{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,16]],"date-time":"2026-10-16T13:28:51Z","timestamp":1792157331521,"version":"4.4.0"},"reference-count":45,"publisher":"American Chemical Society (ACS)","issue":"1","license":[{"start":{"date-parts":[[2015,1,7]],"date-time":"2015-01-07T00:00:00Z","timestamp":1420588800000},"content-version":"vor","delay-in-days":384,"URL":"https:\/\/pubs.acs.org\/page\/policy\/authorchoice_termsofuse.html"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2014,1,8]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>A large amount of (all-E)-lycopene was successfully purified from tomato paste using an improved method that included a procedure to wash crystalline powder with acetone. The total yield of the pure (all-E) form was at least 30%. The melting point of (all-E)-lycopene was determined to be 176.35 \u00b0C by differential scanning calorimetry (DSC) measurements. Bathochromic shifts were observed in the absorption maxima of all solvents tested (at most a 36 nm shift for \u03bb2 in carbon disulfide, as was observed in hexane) and were accompanied by absorbance decreases, namely, a hypochromic effect, showing a higher correlation between the position and the intensity of the main absorption bands. This bathochromic shift was dependent upon the polarizability of the solvent rather than its polarity. The structure of (all-E)-lycopene in CDCl3 and C6D6 was identified on the basis of one- and two-dimensional nuclear magnetic resonance (NMR) spectra, including 1H and 13C NMR, homonuclear correlation spectroscopy (1H\u20131H COSY), heteronuclear multiple-quantum coherence (HMQC), and heteronuclear multiple-bond connectivity (HMBC). The rate constants of the decrease in (all-E)-lycopene with hexane and benzene were calculated to be 3.19 \u00d7 10\u20135 and 3.55 \u00d7 10\u20135 s\u20131, respectively. The equilibrium constants between (all-E) and (13Z) isomers were estimated to be 0.29 in hexane and 0.31 in benzene, respectively, from the point at which the amount of (13Z)-lycopene reached its maximum.<\/jats:p>","DOI":"10.1021\/jf404497k","type":"journal-article","created":{"date-parts":[[2013,12,19]],"date-time":"2013-12-19T16:12:47Z","timestamp":1387469567000},"page":"264-269","source":"Crossref","is-referenced-by-count":89,"title":["Characterization\nand Thermal Isomerization of (\n                    <i>all<\/i>\n                    -\n                    <i>E<\/i>\n                    )-Lycopene"],"prefix":"10.1021","volume":"62","author":[{"given":"Munenori","family":"Takehara","sequence":"first","affiliation":[{"name":"The University of Shiga Prefecture , , , ,","place":["Hassaka, Hikone, Japan, 522-8533"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Masatoshi","family":"Nishimura","sequence":"additional","affiliation":[{"name":"The University of Shiga Prefecture , , , ,","place":["Hassaka, Hikone, Japan, 522-8533"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Takahiro","family":"Kuwa","sequence":"additional","affiliation":[{"name":"The University of Shiga Prefecture , , , ,","place":["Hassaka, Hikone, Japan, 522-8533"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yoshinori","family":"Inoue","sequence":"additional","affiliation":[{"name":"The University of Shiga Prefecture , , , ,","place":["Hassaka, Hikone, Japan, 522-8533"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Chitoshi","family":"Kitamura","sequence":"additional","affiliation":[{"name":"The University of Shiga Prefecture , , , ,","place":["Hassaka, Hikone, Japan, 522-8533"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tsutomu","family":"Kumagai","sequence":"additional","affiliation":[{"name":"The University of Shiga Prefecture , , , ,","place":["Hassaka, Hikone, Japan, 522-8533"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Masaki","family":"Honda","sequence":"additional","affiliation":[{"name":"Kagome Company, Limited , , , ,","place":["Nishitomiyama, Nasushiobara, Japan, 329-2762"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2013,12,19]]},"reference":[{"key":"2026090217594441900_cit1","doi-asserted-by":"crossref","first-page":"803","DOI":"10.1038\/sj.ejcn.1601880","article-title":"Lycopene\nand \u03b2-carotene are\nbioavailable from lycopene \u2018red\u2019 carrots in humans","volume":"58","author":"Horvitz","year":"2004","journal-title":"Eur. J. Clin. Nutr."