From Grape To Bottle Avoiding Haloanisole Taint Napa

From Grape To Bottle: Avoiding Haloanisole Taint Napa Valley Wine Technical Group 26 February 2008 Eric Hervé, Ph. D. E T S Laboratories, St. Helena, CA 1

1. Origins of Haloanisoles 2. Prevention at the Winery 3. Prevention of Cork Taint 2

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Microorganisms Haloanisoles Halophenols Phenols Halogens The Haloanisoles Triangle 4

OH Cl Phenol + Chlorine Cl => Trichlorophenol Cl 5

“Hidden Phenols” - Wood - Water - Grape / wine - Synthetic polymers (phenolic resin) 6

Halogens - Chlorine (bleach, hypochlorite) Trichlorophenol (TCP) - Bromine (tablets) Tribromophenol (TBP) - Iodine ? 7

Microorganisms - Detoxification of halophenols Haloanisoles 8

Microorganisms - Molds/Fungi Trichoderma, Fusarium, Penicillium… (Alvarez-Rodriguez et al. , 2003) - Soil bacteria Streptomyces (Mara et al. , 2005) 9

Microorganisms Haloanisoles Halophenols Phenols Halogens Pesticides, Flame Retardants 10

Chloroanisoles in the Press France, 1998: “La maladie cachee du Vin” Wines “corked” by Te. CA 11

OH Cl Cl 2, 3, 4, 6 Tetrachlorophenol (Te. CP) • Present in pentachlorophenol - based wood preservatives 12

February 2007: “Chile's Viña Errázuriz Confronts Contaminated Cellar - Problem with TBA may be widespread in Chile and Argentina“ James Molesworth 13

2, 4, 6 -Tribromophenol (TBP) OH Br Br Br • Wood preservative and flame retardant • Widely used in South America • Beware of pallets!!! 14

Vineyards • Dichloran (Botran®) NH 2 Cl Cl NO 2 • Traces of TCP, Te. CP and PCP found in one sample • Haloanisoles in treated moldy grapes (TCA > 20 ppt) 15

1. Origins of Haloanisoles 2. Prevention at the Winery 3. Prevention of Cork Taint 16

- Phenols: . few options… - Halogens: . no chlorine or bromine - Microorganisms: . humidity <70% 17

- Halophenols: . Replacing bleach-sanitized items (hoses…). Checking wood materials 18

Risk Assessment Visit Main Control Points: - Water - Air - Wood 19

Water Supply • After “shock” chlorination (well, storage tanks) • Water stored in wooden tanks • Epoxy linings • Contact with hoses 20

A/C Unit Condensates • Concentrate airborne haloanisoles • Drip pan sanitized with bromine tablets • Where does the drip line go? 21

Drains • Wine and bleach mix • TCP TCA • TCA volatilized and distributed by drain system 22

Haloanisoles are airborne contaminants • get in wine via contaminated air or materials • minute amounts (ppt) needed 23

Trap for Atmospheric Haloanisoles • Early detection < 0. 1 ppb best 0. 1 - 0. 3 ppb “trace amounts” (common) ~ 1. 0 ppb danger! > 1. 0 ppb wine contamination probable • Monitoring (efficiency of corrective actions) • “Snapshots” 24

Inventory, Sampling, Analysis (haloanisoles AND halophenols) Barrel runners and chocks, wood tanks, wall paneling, posts stairs, catwalks, beams and rafters, plywood ceiling … 25

Barrels and Winemaking Supplies. Hot issue: TBA . Ask barrel suppliers about QA program. Citric, tartaric, bentonite, DE, filter pads… Use your nose, beware of pallets, ! In doubt… test (traps, soaks, analysis) 26

The Threshold Fallacy: Gradation of Sensory Effects 0 “moldy”, “corked” “muted” “wet concrete” ~2 ~6 Difference Recognition TCA ng/L Sub-recognition levels are of concern 27

Sensory Training 28

Last Line of Defense Analysis right before bottling 29

Remediation Options - Whole milk (0. 2 to 0. 6%) - Half and half (0. 2 to 0. 6%) - Yeast hulls (3 to 7 pounds / 1000 Gal) - Food-grade polyethylene sheets (~ 2 sq. feet / gal) - Commercial “TCA-Removal” offerings 30

1. Origins of Haloanisoles 2. Prevention at the Winery 3. Prevention of Cork Taint 31

Releasable TCA (RTCA) Bulk vs. Individual For a cork, or group of corks, the concentration of TCA reached at equilibrium in a wine soak. Expressed in ng/L (or ppt). (Hervé E. , Price S. and Burns G. - ASEV 1999) 32

Bale G: 3. 8 ng/L No clear-cut line “good cork” / “bad cork” 33

Bulk (group) soaks Individual soaks 34

Bottle TCA after 9 months 35

Thank You! www. etslabs. com 36