220th ACS Syposium, Washington, August 20-24, 2000 Imre Blank

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1 220th AC yposium, Washington, August 20-24, 2000 Imre Blank

2 Major topics of the presentation verview Chemical classes ccurrence Analytical methods Key odorants ensory relevance tructure - activity Flavor simulation Food products Natural Fermented Processed

3 Major classes of sulfur compounds ulfides (~ 440) Thiazoles (100) Thiophenes (100) Thiols (60) Mono (55) Thiane (50) Di (95) Tri (25) thers (265) Thiocyanate (45) Thiolane (25) Dithiazine (20) Total : ~ 700 sulfur compounds 10 % of volatiles listed in TN compilation thers (125)

4 NRC Nestlé Research Center Thiols Number of products Dimethyl Benzo Methyl Thiazole propyl Methyl H2 Dipropyl 2-Acetyl Ethyl Trithiolane Thiazoles Thiophenes 2-Methyl 2-Aldehyde DiMe-D Dimethyl Dimethyl DiMe- Diethyl 2-Acetyl Methional Methyl DiMe-T propyl Methional Diethyl ulfides

5 NRC Nestlé Research Center Monosulfides thers Number of products Dimethyl Methional Diethyl H2 C2 Dithiazine Trithiolane Tetrasulfide C Disulfides Dimethyl Diethyl Methyl propyl Trisulfides Dimethyl Methyl propyl Dipropyl

6 Key odorants : Thiols in natural products Grapefruit ulfury, catty x = µg/l H 2 H Blackcurrant, olive oil ulfury, catty x = µg/l H 2 H (Demole et al., 1982) (Rigaud et al., 1986 Guth & Grosch, 1991) (R)-1-p-Menthene-8-thiol 4-Methoxy-2-methyl-2-butanethiol H H nion ulfury, onion, meaty x = 0.04 µg/l H 2 (Widder et al., 2000) H Buchu leaf oil ulfury, catty (undt et al., 1971) 3-Mercapto-2-methylpentan-1-ol (2R,3) / (2,3R) 8-Mercapto-p-mentane-3-one trans-(1,4) / cis-(1,4r)

7 Key odorants : Thiols by thermal processing H Beer, coffee ulfury, catty x = µg/l H 2 H H Coffee, beer ulfury, catty x = µg/l H 2 (Kuroiwa & Hashimoto, 1961; Holscher et al., 1990) 3-Mercapto-2-buten-1-thiol (Holscher et al., 1990; chieberle, 1991) 3-Mercapto-3-methylbutyl formate H Meat, coffee ulfury, meaty x = µg/l H 2 H Coffee, meat,... ulfury, coffee-like x = 0.01 µg/l H 2 (Gasser & Grosch, 1988; Holscher et al., 1990) 2-Methyl-3-furanthiol (Reichstein & taudinger, 1926; Mottram, 1985) 2-Furfurylthiol

8 ccurrence of key odorants : ulfides N CH 3 hellfish (cooked) hiitake mushroom Meat flavors, chocolate Passion fruit Garlic Potato (boiled) White truffle Vegetables nion (raw) nion (boiled)

9 dor quality and threshold value : ulfides N Roasty 1 x µg/l (Kubota et al., 1991) ulfury, meaty µg/l (Buttery et al., 1982) ulfury, roasty 0.04 µg/l (Mulders, 1976) ulfury, cabbage-like µg/l (Milo,1995) Cooked potato-like 0.2 µg/l (Buttery et al., 1971) ulfury 0.3 µg/l (loot & Harkes, 1975) ulfury, onion 2 µg/l (Boelens & van Gemert, 1993) ulfury, fruity 7 µg/l (Takeoka et al., 1989)

10 Key odorants : Thiazoles, thiophenes, and others N N N N (0.1) (10) (1.0) (Tomato, 3.0) (Watercress) NC N NC N R (1.2) (Fried onion) (Chopped cabbage) NC (Horseradish) N (1.6) N N (1.3) (1.3) (Leek, 7.0) (Radish) NC

11 ensory Directed Chemical Analysis Procedure Method Result Aroma extraction Various Authentic aroma note GC-lfactometry niffing, Charm, AEDA, creening of odorants Identification GC-M, AED, RI, tructure of odorant specific detectors,... Quantification Internal standard, IDA Concentration in food ensory evaluation Triangle test, profiling, dor threshold + quality various matrices, Masking, sens. impact Validation Recombination Flavor simulation (Acree, 1993; Grosch, 1994; chieberle, 1995; Blank, 1996)

12 GC-niffing / GC-lfactometry GC- H Evers et al. (1976) ynthesis GC-M Withcombe & Mussinan (1988) Tuna fish GC-, GC-M Gasser & Grosch (1988) Beef GC- Gasser & Grosch (1990) Chicken GC-, GC-M Holscher et al. (1990) Coffee GC- Gasser & Grosch (1991) Pork GC-...

