Hoppy Aroma and Flavor - Home - 2014 ACS Northwest …norm2014.sites.acs.org/Hop Chemistry.pdf ·...
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Hoppy Aroma and Flavor Daniel C. Sharp, M.S. Food Science and Technology Michael Qian, Thomas H. Shellhammer Oregon State University Department of Food Science and Technology
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How is beer made?
Barley
Hops Yeast
Water
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Hops in Beer: An Overview
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Hops in Beer: An Overview
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What is Hop Aroma/Flavor? Hoppy aroma and flavor in beer is a product of the coordination of physical, biochemical, and chemical phenomena that occur during brewing and psychophysical phenomena during consumption.
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Humulus lupulus fam. Cannabaceae
• Dioecious perennial • Climbing plant (c. 6 meters) • 100+ cultivars
Photo: Indie Hops
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Lupulin glands
SEM Image of Lupulin glands Forster, 2001
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Hops composition Principle Components Concentration (%w/w) Cellulose + lignin 40.0 - 50.0 Protein 15.0 Alpha acids 2.0 - 17.0 Beta acids 2.0 - 10.0 Water 8.0 - 12.0 Minerals 8.0 Polyphenols and tannins 3.0 - 6.0 Lipids and fatty acids 1.0 - 5.0 Hop oil 0.5 - 3.0 Monosaccharides 2.0 Pectin 2.0
European Brewery Convention Hops and Hop Products, Manual of Good Practice; Getranke - Fachverlag Hans Carl: Nurnberg, Germany, 1997.
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Hops composition Principle Components Concentration (%w/w) Cellulose + lignin 40.0 - 50.0 Protein 15.0 Alpha acids 2.0 - 17.0 Beta acids 2.0 - 10.0 Water 8.0 - 12.0 Minerals 8.0 Polyphenols and tannins 3.0 - 6.0 Lipids and fatty acids 1.0 - 5.0 Hop oil 0.5 - 3.0 Monosaccharides 2.0 Pectin 2.0
European Brewery Convention Hops and Hop Products, Manual of Good Practice; Getranke - Fachverlag Hans Carl: Nurnberg, Germany, 1997.
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Hop Acids and their solubility
Peacock, 1998
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The most important reaction in hop chemistry?
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Beer Sample – Iso-alpha acids by HPLC
2.5 5 7.5 10 12
mAU
0
100
200
300
400
DAD1 A, Sig=270,4 Ref=360,100 (VAA 6-18-13\VAA 6-18-13 2013-06-19 12-22-20\002-0301.D)
isocohumulone
isohumulone
isoadhumulone
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Measuring Bitterness in Beer Bitterness Units (IBUs) and [iso-α acids] (IAAs) What does the IBU measure? • Whatever gets extracted by iso-octane • Whatever absorbs at 275 nm. • Combined α, β, iso’s, oxidized materials, polyphenols
1 BU ≠ 1 ppm iso-alpha acid
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y = 1.2x + 2.0 R² = 0.905
0.0
10.0
20.0
30.0
40.0
50.0
60.0
70.0
80.0
90.0
0.0 10.0 20.0 30.0 40.0 50.0 60.0 70.0 80.0
IBU
Iso alpha acids concentration [ppm]
Correlation between total IAA & IBU
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Beer Bitterness Key Points
• Most bitterness attributed to isomerization of α-acids during boiling. Different analogs contribute differently.
• Measured by BUs (spectrophotometric ally)
…but 1 BU ≠ 1 ppm iso-alpha acid • Bitterness also comes from other hop material, eg.
Polyphenols, tannins, oil components, oxidations products.
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Questions so far?
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Design by Victor Algazzali Graphics from http://www.bojensen.net/index.html
Hop Aroma
Table adapted from: Eyres, G.; Dufour, J.
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Hops composition Principle Components Concentration (%w/w) Cellulose + lignin 40.0 - 50.0 Protein 15.0 Alpha acids 2.0 - 17.0 Beta acids 2.0 - 10.0 Water 8.0 - 12.0 Minerals 8.0 Polyphenols and tannins 3.0 - 6.0 Lipids and fatty acids 1.0 - 5.0 Hop oil 0.5 - 3.0 Monosaccharides 2.0 Pectin 2.0
European Brewery Convention Hops and Hop Products, Manual of Good Practice; Getranke - Fachverlag Hans Carl: Nurnberg, Germany, 1997.
