Abstract
Higher alcohols are important flavor compounds in alcoholic beverages. A new method was developed to determinate the main higher alcohols based on dispersive liquid-liquid microextraction (DLLME) coupled with GC/MS. Huangjiu was selected as an example to develop the method. The optimal DLLME parameters were acquired: the sample was diluted one time with water, no pH adjustment was required, 600 μL dichloromethane as extraction solvent, 1.5 mL acetonitrile as dispersant, 3.5 mL of sample volume, 1 min of extraction time and no salt addition. The performance of the method was satisfactory. The results obtained from DLLME were consistent with those from head space solid phase microextration (HS-SPME) and static headspace (SHS). In addition, DLLME is simpler and more time-saving compared with HS-SPME and SHS. These results indicated that the present method is satisfactory and suitable for determination of higher alcohols in Huangjiu, especially for routine inspection and batch analysis.
Similar content being viewed by others
References
Adlnasab L, Ebrahimzadeh H, Yamini Y (2012) A three phase dispersive liquid-liquid microextraction technique for the extraction of antibiotics in milk. Microchim Acta 179:179–184
Almeida C, Fernandes JO, Cunha SC (2012) A novel dispersive liquid–liquid microextraction (DLLME) gas chromatography-mass spectrometry (GC–MS) method for the determination of eighteen biogenic amines in beer. Food Control 25:380–388
Arroyo-Manzanares N, Gámiz-Gracia L, García-Campaña AM (2012) Determination of ochratoxin a in wines by capillary liquid chromatography with laser induced fluorescence detection using dispersive liquid–liquid microextraction. Food Chem 135:368–372
Barboni T, Venturini N, Paolini J, Desjobert J-M, Chiaramonti N, Costa J (2010) Characterisation of volatiles and polyphenols for quality assessment of alcoholic beverages prepared from Corsican Myrtus communis berries. Food Chem 122:1304–1312
Bolaños PP, Romero-González R, Frenich AG, Vidal JLM (2008) Application of hollow fibre liquid phase microextraction for the multiresidue determination of pesticides in alcoholic beverages by ultra-high pressure liquid chromatography coupled to tandem mass spectrometry. J Chromatogr A 1208:16–24
Casale M, Armanino C, Casolino C, Oliveros C, oacute, n C, Forina M (2006) A chemometrical approach for vinegar classification by headspace mass spectrometry of volatile compounds Food Sci Technol Res 12:223–230 doi:https://doi.org/10.3136/fstr.12.223
Chen S, Xu Y, Qian MC (2013) Aroma characterization of Chinese Rice wine by gas chromatography–Olfactometry, chemical quantitative analysis, and aroma reconstitution. J Agric Food Chem 61:11295–11302
de-la Fuente-Blanco A, Sáenz-Navajas M-P, Ferreira V (2016) On the effects of higher alcohols on red wine aroma. Food Chem 210:107–114
Ehsani M, Fernández MR, Biosca JA, Dequin S (2009) Reversal of coenzyme specificity of 2,3-butanediol dehydrogenase from Saccharomyces cerevisae and in vivo functional analysis. Biotechnol Bioeng 104:381–389
Fan Y, Liu S, Xie Q (2014) Rapid determination of phthalate esters in alcoholic beverages by conventional ionic liquid dispersive liquid–liquid microextraction coupled with high performance liquid chromatography. Talanta 119:291–298
Farajzadeh MA, Sorouraddin SM, Mogaddam MRA (2014) Liquid phase microextraction of pesticides: a review on current methods. Microchim Acta 181:829–851
Fariña L, Boido E, Carrau F, Dellacassa E (2007) Determination of volatile phenols in red wines by dispersive liquid–liquid microextraction and gas chromatography–mass spectrometry detection. J Chromatogr A 1157:46–50
Fontana AR, Muñoz de Toro M, Altamirano JC (2011) One-step derivatization and preconcentration microextraction technique for determination of bisphenol A in beverage samples by gas chromatography−mass spectrometry. Journal of agricultural and food chemistry 59:3559–3565
