Formation and Stability of 2,3-Dehydro-1,8-Cineol in a Model Carbonated Beverage System

Lorjaroenphon, Yaowapa; Hausch, Bethany J.; Cadwallader, Keith R.

doi:10.1016/b978-0-12-398549-1.00044-1

Cited by 4 publications

(13 citation statements)

References 7 publications

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“…Review of the chemical reactions susceptible to occur in bitter orange essential oils during growing, ripening, hydrodistillation and storage: hydrations of double bonds, dehydrations, rearrangements, cyclizations, and pyrolysis. Adapted from Baxter et al, Boelens and Jimenez Sindreu, Clark et al, Clark and Chamblee, Cooper et al, Cori et al, Degenhardt et al, Dieckmann and Palamand, Huet, Kimura et al, Lorjaroenphon et al, Mazza, Morin and Richard, Verzera et al, Verzera et al, Williams and Whittaker, Ziegler et al…”

Section: Chemical Reactions Happening During Growing Ripening Storamentioning

confidence: 99%

“…As the storage time increases, the concentration of p ‐cymene increases . In 2014, Lorjaroenphon et al studied the degradation products of citral (mixture of neral and geranial) when stored three days in citric acid solution. They proposed rearrangement pathways for neral and geranial in aqueous acidic solution very similar to the ones by Clark et al dating from 1977.…”

Section: Chemical Reactions Happening During Growing Ripening Storamentioning

confidence: 99%

“…Adapted from the literature, 3,44,69,[77][78][79][80][81][82][83][84][85][86][87][88][89][90][91] the Figure 1 is a review of the different reactions that can happen during growing, ripening and storage of the bitter orange and during hydrodistillation due to heating and acid pH.…”

Section: Chemic Al Re Ac Ti On S Happening During G Rowing Ripenimentioning

confidence: 99%

“…77 During hydrodistillation, the major mechanism by which oxygen is added to the terpenes produced by degradation of linalyl acetate, is not oxidation but acid-catalysed reactions in aqueous acid conditions (due to the acidity of bitter oranges). 89 Baxter et al 86 86 Boelens and Jimenez Sindreu, 44 Clark et al, 89 Clark and Chamblee, 90 Cooper et al, 83 Cori et al, 91 Degenhardt et al, 78 Dieckmann and Palamand, 69 Huet, 3 Kimura et al, 79 Lorjaroenphon et al, 87 Mazza, 80,81 Morin and Richard, 77 Verzera et al, 84 Verzera et al, 85 Williams and Whittaker, 82 Ziegler et al 88 smaller quantities, among which: α-terpineol (3.9%), (Z)-β-terpineol (0.4%) and terpinene-4-ol (1.1%), as well as cis and trans-linalool oxides (0.13%).…”

Section: Chemic Al Re Ac Ti On S Happening During G Rowing Ripenimentioning

confidence: 99%

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Bitter orange peel essential oil: A review of the different factors and chemical reactions influencing its composition

Gaff

Decloux

Giampaoli

2020

Flavour & Fragrance J

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This review summarizes the findings and discusses the results on the different factors that can influence the bitter orange peel oil composition. Small changes in composition can result in noticeable modifications of the odour profile of the essential oil. The analysis method appears to have a crucial effect on the number of compounds identified in the essential oil. Growing location, cultivar, ripening stage, storage conditions and extraction methods are reported to impact the bitter orange essential oil. Bitter orange peel oil should be stored at −21°C to prevent changes in the composition and formation of artefacts when storing for a period of several months. The influence of cultivars should not be neglected, since a few cultivars differ a lot from the main cluster of Citrus aurantium L. The geranyl pyrophosphate forms most of the terpenes present in the bitter orange, especially limonene which is the majority compound, by the action of the terpene synthases during growing of the fruit. The extraction method can also be responsible for some differences in the composition due to the absence of water‐soluble compounds in cold‐pressed oils and to acid‐catalysed reactions in hydrodistilled oils such as the decomposition of the linalyl acetate forming many different terpene derivatives.

