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. 2026 Apr 24;11(17):25110–25118. doi: 10.1021/acsomega.5c10501

Controlled Sorption Studies of Sprayable Films As Barriers to Smoke-Derived Volatile Phenols in Wine Grapes

Lindsay Garcia 1, D Cole Cerrato 1, Lik R Lim 1, Michael H Penner 1, Yanyun Zhao 1, Elizabeth Tomasino 1,*
PMCID: PMC13150660  PMID: 42110742

Abstract

Wildfire events have emerged as a persistent threat to viticulture worldwide, creating an urgent need for effective mitigation and preventative practices. This study investigated the use of spray coatings onto grape surfaces to form a physical barrier against smoke-derived volatile phenols. The four film formulations compared included cellulose nanofiber, β-cyclodextrin, chitosan, and a mix of β-cyclodextrin and chitosan. The effectiveness of these films in reducing volatile phenol uptake was evaluated during controlled laboratory sorption experiments. Results revealed significant differences in film performance (p < 0.05), with the chitosan formulation showing the greatest efficacy. In diffusion tests, guaiacol penetration through the chitosan film measured 4.1 × 106 a.u. compared to 3.9 × 107 a.u. for the β-cyclodextrin film. Syringol and m-cresol followed similar patterns: <300 vs 1.6 × 105 a.u. for syringol and 9.7 × 104 vs 3.2 × 107 a.u. for m-cresol (chitosan vs β-cyclodextrin, respectively). These volatile phenols showed consistent film interaction trends across additional sorption experiments, though their uptake varied by concentration. Overall, these findings highlight the potential of sprayable coatings, particularly chitosan-based formulations, as a practical vineyard-level strategy to prevent smoke taint in wine grapes.

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1. Introduction

Since the 2010s, the United States wine industry has experienced considerable economic setbacks due to wildfire smoke. , Burned lignin from vegetation produces airborne compounds known as volatile phenols (VPs), which are released into smoke. , Previous research has shown that these volatile phenols contribute to the ashy and burnt sensory qualities in wine produced from smoke exposed grapes. , Additional studies have demonstrated that higher levels of smoke taint reduce consumer liking, posing a significant challenge for a winemaker to market and sell smoke-affected wines. − These undesirable sensory attributes compel winegrowers to make difficult decisions regarding the harvest of smoke-exposed grapes. In 2020, concerns about the potential sensory effects of volatile phenols led to the decision not to harvest $601 million worth of wine grapes from California vineyards. The economic impact of wildfires on the wine industry is not limited to the United States; other wine producing countries, such as Australia, have also experienced financial losses due to smoke exposure. In 2003, wildfires in Australia cost the wine industry an estimated $300 million AUD in losses. As wildfires continue to persist, understanding the effects of volatile phenols on smoke-impacted wine is essential for developing effective mitigation techniques.

The initial step in understanding the impact of volatile phenols on wine involved identifying the specific VPs responsible for the distasteful aromas and flavors in smoke-affected wine. Key VPs identified include guaiacol, 4-methylguaiacol, m-cresol, o-cresol, p-cresol, syringol, and 4-methylsyringol. − Building on this knowledge, researchers have focused on developing remediation strategies aimed at reducing the sensory impact of VPs on wine. − These strategies generally fall into three main categories: prevention in the vineyard, mitigation during wine making, and amelioration methods postproduction. Extensive research has been devoted to mitigating smoke taint after harvest. , However, many postharvest techniques have been either impractical or ineffective, often compromising both the removal of smoke compounds and the overall quality of the wine.

A more promising approach involves preventing the uptake of VPs in the vineyard, thereby minimizing the risk of altering a winemaker’s preferred flavor profile. In 2019, van der Hulst et al. tested this approach by applying kaolin to grapevines prior to smoke exposure. The study yielded mixed results with significantly reduced VP levels in Merlot grapes, but no effects on Sauvignon Blanc and Chardonnay grapes. A similar study tested a biofilm made from artificial phospholipid cuticles. The biofilm significantly decreased the uptake of VPs, showing promise as a preventative measure for smoke taint. However, in both cases, further research is needed to assess how these sprays affect grapes at differing developmental stages.

