{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,19]],"date-time":"2025-10-19T16:14:29Z","timestamp":1760890469031,"version":"build-2065373602"},"reference-count":39,"publisher":"MDPI AG","issue":"5","license":[{"start":{"date-parts":[[2022,5,20]],"date-time":"2022-05-20T00:00:00Z","timestamp":1653004800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100008530","name":"European Regional Development Fund and national funds","doi-asserted-by":"publisher","award":["MADFDR-01-0190-FEDER-000010","M1420-01-0247-FEDER-000024","CENTRO-01-0145-FEDER-031568","PTDC\/EEI-EEE\/31568\/2017","UIDP\/50025\/2020","M1420-09-5369-FSE-000001","SFRH\/BD\/145262\/2019"],"award-info":[{"award-number":["MADFDR-01-0190-FEDER-000010","M1420-01-0247-FEDER-000024","CENTRO-01-0145-FEDER-031568","PTDC\/EEI-EEE\/31568\/2017","UIDP\/50025\/2020","M1420-09-5369-FSE-000001","SFRH\/BD\/145262\/2019"]}],"id":[{"id":"10.13039\/501100008530","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Ag\u00eancia Regional para o Desenvolvimento da Investiga\u00e7\u00e3o Tecnologia e Inova\u00e7\u00e3o","award":["MADFDR-01-0190-FEDER-000010","M1420-01-0247-FEDER-000024","CENTRO-01-0145-FEDER-031568","PTDC\/EEI-EEE\/31568\/2017","UIDP\/50025\/2020","M1420-09-5369-FSE-000001","SFRH\/BD\/145262\/2019"],"award-info":[{"award-number":["MADFDR-01-0190-FEDER-000010","M1420-01-0247-FEDER-000024","CENTRO-01-0145-FEDER-031568","PTDC\/EEI-EEE\/31568\/2017","UIDP\/50025\/2020","M1420-09-5369-FSE-000001","SFRH\/BD\/145262\/2019"]}]},{"name":"Funda\u00e7\u00e3o para a Ci\u00eancia e Tecnologia","award":["MADFDR-01-0190-FEDER-000010","M1420-01-0247-FEDER-000024","CENTRO-01-0145-FEDER-031568","PTDC\/EEI-EEE\/31568\/2017","UIDP\/50025\/2020","M1420-09-5369-FSE-000001","SFRH\/BD\/145262\/2019"],"award-info":[{"award-number":["MADFDR-01-0190-FEDER-000010","M1420-01-0247-FEDER-000024","CENTRO-01-0145-FEDER-031568","PTDC\/EEI-EEE\/31568\/2017","UIDP\/50025\/2020","M1420-09-5369-FSE-000001","SFRH\/BD\/145262\/2019"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Processes"],"abstract":"<jats:p>Madeira wine (MW) encompasses an unusual oxidative ageing process that makes it distinctive. Several metabolites have been related to its quality and safety, such as 5-hydroxymethylfurfural (HMF), furfural, sotolon, and ethyl carbamate (EC). These compounds were quantified over a three-year period to assess their formation rate according to the ageing procedure used: canteiro vs. estufagem. Estufagem, which includes thermal processing of young MWs, promoted greater HMF, furfural, and sotolon accumulation, especially in sweet wines, in which sotolon contributed significantly to aroma (odour active values up to 17.5). Tinta Negra revealed a higher predisposition to form EC while Malvasia and Sercial were less prone to its formation. The formation of furfural, HMF, and EC strongly correlated with the ageing time. Sotolon had a strong correlation with the ageing time in canteiro (r = 0.79) and a moderate correlation in estufagem (r = 0.65). In both ageing procedures, sotolon, furfural, and HMF formation trends strongly correlated with each other (r = 0.74\u20130.90). In turn, EC also correlated with all furans (r = 0.51\u20130.85). Yellow tones (b*) correlated with these metabolites only when wines undergo estufagem. This study provides valuable insights to improve MW quality and safety management procedures.