13 Dilution techniques : CHARM and AEDA 1/1 1/3 1/9 erial Dilution response time 1/9 1/3 1/1 dilution value retention index (Acree et al., 1984; Ullrich & Grosch, 1987)

14 ulfur compounds in grapefruit (Demole et al., 1982) H ulfury, catty ( µg/l H 2 ) H (Buettner & chieberle, 1999) H FD = 128 ulfury, catty ( µg/l H 2 ) FD = 128 Cooked potato-like (0.2 µg/l H 2 ) FD = 32

15 Isolation and selective enrichment of thiols with p-hydroxymercuribenzoate CNa CNa CNa Hg-H R-H H 2 Cys-H R-H Hg--R Hg--Cys (Darriet et al., 1995)

16 Isolation and selective enrichment of thiols by covalent chromatography N N R-H N HCl HgCl N N N Hg-R H R -H R-H N N N Hg-R' (Full & chreier, 1995)

17 ensory relevance : dor Activity Value AV = C x T x C x : Concentration T x : Threshold value Rothe & Thomas (1963) Guadagni et al. (1966) Acree et al. (1984) Thresholds : dor (orthonasal) Aroma (retronasal) Perception Recognition Buttery et al. Grosch et al. chieberle et al. : Relative importance of individual odorants estimated olvent Air Water il Food : Interactions remain unknown Flavor recombination studies

18 Threshold values : A very critical step dor Aroma orthonasal (through the nose) retronasal (in the mouth) AV = C x Perception Recognition different from solvent characteristic note perceived T x H olvents: Air (ng/l) n.d Water (µg/l) /1.8, 0.04/10 Model (µg/l) n.d (10% EtH) 0.27 (starch) Food (µg/l) (oil) (wine) 0.05/0.2 (oil) H

19 Effect of the threshold value : Roasted sesame Flavor compound Concentration dor thresholds AV (µg/kg) (µg/kg oil ; water) il Water 2-Acetyl-1-pyrroline Furfurylthiol Phenylethylthiol Furaneol Ethyl-3,5-dimethylpyrazine Guaiacol (E,E)-2,4-Decadienal < (chieberle, 1996)

20 ulfur compounds in natural products Tomato, olive oil, basil dorants : Chemical structure ensory properties Flavor recombination Catty odorants

21 dor characteristics of 2-isobutylthiazole and its impact on the overall tomato flavor Viani et al., 1969 In pure form Green, similar to tomato leafs First identified in tomato fruit (500 kg) N Kazeniac & Hall, 1970 In water Added to canned tomato (juice / paste) poiled wine-like, horseradish-like Threshold of 2-3 µg/kg water More intense fresh tomato note Blended out harsh notes Improved the mouth-feel Effective at µg/kg level

22 Key odorants of fresh tomato Flavor compound Concentration dor threshold AV (µg/kg) (µg/kg water) (Z)-3-Hexenal Hexanal β-ionone Penten-3-one β-damascenone Methylbutanal (E)-2-Hexenal Isobutylthiazole Nitro-2-phenylethane (Buttery et al., 1989)

23 Key odorants of olive oil (pain) Flavor compound Concentration dor Threshold AV (µg/kg) (µg/kg oil) 4-Methoxy-2-methyl-2-butanethiol (Z)-3-Hexenal Ethyl 2-methylbutyrate (Z)-2-Nonenal Ethyl 3-methylbutyrate Ethyl cyclohexanoate Acetic acid Hexanal (Z)-3-Hexenyl acetate Methylbutanol (Guth & Grosch, 1991; 1993)

24 Recombination studies : live oil (pain) Pungent 3 2 Catty 1 0 Fruity il Model Fatty Green imilarity : 2.7 ± 0.3 (21 odorants) (Reiners & Grosch, 1998)

25 Effect of odorants on overall flavor - live oil (pain) Model mixture (21 odorants) No acetaldehyde / propanal amples No acetic acid No 3-/2-methylbutanal No ethyl 2-/3-methylbutyrate imilarity No 4-methoxy-2-methyl- 2-butanthiol H (Reiners & Grosch, 1998)

26 Key odorants and sensory profiling - Fresh basil - Flavor compound AV (Z)-3-Hexenal ,8-Cineol Mercapto-4-methyl-2-pentanone Linalol Allyl-1,2-dimethoxybenzene 9900 Eugenol 8900 α-pinene 90 Clove-like Green Pepper-like Flow ery Herbaceous (Guth & Murgoci, 1997)

27 Recombination studies : Fresh basil aroma Model mixture imilarity AV Complete mixture (11 odorants) 3.0 Compounds ommitted : Eugenol (Z)-3-Hexenal α-pinene H Mercapto-4-methyl-2-pentanone Linalol ,8-Cineol (Guth & Murgoci, 1997)

