Dry Hopping Mythsversus Reality

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1 Dry Hopping Mythsversus Reality 1

2 Major volatile compounds after main fermentation (at start of dry hopping!) 2

3 Compounds present in beer after main fermentation IR CPSil5 Compounds Flavour Samples YEAST GLYCOSILES PRECURSORS HOP CYSTEINES BY PRODUCTS ACTION ON FATTY ACIDS T 0 Day C (ppm) 730 isobutylacetate banana, fruity ethylbutyrate banana, fruity methylbutanoic acid cheese isoamylacetate Banana, apple methylpentanoic acid cheese < hexanoic acid Dry leaves, goaty, fatty acids bière FD methyl-2-pentanoic acid grassy, acid < β-myrcene lemon, sweet < hexylacetate + sulfitic grassy, hop phenylacetaldehyde sweet, hony < linalool lemon < β-phenylethanol rose citronellol lemon < ethylguaiacol spicy ND vinylguaiacol cloves 0.70 <128 3BACKGROUND INFORMATIPON

4 Compounds present in beer after main fermentation IR CPSil5 Compounds Flavour Samples YEAST GLYCOSILES PRECURSORS HOP CYSTEINES BY PRODUCTS ACTION ON FATTY ACIDS T 0J C (ppm) bière FD methyl-2-buten-1-thiol (MBT) hop, cheese ND mercaptopropanol potatoes ND mercaptoethylacetate grilled meat ND mercapto-4-methyl-2-pentanone catty ND <128 Analysis performed at the lab of Prof Sonia Collin UCL 1374 beta -damascenone cooked apple ND < gamma-decalactone peach ND < delta-decalactone coconut ND < vinylsyringol Cloves ND < ethyldodecalactone grassy ND < delta-dodecalactone fruity, olive ND <128 4

5 EBC HOP SYMPOSIUM GDX/JMR/SDK/2009 5

6 ALCOHOLS ALDEHYDES LACTONES TERPENES Monoterpenes Sesquiterpenes MCF-ACIDS (Medium chain fatty acids) LCF-ACIDS GLUCOSIDE OF TERPENES Monoterpenes Sesquiterpenes GLUCOSIDE OF PHENOLS Phenolic acids Polyphenols 6

7 ACIDS ALCOHOLS TERPENES Monoterpenes Sesquiterpenes VOLATILE PHENOLS CYSTEINE DERIVATIVES (THIOLS) MCF-ACIDS LACTONES GLUCOSIDE OF TERPENES Monoterpenes Sesquiterpenes GLUCOSIDE OF PHENOLS Phenolic acids Polyphenols 7

8 Fate of major beer volatiles by dry hopping (maturation) in presence of S.cerevisiae 8

9 MAJOR BEER VOLATILES MONOTERPENES CITRUS FLAVORS 9

10 YEAST GLYCOSILES PRECURSORS HOP IR CPSil5 Compounds Flavour Samples TERPENES T 0J T 14J T 21J C (ppm) bière FD C (ppm) bière FD C (ppm) bière FD 982 β-myrcene Citrus, sweet < < < linalool Citrus < > > citronellol Citrus, fresh < <

11 CITRUS FLAVORS IR CPSil5 Compounds Flavour Samples TERPENES T 0J T 14J T 21J C (ppm) bière FD C (ppm) bière FD C (ppm) bière FD 982 β-myrcene Citrus, sweet < < < linalool Citrus 0.01 < > >1024 = dil1024x 1226 citronellol Citrus, fresh < <

12 DRY HOPPING: evolution of linalool Influenced by : - Time - Temperature - Hop variety(oil content) - Hop quantity added - Hop dispersion methods (static/dynamic) - Beertype and yeasttype Linalool 12

13 CITRUS FLAVOURS IR CPSil5 Compounds Flavour Samples TERPENES T 0J T 14J T 21J C (ppm) bière FD C (ppm) bière FD C (ppm) bière FD 982 β-myrcene Citrus, sweet < < < linalool Citrus < > > citronellol Citrus, fresh < < = dil512x 13

14 DRY HOPPING: evolution of citronellol Influenced by : - Time - Temperature - Hop variety - Hop quantity - Hop dispersion methods (static/dynamic) - Beertype and yeasttype 14

15 PRESENCE OF CITRONELLOL METABOLISM CASCADE OF MONOTERPENE ALCOHOLS BY LAGER AND ALE YEASTS PROPOSED BY KING AND DICKENSON. THE ASTERIC INDICATES A CHIRAL CENTER. 15

16 IN LATE HOPPED WORT (10 min beforeend of boiling) Citation: HAPPOSHU 16

17 G 17

18 Fateof the othervolatilecompounds as the Acids Esters Alcohols Aldehydes Lactones Thiols Others 18

19 CHEESY FLAVOURS HOP YEAST IR CPSil Compounds Flavour Samples SHORT CHAIN FATTY ACIDS 3-methylbutanoic acid 4-methylpentanoic acid cheesy cheesy T 0J T 14J T 21J C (ppm) bière FD C (ppm) bière FD C (ppm) bière FD > < < hexanoic acid mild cheesy > methyl-2- pentanoic acid grassy, acid < <

