SURVIVABLE COMPOUNDS

A BREWER’S HANDBOOK
PRESENTERS

Patrick Jensen has been with YCH for more than three Spencer Tielkemeier is the East Division and Brewing Tessa Schilaty is a Seattleite who brewed beer in
years. He was born in Yakima, Washington and knew Innovations Lead for Yakima Chief Hops. He spent 9 Sweden, Germany, Chile, and Scotland before
nothing of hops and beer until he graduated from years in as a production brewer in Austin, TX, graduating from Heriot-Watt University with an MSc in
Central Washington University with a B.S. in chemistry specializing in hop-forward and continental lager Brewing and Distilling. She is now helping to further
in 2004. He owned a Thai restaurant where he was the styles. Since joining YCH Hops, Spencer has been a develop the YCH sensory program with a special
head chef, but soon after graduation ended up in the key part of their Brewing Innovations team, emphasis on beer sensory. Tessa coordinates with
hop industry. He has managed several hop quality developing new products, honing best-practices for Yakima Chief Hops’ sensory team and brewing
laboratories since, and now manages the research and product usage, and providing tailored customer partners to design, execute, and report on
development laboratory for YCH. He works to develop support in challenging product application scenarios. experiments which help further our collective
analytical methods for hop and brewing research and Spencer believes the best beer pairing is made where understanding of hops and beer flavor. When trying to
provides technical expertise to our growers, production hops meet disc golf. He lives in Yakima, WA with his explain her job to strangers at a dinner party, Tessa
processes, quality control and sales team. Pat believes wife, daughter, and dog. describes what she does as “Drinking beer, but for
all beer is great, because…can you believe brewers pay science”.
me to do what I love? He lives in Yakima, Washington
with his wife, daughter and twin autistic sons.

PAGE 2
CULTURE OF INNOVATION
PEOPLE

• Expanded R&D Lab and Sensory teams with experienced hop

and beer staff

FACILITIES

• State-of-the-art R & D lab responsible for creating and refining

analytical standards in the hop industry

• Research brewery conducts continuous product trialing, allowing

constant improvement of YCH products

Together the talented R & D team dedicated to solutions and novel

brewing innovations led to the survivables research – specifically beer
soluble compounds.

The supportive and creative environment allows YCH to enrich our

entire supply chain through industry-leading hop discoveries.

PAGE 3
Pages 2-3
SURVIVABLE COMPOUNDS
RESEARCH & DEVELOPMENT

• R & D Team utilizing cutting-edge hop analysis techniques to

study and detect maximum potential of aroma hops.

• Discovered the hop survivor technology while exploring aroma

potential of novel hop compounds – specifically beer-soluble
compounds.

• Beer Soluble Hop Compound Research creates a framework for

brewers to select and utilize varieties to their maximum effect.

• Helps to bridge the gap between raw hop aroma and finished
beer aroma.

GROWER NETWORK

• 40 million+ lbs of harvest bales allows YCH to choose the

perfect, most impactful blend components

PAGE 4
Pages 4-7
HOP OIL COMPONENTS
OVER 1,000 DIFFERENT COMPOUNDS

• Terpenes (Hydrocarbons)
• Monoterpenes 40%
• Sesquiterpenes 40%
• Aliphatic Hydrocarbons <1% (straight chains nonaromatic
rings)

• Oxygenated Derivatives
• Esters 15%
• Carboxylic acid 1%
• Monoterpene Alcohols 1%
• Sesquiterpene Oxides 1%
• Aldehydes and Ketones 1%
• Thiols (sulfur-containing compounds)

PAGE 5
Page 26
TERPENES
TERPENES
• Compounds made of one or more isoprene groups (C5 H8)
• Myrcene most prevalent
• Hop analysis focuses on mono- and sesqui- terpenes
• All terpenes are hydrocarbons, not all hydrocarbons are terpenes
• If it ends in “ene” it doesn’t make the scene myrcene