28 tructure - activity relationship : Catty H H H H H H H ( ) (0.0001) (35) (0.001) (0.003) H H H H ( ) (0.2) (0.7) (3.0) (0.0003) H H H H (Thresholds in µg/l water) (0.08) (2.5)

29 Molecular features determining the catty odor H H H H ensory evaluation : Tested in a confusion matrix Factor correspondence analysis ensory panel (n = 15) Results : Tertiary mercapto amyl substructure Keto group is not essential, might be in α- or β-position to H H to C= distance is 2-4 Å (Polak et al., 1988)

30 ulfur compounds in fermented products Wines : White (auvignon, cheurebe) Red (Bordeaux) dorants : Chemical structure ensory properties ( catty ) tereochemistry Precursors Flavor recombination

31 ulfur compounds in wine : auvignon blanc H 4-Mercapto-4-methyl-2-pentanone (Darriet et al., 1993) = 0.1 ng/l water (Darriet et al., 1995) = 1.1 ng/l 10% ethanol = 1.4 ng/l 10% ethanol sucrose (100 g/l) = 3.3 ng/l white / red wine C = ng/l white wine (Bouchilloux et al., 1996) C = 0 ng/l white wine No typical aroma C = 9 ng/l white wine Weak typical note C = 18 ng/l white wine Typical aroma C = 34 ng/l white wine Very typical note

32 Further sulfur compounds in auvignon blanc 3-Mercaptohexyl acetate Passion fruit-like H = 2.3 ng/l water (Tominaga et al., 1996) = 4.3 ng/l 10% EtH H H 3-Mercapto-1-hexanol Passion fruit, grapefruit = 17 ng/l water (Tominaga et al., 1998) = 60 ng/l 10% EtH H H 4-Mercapto-4-methyl- Citrus peel-like 2-pentanol = 20 ng/l water = 55 ng/l 10% EtH H H 3-Mercapto-3-methyl- 1-butanol Cooked leek-like = 1300 ng/l water = 1500 ng/l 10% EtH

33 ensory impact of sulfur compounds in auvignon blanc Concentration (µg/l) dor Activity Value H H H H H H H H (Tominaga et al., 1998)

34 -Cysteine conjugates as precursors of thiols in auvignon blanc HC NH 2 HC NH 2 HC NH 2 H H Alcoholic fermenation (β-lyase of yeast) Thiols released (enhanced auvignon blanc aroma) (Tominaga et al., 1998)

35 Use of the β-lyse activity of yeast - Application to flavour generation - HC NH 2 H + HC NH 2 Yeast H (Tominaga et al., 1998) CH + H 2 N H CH N CH Yeast H (Bel Rhlid & Matthey-Doret., 1998)

36 Use of the yeast β-c-lyse activity in flavour generation H H HN CH Yeast R H H N H (Bel Rhlid & Matthey-Doret., 1998) N H H

37 ulfur compounds in white wine : cheurebe H 4-Mercapto-4-methyl-2-pentanone ulfury, catty Dimethyl sulfide ulfury, tomato-like Dimethyl trisulfide ulfury, cabbage-like H 3-(Methylthio)-1-propanol ulfury, cabbage-like (Guth, 1997)

38 Key odorants in cheurebe wine dor Activity Value H H (Guth, 1997)

39 ensory impact of odorants in the cheurebe wine Model mixture imilarity Complete mixture (42 odorants) 3.0 Compound ommitted : 4-Mercapto-4-methyl-2-pentanone 0.5 H (Guth, 1997)

40 ulfur compounds in Bordeaux red wines H 3-Mercaptohexyl acetate Passion fruit-like = 2.3 ng/l water C = ng/l wine H H 3-Mercapto-1-hexanol Grapefruit-like = 17 ng/l water C = µg/l wine H * H 3-Mercapto-2-methyl- Broth-like, sweaty propanol = 3000 ng/l water C = 1-70 µg/l wine (Bouchilloux et al., 1998)

41 tereochemistry of 3-mercapto-2-methylpropanol H H H H H H (R) () Brothy, sweaty 3-7 µg/l (water) µg/l µg/l (model) µg/l Young red wines: µg/l Aged red wines: 1-4 µg/l White wines: 1-2 µg/l (Bouchilloux et al., 2000)

42 ulfur compounds in red wine (Vitis labrusca) H 3-(Methylthio)-1-propanol ulfury, cabbage-like H trans-2-methylthiophan-3-ol Garlic-like H 4-Mercapto-2,5-dimethyl 3(2H)-thiophenone ulfury, sweet, fruity (Guedes de Pinho et al., 1997)

