title":["Serinol in the\nSolid State: Structural Diversity and\nPacking Motifs in Free Base and Salt Forms"],"prefix":"10.1021","volume":"11","author":[{"ORCID":"https:\/\/orcid.org\/0009-0004-3374-4206","authenticated-orcid":true,"given":"Rachele","family":"Maschio","sequence":"first","affiliation":[{"name":"Universita\u0300 del Piemonte Orientale , , Largo Donegani 2\/3 , ,","place":["Novara, Italy, 28100"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Silvia","family":"Zampini","sequence":"additional","affiliation":[{"name":"Universita\u0300 degli Studi di Milano , , Via Golgi 19; UdR INSTM , ,","place":["Milano, Italy, 20133"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9162-6487","authenticated-orcid":true,"given":"Toni","family":"Grell","sequence":"additional","affiliation":[{"name":"Universita\u0300 degli Studi di Milano , , Via Golgi 19; UdR INSTM , ,","place":["Milano, Italy, 20133"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Marco","family":"Vandone","sequence":"additional","affiliation":[{"name":"Universita\u0300 degli Studi di Milano , , Via Golgi 19; UdR INSTM , ,","place":["Milano, Italy, 20133"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3003-989X","authenticated-orcid":true,"given":"Fabio","family":"Travagin","sequence":"additional","affiliation":[{"name":"Universita\u0300 del Piemonte Orientale , , Largo Donegani 2\/3 , ,","place":["Novara, Italy, 28100"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6577-2595","authenticated-orcid":true,"given":"Luciano","family":"Lattuada","sequence":"additional","affiliation":[{"name":"Bracco Imaging SpA , Via Egidio Folli 50 , ,","place":["Milano, Italy, 20134"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7117-0347","authenticated-orcid":true,"given":"Giovanni B.","family":"Giovenzana","sequence":"additional","affiliation":[{"name":"Universita\u0300 del Piemonte Orientale , , Largo Donegani 2\/3 , ,","place":["Novara, Italy, 28100"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0263-4456","authenticated-orcid":true,"given":"Valentina","family":"Colombo","sequence":"additional","affiliation":[{"name":"Universita\u0300 degli Studi di Milano , , Via Golgi 19; UdR INSTM , ,","place":["Milano, Italy, 20133"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,8,1]]},"reference":[{"issue":"1","key":"2026081811105270100_cit1","doi-asserted-by":"publisher","DOI":"10.1186\/2191-0855-1-12","article-title":"Serinol: Small Molecule - Big Impact","volume":"1","author":"Andree\u00dfen","year":"2011","journal-title":"AMB Express"},{"issue":"6","key":"2026081811105270100_cit2","doi-asserted-by":"publisher","first-page":"1617","DOI":"10.1002\/hlca.19480310624","article-title":"Die Reduktion von \u03b1-Aminocarbonsa\u0308ureestern\nzu Aminoalkoholen mittels Lithiumaluminiumhydrid","volume":"31","author":"Karrer","year":"1948","journal-title":"Helv. Chim. Acta"},{"issue":"11","key":"2026081811105270100_cit3","doi-asserted-by":"publisher","first-page":"4007","DOI":"10.1073\/pnas.73.11.4007","article-title":"Serinol as an Activator\nof Toxin Production in Attenuated\nCultures of Helminthosporium Sacchari","volume":"73","author":"Pinkerton","year":"1976","journal-title":"Proc. Natl. Acad. Sci. U.S.A."},{"issue":"6","key":"2026081811105270100_cit4","doi-asserted-by":"publisher","first-page":"1109","DOI":"10.1093\/oxfordjournals.pcp.a077194","article-title":"Serinol (2-Amino-1,3-Propanediol) and 3-Amino-1,2-Propanediol\nin Soybean Nodules","volume":"27","author":"Minamisawa","year":"1986","journal-title":"Plant Cell Physiol."},{"issue":"11","key":"2026081811105270100_cit5","doi-asserted-by":"publisher","first-page":"4999","DOI":"10.1128\/AEM.67.11.4999-5009.2001","article-title":"DNA Sequence\nand Mutational Analysis of Rhizobitoxine\nBiosynthesis Genes in Bradyrhizobium Elkanii","volume":"67","author":"Yasuta","year":"2001","journal-title":"Appl. Environ. Microbiol."},{"issue":"1","key":"2026081811105270100_cit6","doi-asserted-by":"publisher","first-page":"13","DOI":"10.1016\/S1388-1981(02)00210-X","article-title":"Sphingolipid Functions\nin Saccharomyces Cerevisiae","volume":"1583","author":"Dickson","year":"2002","journal-title":"Biochim. Biophys. Acta, Mol. Cell Biol. 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Pharmaceutics"},{"key":"2026081811105270100_cit39","unstructured":"Nuclear Magnetic Resonance Studies of Protonation\nof Polyamine and\nAminocarboxylate Compounds in Aqueous Solution | Analytical Chemistry\n          2026\n          https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ac60215a006 (accessed Mar 29, 2026)."},{"issue":"6","key":"2026081811105270100_cit40","doi-asserted-by":"publisher","first-page":"1764","DOI":"10.1021\/ja038379n","article-title":"Organic Layered Crystals\nwith Adjustable Interlayer Distances of 1-Naphthylmethylammonium n-Alkanoates\nand Isomerism of Hydrogen-Bond Networks by Steric Dimension","volume":"126","author":"Sada","year":"2004","journal-title":"J. Am. Chem. Soc."},{"issue":"47","key":"2026081811105270100_cit41","doi-asserted-by":"publisher","first-page":"10461","DOI":"10.1021\/jp992279f","article-title":"Comparison\nof the Structures of Ammonium Myristate, Palmitate, and Stearate by\nX-Ray Diffraction, Infrared Spectroscopy, and Infrared Hole Burning","volume":"103","author":"Yu","year":"1999","journal-title":"J. Phys. Chem. B"},{"issue":"21","key":"2026081811105270100_cit42","doi-asserted-by":"publisher","first-page":"6534","DOI":"10.1002\/chem.200800374","article-title":"Two-Component Hydrogels Comprising\nFatty Acids and Amines: Structure, Properties, and Application as\na Template for the Synthesis of Metal Nanoparticles","volume":"14","author":"Basit","year":"2008","journal-title":"Chem. - Eur. 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Solid State Chem."}],"container-title":["ACS Omega"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acsomega.6c06041","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/acsodf\/article-pdf\/11\/32\/48681\/66352884\/acsomega.6c06041.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/acsodf\/article-pdf\/11\/32\/48681\/66352884\/acsomega.6c06041.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,8,18]],"date-time":"2026-08-18T17:16:59Z","timestamp":1787073419000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/acsodf\/article\/11\/32\/48681\/5238218\/Serinol-in-the-Solid-State-Structural-Diversity"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,8,1]]},"references-count":43,"journal-issue":{"issue":"32","published-online":{"date-parts":[[2026,8,1]]},"published-print":{"date-parts":[[2026,8,18]]}},"URL":"https:\/\/doi.org\/10.1021\/acsomega.6c06041","relation":{},"ISSN":["2470-1343"],"issn-type":[{"value":"2470-1343","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,8,1]]}}}