{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,23]],"date-time":"2026-06-23T16:14:32Z","timestamp":1782231272710,"version":"3.54.5"},"reference-count":49,"publisher":"MDPI AG","issue":"19","license":[{"start":{"date-parts":[[2025,10,1]],"date-time":"2025-10-01T00:00:00Z","timestamp":1759276800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100003141","name":"CONAHCYT","doi-asserted-by":"crossref","award":["FOINS-PRONACES-307152"],"award-info":[{"award-number":["FOINS-PRONACES-307152"]}],"id":[{"id":"10.13039\/501100003141","id-type":"DOI","asserted-by":"crossref"}]},{"name":"DGAPA-UNAM PAPIIT","award":["IT200720"],"award-info":[{"award-number":["IT200720"]}]},{"name":"DGAPA-UNAM PAPIIT","award":["IT202125"],"award-info":[{"award-number":["IT202125"]}]}],"content-domain":{"domain":["www.mdpi.com"],"crossmark-restriction":true},"short-container-title":["IJMS"],"abstract":"<jats:p>Curcumin (CUR) is the primary metabolite isolated from the Curcuma longa L. rhizome. Most synthetic and biological studies have focused mainly on the curcumin molecule due to its essential biological activity as an antioxidant, anti-cancer, and anti-Alzheimer\u2019s disease agent. However, the natural extract of turmeric also contains two essential curcuminoids (demethoxycurcumin (DMC) and bisdemethoxycurcumin (BDMC)), which altogether comprise the so-called C-3 complex. They are present in commercial compositions for treating biliary or digestive ailments. The vegetal rhizome\u2019s extraction typically leads to a mixture of the three main curcuminoids, CUR, DMC, and BDMC, in variable proportions, and each of these metabolites has reported specific synthetic routes. Herein, we have performed the synthesis and isolation of the three major curcuminoids using the method called scrambling of aldehydes followed by aldol di-condensation reactions. A density functional theory (DFT) approach supported the experimental results by inspecting the predicted energies for the aldol condensation. Thus, the di-condensation reaction is substantially favoured (\u0394G\u00b0 = \u22122685.9 kJ\/mol) over the mono-condensation reaction (\u0394G\u00b0 = \u22121393.753 kJ\/mol). Our approach allows us to mimic closely the proportions of these curcuminoids found in extracts from natural sources that follow the order CUR &gt; DMC &gt; BDMC, respectively. The proportion of aldehydes can be modified in the scrambling reaction with an adequate mixture of aldehydes to render the order DMC &gt; CUR &gt; BDMC. This is an advantageous way to increase the amount of the unsymmetric DMC metabolite.<\/jats:p>","DOI":"10.3390\/ijms26199599","type":"journal-article","created":{"date-parts":[[2025,10,1]],"date-time":"2025-10-01T12:22:03Z","timestamp":1759321323000},"page":"9599","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["One Pot Synthesis of the C-3 Complex (Curcumin, Demethoxycurcumin, and Bis-Demethoxycurcumin): Their Joint and Independent Biological Actions"],"prefix":"10.3390","volume":"26","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-7932-2958","authenticated-orcid":false,"given":"Marco A.","family":"Obreg\u00f3n-Mendoza","sequence":"first","affiliation":[{"name":"Instituto de Qu\u00edmica, Universidad Nacional Aut\u00f3noma de M\u00e9xico, Circuito Exterior, Ciudad Universitaria, Ciudad de M\u00e9xico 04510, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2046-1766","authenticated-orcid":false,"given":"Rub\u00e9n","family":"S\u00e1nchez-Obreg\u00f3n","sequence":"additional","affiliation":[{"name":"Instituto de Qu\u00edmica, Universidad Nacional Aut\u00f3noma de M\u00e9xico, Circuito Exterior, Ciudad Universitaria, Ciudad de M\u00e9xico 04510, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5501-2496","authenticated-orcid":false,"given":"Rosario","family":"Tavera-Hern\u00e1ndez","sequence":"additional","affiliation":[{"name":"Instituto de Qu\u00edmica, Universidad Nacional Aut\u00f3noma de M\u00e9xico, Circuito Exterior, Ciudad Universitaria, Ciudad de M\u00e9xico 04510, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0007-7187-2569","authenticated-orcid":false,"given":"Leidys L.","family":"P\u00e9rez-Gonz\u00e1lez","sequence":"additional","affiliation":[{"name":"Instituto de Qu\u00edmica, Universidad Nacional Aut\u00f3noma de M\u00e9xico, Circuito Exterior, Ciudad Universitaria, Ciudad de M\u00e9xico 04510, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0900-6017","authenticated-orcid":false,"given":"Antonio","family":"Nieto-Camacho","sequence":"additional","affiliation":[{"name":"Instituto de Qu\u00edmica, Universidad Nacional Aut\u00f3noma de M\u00e9xico, Circuito Exterior, Ciudad Universitaria, Ciudad de M\u00e9xico 04510, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9443-3207","authenticated-orcid":false,"given":"Rogelio","family":"Rodr\u00edguez-Sotres","sequence":"additional","affiliation":[{"name":"Facultad de Medicina, Universidad Nacional Aut\u00f3noma de M\u00e9xico, Ciudad de M\u00e9xico 04510, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4932-2345","authenticated-orcid":false,"given":"Carolina","family":"Escobedo-Mart\u00ednez","sequence":"additional","affiliation":[{"name":"Departamento de Farmacia, Divisi\u00f3n de Ciencias Naturales y Exactas, Universidad de Guanajuato, Campus Guanajuato, Guanajuato 36050, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2317-5466","authenticated-orcid":false,"given":"Irma","family":"Romero","sequence":"additional","affiliation":[{"name":"Departamento de Bioqu\u00edmica, Facultad de Medicina, Universidad Nacional Aut\u00f3noma de M\u00e9xico, Ciudad Universitaria, Ciudad de M\u00e9xico 04510, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2671-615X","authenticated-orcid":false,"given":"Ra\u00fal G.","family":"Enr\u00edquez","sequence":"additional","affiliation":[{"name":"Instituto de Qu\u00edmica, Universidad Nacional Aut\u00f3noma de M\u00e9xico, Circuito Exterior, Ciudad Universitaria, Ciudad de M\u00e9xico 04510, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2025,10,1]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"3177","DOI":"10.1007\/s13738-022-02522-x","article-title":"A Structural and Optical Study of Curcumin and Curcumin Analogs","volume":"19","author":"Tahay","year":"2022","journal-title":"J. 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