{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,13]],"date-time":"2025-10-13T19:59:56Z","timestamp":1760385596133,"version":"build-2065373602"},"reference-count":27,"publisher":"Wiley","issue":"5","license":[{"start":{"date-parts":[[2019,1,22]],"date-time":"2019-01-22T00:00:00Z","timestamp":1548115200000},"content-version":"am","delay-in-days":363,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#am"},{"start":{"date-parts":[[2018,1,24]],"date-time":"2018-01-24T00:00:00Z","timestamp":1516752000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/100000001","name":"National Science Foundation","doi-asserted-by":"publisher","award":["AST-1505502"],"award-info":[{"award-number":["AST-1505502"]}],"id":[{"id":"10.13039\/100000001","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemPhysChem"],"published-print":{"date-parts":[[2018,3,5]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Complex organic molecules are ubiquitous in star\u2010 and planet\u2010forming regions as well as on comets such as on 67P\/Churyumov\u2010Gerasimenko, but their origins have remained largely unexplained until now. Here, we report the first laboratory detection of distinct C<jats:sub>3<\/jats:sub>H<jats:sub>8<\/jats:sub>O (propanol, methyl ethyl ether) and C<jats:sub>4<\/jats:sub>H<jats:sub>8<\/jats:sub>O (<jats:italic>n<\/jats:italic>\u2010butanal, <jats:italic>i<\/jats:italic>\u2010butanal) isomers formed within interstellar analog ices through interaction with ionizing radiation. This study reveals that complex organics with propyl (C<jats:sub>3<\/jats:sub>H<jats:sub>7<\/jats:sub>) and butyl (C<jats:sub>4<\/jats:sub>H<jats:sub>9<\/jats:sub>) groups can be synthesized easily in deep space and may act as key evolutionary tracers of a cosmic ray driven non\u2010equilibrium chemistry in low temperature interstellar ices at 10\u2005K. These processes are of vital importance in initiating a chain of chemical reactions leading to complex organics\u2014some of which are responsible for the flavors of chocolate\u2014not only in the interstellar medium, but also on comet 67P\/Churyumov\u2010Gerasimenko.<\/jats:p>","DOI":"10.1002\/cphc.201701350","type":"journal-article","created":{"date-parts":[[2018,1,22]],"date-time":"2018-01-22T10:44:45Z","timestamp":1516617885000},"page":"556-560","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":12,"title":["On the Synthesis of Chocolate Flavonoids (Propanols, Butanals) in the Interstellar Medium"],"prefix":"10.1002","volume":"19","author":[{"given":"Matthew J.","family":"Abplanalp","sequence":"first","affiliation":[{"name":"Department of Chemistry University of Hawai'i at Manoa  2545 McCarthy Mall Honolulu HI 96822 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"S\u00e1ndor","family":"G\u00f3bi","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Hawai'i at Manoa  2545 McCarthy Mall Honolulu HI 96822 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Alexandre","family":"Bergantini","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Hawai'i at Manoa  2545 McCarthy Mall Honolulu HI 96822 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Andrew M.","family":"Turner","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Hawai'i at Manoa  2545 McCarthy Mall Honolulu HI 96822 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7233-7206","authenticated-orcid":false,"given":"Ralf I.","family":"Kaiser","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Hawai'i at Manoa  2545 McCarthy Mall Honolulu HI 96822 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2018,1,24]]},"reference":[{"key":"e_1_2_2_1_1","unstructured":"\u00a0"},{"key":"e_1_2_2_2_2","doi-asserted-by":"publisher","DOI":"10.1080\/0144235X.2017.1293974"},{"key":"e_1_2_2_3_2","doi-asserted-by":"publisher","DOI":"10.1086\/312881"},{"key":"e_1_2_2_4_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.1256678"},{"key":"e_1_2_2_5_1","doi-asserted-by":"publisher","DOI":"10.1146\/annurev-astro-082214-122348"},{"key":"e_1_2_2_6_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.1604426113"},{"key":"e_1_2_2_7_1","doi-asserted-by":"publisher","DOI":"10.1103\/RevModPhys.85.1021"},{"key":"e_1_2_2_8_1","unstructured":"\u00a0"},{"key":"e_1_2_2_9_2","doi-asserted-by":"publisher","DOI":"10.1146\/annurev-astro-081309-130811"},{"key":"e_1_2_2_10_2","doi-asserted-by":"publisher","DOI":"10.1093\/mnras\/stx1415"},{"key":"e_1_2_2_11_1","unstructured":"\u00a0"},{"key":"e_1_2_2_12_2","doi-asserted-by":"publisher","DOI":"10.1111\/1541-4337.12180"},{"key":"e_1_2_2_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/jf0114177"},{"key":"e_1_2_2_14_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41598-017-00693-9"},{"key":"e_1_2_2_15_1","unstructured":"The processed material of molecular clouds eventually enters circumstellar disks and is at least partially incorporated into planetesimals."},{"key":"e_1_2_2_16_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cplett.2015.11.029"},{"key":"e_1_2_2_17_1","doi-asserted-by":"publisher","DOI":"10.1086\/429119"},{"key":"e_1_2_2_18_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.051502898"},{"key":"e_1_2_2_19_1","doi-asserted-by":"publisher","DOI":"10.1021\/jp5126359"},{"key":"e_1_2_2_20_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.vibspec.2007.12.017"},{"volume-title":"NIST Chemistry WebBook, NIST Standard Reference Database Number 69","author":"Lias S. 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