<\/jats:p>","DOI":"10.3390\/pr10051019","type":"journal-article","created":{"date-parts":[[2022,5,20]],"date-time":"2022-05-20T04:27:22Z","timestamp":1653020842000},"page":"1019","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Unveiling the Evolution of Madeira Wine Key Metabolites: A Three-Year Follow-Up Study"],"prefix":"10.3390","volume":"10","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-0772-8953","authenticated-orcid":false,"given":"Vanda","family":"Pereira","sequence":"first","affiliation":[{"name":"Institute of Nanostructures, Nanomodelling and Nanofabrication (i3N), University of Aveiro, Campus Universit\u00e1rio de Santiago, 3810-193 Aveiro, Portugal"},{"name":"ISOPlexis\u2013Sustainable Agriculture and Food Technology Center, University of Madeira, Campus da Penteada, 9020-105 Funchal, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1704-6745","authenticated-orcid":false,"given":"Jo\u00e3o M.","family":"Le\u00e7a","sequence":"additional","affiliation":[{"name":"Institute of Nanostructures, Nanomodelling and Nanofabrication (i3N), University of Aveiro, Campus Universit\u00e1rio de Santiago, 3810-193 Aveiro, Portugal"},{"name":"ISOPlexis\u2013Sustainable Agriculture and Food Technology Center, University of Madeira, Campus da Penteada, 9020-105 Funchal, Portugal"}]},{"given":"Ana I.","family":"Freitas","sequence":"additional","affiliation":[{"name":"Institute of Nanostructures, Nanomodelling and Nanofabrication (i3N), University of Aveiro, Campus Universit\u00e1rio de Santiago, 3810-193 Aveiro, Portugal"},{"name":"Faculty of Exact Sciences and Engineering, University of Madeira, Campus da Penteada, 9020-105 Funchal, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3097-7704","authenticated-orcid":false,"given":"Ana C.","family":"Pereira","sequence":"additional","affiliation":[{"name":"ISOPlexis\u2013Sustainable Agriculture and Food Technology Center, University of Madeira, Campus da Penteada, 9020-105 Funchal, Portugal"},{"name":"Chemical Process Engineering and Forest Products Research Centre (CIEPQPF), Department of Chemical Engineering, University of Coimbra, P\u00f3lo II\u2013Rua S\u00edlvio Lima, 3030-790 Coimbra, Portugal"}]},{"given":"Marisela","family":"Pontes","sequence":"additional","affiliation":[{"name":"Madeira Wine Company, S.A., Plataforma 3, Pavilh\u00e3o T, Zona Franca Industrial, 9200-047 Cani\u00e7al, Portugal"}]},{"given":"Francisco","family":"Albuquerque","sequence":"additional","affiliation":[{"name":"Madeira Wine Company, S.A., Plataforma 3, Pavilh\u00e3o T, Zona Franca Industrial, 9200-047 Cani\u00e7al, Portugal"}]},{"given":"Jos\u00e9 C.","family":"Marques","sequence":"additional","affiliation":[{"name":"Institute of Nanostructures, Nanomodelling and Nanofabrication (i3N), University of Aveiro, Campus Universit\u00e1rio de Santiago, 3810-193 Aveiro, Portugal"},{"name":"ISOPlexis\u2013Sustainable Agriculture and Food Technology Center, University of Madeira, Campus da Penteada, 9020-105 Funchal, Portugal"},{"name":"Faculty of Exact Sciences and Engineering, University of Madeira, Campus da Penteada, 9020-105 Funchal, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2022,5,20]]},"reference":[{"key":"ref_1","first-page":"419","article-title":"Emerging Trends in Fortified Wines: A Scientific Perspective","volume":"Volume 7","author":"Grumezescu","year":"2019","journal-title":"Alcoholic Beverages"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"11989","DOI":"10.1021\/jf802147z","article-title":"Impact of Forced-Aging Process on Madeira Wine Flavor","volume":"56","author":"Machado","year":"2008","journal-title":"J. Agric. Food Chem."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"122","DOI":"10.1016\/j.foodchem.2014.04.039","article-title":"Volatile Profile of Madeira Wines Submitted to Traditional Accelerated Ageing","volume":"162","author":"Pereira","year":"2014","journal-title":"Food Chem."