The role of oak wood in the mint and floral notes of whisky: identification of common terpenoids by aromatic fractionation
DOI:
https://doi.org/10.58430/jib.v129i1.8Keywords:
whisky maturation, oak wood, floral aromas, mint aromas, terpenoidsAbstract
Understanding the development of the whisky aroma during maturation in oak casks provides a rational basis for improvements in product quality. While oak wood is an important contributor to the spicy, toasted, and smoky aromatic notes, limited studies have focused on its role in floral and mint notes of matured whiskies. However, achieving consistent flavour profiles remains difficult since the odorant molecules are mostly present in low concentration. A semi-preparative ultra-high-performance liquid chromatography (UHPLC) method was applied to whisky and oak wood extracts and used to isolate fractions characterised by floral and mint aromas. To investigate the contribution of terpenoids in these floral and fresh fragrances, a similar analytical process was applied on solutions of targeted reference compounds. This approach, coupled to gas-chromatography/mass-spectrometry analyses, indicated the presence of terpenoids in the fractions of interest as well as selective separation according to chemical structure (i.e., monoterpenes, monoterpenols, ketone monoterpenes, and C13-norisoprenoids). This approach resulted in the detection of respectively, ten and seven new terpenoids in whisky and oak wood. To the best of our knowledge, piperitone, mint lactones, and β-damascone are reported for the first time in whisky and oak wood. Even though raw material, fermentation and distillation processes largely contribute to the presence of terpenoids in new make spirit, this study provides evidence that oak wood enhances floral and mint notes in whisky through chemical and sensory interactions taking place during maturation.
Downloads
References
Adams RP.2007. Identification of essential oil components by gas chromatography/mass spectrometry (Vol. 456, pp. 544-545). 4th Edition Allured Publishing Corporation, Carol Stream.
Black CA, Parker M, Siebert TE, Capone DL, Francis, IL. 2015. Terpenoids and their role in wine flavour: recent advances. Aust J Grape Wine Res 21:582-600. DOI: https://doi.org/10.1111/ajgw.12186
Boothroyd E, Linforth RS, Jack F, Cook DJ. 2014. Origins of the perceived nutty character of new‐make malt whisky spirit. J Inst Brew 120:16-22. DOI: https://doi.org/10.1002/jib.103
Broom, D. 2014. Whisky: The Manual. Hachette, UK.
Burlacu E, Nisca A,Tanase C. 2020. A comprehensive review of phytochemistry and biological activities of Quercus species. Forests 11:10.3390/f11090904 DOI: https://doi.org/10.3390/f11090904
Buśko M, Jeleń H, Góral T, Chmielewski J, Stuper K, Szwajkowska-Michałek L, ..., Perkowski J. 2010. Volatile metabolites in various cereal grains. Food Addit Contam, 27:1574-1581. DOI: https://doi.org/10.1080/19440049.2010.506600
Câmara JS, Marques JC, Perestrelo RM, Rodrigues F, Oliveira L, Andrade, Caldeira M. 2007. Comparative study of the whisky aroma profile based on headspace solid phase microextraction using different fibre coatings. J Chromatogr A 1150:198-207. DOI: https://doi.org/10.1016/j.chroma.2006.09.014
Conner JM, Paterson A, Piggott JR. 1993. Changes in wood extractives from oak cask staves through maturation of Scotch malt whisky. J Sci Food Agric 62:169-174. DOI: https://doi.org/10.1002/jsfa.2740620210
