30 The Art Chemistry of Wine PDF

The Art & Chemistry of Wine
Ralph Obenauf
President, SPEX CertiPrep
Patricia Atkins
Applications Specialist, SPEX CertiPrep
© SPEX CertiPrep, Inc. 2011

Housekeeping
 Everyone in attendance will receive a copy of the slides

 The webinar is being recorded and will be available for
everyone to view on demand
– The recording will be posted about one week after the
event
 Questions will be answered at the end of the presentation
– Type any questions you may have into the question box
and we will answer them during the Q & A portion
 Stay tuned after the Q&A session – we’re giving away a
free gift!

Ralph Obenauf
Making wine and making merry……
…..with some chemistry thrown in.
As Ben Franklin said:

In wine there is wisdom,
In beer there is freedom,
In water there is bacteria.
Viniculture: The science and study of all aspects of wine
grape cultivation and production

Harvesting the Grapes
 A grape’s terroir : affects of season, weather,
soil, mineral, time of harvest, pruning method
and acidity = quality, aroma & flavor
 Harvest time = grape’s level
– sugar (ºBrix) usually >15%
• Later harvest = more sugar
– Acid Levels - Tartaric acid
– pH
 Other harvest factors:
– Tannin development (seed color & taste)
 De-stemming (removal of stems) depends on
winemaking techniques
– Stems and seeds = tannins
• White wines – stems intact
• Red wines – stems removed

Varietals
Original Barrel of Zin #444

Varietals
 Over 10,000 varieties of grapes in world

 Vitis vinifera
– Most common species of grapes
– Almost all the European varieties
– Every continent except Antarctica
 Vitis silvestris: ancestor of modern wine
 Grape Uses
– 71% Wine
– 27% Fresh Fruit
– 2% Dried fruit
 Top wine production regions: Italy,
France, Spain, US & Argentina
 Grafting Root Stocks
Chemistry of the Grape
70-90% Water
18-25% Glucose &

Fructose
0.3-1.5% Tartaric &

Malic Acids
0.7% Amino acids
0.15% Potassium
<0.1% Esters
<0.1% Polyphenols
Trace Amounts 2 ½ lbs of Grapes are needed

Vitamin A, Vitamin C to create a bottle of wine!
Flavor & Aroma Chemistry of
Varietals
Compound Examples Odor Varietals
Methoxypyrazines Cabernet Sauvignon and
Earthy, Grassy, Pepper
Sauvignon blanc.
2‐methoxy‐3‐isobutylpyrazine (IBMP) Bell Peppers
2‐methoxy‐3‐isopropylpyrazine (IPMP) Asparagus, Peas, Earth
Monoterpines
geraniol, linalool and nerol Floral Gewurtramine, Muscat, Riesling
Norisoprenoids megastigmatrienone Spice Chardonnay

zingerone Spice
damascenone Rose Oil Pinot noir
vanillin Vanilla
Cabernet Sauvignon,
Gewürztraminer, Merlot, Muscat,
Mercaptans Onion, Garlic Petit Manseng, Pinot blanc,
Pinot gris, Riesling, Scheurebe,
Thiols Semillon and Sylvaner
4‐mercapto‐4‐methylpentan‐2‐one
(4MMP), 4‐mercapto‐4‐methylpentan‐2‐
Sauvignon blanc
ol, 3‐mercaptohexanol, 3‐mercaptohexyl
acetate
Glycosides Chocolate, Tobacco Ports
Oenology:
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Crushing the Grapes
 Crushing = start liberation

of juice from grape
 The Must = juice, skins,
seeds, pulp
 Must contains molds &
native yeasts
– Natural is not better
 Grape components
crushed = winemaking
method & variety of wine

Crushing the Grapes
White Wines
• Stems can be Intact:
• Increases tannins
• Reduces exposure to color in skins
• Skins directly removed
Rose Wines
• Red skinned grapes with minimal skin contact
• White & red grapes
Red Wines
• Stems usually removed
• Contact with skin encouraged to varying degrees

