hop chemistry - snobs · 2018. 1. 15. · hop oil • hop oil (essential oil) constitutes typically...
TRANSCRIPT
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Hop Chemistry
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DISCLAIMER
1) I am not a hop chemist
2) The field of hop chemistry is vast
3) Some of the published science is sloppy
4) Hop flavors and aromas are subjective
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Why are hops added to beer?
• They add bitterness to balance malt sweetness
• They contribute to foam stability
• Aroma• Microbiological stability
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Many chemical compounds are responsible for the properties of
hops:
• a-acids (humulones)
• b-acids (lupulones)
• Hop oils (or essential oils)
• Polyphenols (tannins)
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An Organic Chemistry Primer—Representing Structures
• Lines represent bonds
• Carbon atoms are present where lines intersect or end
• Each carbon will form four bonds
• Heteroatoms (O, N) are shown; hydrogens are implied
H2C
H2CCH2
CH2
CH2
H2C
H2C
H2CCH2
CH
CH
H2C
H2C
H2CCH2
CH2
CH2
C
O O
CH2
HC
CCH3
CH3
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An Organic Chemistry Primer—Representing Structures
• Organic molecules are three-dimensional
• This can be represented in two-dimensional drawings using wedge-shaped or dashed bonds
• Molecules that are identical except in three dimensions are called stereoisomers
• Stereoisomers can have different physical properties
CH3
CH3
CH3
CH3
CH3
CH3
different molecules!
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a-Acids
• First isolated as lead compounds in 1887 by German chemists
• Humulone was isolated in 1904 as a pure compound
• In 1925 a structure for humulone was proposed—turned out to be incorrect
• The correct structure was elucidated in 1950
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a-Acids
• In 1952 the existence of additional a-acids was proposed
• Cohumulone was isolated in 1952, and the structure confirmed in 1954
• Adhumolone was characterized the same year
• Humulone, cohumulone, and adhumulonemake up 95% of the a-acids in hops
• The structural differences between the three major a-acids are relatively small
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a-Acid Structures-The Big Three
OH
R
OO
O OH
R =
R =
R =
Humulone
Cohumulone
Adhumulone
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a-Acid Isomerization
• a-acids are not themselves bitter
• a-acids have low aqueous solubility (pH-dependent)—6 mg/L
• For bittering, a-acids have to be isomerized
• This can occur at temperatures >100°C (212°F)
• The higher the pH the faster the isomerization
• Also catalyzed by some metal ions (e.g., Mg)
• Photoisomerization (light) is possible--slow
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Structural Changes in Isomerization
OH
R
OO
O OH
heat
R
O
O
OHO
HO
a-acid isoa-acid
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Isomerized a-acids
• When an a-acid isomerizes it generates two iso-a-acids
• The two iso-a-acids are stereoisomers and have different properties—bitterness, stability
OH
R
OO
O OH
heat
R
O
O
OHO
HO
a-acid isoa-acid
R
O
O
OHO
HO
isoa-acid
+
75% 25%
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Isomerized a-acids
• Isomerized a-acids are much more soluble in wort than a-acids
• Maximum conversion from a-acid to iso-a-acid is 60-65% at atmospheric boil
• Utilization is 30-40% (T90 pellets)
• Utilization can be affected by boil time, gravity, pH, oxidation, adsorption, foaming
• More losses occur in fermentation, filtration
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Isomerized a-acids
• The concentration of iso-a-acids in beer is low—15-80 ppm (15-80 mg/L)
• But 80% of beer’s bitterness is derived from iso-a-acids
• Degradation of the iso-a-acids leads to compounds that aren’t as bitter
• This explains the decrease in hoppiness in beers that are mishandled
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Isomerized a-acids
• Iso-a-acids are also sensitive to light
• These degradation products are responsible for the skunky taste of light-struck beer
• But iso-a-acids can be chemically modified to increase their stability
• This allows certain macro beers to be packaged in colorless glass bottles instead of amber bottles
