Citation: LI Mei, YANG Zhaoxia, CHEN Hualei, HAO Junguang. Determination of sweet flavor compounds in wort and beer by ultra-high performance liquid chromatography-tandem mass spectrometry[J]. Chinese Journal of Chromatography, ;2016, 34(3): 258-262. doi: 10.3724/SP.J.1123.2015.10042 shu

Determination of sweet flavor compounds in wort and beer by ultra-high performance liquid chromatography-tandem mass spectrometry

1.
State Key Laboratory of Biological Fermentation Engineering of Beer, Tsingtao Brewery Co. Ltd., Qingdao 266100, China

Received Date: 28 October 2015

Fund Project: 国家高新技术研究发展("863"计划)项目(2013AA102109) ("863"计划)项目(2013AA102109)青岛创业创新领军人才计划项目(13-cx-15). (13-cx-15)

An ultra-high performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS) method was developed for the simultaneous determination of three sweet flavor compounds in wort and beer including 2,5-dimethyl-4-hydroxy-3(2H)-furanone (DMHF), 2(or 5)-ethyl-5(or 2)-methyl-4-hydroxy-3(2H)-furanone (EMHF) and 2-acetylpyrrole (2-AP). C₁₈solid-phase extraction (SPE) tubes were used to clean up samples. The analysis was performed on an ACQUITY UPLC HSS T3 column (50 mm×2.1 mm, 1.8 μm) with gradient elution of mobile phase A (water containing 0.1%(v/v) formic acid) and mobile phase B (acetonitrile containing 0.01%(v/v) formic acid). These three compounds were identified by retention times in positive mode with multiple reaction monitoring (MRM) mode. Good linearities were observed (R²>0.999) in the concentrations less than 1000 μ g/L. The recoveries were in the range of 74.3%-86.7%. The relative standard deviations (RSDs) (n=6) were between 4.8% and 7.3%. Both DMHF and EMHF can be produced by yeast during fermentation, which resulted in apparently higher concentrations in beer than the relevant wort. The concentrations of these compounds may be much higher in certain beer, such as the India Pale (IPA) beer. The method with simple and selective pretreatment measures was sensitive, accurate and reproducible. It may be applied for the quality control in breweries.
- ultra-high performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS),
- furanone,
- 2-acetylpyrrole,
- beer,
- wort
1. [1]
  [1] Lee S M, Jo Y J, Kim Y S. J Agric Food Chem, 2010, 58(5): 3116
2. [2]
  [2] Vandecan S M G, Daems N, Schouppe N, et al. J Am Soc Brew Chem, 2011, 69(3): 150
3. [3]
  [3] Coghe S, Adriaenssens B, Leonard S, et al. J Am Soc Brew Chem, 2004, 62(2): 79
4. [4]
  [4] Hayashida Y, Slaughter J C. Bio Let, 1997, 19: 429
5. [5]
  [5] Mackie A E, Slaughter J C. J Ins Brew, 2002, 108(3): 336
6. [6]
  [6] Sakuma S, Kobayashi K, Tayama T, et al. J Am Soc Brew Chem, 1996, 54(1): 37
7. [7]
  [7] Schutter D P, Saison D, Delvaux F, et al. J Chromatogr A, 2008, 1179(2): 75
8. [8]
  [8] Vandecan S M G, Saison D, Schouppe N, et al. Anal Chim Acta, 2010, 671(1): 55
9. [9]
  [9] Channell G A, Yahya H, Cook D J. J Am Soc Brew Chem, 2010, 68(4): 175
10. [10]
  [10] Dong L, Piao Y Z, Zhang X, et al. J Food Res Int, 2013, 51(2): 783
11. [11]