In 2023, Tran et al. evaluated sprayable cellulose nanofiber coatings. They incorporated β-cyclodextrin and chitosan into the cellulose nanofiber matrix because of their affinity to phenolic compounds. β-cyclodextrin polymers have been shown to remove 23% of guaiacol and 25% of 4-methylguaiacol from smoke tainted wine. Chitosan has also been reported to successfully remove up to 22% of 4-ethylguaiacol in spiked wine. Given these results, it was reasonable to expect that incorporating β-cyclodextrin and chitosan into cellulose nanofiber-based film coatings would promote adsorption of phenolic compounds present in wildfire smoke.

In the work by Tran et al., the liquid formulations were sprayed onto grape surfaces prior to wildfire smoke exposure, forming a dried barrier layer that obstructed VPs from penetrating the grape skins. Their results showed that applying the spray at various developmental stages had no significant effect on berry size, pH, soluble sugar content, or titratable acidity of the fruit, suggesting the film can be applied without compromising grape growth or grape quality. Further research from the group showed the films derived from the coating formulations effectively reduced uptake of larger VPs like guaiacol and syringol, though it was less effective against smaller compounds such as cresols.

To optimize the film formulation in reducing the uptake of volatile phenols of varying sizes in, it is crucial to understand how VPs interact with the surface of the film. A series of targeted experiments is required to examine specific interactions, including the sorption and desorption of VPs from the film, as well as their diffusion through or obstruction by the film matrix. These insights will help identify the limitations of the current formulations and inform future improvements. Thus, the aim of this study was to analyze the sorption behavior of select volatile phenols across four different film formulations. It is expected that all VPs are capable of both sorbing to and desorbing from the films, with smaller VPs are expected to more readily diffuse through the film’s pores due to their smaller molecular size.

2. Experimental Section

Sorption occurs due to the adsorption and/or absorption of aroma vapors at the surface of a matrix, followed by their diffusion through the matrix until an equilibrium state is reached. Four distinct experiments were conducted to assess any sorption activity between the smoke volatile phenols and four film formulations. Preliminary studies were carried out to adapt the methods of Benbettaïeb et al. for this research. Modifications made to the study included adjustments to the duration of film exposure to volatile phenols and the extraction of these phenols from the films using acetone (Supporting Information S.1–S.4).

2.1. Film Preparation

The four different film formulations under investigation consisted of 0.5% w/w wet base cellulose nanofiber (CNF), CNF with 0.5% w/w wet base β-cyclodextrin (BCD), chitosan (1% in 1% acetic acid w/w wet base) added to CNF (CHI), and CNF with 0.5% β-cyclodextrin and 1% chitosan (MIX). The films were prepared as per methodologies described by Tran et al.

2.2. Exposure of Films to Volatile Phenols (Experiment 1)

To evaluate the interaction of volatile phenols with the film matrix – whether through absorption, adsorption, or lack of adherence, 30 × 30 mm films were exposed to pure VPs following the protocol described by Tran et al. Film squares were placed in airtight containers with a VP and incubated for 5 days at ambient temperature (Figure S1). In addition to the three VPs originally selected by the authors, the films were also exposed to four more smoke-related phenols (4-methylguaiacol, o-cresol, p-cresol, and 4-methylsyringol), each at 0.1 g.

Prior to and following VP exposure, films were weighed using an Ohaus Explorer EX224 analytical balance (Ohaus Corporation, Parsippany, NJ, USA) to detect changes in mass indicative of VP uptake. Modifications to the original exposure method were based on preliminary studies, detailed in Supporting Information S.1.

Following exposure, films were transferred into 7 mL amber vials capped with Thermoset PTFE-lined caps (Sigma-Aldrich, St. Louis, MO, USA). Each vial was filled with 4 mL of acetone to extract VPs from the films and stirred with a 10 × 3 mm micro (flea) magnetic stirring bar (VWR, Radnor, PA, USA) on a multipoint stirrer (Cimarec I Poly 15, Thermo Fisher Scientific Inc., Waltham, MA, USA). The extraction was performed twice, with each extraction lasting 30 min. Extracts were subsequently stored at −18 °C to minimize sample degradation and evaporation prior to gas chromatography–mass spectrometry (GCMS) analysis. The choice of solvent, extraction duration, and number of extraction cycles were established based on preliminary studies detailed in Supporting Information S.2–S.4.