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Isomerized a-acids
• Iso-a-acids stabilize beer foam• They inhibit the growth of gram-positive bacteria,
but lactic acid bacteria in beer are not affected by iso-a-acids (they’ve adapted)
• The iso-a-acids derived from cohumulonestabilizes foam less than the iso-a-acids derived from the other a-acids, and reportedly have a lower and less-pleasant bitterness than the other iso-a-acids
• Thus cohumulone levels in hops can be an important consideration—more later
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Reduced Iso-a-acids
• The term “reduction” in organic chemistry can be defined in several ways
• For our discussion of hops chemistry the best definition will be reduction = the addition of hydrogen (H2) across bonds
• There are several bonds in iso-a-acids where hydrogen can be added
• Reduction of iso-a-acids can be carried out to different degrees
• The reduced iso-a-acids have useful properties in the production of beer
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Reduced Iso-a-acids
R
O
O
OHO
HO
isoa-acid
R
O
O
OHHO
HO
dihydroisoacid
R
O
O
OHHO
HO
hexahydroisoacid
R
O
O
OHO
HO
tetrahydroisoacid
1 H2
2 H2
3 H2
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Reduced Iso-a-acids
• Reduction of iso-a-acids improves their stability to light exposure
• Reduced iso-a-acids improve foam stability (more hydrophobic)
• Reduction can also increase the level of bitterness
• Skunk odor formation is prevented
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Skunking of Beer
• The skunk odor in light-struck beer is due to a sulfur-containing compound called 3-methyl-2-butene-1-thiol (MBT)
• It’s generated when light of a certain wavelength interacts with an iso-a-acids
• The immediate degradation products pick up sulfur from another source in beer (cysteine)
• MBT is one component (of seven) in skunk spray (taste threshold ~1 ppt)
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Skunking of Beer
R
O
O
O HO
H O
i s o a - a c i d
l i g h t
R
O
O
O H
H O
S H
S H
3 - m e t h y l - 2 - b u t e n e t h i o l ( M B T )
O
- C O +
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Skunking of Beer
• Reduction prevents the photo reaction:
R
O
O
OHO
HO
isoa-acid
add 1 H2
R
O
O
OHHO
HO dihydroisoacid(rho-isoacid)
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Skunking of Beer
• Reduction prevents the photo reaction:
R
O
O
O HH O
H O
rh o - is o a c id
l ig h t
R
O
O
O H
H OX
O
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Skunking of Beer
• Miller High Life is packaged in colorless glass bottles
• It doesn’t take a lot of light exposure to bring about the skunking reaction—it can occur in as little as 30 seconds
• Miller uses a reduced iso-a-acid—a tetrahydroiso-a-acid—to bitter High Life
• This prevents the skunk formation
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b-acids
• Lupulone was first isolated in pure form in 1863
• Its structure wasn’t confirmed until 1952
• Colupulone and Adlupulone were identified in 1955
• Structurally a-acids and b-acids resemble each other, but their chemical properties are very different
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b-acids
R
OO
OOH
R =
R =
R =
Lupulone
Colupulone
Adlupulone
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b-acids
• b-acids are not themselves very bitter
• Their solubility is lower than that of a-acids, so most of the b-acid charged to the boil is lost on the kettle walls or with the trub
• Unlike a-acids, they don’t isomerize upon heating in wort
• Instead, they oxidize to form bitter compounds—the hulupones
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b-acids
R
OO
O OH
O2
O
R
O
O OH
b-acid
hulupone
+
O O
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b-acids
• Hulupones will also form in stored hops from exposure to oxygen
• Their bitterness is only slightly less than that of iso-a-acids
• The quality of the bittering varies—some beer drinkers like it, some don’t
• This oxidation process can explain why old hops can still produce bitter beer
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Another Source of Bittering
• There is another minor source of bittering in hops: Xanthohumol