COMMONLY FOUND TERPENES

• Myrcene – herbal, woody aroma – can be up to 75% of a hops’ total oil, volatile, low
solubility
• Farnesene – woody aroma – commonly found in Noble Varieties
• α-humulene – grassy, herbal, woody aroma – highly volatile
• β-pinene – pine-like aroma – less abundant in hops, usually around 1% of total oils, volatile
• β-caryophyllene – woody, cedar-like aroma – contributes to Noble Hop aroma and found in
lower levels in newer American Hops, volatile
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Pages 26-27
SURVIVABLE COMPOUNDS
1. MONOTERPENE ALCOHOLS (ex. linalool and geraniol)-
High beer solubility, vital contributors to finished hoppy beer aroma

2. SOLUBLE ESTERS (ex. 2MIB and isoamyl isobutyrate) –

Class of compounds that contain a carboxyl functional group
between two carbon chains. Aromatically this class of compounds
are known to provide tropical, berry, ethereal aromas.

3. POLYFUNCTIONAL THIOLS (ex. 3-mercaptohexanol) –

Organosulfur compounds that contain a sulfhydryl group (-SH)
along with more than one organic functional groups, often
contributing positive beer flavor and aroma. Minute quantities only
detectable via specialized lab equipment.

PAGE 7
Pages 22-29
TERPENE ALCOHOLS

TERPENE ALCOHOLS
• Closely related to terpenes
• Terpene alcohols are oxygenated
• Alcohols are more soluble due to their greater polarity Geraniol

• Hops high in terpene alcohols are thought to benefit hot-side additions

• Terpene alcohols are the subject of recent biotransformation research
• If it ends in “ol” you just might get it all

COMMONLY FOUND TERPENE ALCOHOLS

• Geraniol
• Linalool Linalool

• Nerol

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Pages 27-28
TERPENE ALCOHOLS
GERANIOL
• Monoterpene alcohol
• Commonly survives late boil and whirlpool additions
• Geranium-like and citrusy aroma
• Thought to be at least partially biotransformed by certain strains of yeast into β-citronellol
during fermentation.

PAGE 9
Page 28
TERPENE ALCOHOLS
LINALOOL
• Monoterpene alcohol
• First hop oil discovered in beer
• Commonly survives the brewing process
• High levels act as a ‘booster’ to increase fruity flavors
• Commonly used as a fragrance and flavoring in cosmetics and candy.
• Strong fruity and floral aroma, similar to the aroma of Froot Loops™ cereal

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Page 28
SULFUR-CONTAINING COMPOUNDS
SULFUR COMPOUNDS
• Represent an increasingly important area of study in hop aroma science
• Difficult to detect using a traditional GC-MS
• Usually found in extremely small concentrations in hops
• Human nose is excellent at detecting sulfur compounds
• Common confusion surrounds the prefixes mercapto and sulfanyl
POLYFUNCTIONAL THIOL
• Blanket term for an organic compound containing a sulfhydryl functional group(-SH)
• Often contributing positive beer flavor and aroma

COMMONLY FOUND SULFUR COMPOUNDS

• 4-methyl-4-sulfanylpentan-2one (4MSP or 4MMP)
• 3-sulfanylhexan-1-ol (3SH or 3MH)
• 3-sulfanylhexyl acetate (3SHA or 3MHA)
• 3-sulfanyl-4-methylpentyl acetate (3S4MPA or 3M4MPA)
• 3-sulfanyl-4-methylpentan-1-ol (3S4MP or 3M4MP)
PAGE 11
Pages 28-29
SULFUR-CONTAINING COMPOUNDS
3-MERCAPTOHEXANOL
• Polyfunctional thiol
• Commonly found in hops
• Tropical and grapefruit aroma
• Can be converted by yeast into 3SHA (3MHA)

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Page 29
ESTERS AND KETONES

ESTERS AND KETONES

• 3rd most abundant class of essential oil compounds ~ 15%
• Found in the Bracteoles of hop cone
• Esters typically provide fruity notes
• If it ends in “ate” it probably tastes great

COMMONLY FOUND ESTERS AND KETONES

• 2-methylbutyl isobutyrate
• Methyl geranate
• 2-nonanone
• Butanoic acid 3-methylbutyl ester

PAGE 13
Page 29
ESTERS AND KETONES
2-METHYLBUTYL ISOBUTYRATE
• Ester derived from hops
• Typically survives the brewing process
• Fruity aroma, specifically apricot