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"207","DOI":"10.1016\/B978-0-12-384927-4.00007-5","article-title":"Distinctive Characteristics of Madeira Wine Regarding Its Traditional Winemaking and Modern Analytical Methodologies","volume":"Volume 63","author":"Jackson","year":"2011","journal-title":"Advances in Food and Nutrition Research"},{"key":"ref_5","doi-asserted-by":"crossref","unstructured":"Perestrelo, R., Silva, C., Gon\u00e7alves, C., Castillo, M., and C\u00e2mara, J.S. (2020). An Approach of the Madeira Wine Chemistry. Beverages, 6.","DOI":"10.3390\/beverages6010012"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"11","DOI":"10.1016\/j.aca.2005.05.012","article-title":"Characterization of the Aroma Profile of Madeira Wine by Sorptive Extraction Techniques","volume":"546","author":"Alves","year":"2005","journal-title":"Anal. Chim. Acta"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"180","DOI":"10.1016\/j.aca.2005.10.035","article-title":"Quantitative Gas Chromatography\u2013Olfactometry and Chemical Quantitative Study of the Aroma of Four Madeira Wines","volume":"563","author":"Campo","year":"2006","journal-title":"Anal. Chim. Acta"},{"key":"ref_8","doi-asserted-by":"crossref","unstructured":"Perestrelo, R., Silva, C., and C\u00e2mara, J.S. (2019). Madeira Wine Volatile Profile. A Platform to Establish Madeira Wine Aroma Descriptors. Molecules, 24.","DOI":"10.3390\/molecules24173028"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"99","DOI":"10.1016\/j.foodres.2018.04.034","article-title":"Impact of Storage Time and Temperature on Volatomic Signature of Tinta Negra Wines by LLME\/GC-ITMS","volume":"109","author":"Perestrelo","year":"2018","journal-title":"Food Res. Int."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"188","DOI":"10.1016\/j.aca.2005.10.031","article-title":"Changes in Volatile Composition of Madeira Wines During their Oxidative Ageing","volume":"563","author":"Alves","year":"2006","journal-title":"Anal. Chim. Acta"},{"key":"ref_11","doi-asserted-by":"crossref","unstructured":"Belitz, H.-D., Grosch, W., and Schieberle, P. (2004). Carbohydrates. Food Chemistry, Springer.","DOI":"10.1007\/978-3-662-07279-0"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"71","DOI":"10.1016\/j.foodres.2010.11.011","article-title":"Evolution of 5-Hydroxymethylfurfural (HMF) and Furfural (F) in Fortified Wines Submitted to Overheating Conditions","volume":"44","author":"Pereira","year":"2011","journal-title":"Food Res. Int."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"719","DOI":"10.1016\/j.lwt.2016.10.022","article-title":"Assessment of the Development of Browning, Antioxidant Activity and Volatile Organic Compounds in Thermally Processed Sugar Model Wines","volume":"75","author":"Pereira","year":"2017","journal-title":"LWT"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"1606","DOI":"10.1021\/jf072337r","article-title":"Distribution and Organoleptic Impact of Sotolon Enantiomers in Dry White Wines","volume":"56","author":"Pons","year":"2008","journal-title":"J. Agric. Food Chem."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"540","DOI":"10.1007\/BF01204559","article-title":"Enantiomeric Ratios of Pantolactone, Solerone, 4-Carboethoxy-4-Hydroxy-Butyrolactone and of Sotolon, A Flavour Impact Compound of Flor-Sherry and Botrytized Wines","volume":"195","author":"Guichard","year":"1992","journal-title":"Z. Lebensm. Unters. Forsch."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"475","DOI":"10.1021\/jf00015a023","article-title":"More Clues About Sensory Impact of Sotolon in Some Flor Sherry Wines","volume":"40","author":"Martin","year":"1992","journal-title":"J. Agric. Food Chem."