  [11] Liu X, Jiang W, Zhao S X, et al. Food and Fermentation Industries, 2013, 40(8): 171 刘翔, 江伟, 赵树欣, 等. 食品与发酵工业, 2013, 40(8): 171
12. [12]
  [12] Hu D, Chen C S, Zhang T T, et al. Science and Technology of Food Industry, 2012, 33(22): 162 呼德, 陈存社, 张甜甜, 等. 食品工业科技, 2012, 33(22): 162
13. [13]
  [13] Tang K T, Lin Z P, Liu X, et al. Beer Science and Technology, 2013(11): 18 唐坤甜, 林智平, 刘翔, 等. 啤酒科技, 2013(11): 18
1. [1]
  Zunxiang Zeng , Yuling Hu , Yufei Hu , Hua Xiao . Analysis of Plant Essential Oils by Supercritical CO₂Extraction with Gas Chromatography-Mass Spectrometry: An Instrumental Analysis Comprehensive Experiment Teaching Reform. University Chemistry, 2024, 39(3): 274-282. doi: 10.3866/PKU.DXHX202309069
2. [2]
  Yongqing Kuang , Jie Liu , Jianjun Feng , Wen Yang , Shuanglian Cai , Ling Shi . Experimental Design for the Two-Step Synthesis of Paracetamol from 4-Hydroxyacetophenone. University Chemistry, 2024, 39(8): 331-337. doi: 10.12461/PKU.DXHX202403012
3. [3]
  Xiyuan Zhang , Rui Dong , Yang Yang , Jiapeng Ding , Zhiwei Miao . Palladium-Catalyzed Tandem Cyclization of 4-Vinylbenzoxazinone and Indene-2-carbaldehyde: A Comprehensive Organic Chemistry Experiment. University Chemistry, 2025, 40(9): 361-367. doi: 10.12461/PKU.DXHX202410062
4. [4]
  Yifan Xie , Liyun Yao , Ruolin Yang , Yuxing Cai , Yujie Jin , Ning Li . Exploration and Practice of Online and Offline Hybrid Teaching Mode in High-Performance Liquid Chromatography Experiment. University Chemistry, 2025, 40(11): 100-107. doi: 10.12461/PKU.DXHX202412133
5. [5]
  Zhuoming Liang , Ming Chen , Zhiwen Zheng , Kai Chen . Multidimensional Studies on Ketone-Enol Tautomerism of 1,3-Diketones By ¹H NMR. University Chemistry, 2024, 39(7): 361-367. doi: 10.3866/PKU.DXHX202311029
6. [6]
  Yongzhi LI , Han ZHANG , Gangding WANG , Yanwei SUI , Lei HOU , Yaoyu WANG . A two-dimensional metal-organic framework for the determination of nitrofurantoin and nitrofurazone in aqueous solution. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 245-253. doi: 10.11862/CJIC.20240307
7. [7]
  Yanhui Zhong , Ran Wang , Zian Lin . Analysis of Halogenated Quinone Compounds in Environmental Water by Dispersive Solid-Phase Extraction with Liquid Chromatography-Triple Quadrupole Mass Spectrometry. University Chemistry, 2024, 39(11): 296-303. doi: 10.12461/PKU.DXHX202402017
8. [8]
  Ke Qiu , Fengmei Wang , Mochou Liao , Kerun Zhu , Jiawei Chen , Wei Zhang , Yongyao Xia , Xiaoli Dong , Fei Wang . A Fumed SiO₂-based Composite Hydrogel Polymer Electrolyte for Near-Neutral Zinc-Air Batteries. Acta Physico-Chimica Sinica, 2024, 40(3): 2304036-0. doi: 10.3866/PKU.WHXB202304036
9. [9]
  Mingyang Men , Jinghua Wu , Gaozhan Liu , Jing Zhang , Nini Zhang , Xiayin Yao . Sulfide Solid Electrolyte Synthesized by Liquid Phase Approach and Application in All-Solid-State Lithium Batteries. Acta Physico-Chimica Sinica, 2025, 41(1): 100004-0. doi: 10.3866/PKU.WHXB202309019
10. [10]
  Lihui Jiang , Wanrong Dong , Hua Yang , Yongqing Xia , Hongjian Peng , Jun Yuan , Xiaoqian Hu , Zihan Zeng , Yingping Zou , Yiming Luo . Study on Extraction of p-Hydroxyacetophenone. University Chemistry, 2024, 39(11): 259-268. doi: 10.12461/PKU.DXHX202402056
