{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,21]],"date-time":"2026-09-21T15:03:55Z","timestamp":1790003035530,"version":"4.0.1"},"reference-count":91,"publisher":"MDPI AG","issue":"18","license":[{"start":{"date-parts":[[2026,9,20]],"date-time":"2026-09-20T00:00:00Z","timestamp":1789862400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>A thorough review of pipitzols and isopipitzols, covering the period 1852\u20132026, is presented. Perezone, the precursor of these compounds, is considered to be the first secondary metabolite isolated on the American continent, a phyto-molecule widely studied with regard to its spectra, chemical transformations, and especially its isolation and pharmacological activities. Perezone has several isomers: isoperezone, a synthetic molecule; and \u03b1- and \u03b2-pipitzols, two natural isomers of cedrenoid type achieved by thermal exo [4+2] cycloadditions. Isoperezone can be isomerized to \u03b2-isopipitzol through an endo [4+2] cycloaddition, while \u03b1-isopipitzol can be obtained from perezone by a [1+3] dipole addition. For this review, we conducted a comprehensive literature search, employing the main Scopus, SciFinder\u00ae, and ResearchGate databases, which identified 148 references. We found that the most recent report on \u03b1- and \u03b2-pipitzols appeared in 2024, on \u03b1-isopipitzol appeared on 2 September 2026, and on the four isomers was published on 29 January 2026.<\/jats:p>","DOI":"10.3390\/molecules31183342","type":"journal-article","created":{"date-parts":[[2026,9,21]],"date-time":"2026-09-21T14:12:09Z","timestamp":1789999929000},"page":"3342","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Pipitzols and Isopipitzols, 1852 to 2026: A Review"],"prefix":"10.3390","volume":"31","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-6683-6738","authenticated-orcid":false,"given":"Joel","family":"Mart\u00ednez","sequence":"first","affiliation":[{"name":"Departamento de Ciencias Qu\u00edmicas, Facultad de Estudios Superiores Cuautitl\u00e1n Campo 1, Universidad Nacional Aut\u00f3noma de M\u00e9xico, Cuautitl\u00e1n Izcalli 54740, Estado de M\u00e9xico, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Cristopher Williams","family":"Fuentes Cid","sequence":"additional","affiliation":[{"name":"Departamento de Ciencias Qu\u00edmicas, Facultad de Estudios Superiores Cuautitl\u00e1n Campo 1, Universidad Nacional Aut\u00f3noma de M\u00e9xico, Cuautitl\u00e1n Izcalli 54740, Estado de M\u00e9xico, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7951-1361","authenticated-orcid":false,"given":"Adriana Lizbeth","family":"Rivera Espejel","sequence":"additional","affiliation":[{"name":"Departamento de Ciencias Qu\u00edmicas, Facultad de Estudios Superiores Cuautitl\u00e1n Campo 1, Universidad Nacional Aut\u00f3noma de M\u00e9xico, Cuautitl\u00e1n Izcalli 54740, Estado de M\u00e9xico, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mar\u00eda In\u00e9s","family":"Nicol\u00e1s-V\u00e1zquez","sequence":"additional","affiliation":[{"name":"Departamento de Ciencias Qu\u00edmicas, Facultad de Estudios Superiores Cuautitl\u00e1n Campo 1, Universidad Nacional Aut\u00f3noma de M\u00e9xico, Cuautitl\u00e1n Izcalli 54740, Estado de M\u00e9xico, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6721-7114","authenticated-orcid":false,"given":"Mar\u00eda Z.","family":"Saavedra-Leos","sequence":"additional","affiliation":[{"name":"Coordinaci\u00f3n Acad\u00e9mica Regi\u00f3n Altiplano, Universidad Aut\u00f3noma de San Luis Potos\u00ed, Carretera Cedral km 5+600, Ejido San Jos\u00e9 de las Trojes Matehuala 78700, San Luis Potos\u00ed, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alberto A.","family":"Fajardo de la Rosa","sequence":"additional","affiliation":[{"name":"Laboratorio de Ingenier\u00eda Qu\u00edmica, Facultad de Qu\u00edmica, Universidad Nacional Aut\u00f3noma de M\u00e9xico, Alcald\u00eda Coyoac\u00e1n, Ciudad de M\u00e9xico 04510, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0640-0705","authenticated-orcid":false,"given":"Ren\u00e9 Gerardo","family":"Escobedo-Gonz\u00e1lez","sequence":"additional","affiliation":[{"name":"Department of Industrial Maintenance, Technological University of the City of Ju\u00e1rez, Av. Universidad Tecnol\u00f3gica No. 3051, Col. Lote Bravo II, City of Ju\u00e1rez 32315, Chihuahua, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ren\u00e9","family":"Miranda Ruvalcaba","sequence":"additional","affiliation":[{"name":"Departamento de Ciencias Qu\u00edmicas, Facultad de Estudios Superiores Cuautitl\u00e1n Campo 1, Universidad Nacional Aut\u00f3noma de M\u00e9xico, Cuautitl\u00e1n Izcalli 54740, Estado de M\u00e9xico, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2026,9,20]]},"reference":[{"key":"ref_1","unstructured":"Kinghorn, A.D., Falk, H., Gibbons, S., Asakawa, Y., Liu, J.-K., and Dirsch, V.M. (2021). A timeline of perezone, the first isolated secondary metabolite in the New World, covering the period from 1852 to 2020. 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