43 ulfur compounds in processed foods Food : Meat (stewed beef) Coffee (brew) dorants : Chemical structure ensory properties Flavor recombination

44 Key odorants found in stewed meat juice Flavor compound Concentr. (µg/kg) dor threshold AV Beef Pork (µg/kg water) Beef Pork Methanethiol Methyltridecanal 52 < <1 Furaneol Acetaldehyde Methional (E,E)-2,4-Decadienal Methylbutanal otolone Hexanal Acetic acid 2x10 5 3x10 5 3x Furfurylthiol (Guth & Grosch, 1994; 1995)

45 ensory profiling of stewed meat flavor w eet, caramel 3 Beef w eet, caramel 3 Pork 2 2 Roasty 1 ulfury, meaty Roasty 1 ulfury, meaty 0 0 Fatty Tallow y, beefy Fatty Tallow y, beefy imilarity : 3.0 imilarity : 2.5 Meat Model Meat Model (Guth & Grosch, 1995)

46 Effect of odorants on overall flavor : tewed beef Model mixture (n= 15) No 2-furfurylthiol amples No acetaldehyde No sotolone No acetic acid No 12-methyltridecanal 1 No furaneol No methanethiol imilarity (Guth & Grosch, 1994)

47 Interaction of odorants : tewed beef Flavor compound Model A B C D Methanethiol x x x x Furaneol x x x x 12-Methyltridecanal x x x x Acetic acid x x x x otolone x x x x Acetaldehyde x x x x 2-Furfurylthiol x x x Methional x x x Butyric acid x (E,E)-2,4-Decadienal x x x Diacetyl x x 3-Methylbutanal x x x imilarity : (Guth & Grosch, 1994)

48 ome odorants detected in coffee by GC-olfactometry H 2 CH 3 H H H H R N N R R H R H H H R R H H R-CH : trecker aldehydes (Holscher et al., ; Blank et al., )

49 Key odorants found in Arabica coffee brew (1) Flavor compound Concentration dor threshold AV (µg/kg) (µg/kg water) (x10 3 ) 2-Furfurylthiol Methyl-2-buten-1-thiol Methanethiol Mercapto-3-methylbutyl formate Methyl-3-furanthiol Dimethyltrisulfide Methional (E)-β-Damascenone Homofuraneol Furaneol Diacetyl ,3-Pentanedione (Grosch et al.)

50 Key odorants found in Arabica coffee brew (2) Flavor compound Concentration dor threshold AV (µg/kg) (µg/kg water) (x10 3 ) 3-Isobutyl-2-methoxypyrazine Ethyl-3,5-dimethylpyrazine ,3-Diethyl-5-methylpyrazine Vinylguaiacol Guaiacol Methylbutanal Methylpropanal Acetaldehyde Methylbutanal Propanal (Grosch et al.)

51 ensory profiling of Arabica brew aroma w eet, caramel 3 2 mokey 1 0 Earthy Cof f ee Model Roasty, sulfury imilarity : 2.3 (Czerny et al., 1999)

52 Effect of the base used for sensory profiling w eet, caramel mokey 0 Earthy Roasty, sulfury (Czerny et al., 1999) Coffee Cellulose il Water imilarity : (3.0)

53 Effect of odorants on Arabica coffee brew aroma amples No phenols (4) No guaiacol No 4-vinylguaiacol No 2-furfurylthiol No pyrazines (4) No 2-methyl-3-furanthiol No methanethiol No methional No aldehydes (3) No diones (2) No 3(2H)-furanones (2) No (E)-β-damascenone Positive answers (Grosch et al., 1998)

54 ff-flavor in food products Food : Contamination Prepared meat Food-born Meat, coffee, spinach dorants : Chemical structure ensory properties Formation pathways Decomposition

55 ff-flavors caused by sulfur compounds Meat Beer H 2 H H H H (Patterson, 1969) (Kuroiwa & Hashimoto, 1961) (chieberle, 1991) Milk pinach CH T + NH 2 (Masanetz et al., 1998)

56 Major reactions leading to off-flavor in food Addition of H 2 To double bonds H 2 H To α,β-unsaturated aldehydes R R Thermal degradation Methionine CH Cysteine H NH 2 CH T H 2 NH 2

57 Fish-like off-flavor in dried spinach (Z)-1,5-ctadien-3-one Metallic, geranium-like x = µg/l water Methional Cooked potato-like x = 0.2 µg/l water (Z)-3-hexenal Green leaf-like x = 0.25 µg/l water Compound ample 1 ample 2 Methional (10 µg/l) x x ctadienone ( 0.16 µg/l) x x (Z)-3-Hexenal ( 4.3 µg/l) - x Fishy (2), green (0.5) Fishy (1.5), green (2) Potato (1), metallic (1.5) Potato (1), metallic (1.5) (Masanetz et al., 1998)

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