Fontana A, Rodríguez I, Cela R (2018) Dispersive liquid–liquid microextraction and gas chromatography accurate mass spectrometry for extraction and non-targeted profiling of volatile and semi-volatile compounds in grape marc distillates. J Chromatogr A 1546:36–45
Garrett JM (2008) Amino acid transport through the Saccharomyces cerevisiae Gap1 permease is controlled by the Ras/cAMP pathway. Int J Biochem Cell Biol 40:496–502
Hashemi P, Raeisi F, Ghiasvand AR, Rahimi A (2010) Reversed-phase dispersive liquid–liquid microextraction with central composite design optimization for preconcentration and HPLC determination of oleuropein. Talanta 80:1926–1931
Jiang T-F, Liang T-T, Yue M-E, Wang Y-H, Lv Z-H (2016) Surfactant-free microemulsion reinforced hollow-fiber liquid-phase microextraction combined with micellar electrokinetic capillary chromatography for detection of phthalic acid esters in beverage and urine. Food Anal Methods 9:7–15
Jofré VP, Assof MV, Fanzone ML, Goicoechea HC, Martínez LD, Silva MF (2010) Optimization of ultrasound assisted-emulsification-dispersive liquid–liquid microextraction by experimental design methodologies for the determination of sulfur compounds in wines by gas chromatography–mass spectrometry. Anal Chim Acta 683:126–135
Peinado RA, Moreno JA, Muñoz D, Medina M, Moreno J (2004) Gas chromatographic quantification of major volatile compounds and Polyols in wine by direct injection. J Agric Food Chem 52:6389–6393
Pinho O, Ferreira IMPLVO, Santos LHMLM (2006) Method optimization by solid-phase microextraction in combination with gas chromatography with mass spectrometry for analysis of beer volatile fraction. J Chromatogr A 1121:145–153
Priddy SA, Hanley TR, Effler WT (1999) Separation optimization for the recovery of phenyl ethyl alcohol. In: Davison BH, Finkelstein M (eds) Twentieth symposium on biotechnology for fuels and chemicals: presented as volumes 77–79 of applied biochemistry and biotechnology proceedings of the twentieth symposium on biotechnology for fuels and chemicals held may 3–7, 1998, Gatlinburg. Tennessee. Humana Press, Totowa, pp 473–484
Que F, Mao L, Zhu C, Xie G (2006) Antioxidant properties of Chinese yellow wine, its concentrate and volatiles. LWT Food Sci Technol 39:111–117
Rezaee M, Assadi Y, Milani Hosseini M-R, Aghaee E, Ahmadi F, Berijani S (2006) Determination of organic compounds in water using dispersive liquid–liquid microextraction. Journal of chromatography a 1116:1–9
Rodríguez-Cabo T, Rodríguez I, Ramil M, Cela R (2011) dispersive liquid–liquid microextraction using non-chlorinated, lighter than water solvents for gas chromatography–mass spectrometry determination of fungicides in wine. J Chromatogr A 1218:6603–6611
Rodríguez-Cabo T, Rodríguez I, Ramil M, Silva A, Cela R (2016) Multiclass semi-volatile compounds determination in wine by gas chromatography accurate time-of-flight mass spectrometry. J Chromatogr A 1442:107–117
Sehovic D, Tominac VP, Maric V (2007) On higher alcohols in wine. Period Biol 109:205–217
Soria AC, García-Sarrió MJ, Sanz ML (2015) Volatile sampling by headspace techniques. TrAC trends in analytical chemistry 71:85–99
Souza-Silva ÉA, Gionfriddo E, Pawliszyn J (2015) a critical review of the state of the art of solid-phase microextraction of complex matrices II. Food eanalysis. TrAC Trends Anal Chem 71:236–248
Stupak M, Kocourek V, Kolouchova I, Hajslova J (2017) Rapid approach for the determination of alcoholic strength and overall quality check of various spirit drinks and wines using GC–MS. Food Control 80:307–313
Swiegers JH, Pretorius IS (2005) Yeast modulation of wine flavor. In: advances in applied microbiology, vol 57. Academic press, pp 131–175
Vinas P, Campillo N, Lopez-Garcia I, Hernandez-Cordoba M (2014) Dispersive liquid-liquid microextraction in food analysis. A critical review. Anal Bioanal Chem 406:2067–2099