2.3. Quantification of Volatile Phenol Uptake by Films (Experiment 2)

The experimental setup used to quantify the sorption capacity of films for volatile phenols is shown in Figure S4. Unexposed film samples were placed in 7 mL vials containing 4 mL of a known VP concentration and stirred for 30 min to allow sorption. The phenols guaiacol, m-cresol, and syringol, were evaluated individually. Each film type was tested at both low and high VP concentrations. Table S3 lists the concentrations used for each VP. Following the stirring period, films were removed and transferred to fresh 7 mL vials containing 4 mL of acetone to extract sorbed volatile phenols, as outlined in section . Both the original exposure vial (residual volatile phenol) and the acetone extract vial (desorbed volatile phenol) were analyzed by GCMS.

2.4. Residual Volatile Phenol Analysis Following Film Aeration (Experiment 3)

This experiment aimed to investigate the extent to which volatile phenols desorb from the film surfaces. Films were first exposed to VPs for 5 days following the protocol described in section . After exposure, the films were aerated using a 24-position nitrogen evaporation system equipped with a 0–10 L per minute (LPM) meter (N-EVAP 11250 Organomation, Berlin, MA, USA). To ensure consistent exposure to airflow, each film was suspended 2 cm beneath a blunt needle by attaching it to the base fitting with a piece of string (Figure S5). Films were aerated for varying durations (10, 30, 60, and 120 min) under ambient conditions. Following aeration, films were immediately transferred to amber vials for volatile phenol extraction.

2.5. Evaluation of Film Permeability to Volatile Phenols (Experiment 4)

The final sorption experiment evaluated the permeability of the film in relation to the different volatile phenols (Figure ). The custom-designed box apparatus used to conduct the experiment is described in Tran et al.

1.

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Experimental box apparatus for assessing volatile phenol permeability. The lower chamber contains a crystalline dish with the target volatile phenol, while the upper chamber is fitted with a septum to allow needle access for headspace sampling. A test film is positioned between the chambers to assess volatile phenol diffusion through the film barrier.

2.6. GCMS Calibration Curve Development

The calibration curve was built using methods similar to those described in Callejon et al. Briefly, all seven volatile phenols and their deuterated forms were prepared as standard stock solutions in 100% v/v ethanol. A composite standard was constructed from these stock reference standards. An internal standard (ITSD) was prepared by combining all the stock deuterated standards. A seven-point calibration curve was constructed. The concentrations used for the calibration curve including the internal standard can be found in Table S5. All solutions were stored at −18 °C until used.

2.7. GCMS Analysis of Liquid Samples

GCMS was used for the quantification of VPs from all liquid samples. The analytical instrument utilized was a Shimadzu GCMS-QP2010 Ultra (Shimadzu Scientific Instruments, Columbia, MD, USA) equipped with a CTC Combi-Pal autosampler (CTC-Analytics AG Zwingen, Switzerland) and operated with GCMS Real Time Analysis software (Shimadzu Scientific Instruments). A Stablewax column (30 m × 0.25 mm ID × 0.25 μm film thickness, Restek Corp., Bellefonte, PA, USA) connected to an Rxi column (15 m × 0.25 mm ID × 0.25 μm film thickness, Restek Corp.) with a universal press-tight connector (Restek Corp.) was used to facilitate the separation of volatile phenols. GCMS parameters utilized were adapted from Liu et al. and are described as follows: A 5 μL syringe (Hamilton, Reno, NV, USA) was used to inject 2 μL of liquid sample into the inlet set to 250 °C in splitless mode. The linear velocity of the helium carrier gas was fixed at 30.8 cm/s. The oven temperature program started at 50 °C and held for 5 min, then raised to 165 °C at 4 °C/min, held for 5 min, and finally increased to 250 °C at the same rate, where it was held for 5 min. The temperatures for the interface and MS source were set to 250 and 200 °C, respectively. MS was operated in electron impact mode (EI) at an ionization energy of 0.8 kV, with full scan mode applied to all samples. Limit of detection (LOD) and limit of quantitation (LOQ) were calculated using methods described in Callejon et al. and Miller et al. Volatile phenols were identified through comparing their retention times and mass spectrum with NIST11 mass spectra library and their reference standard. Details of the retention times, target ions, and qualifier ions are listed in Table S5. All samples were analyzed in duplicate and in random order.