},{"key":"2026090217594441900_cit2","doi-asserted-by":"crossref","first-page":"2479","DOI":"10.1271\/bbb.66.2479","article-title":"Carotenoid\npigments in GAC fruit (Momordica cochinchinensis SPRENG)","volume":"66","author":"Aoki","year":"2002","journal-title":"Biosci., Biotechnol., Biochem."},{"key":"2026090217594441900_cit3","doi-asserted-by":"crossref","first-page":"609","DOI":"10.1104\/pp.122.2.609","article-title":"Exposure to low\nirradiances favors the synthesis of\n9-cis \u03b2,\u03b2-carotene in Dunaliella salina (Teod.)","volume":"122","author":"Orset","year":"2000","journal-title":"Plant Physiol."},{"key":"2026090217594441900_cit4","doi-asserted-by":"crossref","first-page":"585","DOI":"10.1007\/s10295-004-0179-9","article-title":"Lycopene accumulation and cyclic carotenoid deficiency in heterotrophic Chlorella treated with nicotine","volume":"31","author":"Ishikawa","year":"2004","journal-title":"J. Ind. Microbiol. Biotechnol."},{"key":"2026090217594441900_cit5","doi-asserted-by":"crossref","first-page":"282","DOI":"10.3109\/08923973.2012.742534","article-title":"Anti-inflammatory activity of lycopene\nisolated from Chlorella marina on type\nII collagen induced arthritis in Sprague Dawley rats","volume":"35","author":"Renju","year":"2013","journal-title":"Immunopharmacol. Immunotoxicol."},{"key":"2026090217594441900_cit6","doi-asserted-by":"crossref","first-page":"157","DOI":"10.1016\/j.tca.2004.01.026","article-title":"Natural lycopene\nfrom Blakeslea trispora: all-trans lycopene themochemical and structural properties","volume":"417","author":"Estrella","year":"2004","journal-title":"Thermochim. Acta"},{"key":"2026090217594441900_cit7","doi-asserted-by":"crossref","first-page":"153","DOI":"10.1007\/s00253-004-1669-4","article-title":"Biotechnological lycopene production\nby mated fermentation of Blakeslea trispora","volume":"66","author":"Lo\u0301pez-Nieto","year":"2004","journal-title":"Appl. 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Soc."},{"key":"2026090217594441900_cit19","first-page":"38","article-title":"Carotenoid","volume-title":"Chemistry and Biochemistry of Plant Pigments","author":"Davis","year":"1976"},{"key":"2026090217594441900_cit20","doi-asserted-by":"crossref","first-page":"468","DOI":"10.1073\/pnas.27.10.468","article-title":"Prolycopene, a naturally\noccuring stereoisomer of lycopene","volume":"27","author":"Zechmeister","year":"1941","journal-title":"Proc. Natl.\nAcad. Sci. U. S. A."},{"key":"2026090217594441900_cit21","doi-asserted-by":"crossref","first-page":"1176","DOI":"10.1093\/jn\/129.6.1176","article-title":"cis-Lycopene is more bioavailable\nthan trans-lycopene in vitro and in vivo in lymph-cannulated\nferrets","volume":"129","author":"Boileau","year":"1999","journal-title":"J. Nutr."},{"key":"2026090217594441900_cit22","doi-asserted-by":"crossref","first-page":"482","DOI":"10.1093\/jn\/138.3.482","article-title":"In vitro\nmicellarization and intestinal\ncell uptake of cis isomers of lycopene exceed those\nof all-trans lycopene","volume":"138","author":"Failla","year":"2008","journal-title":"J. Nutr."},{"key":"2026090217594441900_cit23","doi-asserted-by":"crossref","first-page":"8997","DOI":"10.1021\/jf051672h","article-title":"Kinetic studies of lycopene isomerization in a tributyrin\nmodel system at gastric pH","volume":"53","author":"Moraru","year":"2005","journal-title":"J. Agric. Food Chem."