Potassium metabisulfite & SO2
 Added during many stages

– Campden tablets = ½ g potassium or sodium
metabisulfite
 Levels in wine
– Commercial wine = 20 to 40 ppm
– Natural wines as low as 6 ppm
• Obie’s wines: no added sulfites; drink within
3-4 years
 Produces SO2
− Kills native yeast = antimicrobial
− Anti-oxidant
• Binds w/ acetaldehyde
• Binds w/ anthocyanins
• red wine = problem
• Anthocyanins bind to tannins © SPEX CertiPrep, Inc. 2011
Sulfites
 K2S2O5, contributes to sulfites in wine

 ‘Contains Sulfites’ = added sulfite
compounds
– Warning labels
• 1987 US
• 2005 EU
 All wines have sulfites
– Sweet & White > Reds
– Fermentation process = 6 to 40 ppm
sulfites
– US levels allowed = 350 ppm

Red Wine Headaches
 Occurs after drinking red wine

− As little as one glass
 Usually blamed on sulfites
− Only 0.01% population are allergic
to sulfites = asthmatics
 Un-metabolized acetaldehyde causes
headaches
 Possible other causes:
− Histamines
− Tannins
• Cause release of serotonin
− Prostaglandin release
• Cause pain and swelling
− Strains of yeast or bacteria

Punching Down the Must
 ‘Cap’ – skins, seeds etc. top of juice - CO2
 Punching down the must
– Juice mix with skins = color & flavor
extraction
– introduce O2 to yeast = fermentation
– prevent harmful bacterial growth
– lower the must temperature
• Preserve delicate aroma compounds
• Increases production of esters
• Keep yeast growing
Red wines: 22 to 25° C
White wines: 15 to 18° C
 Cultured, selected yeast added
– Beginning of primary fermentation
• 1-2 weeks
• Converts most of sugar to ethanol © SPEX CertiPrep, Inc. 2011
The most Important Chemical
Reaction in Wine Making!
C6H12O6 → 2 C2H5OH + 2 CO2

Fermentation Reactions
Bacteria or yeast consumes one compound and
excretes different product(s)
Fruit Milk Flour Ethanol

(sucrose / (lactose) (sugars) +
fructose / + + Yeast
glucose) Bacteria Yeast =
+ = = Acetic acid
Yeast Cheese Bread (Vinegar)
=
Alcohol
(Ethanol)
Sugars
 Sugar level in wine = ºBrix

 1.0º Brix = 1% Sugar = 0.55%
EtOH
 Sugar level = alcohol content
 Sugars = 1º fuel fermentation
 Non-fermentable sugars (5 C ring)
– Arabinose, Rhamnose & Xylose
– Still present after fermentation
– No wine is ever completely ‘dry’
 Chaptalization: Sucrose added to
boost fermentable sugar content –
boost alcohol content
– 17-18% alcohol highest level
w/o added sucrose
Fermentable Sugars (6 C ring)
 Glucose
− One of primary sugars of wine
− 1st sugar metabolized by yeast
− Tastes < sweet than Fructose
− % Glucose beginning of ripening of
grape (>5x Fructose)
− At harvest glucose = Fructose
 Fructose
− Over ripen grapes > Fructose
− Twice as sweet as glucose
• Important for dessert wines
 Sucrose
− Minimal in wine, except champagne
& sparkling wines

Alcohol - Ethanol
 Alcohol content limited to 18% w/o Wine % Alcohol
sucrose addition
Table Wine 8-14%
 During fermentation, >9% Alcohol Claret 6-10%
needed to prevent bacterial growth
Shiraz 10-14%
– Mother of Vinegar (Acetobacter)
Rose 10%
 Target alcohol = 13% Alcohol (24º Brix)
White, medium 11%
 Final Ethanol Content varies by variety White, dry 11%
Red, medium 12%
White, sparkling 12%
White, sweet 12%
Cabernet, Pinot Noir 11–14%
Dessert Wine 14-20%
Zinfandel 17-22%
Vermouth 17-22%
Syrah 17-23%
Port 20%
http://alcoholcontents.com/wine/wine.html

Pressing the Grape
 Pressure removes juice from pulp & skins
 Gains 15-30% more juice
 Pressed juice has lower acidity (higher pH)
than drained juice
 Red wines pressed after fermentation
 White wines pressed before fermentation
 Pressing releases different compounds
from layers of the grape
 pH adjusted (3.0-3.7)
– Tartaric or Malic Acid
– Prevents bacterial growth
– Gives tart flavor or zing
 <1º Brix before pumping into barrel
– Sweet wine >1º Brix
• Stabilized with Potassium Sorbate
 Bubbler at top of barrel to release CO2
Chemical Anatomy of the Grape
Seeds & Stems

