September2012. XIV Jean De Clerckchair Sotolon and Madeira. off-flavour in beer. Caroline Scholtes PhD Student, brewing department UCLouvain

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1 Sotolon and Madeira XIV Jean De Clerckchair September2012 off-flavour in beer Caroline Scholtes PhD Student, brewing department UCLouvain

2 Contents Sotolon State of the art in food chemistry In alcoholic beverages New insights Madeira off-flavour in beer Context of this study Evolution of sotolon concentrations during aging for a panel of beers Evidence of efficient pathways in beer Perspectives XIV Jean De Clerckchair 12-14

3 Sotolon H state of the art in food chemistry

4 Significantcontribution to variousfoodand beverages flavours Madeirised, burnt, dried fruit, nutty, rancio, curry, spicy, Thr= 8 ppb (in wine(lavigne et al., 2008)) Many precursors described under various conditions Generally results from mild oxydation during aging H

5 In alcoholic beverages Jura flor-sherry wines, Yellow wines(120 to 268 ppb),sherry (Xeres) Porto, Madeira and other fortified wines H 3 C H 6 yearsand 3 monthsin re-usedoak barrel Development of yeast film (Saccharomyces genus) NH 2 H H 3 C H 3 C Dry white wines + H Agingin woodbarrel oxydative aging conditions (acetaldehyde (Cantarelli, 1967)) H 3 C H 3 C H (Kobayashi et al., 1989) No flor (liquoraddition) no microbialintervention afterthe end of alcoholic fermentation Temperature - residual Maillard reactions sugar content (> 25g/L) (Hofman, T.& Schieberle, P., 1997)

6 ( Perez Locas & Yaylayan, 2004 )

7 New insights : Dry white wines and citrus soft drinks Vinification conducted under limited oxygen contact No alcohol but citrus essence ethanolic extracts Ascorbic acid degradation (Pons et al., 2010) liberation of high quantities of α-ketobutyric acid Identification of 2 degradation pathways of ascorbic acid leading to sotolon (Koning et al., 1999) (Pons et al., 2007) (Koning et al. 1999)

8

9 Madeira flavour In beer

10 Context of this study (1) In industry: prematureagingof specialtybeers(3-5m) causing off-flavors ( Madeira, nut, curry) Identifiedby GC-MS as sotolon.

11 Context of this study (2) 160 Analyses of a 6 yearsaged specialty beer Yellow wine! Formation pathways not clear No data about sotolon in beer Concentration of sotolon (ppb) years Flor Sherry wine

12 In beer Biochemical origin: Yeast Threonin desamination by saccharomyces Chemical origin: 2 content Low (<0,05 ppm) Diacetyl + amino acids H H H H H Pro-oxydants Ascorbic acid and oxygen radicals Fenton reactions Antioxydants Ascorbic acid S2 Ascorbic acid Polyphenols(catechin, epicatechin) Dehydroascorbic acid

13 Sulfites Combine to acetaldehyde Blouin (1965) LimitH 2 2 disponibility Combine to α- ketobutyric acid (Kaneda et al., 1999) Pons (2007)

14 Incriminated compounds in beer : Bio-chemical origin: Refermentation yeast Chemical origin: - Ethanal peroxydation -Ascorbicacid!

15 Madeira flavour Evolution of sotolon concentrations during aging for a panel of beers

16 Material : 7 Belgian special beers BL1 BL2 BL3 BL4 Blond AM1 Amber Conventional Triple rganic TR-dh Blond Trappist dry-hopped BR1 Brown Amber Dry-hopped Trappist Brown

17 Method : 50 ml beer at ph 11,5 + 2g XAD 2 resin, agitation 2h Percolated beer + 50 ml washing resin waters collected and adjusted at ph 3 T.Claes, 2011 L:L extraction with dichloromethane and concentration to 500 µl Extractswereanalysedby GC-MS on FFAP polar column(sim Mode)

18 Results : [sotolon] (ppb) Veryrichin 4 polyphenols & sulfites treatment 2 Ascorbic acid treatment fresh 6 month 0 AM 1 BL 1 BL 2 BL 3 BL 4 TR-dh BR 1 Beer

19 Results : Bottle refermented [sotolon] (ppb) 5 0 AM 1 BL 1 BL 2 BL 3 BL 4 TR-dh BR 1 Beer fresh 6 month 1 year

20 Madeira flavour Evidence of efficient pathways in beer

21 In beer Biochemical origin: Yeast Threonin desamination by saccharomyces Chemical origin: 2 content Low (<0,05 ppm) Diacetyl + amino acids H H H H H Pro-oxydants Ascorbic acid and oxygen radicals Fenton reactions Antioxydants Ascorbic acid S2 Ascorbic acid Polyphenols(catechin, epicatechin) Dehydroascorbic acid

22 Sulfites Combine to acetaldehyde Blouin (1965) LimitH 2 2 disponibility Combine to α- ketobutyric acid (Kaneda et al., 1999) Pons (2007)

23 Incriminated compounds in beer : Bio-chemical origin: Refermentation yeast Chemical origin: - Ethanal peroxydation -Ascorbicacid!

24 Material : KMS 5mM AA (Ascorbic acid) 5mM Trolox 5mM Fe 2+ 5mM H 2 2 Ageing30 days-40 C

25 1. xygen Concentration (ppb) Blanco- no 2 Blanco - 2 Treatment

26 2. Ascorbicacid Concentration (ppb) Blanco - 2 AA-2 AA-S2-2 Treatment

27 3.Pro-oxydant species Concentration (ppb) Blanco - 2 AA-2 AA-Fe-H22-2 Fe-H22-2 Trolox-2 Treatment

28 Sulfites fight! Concentration (ppb) Blanco - 2 AA-2 AA-S2-2 Treatment

29 Perspectives

30 Assessment of the impact of technological practices on sotolon concentration Determination of the relative contribution of each sotolon synthesis pathway Determination of the impact of yeast strain and yeast metabolism state on sotolon synthesis

31 Thank you for your attention Thanks to CNSALIM Project and brewers for their kind collaboration!

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