• Xanthohumol is a polyphenol, but it undergoes a change during the boil that converts it to a bitter substance, Isoxanthohumol
• Isoxanthohumol is 8-30% as bitter as iso-a-acids
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Another Source of Bittering
• Note the lack of a five-membered ring—compare to iso-a-acids and hulupones
OHHO
OCH3O
OH
XanthohumolIsoxanthohumol
heatHO
OCH3
O
O
OH
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Hop Oil
• Hop oil (essential oil) constitutes typically 0.5-2.5% of hops by weight
• There are between 400 and 1000 different compounds in hop oil
• Because they are volatile relative to a-acids and b-acids they are responsible for the aroma of hops
• There are three main types of compounds in hop oil:
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Hop Oil
1) Hydrocarbons (major)
2) Oxygen-containing compounds
3) Sulfur-containing compounds
• An entire series of lectures could be devoted to hop oil constituents
• We’ll only discuss a few—those found on a typical hop certificate of analysis
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Hop Oil: Hydrocarbons
• Composed of carbon and hydrogen only
m y r c e n eh u m u l e n e
b - p i n e n e
c a r y o p h y l l e n e f a r n e s e n e
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Hop Oil: Hydrocarbon Aromas
• Myrcene green, balsam, slightly metallic
• Humulene woody
• b-pinene coniferous pine, woody
• Caryophyllene woody, carrot
• Farnesene green, woody, weedy, herbal, pine, gin
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Hop Oil: Oxygenated Compounds
• These are derived from hydrocarbons by oxidation (addition of oxygen)
OH
linaloolgeraniol
HO
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Hop Oil: O.C. Aromas
• Geraniol sweet floral, perfumy
• Linalool floral, orange
OH
linaloolgeraniol
HO
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Hop Oil Volatility
• The hydrocarbon aroma compounds are quite volatile and will not survive the boil and fermentation
• They will distill off during the boil, and be sparged off by CO2 during fermentation
• Most oxygen- and sulfur-containing compounds will survive the boil and fermentation
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Hop Oil Volatility
• Bitterness is a function of a-acid levels and boil time
• Aroma level is a function of volatilization
Floral Citrus Spicy Resinous
Kettle hop + +
Late hop ++ ++ ++
Dry hop +++ +++ +++ +
From Shellhammer 2014
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Hop Certificates of Analysis
• Hop Cs of A will show you the content of certain chemical compounds for a given lot of hops
• Typically 10 or so compounds are included: a-acids, b-acids, cohumulone, b-pinene, myrcene, linalool, caryophyllene, farnesene, humulene, and geraniol
• Total oil (mL/100 g) is also included
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Hop Certificates of Analysis
• Aroma Hop: Cascade (YCH)
Alpha Acid 5.5 - 9%Beta Acid 6 - 7.5%Cohumulone 30 - 35%Total Oil 0.8 - 2.5 mL/100gb-Pinene 0.5 - 0.8% of total oilMyrcene 45 - 60% of total oil
Linalool 0.3 - 0.6% of total oilCaryophyllene 5 - 9% of total oilFarnesene 6 - 9% of total oilHumulene 14 - 20% of total oilGeraniol 0.2 - 0.2% of total oil
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Hop Certificates of Analysis
• Bittering Hop: Warrior
Alpha Acid 15.5 - 18%Beta Acid 4.4 - 6%Cohumulone 25 - 28%Total Oil 1 - 2.5 mL/100gB-Pinene 0.5 - 0.7% of total oilMyrcene 40 - 50% of total oil
Linalool 0.4 - 0.7% of total oilCaryophyllene 11 -14% of total oilFarnesene < 1.0% of total oilHumulene 15 - 18% of total oilGeraniol 0.4 - 0.8% of total oil
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Hop Certificates of Analysis
Major differences between Warrior (l) and Cascade (r)
Alpha Acid 15.5 - 18%Beta Acid 4.4 - 6%Cohumulone 25 - 28%
Myrcene 40 - 50%Caryophyllene 11 -14%Farnesene < 1.0%
Alpha Acid 5.5 – 9%Beta Acid 6 – 7.5%Cohumulone 30 –35%Myrcene 45 - 60% Caryophyllene 5 - 9%
Farnesene 6 - 9%
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Hop Certificates of Analysis
• Chemistry will only get you so far when deciding what hops and how much hops to use in a beer
• Many of the most interesting aroma compounds aren’t included on Cs of A
• Smelling and tasting hops still has great value in brewing
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Questions?