20 HOP CONDITIONNING AND STORAGE CONDITIONS CHEESY: linked to bad storage of hop bales and/or pellets and to the use of aged hop (presence of degradation products as 2-methylpropionic acid/ isobutyric acid and of 2-methylbutyricacid/ isovalericacid) 20

21 FRUITY, FLORAL FLAVOURS YEAST HOP IR CPSil5 Compounds Flavour Samples ESTERS T 0J T 14J T 21J C (ppm) bière FD C (ppm) bière FD C (ppm) bière FD 730 isobutylacetate banana, fruity > ethylbutyrate 852 isoamylacetate banana, fruity, flowery banana, sweet > > > hexylacetate grassy, hop

22 FRUITY, FLORAL FLAVOURS YEAST HOP GLYCOSILES PRECURSORS CYSTEINES BY PRODUCTS ACTION ON FATTY ACIDS IR CPSil5 Compouds Flavour Samples HIGHER ALCOHOLS T 0J T 14J T 21J C (ppm) bière FD C (ppm) bière FD C (ppm) bière FD 1101 β-phenylethanol rose >1024 IR CPSil5 Compouds Flavour Samples ALDEHYDES T 0J T 14J T 21J C (ppm) bière FD C (ppm) bière FD C (ppm) bière FD 1018 phenylacetaldehyde sweetened, honey < <

23 23

24 YEAST HOP GLYCOSILES PRECURSORS CYSTEINES BY PRODUCTS ACTION ON FATTY ACIDS FRUITY, FLORAL FLAVOURS IR CPSil5 Compounds Flavour Samples LACTONES gammadecalactone deltadecalactone Ethyldodecalactone deltadodecalactone T 0J T 14J T 21J C (ppm) bière FD C (ppm) bière FD C (ppm) bière FD peach ND <128 ND <128 ND 512 coconut ND <128 ND <128 ND 512 grassy ND <128 ND <128 ND 512 fruity, olive ND <128 ND <128 ND

25 WHY LACTONES? FRUITY FLAVORS 25

26 FRUITY FLAVORS BIOSYNTHESIS YEAST PEROXISOME 26

27 FRUITY FLAVORS YEAST PEROXISOME BIOSYNTHESIS 27

28 SULFITIC FLAVOURS CYSTEINES BY PRODUCTS YEAST IR CPSil5 Compounds Flavour Samples T 0J T 14J T 21J C (ppm) bière FD C (ppm) bière FD C (ppm) bière FD methyl-2-buten-1-thiol (MBT) hop, cheese ND 512 ND >1024 ND > mercapto-propanol potatoes ND 512 ND >1024 ND > mercapto-ethylacetate mercapto-4-methyl- 2-pentanone grilled meat ND 512 ND >1024 ND >1024 catty ND <128 ND <128 ND

29 Concentration of major non-volatile compounds after maturation in presence of raw hops Polyphenols Glucosides 29

30 Non volatile compounds extracted POLYPHENOLS Year

31 POLYPHENOLS MOST INTERESTING PHENOLIC COMPOUNDS Phenolic acids Flavonoids Flavanoids Proanthocyanidin = anthocyanogen Resveratrol 31

32 POLYPHENOLS PHENOLIC ACIDS HOP YEAST ACTION ON PHENOLIC ACIDS ONLY IF PRESENCE OF BRETTANOMYCES sp (Vinyl reductase activity) CLOVES AND SPICY FLAVORS PRESENCE OF POF or PAD YEASTS (Phenolic acid decarboxylase activity) Several TOP fermenting yeasts FERULIC ACID = Phenolic acid (Barley, Hops) IR CPSil5 Compounds Flavour Samples PHENOLS T 0J T 14J T 21J C (ppm) bière FD C (ppm) bière FD C (ppm) bière FD ethylguaiacol spicy ND ND > vinylguaiacol Cloves, dentist 0.70 < < >

33 Formation of vinylguaiacol vinylphenol and styrene from phenylalanine by S. cerevisiae! 33

34 POLYPHENOLS FLAVANOIDS WHY ARE FRESH FLAVANOIDS INTERESTING! BECAUSE. 34

35 Non volatile compounds extracted - POLYPHENOLS - GLUCOSIDES 35

36 NON VOLATILE COMPOUNDS EXTRACTED POLYPHENOLS PHENOLIC ACIDS FLAVANOIDS GLUCOSIDES GLYCOSIDES IMPORTANCE OF THE HOPS INFLUENCE OF THE YEAST STRAINS CULTURE YEASTS WILD YEASTS Brettanomyces sp 36

37 - GLUCOSIDES A few theory Glucosidic bound can be hydrolysed by : - High temperature - Enzymatic activity - endogenouspresence(yeastby maturation, bottle refermentation) - (addition of exogenous betaglucosidase during the process) Non volatile compounds extracted 37