2.8. GCMS Headspace Analysis of Samples

The previously mentioned GCMS instrument was used to analyze headspace samples, with a modified liquid sample method. Differing from liquid samples, a 500 μL volume of headspace samples were injected into the inlet via a 1 mL PTFE Tipped gastight syringe (Hamilton Company, Reno, NV, USA). The inlet temperature was set to 220 °C in direct mode. The helium carrier gas was maintained at a steady linear velocity of 20.5 cm/s. The column oven was programmed to start at 50 °C for 5 min, then raised to 140 °C at 15 °C/min and held for 5 min, followed by a final increase to 250 °C at 3 °C/min and maintaining that temperature for 5 min.

2.9. Statistical Analysis

Analysis of variance (ANOVA) was performed to evaluate statistical differences among treatment groups at a significance level of 5%. When significant effects were detected, Tukey’s post hoc test was used to identify specific pairwise differences. All statistical analysis was conducted using RStudio software (Version 4.4.1, Boston, MA, USA).

3. Results and Discussion

Four different films (CNF, BCD, CHI, and MIX) were evaluated in different experimental settings to determine their efficacy at adsorbing important smoke compounds related to smoke taint in wine. CNF was selected as the film matrix material as it can be used in conjunction with other additives to enhance the gas barrier properties of coatings. On its own, CNF forms a porous network of entangled fibers held primarily by hydrogen bonds. , Without a secondary polymer to fill the gaps, voids remain between fibers, allowing VPs to diffuse freely through the film. , As shown in Figure A, films made only with CNF had the highest concentration of VPs diffuse through the film, confirming that CNF alone is ineffective at blocking smoke VP’s from reaching the grapes.

2.

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Guaiacol results for diffusion experiment. (A) Mean peak area (in arbitrary units) of headspace samples collected at different time points. (B) Mean concentration extracted from films used in part (A). Identical letters indicate no significant differences between films at each time point (one-way ANOVA followed by Tukey’s Test, p < 0.05).

In contrast, incorporating β-cyclodextrin and chitosan into the CNF matrix improved the film’s ability to absorb VPs. , To confirm this, the films were exposed to VPs and the absorbed compounds were then extracted with acetone. Figure shows the various extraction concentrations of the seven volatile phenols absorbed to the films (Table S1). Of note, films containing chitosan (CHI and MIX) had statistically significantly lower concentrations of guaiacol, 4-methylguaiacol, and syringol compared to films without chitosan (CNF and BCD). However, these results alone do not indicate whether chitosan binds VPs more strongly or simply blocks them more effectively.

3.

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Average concentration of seven volatile phenols extracted from four different film formulations (CNF = cellulose nanofiber, BCD = β-cyclodextrin, CHI = chitosan, MIX = chitosan and β-cyclodextrin). For each volatile phenol, different letters above error bars denote statistical difference (p = 0.05, one-way ANOVA) between film types, as determined by Tukey HSD comparison of means.

When considering the data from experiment 3, the results point to stronger binding with the film structure containing chitosan. Figure shows no statistical differences between BCD and CHI in the percentage of VPs remaining in the vial after the film removal, indicating that both films absorbed similar amounts. Yet, when the films were analyzed, more VPs were extracted from BCD than from CHI (Table S4). This suggests that while both films absorb similar quantities of VPs, chitosan holds onto them more tightly, making it the more effective binding material.

4.

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Each bar represents 100% of the initial guaiacol concentration added to a 7 mL vial. Bars are divided into three color-coded segments: green indicates the percentage recovered from the film after removal from the vial (not discernible at the plotted scale), red shows the percentage remaining in the vial after film removal, and blue represents the unaccounted fractioncalculated as the difference between 100% and the sum of the recovered and remaining amounts. Data shown for (A) guaiacol, (B) m-cresol, (C) syringol.

