SURVIVABLE COMPOUNDS

A BREWER’S HANDBOOK
 PRESENTERS

Patrick Jensen has been with YCH for more than three Spencer Tielkemeier is the Director of North Tessa Schilaty is a Seattleite who brewed beer
years. He was born in Yakima, Washington and knew American Sales for Yakima Chief Hops. He spent in Sweden, Germany, Chile, and Scotland before
nothing of hops and beer until he graduated from Central 9 years in as a production brewer in Austin, TX, graduating from Heriot-Watt University with an
Washington University with a B.S. in chemistry in 2004. He specializing in hop-forward and continental lager MSc in Brewing and Distilling. She is now helping
owned a Thai restaurant where he was the head chef, but styles. Since joining YCH Hops, Spencer has to further develop the YCH sensory program with
soon after graduation ended up in the hop industry. He has been a key part of their Brewing Innovations a special emphasis on beer sensory. Tessa
managed several hop quality laboratories since, and now team, developing new products, honing best- coordinates with Yakima Chief Hops’ sensory
manages the research and development laboratory for YCH. practices for product usage, and providing team and brewing partners to design, execute,
He works to develop analytical methods for hop and brewing tailored customer support in challenging product and report on experiments which help further our
research and provides technical expertise to our growers, application scenarios. Spencer believes the best collective understanding of hops and beer flavor.
production processes, quality control and sales team. Pat beer pairing is made where hops meet disc golf. When trying to explain her job to strangers at a
believes all beer is great, because…can you believe He lives in Yakima, WA with his wife, daughter, dinner party, Tessa describes what she does as
brewers pay me to do what I love? He lives in Yakima, and dog. “Drinking beer, but for science”.
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
Handbook 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
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
Handbook page 6
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

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
PAGE 6
Handbook 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
Handbook pages 22 - 29
SURVIVABLE COMPOUNDS SENSORY EXPERIENCE
• There are labeled fragrance strips on
your table.
• We will come around with the
corresponding colored vial of each
aroma standard.
• Place the bundled matching fragrance
strips in the vial and allow full contact
with the liquid. Then remove the strips
and pass them around the table.
• Wave off excess and allow alcohol
dilution to evaporate.
• Smell the fragrance strip.
PAGE 8
TERPENE ALCOHOLS

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

PAGE 9
Handbook 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 10
Handbook 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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Handbook page 28
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

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

PAGE 13
Handbook page 29
ESTERS AND KETONES

ISOAMYL ISOBUTYRATE
• Hop-derived ester
• Typically survives the brewing process
• Fruity and tropical fruit aromas

PRESENTATION NAME 9/1/2022 PAGE 14

Handbook page 29
ESTERS AND KETONES

ISOBUTYL ISOBUTYRATE
• Hop-derived ester
• Typically survives the brewing process
• Fruity and pineapple aromas

PRESENTATION NAME 9/1/2022 PAGE 15

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

PAGE 16
Handbook 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
Handbook page 29
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 18
Handbook page 29
SULFUR-CONTAINING COMPOUNDS
3-MERCAPTOHEXANOL
• Polyfunctional thiol
• Commonly found in hops
• Tropical and grapefruit aroma
• Can be converted by yeast into 3SHA (3MHA)

PAGE 19
THE SURVIVABLES GRAPH
Crop Year 2021

PAGE 20
Handbook pages 8 - 9
 1. USE HIGH SURVIVABLES HOPS EARLY (OR LATE)
THE SURVIVABLES GRAPH Hops with higher concentrations of survivable compounds
have a better likelihood of being successful when used
Crop Year 2021 earlier in the brewing process than hops with
low concentrations of these same compounds. Early
additions include late kettle, whirlpool, and active
fermentation dry hopping (AFDH).
EXAMPLE
Ekuanot® is likely a better choice for high-impact whirlpool
hopping than Palisade®.
This is because Ekuanot® contains higher concentrations
of beer soluble compounds that can survive heat and
fermentation activity.

PAGE 21
Handbook pages 8 - 9
 2. USE LOW SURVIVABLES HOPS LATE
THE SURVIVABLES GRAPH Similarly, we can say that hops with lower concentrations
are likely to find better success and a more positive
Crop Year 2021 impact in beer when used later in the process, such as
post fermentation dry hopping (PFDH).
EXAMPLE
Willamette will likely make a higher impact in finished beer
if used later in the brewing process.

This is because Willamette contains smaller

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

PAGE 22
Handbook 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 23
Handbook pages 8 - 10
 4. LOAD WORT STREAMS WITH SURVIVABLES
THE SURVIVABLES GRAPH EARLY

Crop Year 2021 High concentrations of survivables in whirlpool and active

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 24
Handbook pages 8 - 10
CRYO POP® ORIGINAL BLEND
Crop Year 2021

PAGE 25
Handbook pages 8 - 9
Handbook pages
PAGE20-21
26
CRYO POP® ORIGINAL BLEND
CONVENTIONAL USAGE

• Brewer looking for a “go-to” solution for all juicy,

hazy, fruit-forward beers

• Brewer needing a user-friendly solution to help

them make market-relevant beer

STRATEGIC USAGE

• Brewer focused on maximizing contributions from

individual hop compounds

• Brewer desiring to bridge the gap between raw

hop and finished beer aromas

PAGE 27
Handbook pages 14 - 19
 Join Code: K71P9

PRESENTATION NAME 9/1/2022 PAGE 28

PRESENTATION NAME 9/1/2022 PAGE 29
CRYO POP® ORIGINAL BLEND
BEER SENSORY ANALYSIS

Active Fermentation
Peach, Pineapple, Strawberry (50% each)
Guava, Mango, Orange (38% each)

Post Fermentation
Peach, Grapefruit (50% each)
Mango, Pineapple, Pine, Sweetgrass (38% each)

Cryo Pop® Cryo Pop®

Original Blend Original Blend
Active Post

PAGE 30
Handbook pages 22 - 24
CRYO POP® ORIGINAL BLEND
BEER SENSORY ANALYSIS

• Trial designed to test the impact of synergies

between components

• Cryo Pop® Original Blend showed significantly

higher incidence of desirable aromas in Berry,
Stone Fruit, Floral, and Sweet Aromatic

• Superior performance is believed to be

created by synergies between beer-soluble
components

Post-Package Blend of Constituents Cryo Pop®

Original Blend

PAGE 31
Handbook pages 15
9/1/2022