Creyaufmüller FC, Chassignet I, Delb H, Dounavi A, Gailing O, Leinemann L, ..., Vornam, B (2018). Terpene Synthase Genes in Quercus robur–Gene Characterization, Expression and Resulting Terpenes Due to Cockchafer Feeding. Front Plant Sci 9:1753. DOI: https://doi.org/10.3389/fpls.2018.01753
Davies NW. 1990. Gas chromatographic retention indices of monoterpenes and sesquiterpenes on methyl silicon and Carbowax 20M phases. J Chromatogr A 503:1-24. DOI: https://doi.org/10.1016/S0021-9673(01)81487-4
Dudareva N, Pichersky E. 2006. Floral scent metabolic pathways: their regulation and evolution. In Biology of floral scent (pp. 55-78). Boca Raton, FL: CRC Press. DOI: https://doi.org/10.1201/9781420004007.sec2
Escudero A, Campo E, Fariña L, Cacho J, Ferreira V. 2007. Analytical characterization of the aroma of five premium red wines. Insights into the role of odor families and the concept of fruitiness of wines. J Agric Food Chem 55:4501-4510. DOI: https://doi.org/10.1021/jf0636418
Esteban‐Decloux M, Tano N. G. C. R, Grangeon H. 2022. Simulation of the behaviour of volatile compounds during batch multi‐stage distillation of whisky. J Inst Brew 128:171-187. DOI: https://doi.org/10.1002/jib.704
Ferreira V, Hernández-Orte P, Escudero A, Lopez R, Cacho J .1999. Semipreparative reversed-phase liquid chromatographic fractionation of aroma extracts from wine and other alcoholic beverages. J Chromatogr A 864:77-88. DOI: https://doi.org/10.1016/S0021-9673(99)01004-3
Frérot E, Bagnoud A, Vuilleumier C .2002. Menthofurolactone: a new p‐menthane lactone in Mentha piperita L.: analysis, synthesis and olfactory properties. Flavour Fragr J 17:218-226. DOI: https://doi.org/10.1002/ffj.1089
Ghadiriasli R, Wagenstaller M, Buettner A.2018. Identification of odorous compounds in oak wood using odor extract dilution analysis and two-dimensional gas chromatography-mass spectrometry/olfactometry. Anal Bioanal Chem 410:6595-6607. DOI: https://doi.org/10.1007/s00216-018-1264-7
Ghadiriasli R, Mahmoud MA, Wagenstaller M, van de Kuilen JW, Buettner A. 2021. Chemo-sensory characterization of aroma active compounds of native oak wood in relation to their geographical origins. Int Food Res J 150:110776. DOI: https://doi.org/10.1016/j.foodres.2021.110776
González‐Robles IW, Cook DJ. 2016. The impact of maturation on concentrations of key odour active compounds which determine the aroma of tequila. J Inst Brew 122:369-380. DOI: https://doi.org/10.1002/jib.333
Gonzalez-Robles IW. 2018. Flavour Interactions between the estery and mature/woody characters of whisky, bourbon & tequila. PhD thesis, University of Nottingham.
Hjelmeland AK, Ebeler SE. 2015. Glycosidically bound volatile aroma compounds in grapes and wine: a review. Am J Enol Vitic 66:1-11. DOI: https://doi.org/10.5344/ajev.2014.14104
Hock R, Benda I, Schreier P. 1984. Formation of terpenes by yeasts during alcoholic fermentation. Zeitschrift für Lebensmittel-Untersuchung und-Forschung, 179:450-452. DOI: https://doi.org/10.1007/BF01043423
Högnadóttir Á, Rouseff RL. 2003. Identification of aroma active compounds in orange essence oil using gas chromatography–olfactometry and gas chromatography–mass spectrometry. J Chromatogr A 998:201-211. DOI: https://doi.org/10.1016/S0021-9673(03)00524-7
Jackson, M. 2017. Whisky: The definitive world guide. Dorling Kindersley Ltd.