(Optional Inclusion)
• Tannins
Skin
• Anthocyanins
• Quercetin
• Resveratrol
• Tannins
• Catechins

Grape Skin & Seed Compounds:
Tannins
 Plant polyphenol
 Binds and precipitates proteins & other compounds
 3 types: hydrolysable, condensed & complex
 Bad tannins (skins, seeds & stems)
− Don’t polymerize
− Produce bitter taste = astringency
 Beneficial Tannins (Oak barrels)
− Preservative
− Wine clarification (Fining agents)
• Proteins bind to tannins
• Clarify wine: egg whites, gelatin, bentonite
− Young Oak barrels = more tannins
 Red wines (>tannins) pair with meats = hydrolysable tannins
 As tannins age – lose binding
− fall to bottom of bottle
− wine mellows © SPEX CertiPrep, Inc. 2011
Catechins
 Flavanols
 Also found in chocolate
 React with tannins to make primary
flavor components in wine
 Larger flavanol – tannin complexes –
mellow
 Smaller flavanol – tannin complexes –
bitter
 Concentrations in red wine 10 mg/L to
250 mg/L
− Lighter bodied wine > catechin
content

Anthocyanins
 Water soluble pigments of red, purple

or blue (pH)
 Flavenoids
 Antioxidants
 Odorless and almost flavorless
 Polymerize with tannins
 Important in tannin retention and aging
of wine
 Five groups of anthocyanins and
presence dependent on varietal of
grape & wine
− > free hydroxyl groups = blueness
− > methyl groups = redness
− Malvin group – red grapes
Other Grape Skin & Seed
Compounds
 Quercertin
− Flavanoid
− Antioxidant
− Found in skin of grape
− Reacts with anthocyanins
• deeper vibrant color
 Resveratrol (3,5,4'-trihydroxy-trans-
stilbene)
− Phenol produced by plants when
under attack by bacteria and fungi
− Found on skin of grape
− Antioxidant works in conjunction
with Quercertin
− Reported health benefits
Other Grape Skin & Seed
Compounds
 Gallic Acid: Phenolic compound
− Antifungal & Antiviral compound
− Found in seeds & from exposure to new oak
− 10 – 100 g/L in wine
 Succinic Acid: Dicarboxylic acid
− Considered flavor component
− Salty bitter flavor in wine elsewhere for
sweetness
− Reacts to form esters
− Acid + Ethanol = mono-ethyl succinate (fruit
aroma)
− In grape & by-product of alcohol and sugar rxn
 Caffeic Acid & Caftaric Acid: Cinnamates
− Yellow gold color in white wine
− Esterifcation rxn: Caffeic Acid + Tartaric Acid =
Caftaric Acid
− Oxidation > reaction
• Pressed wine have little to no Caftaric Acid
Chemical Anatomy of the Grape
Peripheral Zone
Intermediate Zone
• Potassium
• Tartaric Acid • Sugars
• Sugars • Oxidases
• Acids
• Astringents
• Tannins
• Aroma Compounds
Central Zone
• Malic Acid
• Sugars
Grape Flesh Compounds:
Acids
 Acids are important in

winemaking and the finished wine
 Primary Acids in Wine
− Malic Acid
− Tartaric Acid
 Other Acids in Wine
− Acetic Acid
− Ascorbic Acid
− Butyric Acid
− Citric Acid
− Lactic Acid
− Sorbic Acid

Tartaric Acid
 Most important acid in wine

 Maintains chemical stability of wine
 Influences Taste & Color
 Grape vines -few sources of natural
high concentrations
 Majority of acid = potassium acid salt
(cream of tartar)
 During fermentation acid binds with
pulp debris (lees), tannins, and
pigments
 Acid crystals can precipitate out
− Wine Diamonds
− Cold stabilization precipitates
crystals
Malic Acid
 One of two Primary Acids in Wine

 Carboxylic Diacid
 Bitter, Tart taste
 Associated with Green Apple Flavor
 Riesling – high Malic Acid
 Cooler growing conditions > Malic Acid
 Decreases as grape ripens
 Low Malic Acid = flat taste
 High Malic Acid = sharp bite