11. [11]
  Anqiu LIU , Long LIN , Dezhi ZHANG , Junyu LEI , Kefeng WANG , Wei ZHANG , Junpeng ZHUANG , Haijun HAO . Synthesis, structures, and catalytic activity of aluminum and zinc complexes chelated by 2-((2,6-dimethylphenyl)amino)ethanolate. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 791-798. doi: 10.11862/CJIC.20230424
12. [12]
  Kangmin Wang , Liqiu Wan , Jingyu Wang , Chunlin Zhou , Ke Yang , Liang Zhou , Bijin Li . Multifunctional 2-(2′-hydroxyphenyl)benzoxazoles: Ready synthesis, mechanochromism, fluorescence imaging, and OLEDs. Chinese Chemical Letters, 2024, 35(10): 109554-. doi: 10.1016/j.cclet.2024.109554
13. [13]
  Jiayao Wang , Guixu Pan , Ning Wang , Shihan Wang , Yaolin Zhu , Yunfeng Li . Preparation of donor-π-acceptor type graphitic carbon nitride photocatalytic systems via molecular level regulation for high-efficient H₂O₂ production. Acta Physico-Chimica Sinica, 2025, 41(12): 100168-0. doi: 10.1016/j.actphy.2025.100168
14. [14]
  Yue Zhao , Yanfei Li , Tao Xiong . Copper Hydride-Catalyzed Nucleophilic Additions of Unsaturated Hydrocarbons to Aldehydes and Ketones. University Chemistry, 2024, 39(4): 280-285. doi: 10.3866/PKU.DXHX202309001
15. [15]
  Liangzhen Hu , Li Ni , Ziyi Liu , Xiaohui Zhang , Bo Qin , Yan Xiong . A Green Chemistry Experiment on Electrochemical Synthesis of Benzophenone. University Chemistry, 2024, 39(6): 350-356. doi: 10.3866/PKU.DXHX202312001
16. [16]
  Guojie Xu , Fang Yu , Yunxia Wang , Meng Sun . Introduction to Metal-Catalyzed β-Carbon Elimination Reaction of Cyclopropenones. University Chemistry, 2024, 39(8): 169-173. doi: 10.3866/PKU.DXHX202401060
17. [17]
  Yuexiang Liu , Xiangqiao Yang , Tong Lin , Guantian Yang , Xiaoyong Xu , Bubing Zeng , Zhong Li , Weiping Zhu , Xuhong Qian . Efficient continuous synthesis of 2-[3-(trifluoromethyl)phenyl]malonic acid, a key intermediate of Triflumezopyrim, coupling with esterification-condensation-hydrolysis. Chinese Chemical Letters, 2025, 36(1): 109747-. doi: 10.1016/j.cclet.2024.109747
18. [18]
  Qiang HU , Zhiqi CHEN , Zhong CHEN , Xu WANG , Weina WU . Pyridinium-chalcone-based ClO^- fluorescent probe: Preparation and biological imaging applications. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1789-1795. doi: 10.11862/CJIC.20250086
19. [19]
  Runjie Li , Hang Liu , Xisheng Wang , Wanqun Zhang , Wanqun Hu , Kaiping Yang , Qiang Zhou , Si Liu , Pingping Zhu , Wei Shao . 氨基酸的衍生及手性气相色谱分离创新实验. University Chemistry, 2025, 40(6): 286-295. doi: 10.12461/PKU.DXHX202407059
20. [20]
  Zhaoyang WANG , Chun YANG , Yaoyao Song , Na HAN , Xiaomeng LIU , Qinglun WANG . Lanthanide(Ⅲ) complexes derived from 4′-(2-pyridyl)-2, 2′∶6′, 2″-terpyridine: Crystal structures, fluorescent and magnetic properties. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1442-1451. doi: 10.11862/CJIC.20240114

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(796)
HTML views(79)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142