Jordão AM, Ricardo-da-Silva JM, Laureano O, Adams A, Demyttenaere J, Verhé R, De Kimpe N. 2006. Volatile composition analysis by solid-phase microextraction applied to oak wood used in cooperage (Quercus pyrenaica and Quercus petraea): effect of botanical species and toasting process. J Wood Sci 52:514-521. DOI: https://doi.org/10.1007/s10086-005-0796-6
Jordan MJ, Margaria CA, Shaw PE, Goodner KL. 2002. Aroma active components in aqueous kiwi fruit essence and kiwi fruit puree by GC-MS and multidimensional GC/GC-O. J Agric Food Chem 50: 5386-5390. DOI: https://doi.org/10.1021/jf020297f
Khan M, Mousa AA, Syamasundar KV, Alkhathlan, HZ. 2012. Determination of chemical constituents of leaf and stem essential oils of Artemisia monosperma from central Saudi Arabia. Nat Prod Commun, 7, 1934578X1200700829. DOI: https://doi.org/10.1177/1934578X1200700829
Klesk K, Qian M, Martin, RR.2004. Aroma extract dilution analysis of cv. Meeker (Rubus idaeus L.) red raspberries from Oregon and Washington. J Agric Food Chem 52: 5155-5161. DOI: https://doi.org/10.1021/jf0498721
Kovats VE. 1958. Gas‐chromatographische charakterisierung organischer verbindungen. Teil 1: retentionsindices aliphatischer halogenide, alkohole, aldehyde und ketone. Helv. Chim. Acta 41:1915-1932. DOI: https://doi.org/10.1002/hlca.19580410703
LaRoe EG, Shipley PA. 1970. Whiskey composition: formation of alpha-and beta-ionone by the thermal decomposition of beta-carotene. J Agric Food Chem 18:174-175. DOI: https://doi.org/10.1021/jf60167a012
Lee KYM, Paterson A, Piggott JR, Richardson GD.2001. Origins of flavour in whiskies and a revised flavour wheel: A review. J Inst Brew 107:287-313. DOI: https://doi.org/10.1002/j.2050-0416.2001.tb00099.x
Leffingwell, JC, Alford, ED. 2005. Volatile constituents of perique tobacco. Elec J Env Agricult Food Chem 4:899-915.
Loreto F. 2002. Distribution of isoprenoid emitters in the Quercus genus around the world: chemo-taxonomical implications and evolutionary considerations based on the ecological function of the trait. Perspect Plant Ecol Evol 5:185-192. DOI: https://doi.org/10.1078/1433-8319-00033
Loreto F, Bagnoli F, Fineschi, S. (2009). One species, many terpenes: matching chemical and biological diversity. Trends Plant Sci 14:416-420. DOI: https://doi.org/10.1016/j.tplants.2009.06.003
Lytra G, Tempere S, Revel GD, Barbe JC. 2012. Impact of perceptive interactions on red wine fruity aroma. J Agric Food Chem 60:12260-12269. DOI: https://doi.org/10.1021/jf302918q
Maarse, H. 1983. Volatile Compounds in Food. Quantitative Data. Division for Nutrition and Food Research (vol 2), TNO-CIVO Food Analysis Institute: Zeist, The Netherlands.
Mahmoud SS, Croteau RB. 2003. Menthofuran regulates essential oil biosynthesis in peppermint by controlling a downstream monoterpene reductase. PNAS 100 :14481-14486. DOI: https://doi.org/10.1073/pnas.2436325100
Masuda Y, Mori K, Hirohata T, Kuratsune M. 1966. Carcinogenesis in the esophagus III. Polycyclic aromatic hydrocarbons and phenols in whisky. Jpn J Cancer Res 57:549-557.
Marais J. 1983. Terpenes in the aroma of grapes and wines: a review. South African J Enol Vitic 4:49-58. https://doi.org/10.21548/4-2-2370 DOI: https://doi.org/10.21548/4-2-2370
Masson G, Baumes R, Puech JL, Razungles A. 1997. Demonstration of the presence of carotenoids in wood: quantitative study of cooperage oak. J Agric Food Chem 45:1649-1652. DOI: https://doi.org/10.1021/jf960668q
Mateo JJ, Jiménez M. 2000. Monoterpenes in grape juice and wines. J Chromatogr A 881(1-2):557-567. DOI: https://doi.org/10.1016/S0021-9673(99)01342-4
Mendes-Pinto MM. 2009. Carotenoid breakdown products the—norisoprenoids—in wine aroma. Arch Biochem Biophys 483:236-245. DOI: https://doi.org/10.1016/j.abb.2009.01.008
Michelozzi M.1999. Defensive roles of terpenoid mixtures in conifers. Acta bot Gall 146:73-84. DOI: https://doi.org/10.1080/12538078.1999.10515803
Nishimura K, Ohnishi M, Masuda M, Koga K, Matsuyama R. 1983. Reactions of wood components during maturation. In Piggott JR. (ed) Flavour of Distilled Beverages: Origin and Development (Food Science and Technology), Ellis Horwood.