38 - GLyCOSIDES In beer, the aglycon part is liberated by two different types of activities -by β-1-3-glucanase activity in case of S. cerevisiae strains -by β -glucosidase activity in case of Brettanomyces sp. strains Non volatile compounds extracted 38

39 Glycosidic bounds hydrolysed by endogenous presence (by yeast during maturation and/or during bottle fermentation) Preferential links detected in hops Terpenes TERPENIC SUB UNIT + SUGAR : FLAVOUR PRECURSOR linalool- β-d- glucoside α terpineol β D -glucoside 1-octen-3-ol- β D glucoside 3 hydroxy β damascenone D glucoside PHENOLIC SUB UNIT + SUGAR : SHELF LIFE PROTECTOR PRECURSOR Flavonoids Kaempferoland Quercetin 3 glycosides glycosidic sub-unit : mono or di- glycosides glucose, galactose, rhamnose Flavanoids As yet, flavanol dimers or multimers glucoside aren t detected nor described Non volatile compounds extracted 39

40 Glucosidic bound hydrolyses by endogenous presence (yeast by maturation, bottle refermentation) Importance of the yeaststrainand yeast species Non volatile compounds extracted 40

41 Influence of hop quantity and of yeast strain TYPICAL YEASTS β-glucanase and βglucosidase activities of different yeast strains and yeast species LEGEND : SC: S.CEREVISIAE(ALE YEAST) BB: BRETTANOMYCES BRUXELLENSIS BC: BRETTANOMYCES CUSTERSII *SC+ D : S. CEREVISIAE+ CARBOHYDRATE SOURCE(GLUCOSE) AR: AR 2000 GLYCOSIDASIC CONCENTRATE OF ASPERGILLUS NIGER(COMMERCIALLY AVAILABLE) 41

42 Glucosidic bound hydrolyses by endogenous presence (yeast by maturation, bottle refermentation) Importance of the aglycon moiety (glucoside of higher alcohols) 1-octen-3-ol cis-3-hexen-1-ol Non volatile compounds extracted 42

43 HOP GLYCOSILES PRECURSORS YEAST FRUITY, FLORAL FLAVOURS IR CPSil5 Compounds Flavour Samples OTHERS T 0J T 14J T 21J C (ppm) bière FD C (ppm) bière FD C (ppm) bière FD 1374 beta - damascenone cooked apple, rose ND <128 ND <128 ND >

44 BEER DRY HOPPING IS A CONFLICTUAL ART WHEN RAW HOP EXTRACTION TAKES PLACE IN PRESENCE OF ACTIVE YEAST ACTIVE YEAST BY DRY HOPPINGIMPROVES THE BEER VALUE BY : - PROTECTING BEER FROM OXIDATION BY CAPTURING MOLECULAR OXYGEN - PROTECTING BEER BY EXERTING A REFRESHING EFFECT - IMPROVING (IN A FIRST STEP) THE BEER FLAVOUR BY : increasing the content of citronellol synthesizing nice flavours as lactones liberating aglycons from glucosides: - Linalool, Geraniol, 44

45 BEER DRY HOPPING IS A CONFLICTUAL ART WHEN RAW HOP EXTRACTION TAKES PLACE IN PRESENCE OF ACTIVE YEAST ACTIVE YEAST by dry hopping DECREASES THE BEER VALUE BY : - LIBERATING ESTERASES THAT DECREASE THE AROMA - METABOLIZING H + ACCEPTORS AS SOME ALDEHYDES AND OTHER POTENT SUBTILE FLAVOURS AS LACTONES 45

46 BEER DRY HOPPING IS A CONFLICTUAL ART WHEN BOTTLING TAKES PLACE IN PRESENCE OF ACTIVE YEASTs 46

47 Orval A B C TRADITIONNAL EUROPEAN METHODS Methods by batch dry hopping D A : Parts of 4 KG of dried hop cones are compacted under inert gas (N2) in onion bags that are sealed in aluminium packets by the hop supplier. of 4 KG. These are stored in the fridge of the brewery at + 2 /+ 4 C. B : Just before use, the aluminium packets are opened and the onion bags containing the hop cones are decompressed. C : Before introduction in the empty tank, E the hop cones are decompacted too D : In order to improve the contact between the beer and the hop bells, the hop bag can be attached to the tank. E : Hop plugs of 5 Oz ( 140 Gr) are also available by hop suppliers and can be added to beer casks directly. Sierra Nevada 47

48 Methods by continuous extraction in separated vessels 1.1. by hop cones Sierra Nevada Brewery NEW AMERICAN METHODS 1.2. by hop pellets Stone Brewery (designed plant) New Belgium Brewery Pneumatic Method = dry method Out-Indoorhop cellar canoon Lagunitas Brewery 48 With authorization of Steven Pauwels, CBC Dry hopping subcommittee

49 HOP and BEER 49

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