Similar adsorption behavior has been observed in studies using chitosan to remove phenolic compounds. In white wine, chitosan-based adsorbents have been shown to remove unwanted phenolic compounds, and chitosan has also been used to purify water contaminated with phenols. The adsorption capacity of chitosan is largely attributed to its ability to form hydrogen bonds with phenolic compounds. Both chitosan and CNF contain hydroxyl and amine groups that can form strong hydrogen bonds with the hydroxyl groups of VPs. The formation of these intermolecular hydrogen bonds were confirmed using FT-IR spectroscopy and phenolic release was further examined with the equilibrium dialysis technique. The results revealed a two-phase release profile: an initial fast release within the first 10 h, followed by a slower release between 10 and 48 h. A similar trend was observed in experiment 2 (Figure ), where no significant differences in guaiacol released from the film were detected within the first hour, but a clear difference emerged after 12 h.

5.

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Mean guaiacol concentration extracted from films aerated after exposure to volatile phenols. Different letters indicate statistical significant differences between films at each time point (one-way ANOVA followed by Tukey’s Test, p < 0.05).

The slow release of phenolics from CHI films offers insight into the underlying diffusion mechanism. It has been proposed that the transport of phenolics through CHI films follows pseudo-Fickian diffusion, which describes the particle movement through a medium by taking into account the surface area, concentration difference, and the medium thickness. In experiment 4, the prolonged diffusion of VPs in chitosan films showed a noticeable increase in headspace VP concentration after 16 h, while CNF and BCD exhibited a more gradual increase over a 24-h period. As a result, chitosan-containing films maintained significantly lower headspace VP levels than nonchitosan films after just 8 h.

This reduced diffusion of VPs can also be attributed to the low porosity of chitosan films. Chitosan’s linear structure enables it to form strong intermolecular bonds, allowing it to fill voids between CNF fibers and create a denser film matrix (Figure ). Additionally, chitosan forms hydrogen bonds with CNF surfaces, further compacting the fiber network. , Together, these structural interactions limit VP diffusion through CHI film, effectively reducing the amount that reaches the grape surface.

6.

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Schematic representation of intermolecular hydrogen bonds (shown in blue) formed between chitosan and cellulose nanofibers.

While chitosan contributes to a denser, less permeable film structure, β-cyclodextrin has the opposite effect. Due to its bulky, conical shape, β-cyclodextrin disrupts the tight packing of CNF fibrils, creating a more porous surface layer. , This structural difference helps explain the higher VP diffusion observed after 8 h in experiment 4. Additionally, the interaction between β-cyclodextrin and VPs is relatively weak. VPs interact with β-cyclodextrin primarily through hydrophobic interactions within its inner cavity, which allows the VPs to be more easily released. This is reflected in the consistently high VP extraction concentrations across all four experiments. Although VPs can form stable host–guest inclusion complexes with β-cyclodextrin, these interactions are not as strong or persistent as the hydrogen bonds formed with chitosan.

When comparing the effectiveness of the film across different volatile phenols, syringol consistently showed the lowest extraction concentration. However, this is largely because syringol is a heavier molecule with a higher boiling point, making it less volatile. While the low levels might suggest that the films are especially effective at blocking syringol, the real reason is its limited initial volatility.

Comparing guaiacol and m-cresol, it seems that m-cresol generally forms weaker interactions with the films. In experiment 1, m-cresol showed the highest extraction concentrations ranging from 179 to 456 mg/L compared to guaiacol’s 19 to 146 mg/L (Figure ). Notably, in experiment 2, although m-cresol had a lower overall absorption than guaiacol, it still had a higher extraction rate of 0.3% versus 0.08% of guaiacol. In contrast, experiment 3 showed higher extraction for guaiacol after the VP exposed films were aerated. This may be due to guaiacol’s ability to form more hydrogen bonds with the film, allowing it to desorb at lower concentrations.

Unexpectedly, guaiacol showed higher headspace levels than m-cresol in experiment 4. Previous work has linked higher m-cresol headspace concentrations to its smaller molecular size, which allows it to permeate the film more easily. However, diffusion is influenced by more than just size; it also depends on molecular shape, functional groups, and polarity. For example, CO2 has been shown to exhibit a higher diffusion coefficient than other gases despite its higher molecular weight. This behavior pointed to facilitated transport, which is likely driven by favorable interactions between CO2 and the membrane. The low solubility of CO2 also allowed it to pass through the membrane quickly, while saturating it rapidly. A similar mechanism may explain the high concentration of guaiacol extracted from the film in the diffusion experiment.