},{"key":"2026090217594441900_cit24","doi-asserted-by":"crossref","first-page":"12784","DOI":"10.1021\/jf102934u","article-title":"Lycopene\ndegradation and isomerization kinetics during thermal processing of\nan olive oil\/tomato emulsion","volume":"58","author":"Colle","year":"2010","journal-title":"J. Agric. Food\nChem."},{"key":"2026090217594441900_cit25","first-page":"13","article-title":"UV\/visible spectroscopy","volume-title":"Carotenoids","author":"Britton","year":"1995"},{"key":"2026090217594441900_cit26","doi-asserted-by":"crossref","first-page":"459","DOI":"10.1016\/S0308-8146(96)00177-X","article-title":"Content and isomeric ratio of lycopene\nin food and human blood plasma","volume":"59","author":"Schierle","year":"1997","journal-title":"Food Chem."},{"key":"2026090217594441900_cit27","doi-asserted-by":"crossref","first-page":"194","DOI":"10.1002\/pca.576","article-title":"A simple,\nrapid method for HPLC analysis of lycopene\nisomers","volume":"12","author":"Ishida","year":"2001","journal-title":"Phytochem. Anal."},{"key":"2026090217594441900_cit28","doi-asserted-by":"crossref","first-page":"1632","DOI":"10.1021\/jp9728058","article-title":"Vibrational relaxation\nand redistribution\nin the 2Ag\u2013 state of all-trans-lycopene as revealed by picosecond time-resolved absorption\nspectroscopy","volume":"102","author":"Zhang","year":"1998","journal-title":"J. Phys. Chem. B"},{"key":"2026090217594441900_cit29","doi-asserted-by":"crossref","first-page":"289","DOI":"10.1080\/10942910601052699","article-title":"A review on lycopene\u2500Extraction,\npurification,\nstability and applications","volume":"10","author":"Choksi","year":"2007","journal-title":"Int. J. Food Prop."},{"key":"2026090217594441900_cit30","doi-asserted-by":"crossref","first-page":"431","DOI":"10.1021\/jf00015a013","article-title":"Relative solubility, stability, and\nabsorptivity of lutein and \u03b2-carotene in organic solvents","volume":"40","author":"Craft","year":"1992","journal-title":"J. Agric. Food Chem."},{"key":"2026090217594441900_cit31","doi-asserted-by":"crossref","first-page":"1522","DOI":"10.1021\/ja01248a025","article-title":"cis\u2013trans Isomerization\nand spectral characteristics of carotenoids and some related compounds","volume":"65","author":"Zechmeister","year":"1943","journal-title":"J. Am. Chem. Soc."},{"key":"2026090217594441900_cit32","doi-asserted-by":"crossref","first-page":"29","DOI":"10.1246\/nikkashi1948.75.29","article-title":"Relation between\nchemical structure and visible and ultra-violet spectra. I\u2013II.\nII. Polyenes and alkylated polyenes","volume":"75","author":"Hirayama","year":"1954","journal-title":"Nippon\nKagaku Zassi"},{"key":"2026090217594441900_cit33","doi-asserted-by":"crossref","first-page":"667","DOI":"10.1246\/nikkashi1948.75.667","article-title":"Relation between\nchemical structure and visible and ultra-violet spectra. III. Solvents\neffects on absorption of polyenes","volume":"75","author":"Hirayama","year":"1954","journal-title":"Nippon Kagaku\nZassi"},{"key":"2026090217594441900_cit34","doi-asserted-by":"crossref","first-page":"674","DOI":"10.1246\/nikkashi1948.75.674","article-title":"Relation between\nchemical structure and visible and ultra-violet spectra. IV. Effects\nof substituents and special structures","volume":"75","author":"Hirayama","year":"1954","journal-title":"Nippon\nKagaku Zassi"},{"key":"2026090217594441900_cit35","first-page":"37","article-title":"Extraction of pure lycopene from industrial tomato\nwaste in water using the extractor Naviglio","volume":"2","author":"Naviglio","year":"2008","journal-title":"Afr. J. Food Sci."},{"key":"2026090217594441900_cit36","doi-asserted-by":"crossref","first-page":"15","DOI":"10.3891\/acta.chem.scand.21-0015","article-title":"Bacterial carotenoids: The carotenoids of Mycobacterium phlei strain Vera. 2. The structure\non the phlei-xanthophylls\u2500two novel tertiary glycoside","volume":"21","author":"Hertzberg","year":"1967","journal-title":"Acta Chem. Scand."