Other Acids
Lactic Acid
• Controlled by the winemaker

• Milder than Tartaric or Malic Acid
• Creates milky flavor
• Rxn Lactic acid bacteria (LAB) &
Malic Acid
• Chardonnays & other white
wines
• Some LAB -histamines cause
RWH
Citric Acid
• Very small quantities in wine

• Supplement for sucrose addition

Other Acids
Acetic Acid
• Produced during or after fermentation

• Vinegar taste above 300 mg/L
• Acetobacter
Ascorbic Acid
• Vitamin C
• Found in young grapes
• Lost to ripening
• Added with SO2 as antioxidant (EU limit 150
mg/L)
Butyric Acid
• Bacteria Induced wine fault

• Smells like rancid butter or blue cheese
Sorbic Acid
• Used as a preservative
Sampling Young Wine

Chemistry in a Glass
70-90% Water
6-23% Ethanol by
Variety
1-3% Pectins,
Proteins, Acids
1% Vitamins &
Minerals
1% Polyphenols,
Flavenoids, Tannins
& flavor compounds
Aging the Wine
The average age of a French
Oak tree used for wine barrels
is 170 years old

Oak Barrels
 Two major origins for Oak barrels
– French & American
 Seasoning
– French oak traditionally aged or
seasoned for two years
– American oak kiln dried
 Harvest
– French Oak is split
– American Oak is sawed
• Ruptures xylem cells =
release of lactones
 Flavor: American Oak > French
Oak
– 2-4x > lactones – vanilla
Oak Barrels
 First widespread use - Roman Empire
 400 species of Oak
 20 species used for wine barrels
 One tree = 2 barrels
 5% of the trees used for barrels
 Oak barrels are source for tannins
– New barrels = high tannins
– Green oak = bad tannins
 Porousness: oxidation & evaporation
– 5-6 gal loss (59 gal barrel)
– Angel’s Share
 3-5 vintages before oak character
absent
– Staves sanded to open oak
– Oak strips added to impart aroma © SPEX CertiPrep, Inc. 2011
Other Flavor & Aroma influence of
the Barrel
 Toasting – exposure of oak barrel to

fire & high temperatures
– Reduces lactones (fresh oak
aromas)
– Increases vanilla & caramel
aromas
Vanillin
Furfual
5-methyfurfal
– High toast levels = spicy & smoky
notes
Eugeol & Isoeugenol (spicy)
4-methyl guaiacol (spicy &
smoky)
Guaiacol (smoky)
 Add oak chips to increase aromas
Racking the Wine
Barking at the moon referred to a process of racking the

wine under the clear light of the full moon
 Racking:
Separate the wine from
the solids, “lees”,
settled at the bottom of
the barrel
 Clearing:
Settling of small
particulates and matter
in wine over time.

Sampling

Bottling Process
 Bottle Rinsing
– Rinsed with Potassium
metabisulfate
 Bottles Filling
– Wine dispensed into
bottles
 Corks are placed in the

bottles
– Headspace
 Capsules placed on bottles

– Heat sealed
Bottles
Volume
(liters)
# Standard Bottles Name  Shape: traditional, cultural or
0.1875 0.25 Piccolo marketing
0.25 0.33 Chopine
0.375 0.5 Demi  Before corks bottles were squat &
0.378 0.505 Tenth flat bottomed
0.5 0.67 Jennie
0.62 0.83 Clavelin  After corks: store on side: long &
0.75 1 Standard cylindrical
0.757 1.01 Fifth
1.5 2 Magnum
2.25 3 Marie Jeanne
3 4 Jeroboam
4.5 6 Rehoboam
6 8 Methuselah
9 12 Mordechai
9 12 Salmanazar
12 16 Balthazar
15 20 Nebuchadnezzar
18 24 Melchior
20 26.66 Solomon
25 33.33 Sovereign
27 36 Primat
30 40 Melchizedek
Corks
 The primary tree for corks is the

Cork Oak, Quercus suber
 Trees are 25 years old before
cork is stripped from the trunks
every ten years
 The trees live for about 200
years
 Cork production
− 52.5% Portugal
− 29.5% Spain
− 5.5% Italy