Nishimura O. 1995. Identification of the characteristic odorants in fresh rhizomes of ginger (Zingiber officinale Roscoe) using aroma extract dilution analysis and modified multidimensional gas chromatography-mass spectroscopy. J Agric Food Chem 43:2941-2945. DOI: https://doi.org/10.1021/jf00059a031
Nonier MF, De Gaulejac NV, Vivas N, Vitry C. 2004. Characterization of carotenoids and their degradation products in oak wood. Incidence on the flavour of wood. Comptes Rendus Chimie 7: 689-698. DOI: https://doi.org/10.1016/j.crci.2004.03.010
Nonier MF, de Gaulejac NV, Vivas N, Vitry C. 2005. Glycosidically bound flavour compounds in Quercus petraea Liebl. wood. Flavour Fragr J 20:567-572. DOI: https://doi.org/10.1002/ffj.1488
Nykänen L. 1986. Formation and occurrence of flavor compounds in wine and distilled alcoholic beverages. Am J Enol Vitic 37:84-96. DOI: https://doi.org/10.5344/ajev.1986.37.1.84
Oller-Ruiz A, Viñas P, Campillo N, Fenoll J, Hernández-Córdoba M. 2017. Triple quadrupole mass spectrometry with Liquid Chromatography and Dispersive Liquid-Liquid Microextraction for the determination of monoterpenes in alcoholic drinks. Food Anal Methods, 10:3615-3622. DOI: https://doi.org/10.1007/s12161-017-0937-8
Picard M, Lytra G, Tempere S, Barbe JC, de Revel, G, Marchand S. 2016. Identification of piperitone as an aroma compound contributing to the positive mint notes perceived in aged red Bordeaux wines. J Agric Food Chem 64:451-460. DOI: https://doi.org/10.1021/acs.jafc.5b04869
Picard M, de Revel G, Marchand, S. 2017. First identification of three p-menthane lactones and their potential precursor, menthofuran, in red wines. Food Chem 217:294-302. DOI: https://doi.org/10.1016/j.foodchem.2016.08.070
Picard M, Franc C, De Revel G, Marchand S. 2018. Dual solid-phase and stir bar sorptive extraction combined with gas chromatography-mass spectrometry analysis provides a suitable tool for assaying limonene-derived mint aroma compounds in red wine. Anal Chim Acta 1001:168-178. DOI: https://doi.org/10.1016/j.aca.2017.11.074
Piggott JR, Conner JM.2003. Whiskies. P 239-262. In Lea AGH, Piggott JR (eds) Fermented Beverage Production. Springer, Boston, MA. DOI: https://doi.org/10.1007/978-1-4615-0187-9_11
Pineau B, Barbe JC, Van Leeuwen C, Dubourdieu D. 2009. Examples of perceptive interactions involved in specific ‘red-’ and ‘black-berry’ aromas in red wines. J Agric Food Chem 57: 3702-3708. DOI: https://doi.org/10.1021/jf803325v
Pino JA, Mesa J, Muñoz Y, Martí MP, Marbot R. 2005. Volatile components from mango (Mangifera indica L.) cultivars. J Agric Food Chem 53:2213-2223. DOI: https://doi.org/10.1021/jf0402633
Poisson L, Schieberle P. 2008. Characterization of the most odor-active compounds in an American Bourbon whisky by application of the aroma extract dilution analysis. J Agric Food Chem 56:5813-5819. DOI: https://doi.org/10.1021/jf800382m
Rapp A, Mandery H.1986. Wine aroma. Experientia 42(8):873-884. DOI: https://doi.org/10.1007/BF01941764
Rapp A. 1998. Volatile flavour of wine: Correlation between instrumental analysis and sensory perception. Nahrung 42:351-363. DOI: https://doi.org/10.1002/(SICI)1521-3803(199812)42:06<351::AID-FOOD351>3.3.CO;2-U
Reazin, G. H. (1981). Chemical mechanisms of whiskey maturation. Am J Enol Vitic 32:283-289. DOI: https://doi.org/10.5344/ajev.1981.32.4.283
Ribéreau-Gayon P, Boidron JN, Terrier A. 1975. Aroma of Muscat grape varieties. J Agric Food Chem 23:1042-1047. DOI: https://doi.org/10.1021/jf60202a050
