Acid-Catalyzed Reactions of Citrus Oils and Other Terpene-Containing Flavors

Clark, Benjamin C.; Chamblee, Theresa S.

doi:10.1016/b978-0-444-88558-6.50015-5

Cited by 58 publications

(88 citation statements)

References 80 publications

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“…1 Distilled key lime oil accounts for about 95% of total lime oil use, whose harsh terpenic aroma is the result of the formation of hydration, rearrangement and elimination products during the acid-catalysed distillation. [2][3][4][5] Commercial coldpressed lime oil has a fresh fragrant citrus aroma and is used as a perfumery ingredient, in addition to its use as a flavourant. 6 Recent studies have identified and quantified over 65 volatile compounds in cold-pressed key lime oil and more than 110 compounds in the distilled oil.…”

Section: Introductionmentioning

confidence: 99%

“…The differences in the aroma of the cold-pressed and distilled lime oils are known to be the result of the changes in the composition of oxygenates caused by the acid-catalysed distillation. 1,4 A GC sniffport technique has been used to measure the intensities of lemon and lime oil oxygenates. [15][16][17][18] Neral, geranial and linalool were found to be responsible for the characteristic fresh aroma of cold-pressed lime oil, and are mostly lost on distillation.…”

Section: Introductionmentioning

confidence: 99%

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Characterization of aroma volatiles in key lime essential oils (Citrus aurantifolia Swingle)

Chisholm

Wilson

Gaskey

2003

Flavour & Fragrance J

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The most intense aroma volatiles of extracted and distilled oils from the peels of key lime (Citrus aurantifolia Swingle) were identified using gas chromatography-olfactometry (GC-O) and gas chromatographymass spectrometry (GC-MS). Over 50 odour-active volatiles were detected in the extracted oil, and over 60 in the distilled oil. Geranial, neral and linalool were found to dominate the lime oil aroma in both oils, which accounted for their fresh, floral citrus-like character. Many simple aldehydes contributed to the aroma of the extracted oil, giving it a characteristic lime tone. The distilled oil contained many new odourants, resulting from the acid-catalysed distillation, which imparted woody, musty, spicy and balsamic notes to its aroma. These are C 10 alcohols and ethers and many sesquiterpenes, most of which possess lower odour activity and contribute to the more intense piney aroma of the distilled oil. 7-Methoxycoumarin was found to be one of the more intense odourants in the extracted oil. Caryophyllene oxide and humulene oxide II were found to be major odourants in the distilled oil; their intensities varied with the method of analysis of the oil. They contribute a sawdust-like and skunky odour, respectively, to the distilled lime oil. Many sesquiterpenes were found to possess some odour activity.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Characterization of aroma volatiles in key lime essential oils (Citrus aurantifolia Swingle)

Chisholm

Wilson

Gaskey

2003

Flavour & Fragrance J

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“…This work has also demonstrated that acetates are not important flavour constituents of coldpressed grapefruit oils. Since aldehydes are susceptible to acid-catalysed reactions and oxidation, 37 precautions should be taken in flavour application of the cold-pressed grapefruit oils to avoid their degradation, which will alter their distinctive flavour contribution.…”

Section: Aldehydesmentioning

confidence: 99%

Characterization of aroma‐impact compounds in cold‐pressed grapefruit oil using time–intensity GC–olfactometry and GC–MS

Lin

Rouseff

2001

Flavour & Fragrance J

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Thirty-eight aroma-active compounds were detected in commercial cold-pressed grapefruit oil using a time-intensity GC-olfactometry procedure. Identification of the aroma-active components was based on the combination of sensory descriptors, linear retention index values from DB-Wax and DB-1 columns and GC-MS data. Thirteen flavour components, which had not been previously reported in grapefruit oil, were identified. Compounds with the greatest aroma intensities include: 1,8-cineole, octanal, dodecanal, trans-4,5-epoxy-(E)-2-decenal,ˇ-sinensal and nootkatone. The aroma activities of sulphur compounds such as 4-mercapto-4-methyl-2-pentanol and methional were surprisingly low and neither of the two putative grapefruit aroma impact compounds, 4-mercapto-4-methyl-2-pentanone and 1-p-menthene-8-thiol, was detected. Over 200 volatiles have been reported in grapefruit oil, but only 38 have significant aroma activity and 22 of these can be considered major aroma impact compounds.

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“…Candidate compounds were selected from the list of components contained in lemon juice [9] or deteriorated lemon juice [10][11][12][13]. Unless the position on the 2-D map agreed exactly with those of the authentic components, the spots were recorded as unidentified.…”

Section: Identification Of Componentsmentioning

confidence: 99%

“…Thus, the presence of such alcohol components, not observed in fresh juice, may plausibly be due to the deterioration of some terpenic compounds under aqueous acidic conditions, common to lemon-flavored beverages. In order to identify these deterioration products, if present in the samples even without heat challenge, known deterioration compounds from citral [10][11][12][13] were injected and analyzed by GC6GC. The presence of pcymen-8-ol (s20), and p-methylacetophenone (s19) were confirmed.…”

Section: Components In Soft Drinks and In A Lowalcoholic Rtd Beveragementioning

confidence: 99%

Comprehensive two‐dimensional gas chromatographic analysis of commercial lemon‐flavored beverages

Komura

2006

J of Separation Science

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Fresh lemon juice and lemon-flavored beverages were analyzed by using comprehensive 2-D GC (GC x GC) with flame-ionization detection, with a nonpolar-polar column combination. A low-alcohol, ready-to-drink (RTD) beverage was also analyzed as fresh, and after deterioration for 12 days at 50 degrees C. Identification of some of the components in the 2-D plots was performed by comparison of peak positions of authentic standards and comparison with 1-D GC. However, without the aid of GC x GC-mass spectral data, only 24 components were identified; a large number of components remained unassigned. In some soft drinks obtained in the market, components indicative of deterioration, such as p-methylacetophenone and p-cymen-8-ol were already present in the products. In contrast, even upon heat challenge, a low-alcohol RTD beverage did not generate deterioration products of citral, such as p-methylacetophenone and the intermediates, p-menth-2-ene-1,8-diols. This was apparently related to the fact that the original formulation contained only a minute amount of the citral ingredient.

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Acid-Catalyzed Reactions of Citrus Oils and Other Terpene-Containing Flavors

Cited by 58 publications

References 80 publications

Characterization of aroma volatiles in key lime essential oils (Citrus aurantifolia Swingle)

Characterization of aroma volatiles in key lime essential oils (Citrus aurantifolia Swingle)

Characterization of aroma‐impact compounds in cold‐pressed grapefruit oil using time–intensity GC–olfactometry and GC–MS

Comprehensive two‐dimensional gas chromatographic analysis of commercial lemon‐flavored beverages

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