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Essential Oil
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Hop Oil Composition
Schönberger, C.; Kostelecky, T. 125th Anniversary Review: The Role of Hops in Brewing. J. Inst. Brew 2011, 117, 259–267.
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Hop Oil Composition
Schönberger, C.; Kostelecky, T. 125th Anniversary Review: The Role of Hops in Brewing. J. Inst. Brew 2011, 117, 259–267.
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Physical Effects Objective: Identify the effect of hopping regime on the contribution of hop volatiles to hop aroma in beer.
CC
V
Kettle Whirlpool
• Factors • Hopping Regime • Hop Cultivar (Simcoe, Hallertau Mittlefrueh)
• Response • (Chemical) Volatiles • (Sensory) Descriptive Analysis
60 minute boil ~100 C, 20 min 18 C, 48 hours
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Stir Bar Sorptive Extraction GC-MS Analysis Target Analytes α-pinene β-pinene 3-carene β-myrcene Limonene p-cymene β-citronellal Linalool β-caryophyllene β-farnesene α-humulene E-citral α-terpineol Z-citral geranyl acetate β-citronellol Nerol E-β-damascenone Geraniol β-ionone Eugenol α-eudesmol β-eudesmol Terpinen-4-ol
Significant Analytes
3-carene
β-myrcene
Linalool
β-farnesene
α-humulene
geranyl acetate
β-citronellol
Geraniol
Eugenol
Terpinen-4-ol
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Biochemical Effects
O
HO
OH
OH
OOH
Yeast OH
OHO
HO
HO
OH
OHH2O
Non-Odor Active Odor Active
• Factors – Yeast strain → glycosidase activity
• Response – Change in volatile composition
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Homework
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HS-SPME GC-MS of Big Sky IPA and Budlight
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HS-SPME GC-MS of Big Sky IPA and Budlight
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HS-SPME GC-MS of Big Sky IPA and Budlight
β-M
yrce
ne Lina
lool
β-C
itron
ello
l
Ger
anio
l
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Big Sky IPA hop aroma – Principle compounds (by conc.)
Compound ~Conc. (ppm) Sensory Threshold Description
Myrcene 0.160 ppm 0.01 ppm Metallic, Green, Slight Pine
Linalool 0.174 ppm 0.008 ppm Fruity and Floral. Fruit Loops
α-terpineol 0.071 ppm 0.33 ppm Pine β-citronellol 0.016 ppm 0.04 ppm Citrus Floral Geraniol 0.026 ppm 0.004 ppm Floral Citrus
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References • Forster, A. The quality chain from hops to hop products. In 48th IHGC Congress, Canterbury, Barth-
Haas Research & Publications (http://www. barthhaas. com); 2001.
• European Brewery Convention Hops and Hop Products, Manual of Good Practice; Getranke - Fachverlag Hans Carl: Nurnberg, Germany, 1997.
• Peacock, V. Fundamentals of Hop Chemistry. Tech. Q.-Master Brew. Assoc. Am. 1998, 35, 4–8.
• Eyres, G.; Dufour, J. Hop Essential Oil: Analysis, Chemical Composition and Odor Characteristics. In Beer in Health and Disease Prevention; Preedy, V. R., Ed.; Academic Press: San Diego, 2009; pp. 239-254.
• Schönberger, C.; Kostelecky, T. 125th Anniversary Review: The Role of Hops in Brewing. J. Inst. Brew 2011, 117, 259–267.
• ASBC Methods of Analysis – Beer Flavor Database http://www.asbcnet.org/MOA/Flavors_Database.aspx (accessed June 15, 2014)
• Kishimoto, T.; Kobayashi, M.; Yako, N.; Iida, A.; Wanikawa, A. Comparison of 4-Mercapto-4-Methylpentan-2-One Contents in Hop Cultivars from Different Growing Regions. J. Agric. Food Chem. 2008, 56, 1051–1057.