Rocha SM, Coelho E, Zrostlíková J, Delgadillo I, Coimbra MA. 2007. Comprehensive two-dimensional gas chromatography with time-of-flight mass spectrometry of monoterpenoids as a powerful tool for grape origin traceability. J Chromatogr A 1161:292-299. DOI: https://doi.org/10.1016/j.chroma.2007.05.093
Rodrigues F, Caldeira M, Câmara JDS. 2008. Development of a dynamic headspace solid-phase microextraction procedure coupled to GC–qMSD for evaluation the chemical profile in alcoholic beverages. Anal Chim Acta 609:82-104. DOI: https://doi.org/10.1016/j.aca.2007.12.041
Sefton MA, Francis IL, Williams PJ.1990. Volatile norisoprenoid compounds as constituents of oak woods used in wine and spirit maturation. J Agric Food Chem 38:2045-2049. DOI: https://doi.org/10.1021/jf00101a009
Schieberle P, Grosch W.1988. Identification of potent flavor compounds formed in an aqueous lemon oil/citric acid emulsion. J Agric Food Chem 36:797-800. DOI: https://doi.org/10.1021/jf00082a031
Shrivastava A, Gupta VB. 2011. Methods for the determination of limit of detection and limit of quantification of the analytical methods. Chron Young Sci 2:21-25. DOI: https://doi.org/10.4103/2229-5186.79345
Slaghenaufi D, Perello MC, Marchand S, de Revel G. 2016. Quantification of megastigmatrienone, a potential contributor to tobacco aroma in spirits. Food Chem 203:41-48. DOI: https://doi.org/10.1016/j.foodchem.2016.02.034
Slaghenaufi D, Ugliano M. 2018. Norisoprenoids, sesquiterpenes and terpenoids content of Valpolicella wines during aging: Investigating aroma potential in relationship to evolution of tobacco and balsamic aroma in aged wine. Front Chem 6: article 66. DOI: https://doi.org/10.3389/fchem.2018.00066
Stamatopoulos P, Frerot E, Tempere S, Pons A, Darriet P.2014. Identification of a new lactone contributing to overripe orange aroma in Bordeaux dessert wines via perceptual interaction phenomena. J Agric Food Chem 62:2469-2478. https://doi.org/10.1021/jf405397c DOI: https://doi.org/10.1021/jf405397c
Strauss CR, Wilson B, Gooley PR, Williams PJ.1986. Role of monoterpenes in grape and wine flavor. ACS Symposium Series 317:222-242. DOI: https://doi.org/10.1021/bk-1986-0317.ch018
Takahashi K, Someya T, Muraki S, Yoshida T.1980. A New Keto-alcohol, (−)-Mintlactone, (+)-iso mintlactone and minor components in peppermint oil. Agric Biol Chem 44:1535-1543. DOI: https://doi.org/10.1080/00021369.1980.10864154
Thibaud F, Courregelongue M, Darriet, P. 2020. Contribution of volatile odorous terpenoid compounds to aged cognac spirits aroma in a context of multicomponent odor mixtures. J Agric Food Chem 68:13310-13318. DOI: https://doi.org/10.1021/acs.jafc.9b06656
Typ B, Ym C.1999. Oxidation and thermal degradation of carotenoids. J Oil Palm Res 11:62-78.
Vivas N, de Gaulejac, NV, Nonier, MF, Picard M. 2019. Selecting oakwood for cooperage based on the wood grain-meaning, methodology and consequences for ageing wine and spirits. Rev For Fr 71:153-171. DOI: https://doi.org/10.4267/2042/70626
Wishart D.2009. The flavour of whisky. Significance 6:20-26. DOI: https://doi.org/10.1111/j.1740-9713.2009.00337.x
Downloads
Published
How to Cite
Issue
Section
License
Copyright (c) 2023 The Institute of Brewing & Distilling
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.
This is an open access article which permits non-commercial re-use, distribution, and reproduction in any medium, provided the original work is properly cited, and is not altered, transformed or built upon in any way.
Permission will be required if the proposed reuse is not covered by the terms of the License. In this event, email the Editor in Chief - david.quain@ibd.org.uk - with details of your request.