Wu Q, Wang C, Liu Z, Wu C, Zeng X, Wen J, Wang Z (2009) dispersive solid-phase extraction followed by dispersive liquid–liquid microextraction for the determination of some sulfonylurea herbicides in soil by high-performance liquid chromatography. J Chromatogr A 1216:5504–5510
Xiao Q, Yu C, Xing J, Hu B (2006) Comparison of headspace and direct single-drop microextraction and headspace solid-phase microextraction for the measurement of volatile sulfur compounds in beer and beverage by gas chromatography with flame photometric detection. J Chromatogr A 1125:133–137
Xiong J, Hu B (2008) Comparison of hollow fiber liquid phase microextraction and dispersive liquid–liquid microextraction for the determination of organosulfur pesticides in environmental and beverage samples by gas chromatography with flame photometric detection. J Chromatogr A 1193:7–18
Xu Y, Wang D, Fan WL, Mu XQ, Chen J (2010) Traditional Chinese biotechnology. In: Tsao GT, Ouyang P, Chen J (eds) Biotechnology in China II: chemicals. Energy and Environment. Springer, Berlin Heidelberg, Berlin, Heidelberg, pp 189–233
Xu X et al (2011) Determination of formaldehyde in beverages using microwave-assisted derivatization and ionic liquid-based dispersive liquid–liquid microextraction followed by high-performance liquid chromatography. Talanta 85:2632–2638
Xu E et al (2015) Characterization of volatile flavor compounds in Chinese rice wine fermented from enzymatic extruded rice. J Food Sci 80:1476–1489
Yan HY, Wang H (2013) Recent development and applications of dispersive liquid-liquid microextraction. J Chromatogr A 1295:1–15
Yilmaz E, Soylak M (2016) Latest trends, green aspects, and innovations in liquid-phase based microextraction techniques: a review. Turk J Chem 40:868–893. https://doi.org/10.3906/kim-1605-26
Zhu J, Shi J, Lu Y, Liu L, Liu Y (2016) Application of strains of Geotrichum spp. to decrease higher alcohols and to increase esters. J Inst Brew 122:147–155
Funding
The authors are grateful for the financial support from National Key Research and Development Program of China (No. 2017YFD0400103, 2016YFD0400504, 2018YFD0400400), National Natural Science Foundation of China (No. 31571823), Natural Science Foundation of Jiangsu Province, China (No. BK20161293, BK20171405), the National First-Class Discipline Program of Light Industry Technology and Engineering (LITE2018-13), the Fundamental Research Funds for the Central Universities (JUSRP11810), the funding from Beijing Advanced Innovation Center for Food Nutrition and Human Health of Beijing Technology and Business University(20161041).
Author information
Authors and Affiliations
Corresponding authors
Ethics declarations
Conflict of Interest
Zhilei Zhou declares that he has no conflict of interest. Wei Ni declares that she has no conflict of interest. Zhongwei Ji declares that he has no conflict of interest. Shuangping Liu declares that he has no conflict of interest. Xiao Han declares that she has no conflict of interest. Xiuting Li declares that she has no conflict of interest. Jian Mao declares that he has no conflict of interest.
Ethical Approval
This article does not contain any studies with human participants or animals performed by any of the authors.
Informed Consent
Not applicable.
Additional information
Publisher’s Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Electronic supplementary material
ESM 1
(DOCX 20 kb)
Rights and permissions
About this article
Cite this article
Zhou, Z., Ni, W., Ji, Z. et al. Development of a Rapid Method for Determination of Main Higher Alcohols in Fermented Alcoholic Beverages Based on Dispersive Liquid-Liquid Microextraction and Gas Chromatography-Mass Spectrometry. Food Anal. Methods 13, 591–600 (2020). https://doi.org/10.1007/s12161-019-01668-4
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12161-019-01668-4