ACS Publications. Most Trusted. Most Cited. Most Read
My Activity
CONTENT TYPES

Figure 1Loading Img

Formation of 2-Alkyl-(2H)-thiapyrans and 2-Alkylthiophenes in Cooked Beef and Lamb

View Author Information
Department of Food Science and Technology, The University of Reading, Whiteknights, Reading RG6 6AP, United Kingdom
Cite this: J. Agric. Food Chem. 2000, 48, 6, 2420–2424
Publication Date (Web):May 13, 2000
https://doi.org/10.1021/jf000124v
Copyright © 2000 American Chemical Society

    Article Views

    409

    Altmetric

    -

    Citations

    LEARN ABOUT THESE METRICS
    Other access options

    Abstract

    2-Alkyl-(2H)-thiapyrans and 2-alkylthiophenes have been identified in the volatiles of cooked beef and lamb. The quantities of both groups of compounds were higher in the meat of animals fed lipid supplements high in n−3 polyunsaturated fatty acids. 2-Alkyl-(2H)-thiapyrans were formed when (E,E)-2,4-dienals (C6−C11) and hydrogen sulfide were heated at 140 °C for 30 min. This confirmed their proposed route of formation in cooked meat from lipid-derived aldehydes and hydrogen sulfide; the latter was produced from the degradation of cysteine, via the Maillard reaction. The mass spectra and NMR spectra of these thiapyrans are reported for the first time. Although 2-alkyl-(2H)-thiapyrans were found to have only low odor potency, the reactions by which they are formed may have important implications for meat flavor. These reactions may remove potent aroma compounds and their intermediates from meat, thus modifying the overall aroma profile.

    Keywords: Flavor; 2-alkyl-(2H)-thiapyrans; 2-alkylthiophenes; meat; Maillard reaction; lipids; alkadienals

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. You can change your affiliated institution below.

    *

     Author to whom correspondence should be addressed (fax +44 118 931 0080; e-mail [email protected]).

    Cited By

    This article is cited by 31 publications.