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Section: Chemical Reactions Happening During Growing Ripening Storamentioning

confidence: 99%

Section: Chemical Reactions Happening During Growing Ripening Storamentioning

confidence: 99%

Section: Chemic Al Re Ac Ti On S Happening During G Rowing Ripenimentioning

confidence: 99%

Section: Chemic Al Re Ac Ti On S Happening During G Rowing Ripenimentioning

confidence: 99%

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Bitter orange peel essential oil: A review of the different factors and chemical reactions influencing its composition

Gaff

Decloux

Giampaoli

2020

Flavour & Fragrance J

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“…Among those many factors, heat and light are the major ones. Most of the studies investigating citral degradation have focused on the thermal degradation of citral in the presence of acid. − It has been established that citral in acidic solutions and under a wide range of temperature undergoes cyclization and oxidation reactions, leading to the formation of many identified compounds, for instance, p -cymene, one compound responsible for the off-flavor of deteriorated citral. Other studies investigated the citral photodegradation. − They reported that the degradation of citral under light and UV irradiation generates photoproducts through a cyclization reaction.…”

Section: Introductionmentioning

confidence: 99%

Citral Photodegradation in Solution: Highlighting of a Radical Pathway in Parallel to Cyclization Pathway

Gerard

Graff

et al. 2019

J. Agric. Food Chem.

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Citral, a lemon flavor molecule often used in the beverage and fragrance industry, is known to be unstable under light irradiation. Its deterioration is considered to be an important issue for the stabilization of lemon-flavored drinks. The aim of this study is to understand the degradation mechanisms of citral under light irradiation with the variation of three parameters: the solvent (citrate buffer solution at pH 3 vs ethanol), the atmosphere (air vs N2), and the concentration of citral. The photodegradation has been studied using UV–visible spectroscopy after photolysis, nuclear magnetic resonance spectrometry, and electron spin resonance spectroscopy. To extend the investigation, molecular orbitals and bond dissociation energies have also been calculated. They give an insight into the light absorption properties and the possible cleavage of citral molecular bonds. In addition, UV-light absorption and radical scavenging activities of two additives, potassium sorbate and ascorbic acid, have been studied for the inhibition of the citral photodecomposition by UV-light irradiation. Both theoretical and experimental results highlight a new degradation pathway involving free-radical intermediates in parallel to the already reported cyclization one, which could be prevented by the addition of stabilizers such as ascorbic acid or sorbate.

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Flavor Chemistry of Lemon-Lime Carbonated Beverages

Hausch

Lorjaroenphon

Cadwallader

2014

J. Agric. Food Chem.

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The most potent aroma-active components of Sprite ® (SP), Sierra Mist ® (SM), and 7UP ® (7UP) were identified. Aroma extracts were prepared by liquid-liquid continuous extraction/solvent-assisted flavor evaporation (LLCE/SAFE). Twenty eight compounds were detected by gas chromatography-olfactometry (GCO) with linalool (floral, lavender), octanal (pungent orange) and 2,3-dehydro-1,8-cineole (minty) determined to be predominant aroma compounds based on their high flavor dilution (FD) factors by aroma extract dilution analysis (AEDA). The data indicate that lemon-lime is composed of a small number of compounds (22 at the most in SM) and only a subset of these may be important since many compounds were only detected at low FD factors.Predominant aroma compounds in three commercial brands of lemon-lime carbonated beverages were quantified using static headspace solid phase microextraction (SPME) combined with stable isotope dilution assays (SIDA). The compounds chosen for quantification were 2,3-dehydro-1, 8-cineole, 1,8-cineole, octanal, nonanal, decanal, linalool, borneol, isoborneol, neral, geranial, nerol, geraniol and p-cresol. Benzoic acid was quantified separately by HPLC using an external standardization method.Concentrations of the all compounds, except neral, differed between at least two brands.Concentrations of 1,8-cineole, octanal, nonanal, decanal, linalool, isoborneol, geraniol and benzoic acid differed among all brands. In contrast to FD factors, the calculated odor-activity values (OAVs) indicated that decanal was the most potent aroma compound, followed by octanal and dehydrocineole; with linalool and nonanal being moderately important to the aroma of lemon-lime carbonated beverages. Possible errors in the determination of threshold values and the nature of GCO analysis preclude the iii results of the two methodologies from matching exactly. The results demonstrate that lemon-lime carbonated beverages share many of the same compounds but the relative abundance of these compounds varies by brand. Recommendations for further research include conducting sensory model studies based on the quantification data and determining compound thresholds in a carbonated matrix.iv

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Formation and Stability of 2,3-Dehydro-1,8-Cineol in a Model Carbonated Beverage System

Cited by 4 publications

References 7 publications

Bitter orange peel essential oil: A review of the different factors and chemical reactions influencing its composition

Bitter orange peel essential oil: A review of the different factors and chemical reactions influencing its composition

Citral Photodegradation in Solution: Highlighting of a Radical Pathway in Parallel to Cyclization Pathway

Flavor Chemistry of Lemon-Lime Carbonated Beverages

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