It has also been suggested that a methoxy group in the ortho position may significantly interfere with the hydroxy group’s ability to form frequent and strong hydrogen bonds. Guaiacol may potentially form intramolecular hydroxy to methoxy hydrogen bonds, which could make the molecule more compact and less prone to strong intermolecular interactions. With fewer intermolecular interactions, guaiacol’s diffusion rate increases. Further studies determining the diffusion coefficient of guaiacol and m-cresol are needed to better understand this phenomenon.

Despite differences in headspace and extraction concentrations, the films had a consistent effect on all three compounds across all experiments. In experiment 3, for instance, all three VPs had significantly lower extraction levels from CHI films compared to BCD films (Figure and Figure S6). A similar trend appeared in experiment 4, where CHI films had lower headspace levels than BCD (Figure A, Figure S7A and Figure S8A). These results suggest the VPs relevant to smoke taint interact in similar ways across the different film types, indicating that a single formulation could potentially prevent a broad range of VPs from entering wine grapes.

This study was conducted under controlled lab conditions that could differ significantly from those in vineyards exposed wildfire smoke. The films were tested at 20 and 40 °C with 30–40% relative humidity (RH), whereas smoke exposed vineyard conditions face variable temperature and RH conditions, depending on their proximity to the fire. − These environmental shifts could alter the films’ sorption behavior, leading to outcomes that differ from those observed in the lab. Smoke also contains additional components, including particles and other gases, that could change how the films perform in the field. Additionally, the films were exposed to volatile phenol concentrations far higher than those typically found in wildfire smoke. , This was intentional, as it allowed to push the limits of the film’s capacity and evaluate their maximum performance. In real wildfire conditions, the films may therefore perform even more effectively and offer greater protection against volatile phenols. Other critical variables, such as the duration and intensity of smoke exposure and the presence of additional smoke compounds, were not replicated, further limiting the applicability of the findings to field conditions.

4. Conclusion

This work offers new insight into how these film materials interact with volatile phenols. For managing smoke-related VPs, CHI was the most effective film matrix because it both adsorbed VPs and reduced their diffusion through the film. Future work is still needed to fully prevent VP transfer since any retained compounds could be released into the wine during fermentation if the films remain on the grapes postharvest. This is a key consideration, as winemakers typically do not wash their fruit before processing. The ability to leave films in place would provide a practical, low intervention option for winemakers. Chitosan fits well with this approach since it is already used in winemaking as a fining agent to remove unwanted compounds. If applied to grapes, chitosan would naturally be removed from the system through the winemaking process. Further research is needed to enhance the blocking efficiency of CNF-based films, especially across a broader range of VP sizes. Once optimized, sensory studies will be essential to ensure the films do not alter the wine’s flavor profile. If successful, this technology could offer a groundbreaking, preventative vineyard strategy that has the potential to save the wine industry millions of dollars in losses following wildfire smoke exposure.

Supplementary Material

ao5c10501_si_001.pdf (858KB, pdf)

Acknowledgments

We would like to acknowledge Trung Tran and Sarah Caballero for making the films that were used in this research.

Glossary

Abbreviations

VP

volatile phenols

CHI

chitosan

CNF

cellulose nanofibers

BCD

β-cyclodextrin

GCMS

gas chromatography mass spectrometry

ANOVA

analysis of variance.

The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acsomega.5c10501.

  • Additional experimental methods and results, including images of experimental setup; retention time, qualifier ions, and calibration information for GCMS; results for m-cresol and syringol (PDF)

ET initiated the proposal; LG and LRL conducted the research, LG, DCC, and ET analyzed the data, LG, DCC, and ET, contributed to writing the paper. All authors contributed to the experimental design and discussion, provided feedback on the results, and contributed to the paper.

This work is supported by Assessment and management of risk associated with wildfire smoke exposure of grapes in the vineyard, project award no. 2021-51181-35862, from the U.S. Department of Agriculture’s National Institute of Food and Agriculture.

Any opinions, findings, conclusions, or recommendations expressed in this publication are those of the authors and should not be construed to represent any official USDA or U.S. Government determination or policy.

The authors declare no competing financial interest.

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