},{"key":"2026090217594441900_cit37","doi-asserted-by":"crossref","first-page":"219","DOI":"10.1016\/0009-2614(92)85291-H","article-title":"Quantitative analysis\nof the solvent effect on the relaxation processes of carotenoids showing\ndual emissive characteristics","volume":"191","author":"Mimuro","year":"1992","journal-title":"Chem. Phys. Lett."},{"key":"2026090217594441900_cit38","doi-asserted-by":"crossref","first-page":"1848","DOI":"10.1002\/hlca.19920750611","article-title":"Synthesis,\nisolation, and NMR-spectroscopic characterization of fourteen (Z)-isomers of lycopene and of some acetylenic didehydro-\nand tetradehydrolycopenes","volume":"75","author":"Hengartner","year":"1992","journal-title":"Helv. Chim. Acta"},{"key":"2026090217594441900_cit39","volume-title":"The Merck Index","author":"Budavari","year":"2001","edition":"13"},{"key":"2026090217594441900_cit40","doi-asserted-by":"crossref","first-page":"6094","DOI":"10.1021\/jf061154m","article-title":"Profiling\nof carotenoids in tomato\njuice by one- and two-dimensional NMR","volume":"54","author":"Tiziani","year":"2006","journal-title":"J. Agric.\nFood Chem."},{"key":"2026090217594441900_cit41","doi-asserted-by":"crossref","first-page":"369","DOI":"10.1024\/0300-9831.77.6.369","article-title":"Isolation\nand structural elucidation of different geometrical\nisomers of lycopene","volume":"77","author":"Fro\u0308hlich","year":"2007","journal-title":"Int. J. Vitam. Nutr. Res."},{"key":"2026090217594441900_cit42","doi-asserted-by":"crossref","first-page":"2122","DOI":"10.1271\/bbb.69.2122","article-title":"Analysis of carotenoid\ncomposition in petals of calendula (Calendula officinalis L.)","volume":"69","author":"Kishimoto","year":"2005","journal-title":"Biosci., Biotechnol., Biochem."},{"key":"2026090217594441900_cit43","first-page":"147","article-title":"NMR spectroscopy","volume-title":"Carotenoids","author":"Englert","year":"1995"},{"key":"2026090217594441900_cit44","doi-asserted-by":"crossref","first-page":"2747","DOI":"10.1021\/ja00115a010","article-title":"Thermal interconversions\namong 15-cis-, 13-cis-, and all-trans-\u03b2-carotene: Kinetics, Arrhenius\nparameters, thermochemistry, and potential relevance to anticarcinogenicity\nof all-trans-\u03b2-carotene","volume":"117","author":"Doering","year":"1995","journal-title":"J. Am. Chem. Soc."},{"key":"2026090217594441900_cit45","doi-asserted-by":"crossref","first-page":"3656","DOI":"10.1021\/jf981319u","article-title":"Isomerization of trans-astaxanthin to cis-isomers in organic solvents","volume":"47","author":"Yuan","year":"1999","journal-title":"J. Agric. Food\nChem."}],"container-title":["Journal of\nAgricultural and Food Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/jf404497k","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/jafcau\/article-pdf\/62\/1\/264\/18074905\/jf404497k.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/jafcau\/article-pdf\/62\/1\/264\/18074905\/jf404497k.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,2]],"date-time":"2026-09-02T21:59:54Z","timestamp":1788386394000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/jafcau\/article\/62\/1\/264\/1363448\/Characterization-and-Thermal-Isomerization-of-all"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2013,12,19]]},"references-count":45,"journal-issue":{"issue":"1","published-online":{"date-parts":[[2013,12,19]]},"published-print":{"date-parts":[[2014,1,8]]}},"URL":"https:\/\/doi.org\/10.1021\/jf404497k","relation":{},"ISSN":["0021-8561","1520-5118"],"issn-type":[{"value":"0021-8561","type":"print"},{"value":"1520-5118","type":"electronic"}],"subject":[],"published":{"date-parts":[[2013,12,19]]}}}