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"4356","DOI":"10.1021\/jf0342932","article-title":"3-Hydroxy-4,5-dimethyl-2(5H)-furanone:\u2009 A Key Odorant of the Typical Aroma of Oxidative Aged Port Wine","volume":"51","author":"Barbe","year":"2003","journal-title":"J. Agric. Food Chem."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"6765","DOI":"10.1021\/jf049547d","article-title":"3-Hydroxy-4,5-dimethyl-2(5H)-furanone Levels in Fortified Madeira Wines: Relationship to Sugar Content","volume":"52","author":"Marques","year":"2004","journal-title":"J. Agric. Food Chem."},{"key":"ref_19","doi-asserted-by":"crossref","unstructured":"Gaspar, J.M., Freitas, A.I., Zhao, Q., Le\u00e7a, J.M., Pereira, V., and Marques, J.C. (2019). Is Sotolon Relevant to the Aroma of Madeira Wine Blends?. Biomolecules, 9.","DOI":"10.3390\/biom9110720"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"162","DOI":"10.5344\/ajev.1999.50.2.162","article-title":"Determination of Volatile Compounds in Hydroalcoholic Extracts of French and American Oak Wood","volume":"50","author":"Sanz","year":"1999","journal-title":"Am. J. Enol. Vitic."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"40","DOI":"10.1016\/j.lwt.2016.10.041","article-title":"Impact of Storage Time and Temperature on Furanic Derivatives Formation in Wines Using Microextraction by Packed Sorbent Tandem with Ultrahigh Pressure Liquid Chromatography","volume":"76","author":"Perestrelo","year":"2017","journal-title":"LWT"},{"key":"ref_22","doi-asserted-by":"crossref","unstructured":"Farag, M.R., Alagawany, M., Bin-Jumah, M., Othman, S.I., Khafaga, A.F., Shaheen, H.M., Samak, D., Shehata, A.M., Allam, A.A., and Abd El-Hack, M.E. (2020). The Toxicological Aspects of the Heat-Borne Toxicant 5-Hydroxymethylfurfural in Animals: A Review. Molecules, 25.","DOI":"10.3390\/molecules25081941"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"667","DOI":"10.1002\/mnfr.201000564","article-title":"Toxicology and Risk Assessment of 5-Hydroxymethylfurfural in Food","volume":"55","author":"Abraham","year":"2011","journal-title":"Mol. Nutr. Food Res."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"e2012016","DOI":"10.5620\/eht.2012.27.e2012016","article-title":"The Margin of Exposure of 5-Hydroxymethylfurfural (HMF) in Alcoholic Beverages","volume":"27","author":"Monakhova","year":"2012","journal-title":"Environ. Anal. Health. Toxicol."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"35","DOI":"10.1186\/s13065-018-0408-3","article-title":"5-Hydroxymethylfurfural (HMF) Levels in Honey and other Food Products: Effects on Bees and Human Health","volume":"12","author":"Shapla","year":"2018","journal-title":"Chem. Cent. J."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"545","DOI":"10.1080\/15569543.2020.1756857","article-title":"5-Hydroxymethylfurfural (HMF) Formation, Occurrence and Potential Health Concerns: Recent Developments","volume":"40","author":"Choudhary","year":"2020","journal-title":"Toxin Rev."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"3441","DOI":"10.1016\/j.chroma.2010.03.027","article-title":"Comprehensive Two-Dimensional Gas Chromatography with Time-Of-Flight Mass Spectrometry Combined with Solid Phase Microextraction as a Powerful Tool for Quantification of Ethyl Carbamate in Fortified Wines. The Case Study of Madeira Wine","volume":"1217","author":"Perestrelo","year":"2010","journal-title":"J. Chromatogr. A"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"327","DOI":"10.1007\/s12161-017-1002-3","article-title":"A Sensitive Method for the Rapid Determination of Underivatized Ethyl Carbamate in Fortified Wine by Liquid Chromatography-Electrospray Tandem Mass Spectrometry","volume":"11","author":"Pereira","year":"2018","journal-title":"Food Anal. Methods"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"611","DOI":"10.1111\/1541-4337.12084","article-title":"Ethyl Carbamate in Fermented Beverages: Presence, Analytical Chemistry, Formation Mechanism, and Mitigation Proposals","volume":"13","author":"Jiao","year":"2014","journal-title":"Compr. Rev. Food Sci. Food Saf."