PAGE 14
Page 29
ESTERS AND KETONES
ISOAMYL ISOBUTYRATE
• Hop-derived ester
• Typically survives the brewing process
• Fruity and pineapple aromas

PAGE 15
Page 29
ESTERS AND KETONES
METHYL GERANATE
• Methyl ester
• Derived from hops
• Typically survives the brewing process
• Fruity and floral aroma

PAGE 16
Page 29
ESTERS AND KETONES
2-NONANONE
• Ketone
• Variety of different aromas
• Can be sweet and fruity
• Can be cheesy, buttery, and waxy

PAGE 17
Page 29
SURVIVABLE COMPOUNDS
THE SURVIVABLES GRAPH

PAGE 18
Pages 8-9
 1. USE HIGH SURVIVABLES HOPS EARLY (OR LATE)
SURVIVABLE COMPOUNDS Hops with higher concentrations of survivable compounds
have a better likelihood of being successful when used
earlier in the brewing process than hops with
THE SURVIVABLES GRAPH
low concentrations of these same compounds. Early
additions include late kettle, whirlpool, and active
fermentation dry hopping (AFDH).
EXAMPLE
Idaho 7® is likely a better choice for high-impact whirlpool
hopping than Cascade.
This is because Idaho 7® contains higher concentrations
of beer soluble compounds that can survive heat and
fermentation activity.

PAGE 19
Pages 8-9
 2. USE LOW SURVIVABLES HOPS LATE
SURVIVABLE COMPOUNDS Similarly, we can say that hops with lower concentrations
are likely to find better success and a more positive
impact in beer when used later in the process, such as
THE SURVIVABLES GRAPH
post fermentation dry hopping (PFDH).
EXAMPLE
Cashmere will likely make a higher impact in finished beer
if used later in the brewing process.

This is because Cashmere contains smaller

concentrations of beer soluble compounds that can
survive heat and fermentation activity.

PAGE 20
Pages 8-9
SURVIVABLE COMPOUNDS
3. BLEND HOPS TO MAXIMIZE BENEFICIAL
CONCENTRATIONS
Focus on balancing high concentrations when creating
blends.
EXAMPLE
Because Loral® is high in linalool and Talus™ is high in
geraniol, the two of them are likely to work well in
concert. Loral® and Crystal are both high in linalool and
would therefore likely create a less dynamic
and more one-dimensional blend.

PAGE 21
Pages 8-10
 4. LOAD WORT STREAMS WITH SURVIVABLES
SURVIVABLE COMPOUNDS EARLY
High concentrations of survivables in whirlpool and active
THE SURVIVABLES GRAPH fermentation dry hopping can create conditions necessary
for beneficial biotransformation.
EXAMPLE
A whirlpool addition of Idaho 7® combined with an active
fermentation dry hopping addition of Sabro® and
Simcoe® is likely to yield huge flavor impact because it
loads the wort stream with a diverse array of “raw
materials” needed to favor biotransformation.

PAGE 22
Pages 8-10
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PAGE 23
Page 14
CRYO POP™ ORIGINAL BLEND
THE SURVIVABLES GRAPH

PAGE 24
Pages 8-9
CRYO POP™ ORIGINAL BLEND
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PAGE 25
Pages 14-19
 PAGE 26
Page 17
Page 18 PAGE 27
Page 19 PAGE 28
CRYO POP™ ORIGINAL BLEND
BEER SENSORY ANALYSIS

BERRY Active Fermentation

SWEET AROMATIC STONEFRUIT Peach, Pineapple, Strawberry (50% each)
80
Guava, Mango, Orange (38% each)
CEREAL 60 POMME

40 Post Fermentation
20
Peach, Grapefruit (50% each)
WOODY
MELON
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EARTHY TROPICAL

VEGETAL
CITRUS

HERBAL FLORAL

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PAGE 29
Pages 22-24
CRYO POP™ ORIGINAL BLEND
BEER SENSORY ANALYSIS BERRY

SWEET AROMATIC STONEFRUIT

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between components 60

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WOODY POMME
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PAGE 30
Page 15
Pages 20-21
PAGE 31
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PAGE 32