    1. Valentina Vasta,, Jeremy Ratel, and, Erwan Engel. Mass Spectrometry Analysis of Volatile Compounds in Raw Meat for the Authentication of the Feeding Background of Farm Animals. Journal of Agricultural and Food Chemistry 2007, 55 (12) , 4630-4639. https://doi.org/10.1021/jf063432n
    2. Tuong Huynh-Ba,, Walter Matthey-Doret,, Laurent B. Fay, and, Rachid Bel Rhlid. Generation of Thiols by Biotransformation of Cysteine−Aldehyde Conjugates with Baker's Yeast. Journal of Agricultural and Food Chemistry 2003, 51 (12) , 3629-3635. https://doi.org/10.1021/jf026198j
    3. J. Stephen Elmore,, Maria M. Campo,, Michael Enser, and, Donald S. Mottram. Effect of Lipid Composition on Meat-like Model Systems Containing Cysteine, Ribose, and Polyunsaturated Fatty Acids. Journal of Agricultural and Food Chemistry 2002, 50 (5) , 1126-1132. https://doi.org/10.1021/jf0108718
    4. Wender L. P. Bredie,, Donald S. Mottram, and, Robin C. E. Guy. Effect of Temperature and pH on the Generation of Flavor Volatiles in Extrusion Cooking of Wheat Flour. Journal of Agricultural and Food Chemistry 2002, 50 (5) , 1118-1125. https://doi.org/10.1021/jf0111662
    5. Xingang Zhao, Shuxian Zuo, Yanping Guo, Can Zhang, Yuejun Wang, Sijia Peng, Ming Liu, Bing Wang, Hao Zhang, Hailing Luo. Carcass meat quality, volatile compound profile, and gene expression in Tan sheep under different feeding regimes. Food Bioscience 2023, 56 , 103213. https://doi.org/10.1016/j.fbio.2023.103213
    6. Mónica Flores. The eating quality of meat: III—Flavor. 2023, 421-455. https://doi.org/10.1016/B978-0-323-85408-5.00014-5
    7. Zheqi Zhang, Mingwu Zang, Kaihua Zhang, Shouwei Wang, Dan Li, Xiaoman Li. Effects of phospholipids and reheating treatment on volatile compounds in phospholipid-xylose-cysteine reaction systems. Food Research International 2021, 139 , 109918. https://doi.org/10.1016/j.foodres.2020.109918
    8. Can Zhang, Hao Zhang, Ming Liu, Xin’gang Zhao, Hailing Luo. Effect of Breed on the Volatile Compound Precursors and Odor Profile Attributes of Lamb Meat. Foods 2020, 9 (9) , 1178. https://doi.org/10.3390/foods9091178
    9. Xueping Ma, Ping Zhan, Honglei Tian, Zhisheng Wei, Peng Wang. Effects of Different Enzymatic Hydrolyses of Mutton Tallow on the Aroma Characteristics of the Maillard Reaction of Xylose–Cysteine Based on GC‐MS, E‐Nose, and Statistical Analysis. European Journal of Lipid Science and Technology 2020, 122 (3) https://doi.org/10.1002/ejlt.201900212
    10. Tianze Wang, Dawei Zhen, Jia Tan, Jianchun Xie, Jie Cheng, Jian Zhao. Characterization of initial reaction intermediates in heated model systems of glucose, glutathione, and aliphatic aldehydes. Food Chemistry 2020, 305 , 125482. https://doi.org/10.1016/j.foodchem.2019.125482
    11. Franco Doro, Niels Akeroyd, Franc Schiet, Anubhav Narula. The Prins Reaction in the Fragrance Industry: 100th Anniversary (1919–2019). Angewandte Chemie 2019, 131 (22) , 7248-7253. https://doi.org/10.1002/ange.201814470
    12. Franco Doro, Niels Akeroyd, Franc Schiet, Anubhav Narula. The Prins Reaction in the Fragrance Industry: 100th Anniversary (1919–2019). Angewandte Chemie International Edition 2019, 58 (22) , 7174-7179. https://doi.org/10.1002/anie.201814470
    13. Joseph William Holloway, Jianping Wu. Flavor Intrinsic Character. 2019, 151-200. https://doi.org/10.1007/978-981-13-7860-7_7
    14. Jane K. Parker. Meat. 2017, 29-30. https://doi.org/10.1007/978-3-319-26932-0_10
    15. D. Frank, Y. Oytam, J. Hughes. Sensory Perceptions and New Consumer Attitudes to Meat. 2017, 667-698. https://doi.org/10.1016/B978-0-08-100593-4.00028-X
    16. Mónica Flores. The Eating Quality of Meat. 2017, 383-417. https://doi.org/10.1016/B978-0-08-100694-8.00013-3
    17. C. Cerny. The role of sulfur chemistry in thermal generation of aroma. 2015, 187-210. https://doi.org/10.1016/B978-1-78242-103-0.00009-6
    18. Angelina Sansone-Land, Gary R. Takeoka, Charles F. Shoemaker. Volatile constituents of commercial imported and domestic black-ripe table olives (Olea europaea). Food Chemistry 2014, 149 , 285-295. https://doi.org/10.1016/j.foodchem.2013.10.090
    19. Shiqing Song, Qi Tang, Khizar Hayat, Eric Karangwa, Xiaoming Zhang, Zuobing Xiao. Effect of enzymatic hydrolysis with subsequent mild thermal oxidation of tallow on precursor formation and sensory profiles of beef flavours assessed by partial least squares regression. Meat Science 2014, 96 (3) , 1191-1200. https://doi.org/10.1016/j.meatsci.2013.11.008
    20. Hoa Van Ba, Touseef Amna, Inho Hwang. Significant influence of particular unsaturated fatty acids and pH on the volatile compounds in meat-like model systems. Meat Science 2013, 94 (4) , 480-488. https://doi.org/10.1016/j.meatsci.2013.04.029
    21. Shiqing Song, Xiaoming Zhang, Zuobing Xiao, Yunwei Niu, Khizar Hayat, Karangwa Eric. Contribution of oxidized tallow to aroma characteristics of beeflike process flavour assessed by gas chromatography–mass spectrometry and partial least squares regression. Journal of Chromatography A 2012, 1254 , 115-124. https://doi.org/10.1016/j.chroma.2012.07.056
    22. Valentina Vasta, Valentina Ventura, Giuseppe Luciano, Valeria Andronico, Renato I. Pagano, Manuel Scerra, Luisa Biondi, Marcella Avondo, Alessandro Priolo. The volatile compounds in lamb fat are affected by the time of grazing. Meat Science 2012, 90 (2) , 451-456. https://doi.org/10.1016/j.meatsci.2011.09.006
    23. Yongxia Xu, Qingchan Chen, Shengjiao Lei, Peng Wu, Gang Fan, Xiaoyun Xu, Siyi Pan. Effects of lard on the formation of volatiles from the Maillard reaction of cysteine with xylose. Journal of the Science of Food and Agriculture 2011, 91 (12) , 2241-2246. https://doi.org/10.1002/jsfa.4445
    24. T. T. N. Dinh, J. R. Blanton, D. G. Riley, C. C. Chase, S. W. Coleman, W. A. Phillips, J. C. Brooks, M. F. Miller, L. D. Thompson. Intramuscular fat and fatty acid composition of longissimus muscle from divergent pure breeds of cattle. Journal of Animal Science 2010, 88 (2) , 756-766. https://doi.org/10.2527/jas.2009-1951
    25. J.S. Elmore, D.S. Mottram. Flavour development in meat. 2009, 111-146. https://doi.org/10.1533/9781845695439.1.111
    26. J.D. Hepworth, B.M. Heron. Thiopyrans and their Benzo Derivatives. 2008, 727-954. https://doi.org/10.1016/B978-008044992-0.00610-6
    27. V. Vasta, A. Priolo. Ruminant fat volatiles as affected by diet. A review. Meat Science 2006, 73 (2) , 218-228. https://doi.org/10.1016/j.meatsci.2005.11.017
    28. J. Stephen Elmore, Donald S. Mottram. The role of lipid in the flavour of cooked beef. 2006, 375-378. https://doi.org/10.1016/S0167-4501(06)80089-0
    29. A. Arnoldi. The Maillard reaction as a source of off-flavours. 2003, 162-175. https://doi.org/10.1533/9781855736979.162
    30. . Current Awareness. Flavour and Fragrance Journal 2000, 362-369. https://doi.org/10.1002/1099-1026(200009/10)15:5<362::AID-FFJ899>3.0.CO;2-A
    31. Donald S. Mottram. The Maillard Reaction: Source of Flavour in Thermally Processed Foods. , 269-283. https://doi.org/10.1007/978-3-540-49339-6_12

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    You’ve supercharged your research process with ACS and Mendeley!

    STEP 1:
    Click to create an ACS ID

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    MENDELEY PAIRING EXPIRED
    Your Mendeley pairing has expired. Please reconnect