},{"key":"ref_30","unstructured":"International Agency for Research on Cancer (2010). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans: Alcohol Consumption and Ethyl Carbamate, International Agency for Research on Cancer."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"233","DOI":"10.1007\/s10311-008-0168-8","article-title":"Ethyl Carbamate in Foods and Beverages: A Review","volume":"7","author":"Weber","year":"2009","journal-title":"Environ. Chem. Lett."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"1204","DOI":"10.1002\/jssc.200900784","article-title":"HPLC-DAD Methodology for the Quantification of Organic Acids, Furans and Polyphenols by Direct Injection of Wine Samples","volume":"33","author":"Pereira","year":"2010","journal-title":"J. Sep. Sci."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"4393040","DOI":"10.1155\/2018\/4393040","article-title":"Rapid Determination of Sotolon in Fortified Wines Using a Miniaturized Liquid-Liquid Extraction Followed by LC-MS\/MS Analysis","volume":"2018","author":"Pereira","year":"2018","journal-title":"J. Anal. Methods Chem."},{"key":"ref_34","unstructured":"International Organization of Vine and Wine (2018). Compendium of International Methods of Spirituous Beverages of Vitivinicultural Origin, International Organization of Vine and Wine."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"5371","DOI":"10.1021\/jf4005109","article-title":"Port Wine Oxidation Management: A Multiparametric Kinetic Approach","volume":"61","author":"Martins","year":"2013","journal-title":"J. Agric. Food Chem."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"494285","DOI":"10.1155\/2015\/494285","article-title":"Amino Acids and Biogenic Amines Evolution during the Estufagem of Fortified Wines","volume":"2015","author":"Pereira","year":"2015","journal-title":"J. Chem."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"111566","DOI":"10.1016\/j.lwt.2021.111566","article-title":"New Insights into Ethyl Carbamate Occurrence in Fortified Wines","volume":"150","author":"Pereira","year":"2021","journal-title":"LWT"},{"key":"ref_38","doi-asserted-by":"crossref","unstructured":"Ramawat, K.G., and M\u00e9rillon, J.-M. (2013). Tannins and Anthocyanins of Wine: Phytochemistry and Organoleptic Properties. Natural Products: Phytochemistry, Botany and Metabolism of Alkaloids, Phenolics and Terpenes, Springer.","DOI":"10.1007\/978-3-642-22144-6"},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"2309","DOI":"10.1007\/s11947-015-1585-x","article-title":"Evaluation of Wine Colour Under Accelerated and Oak-Cask Ageing Using CIELab and Chemometric Approaches","volume":"8","author":"Carvalho","year":"2015","journal-title":"Food Bioprocess Technol."}],"container-title":["Processes"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/2227-9717\/10\/5\/1019\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T23:15:11Z","timestamp":1760138111000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/2227-9717\/10\/5\/1019"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,5,20]]},"references-count":39,"journal-issue":{"issue":"5","published-online":{"date-parts":[[2022,5]]}},"alternative-id":["pr10051019"],"URL":"https:\/\/doi.org\/10.3390\/pr10051019","relation":{},"ISSN":["2227-9717"],"issn-type":[{"type":"electronic","value":"2227-9717"}],"subject":[],"published":{"date-parts":[[2022,5,20]]}}}