Cork Taint
 “Corked Wine”
− Cork industry claims only 0.7 –
1.2% cork taint
 Trichlorophenol compounds
 Found in cork & methylated by fungi
 Product is 2,4,6 trichloroanisole, TCA
 Damp moldy odor

 Human detection limit of TCA is 1ppt
 Eliminate with synthetic corks, screw
caps
– Also eliminates the “POP”
Cork Taint Standards
Single Component:
Part# Compound
S-133 Acetic Acid
S-1885 Ethanol
S-1983 2-Ethylphenol
S-1985 4-Ethylphenol
S-2050 2-Fluorophenol
S-2930 2,3,4,5,6-Pentachloroanisole
S-2950 Pentachlorophenol
S-3405 2,3,4,6-Tetrachlorophenol Multi-Component:
S-3555 2,4,6-Tribromophenol
Part# Compound
S-3586 2,4,6-Trichloroanisole
2,4,6-Tribromoanisole-d5
S-3645 2,4,6-Trichlorophenol WINE-1 Pentachloroanisole-d3
S-4168 Malic Acid 2,4,6-Trichloroanisole-d5
S-4183 4-Ethyl-2-Methoxyphenol 2,3,4,5,6-Pentachloroanisole
S-4309 2,4,6-Tribromoanisole WINE-2 2,3,4,6-Tetrachloroanisole
2,4,6-Trichloroanisole
S-5005 Dextrose
Carbon Disulfide
S-609 2,3-Butanedione
Ethyl Sulfide
Ethanethiol
Ethyl Disulfide
Ethyl Methyl Sulfide
2-Ethylthiophene
Methanethiol
WINE-3
Methyl Disulfide
Methyl Sulfide
2-Methyl-2-Propanethiol
2-Methylthiophene
1-Pentanethiol
2-Propanethiol
Thiophene

Storage
Titanic sits at 12,000 to 13,000 feet below the ocean's surface.
Many of the wine bottles in the cellar were intact.
 Most modern wines are consumed

within 24 hours after purchase (near
term consumption)
 Most important factors:
– Light: light rxn with phenolic
compounds
– Temperature:
Chemical rxns 2x every 8 °C increase
Ideal: 10 to 15 °C
– Humidity (75%): corks from drying
 Wine refrigerators or Wine cellars keep
constant light, temperature & humidity

Enjoy
Breathing the wine: removes hydrogen sulfides from

stinky or young reds; rarely helps whites

Health Benefits
Food & Wine Magazine’s 8 Benefits of
Drinking Wine (2007)
Reduces Heart Attack rate
•30% lower risk (Harvard Public Health Study)
Promotes Longevity
•34% lower mortality rate (Finnish Study)
Lowers Heart Disease

•Queen Mary University, London
Reduces Risk of Type 2 Diabetes

•30% lower risk (Amsterdam VU Univ. Medical Center)
Lowers Risk of Stroke

•Clot risk drops 50% (Columbia University)
Cuts Risk of Cataracts

•32% risk reduction (Nature 2003)
Cuts Risk of Colon Cancer

•45% risk reduction (especially red) (Stony Brook)
Slows Brain Decline

•Reduced risk (Columbia University)
Calories in Wine & Alcohol
 Recent studies report alcohol is not efficiently metabolized in the
body
 To calculate the metabolized calories (N):
N = T – (7cal/g)*(0.28g/oz%)*P*X = T- 2*P*X
N = net calories
T = Total calories
X = #oz
P = % Alcohol
Dry Wine (4oz, 13% abv) Beer (12oz, 5.5% abv) Light Beer (12oz, 4% abv)
T=115, N=9 calories T=150, N=18 calories T=105, N=9 calories

Pesticides in Wine
 Grapes: one of the ‘Dirty Dozen’ of produce
 2008 Pesticide Action Network (PAN) Europe:
– 128 pesticide residues in 40 bottles EU wine
– Low ppm to ppb range
 Studies being conducted to find out if the
pesticide levels are of concern in wine
SPEX CertiPrep Pesticide Standards:

Part# Pesticide Part# Pesticide
S-3970 Dimethomorph S-3984 Azoxystrobin
S-5225 Pyrimethanil S-4962 Fenhexamid
S-4622 Cyprodinil S-4815 Boscalid
S-3871 Procymidone S-2369 Metalaxyl
S-2056 Tebuconazole S-1997 Fenarimol
S-2272 Iprodione S-5469 Spiroxamine
S-733 Carbendazim S-4262 Benalaxyl
S-2061 Fludioxonil S-4267 Penconazole
S-103 Bromopropylate S-4832 Flusilazole
S-3450 Tetradifon
Heavy Metals in Wine
 Studies have found Hazardous
levels of metals in wine
– Exceed EPA THQ (Target
Hazard Quotients)
• Vanadium
• Copper
• Manganese
• Zinc
• Chromium
• Nickel
• Lead
 Worst countries for metal levels:
– Hungary, Slovakia, France,
Austria, Spain, Germany,
Portugal, Greece
Heavy Metals Standards
 SPEX CertiPrep carries full line of
Inorganic standards
− Heavy Metal Mixes
− Heavy Metal Standards
 UL and A2LA Stamp of Approval:
− Certified by UL-DQS for ISO 9001
− Accredited by A2LA for ISO 17025
and ISO Guide 34
 Inorganic CRMs for:
− AA & GFAA
− ICP & ICP-MS
− IC
− XRF
− Classical Wet Chemistry Techniques
 Single element standards 1,000 mg/L
and 10,000 mg/L concentrations
 Custom standards at almost any
concentration
Questions?

New in 2011
2011-2012 Catalog – Now New Consumer Safety

available on CD! standards kit for USP 232
(Part# USP-TXM1)
Visit www.spexcertiprep.com for more information!

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The Art & Chemistry of Wine

© SPEX CertiPrep, Inc. 2011

 Everyone in attendance will receive a copy of the slides

© SPEX CertiPrep, Inc. 2011

As Ben Franklin said:

© SPEX CertiPrep, Inc. 2011

© SPEX CertiPrep, Inc. 2011

Original Barrel of Zin #444

© SPEX CertiPrep, Inc. 2011

 Over 10,000 varieties of grapes in world

18-25% Glucose &

0.3-1.5% Tartaric &

0.7% Amino acids

Trace Amounts 2 ½ lbs of Grapes are needed

Norisoprenoids megastigmatrienone Spice Chardonnay

© SPEX CertiPrep, Inc. 2011

 Crushing = start liberation

© SPEX CertiPrep, Inc. 2011

© SPEX CertiPrep, Inc. 2011

 Added during many stages

 K2S2O5, contributes to sulfites in wine

© SPEX CertiPrep, Inc. 2011

 Occurs after drinking red wine

© SPEX CertiPrep, Inc. 2011

C6H12O6 → 2 C2H5OH + 2 CO2

© SPEX CertiPrep, Inc. 2011

Fruit Milk Flour Ethanol

 Sugar level in wine = ºBrix

© SPEX CertiPrep, Inc. 2011

© SPEX CertiPrep, Inc. 2011

Seeds & Stems

© SPEX CertiPrep, Inc. 2011

© SPEX CertiPrep, Inc. 2011

 Water soluble pigments of red, purple

 Acids are important in

© SPEX CertiPrep, Inc. 2011

 Most important acid in wine

 One of two Primary Acids in Wine

© SPEX CertiPrep, Inc. 2011

• Controlled by the winemaker

• Very small quantities in wine

© SPEX CertiPrep, Inc. 2011

• Produced during or after fermentation

• Bacteria Induced wine fault

© SPEX CertiPrep, Inc. 2011

© SPEX CertiPrep, Inc. 2011

 Toasting – exposure of oak barrel to

Barking at the moon referred to a process of racking the

© SPEX CertiPrep, Inc. 2011

© SPEX CertiPrep, Inc. 2011

 Corks are placed in the

 Capsules placed on bottles

 The primary tree for corks is the

© SPEX CertiPrep, Inc. 2011

 Damp moldy odor

© SPEX CertiPrep, Inc. 2011

 Most modern wines are consumed

© SPEX CertiPrep, Inc. 2011

Breathing the wine: removes hydrogen sulfides from

© SPEX CertiPrep, Inc. 2011

Lowers Heart Disease

Reduces Risk of Type 2 Diabetes

Lowers Risk of Stroke