An Investigation of the Chemical Constituents of Distilled Lime Oil (Citrus Medica, L., Var. Acida, Brandis) (Citrus Aurantifolia, Swingle)<sup>*</sup>

Guenther, Ernest; Langenau, Edward E.

doi:10.1021/ja01245a053

Cited by 16 publications

(7 citation statements)

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“…A number of sesquiterpenes, α-santalene, α-amorphene, epi-β-santalene, β-sesquiphellandrene, 4(14),7(11)selinadiene, (E)-α-bisabolene, germacrene B and bicyclogermacrene have also been reported to be present in lime oil [7,8]. Generally, the quality of lime oil is related to the content of total aldehydes, and in particular, citral, which is in the region of 5% [9,10].…”

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confidence: 99%

Comparative Study of the Chemical Profiles of the Essential Oils of Ripe and Rotten Fruits of Citrus Aurantifolia Swingle

Afolayan

Asekun

2008

Natural Product Communications

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Most often during the processing of lime fruits for essential oil extraction, rotten fruits are used along with ripe ones. In this study, we examine the volatile constituents of the essential oils from both ripe and rotten lime fruits (Citrus aurantifolia Swingle) from Nigeria. The oils were isolated by hydrodistillation and analyzed using GC-MS. The ripe and rotten lime oils contained 55 and 49 components, respectively. Both oils were rich in limonene (21.0%, ripe lime; 21.3% rotten lime), α-terpineol (11.7%, ripe; 14.1%, rotten), γ-terpinene (8.3%, ripe; 8.9% rotten lime), α-terpinolene (2.5%, ripe; 8.5%, rotten) and (E)-α-farnesene (6.3% ripe lime; 4.8% rotten lime). The other major components, α-pinene (11.1%), and linalool (5.5%) were identified in ripe lime oil only. Limonene and citral, which are believed to be the two major citrus odour contributors, were present in both ripe and rotten lime oils. Aldehydes like decanal and the farnesenes, which are also important in citrus flavor, were represented in both lime oils. Some notable components of ripe lime fruit oil, like trans-β-ocimene, linalool, myrcenol, dodecanal, trans-β-bergamotene and trans-γ-bisabolene, were absent in the rotten fruit oil. It could be suggested that some compounds like cis-ocimene, trans-linalool oxide, p-mentha-3-en-1-ol, mentha-1,4,8-triene, citronellal, trans-β-bergamotene and α-copaene, which were not identified in the ripe fruit oil, were introduced into the lime oil by the incorporation of rotten fruits in the distilled samples.

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confidence: 99%

Comparative Study of the Chemical Profiles of the Essential Oils of Ripe and Rotten Fruits of Citrus Aurantifolia Swingle

Afolayan

Asekun

2008

Natural Product Communications

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“…1) calculated as 0.1% and having a relative retention time different from that of any of the reported constituents of lime oil (Guenther, 1947a ;Guenther and Langenau, 1943 ;Slater, 1961a identical with those of purified commercial p,a-dimethylstyrene (Max 247~) as well as spectral data given in the literature (Barnes et al, 1943;Elliott and Cook, 1944). The VPC relative retention time (Ambrose, 1958) was identical to that of the unknown peak in the intact oil under two different conditions of temperature and flow rate.…”

Section: Resultsmentioning

confidence: 82%

“…Indeed, other than in recent reports by Teranishi et al (1963) and Kov6ts (1963), the literature does not indicate its identification in any of the essential oils (Guenther, 1947a;Gildemeister, 1929;Ikeda et al, 1962) ; yet, in accordance with the classically accepted definition of "terpenes" (Haagen-Smit, 1948)) there is no reason not to consider it as a member of this class of compounds.…”

Section: Recent Investigationsmentioning

confidence: 85%

“…This was considered to be ample evidence that the presence of p-a-dimethylstyrene in the steam-distilled oils was not due to the methods of isolation and identification used. Since the major difference between the steam-distilled oils and the cold-pressed oils is steam-distillation in the presence of natural fruit acids, and since acid conditions are known to alter the properties of the citrus oils (Guenther and Langenau, 1943 ;Guenther, 1943;Guenther, 1947b), it is reasonable to postulate that acid-catalyzed reactions of lime constituents may result in the formation of p,a-dimethylstyrene.…”

Section: Resultsmentioning

confidence: 99%

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The Mechanism of Formation of p,α‐Dimethylstyrene in the Essential Oil of Distilled Lime (Citrus Aurantifolia)

Loori¹,

Cover²

1964

Journal of Food Science

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SUMMARY The terpene p,α‐dimethylstyrene was isolated and identified in the essential oil of distilled Mexican lime (Citrus aurantifolia, Swingle) but could not be demonstrated in oil expressed from Citrus aurantifolia. Experimental evidence is presented supporting a nonbiogenetic mechanism of formation of p,α‐dimethylstyrene in distilled lime oil from the acid‐catalyzed cyclization of citral. The mechanism involves novel reactions of citral and its reaction products that are not consistent with the classically accepted acid‐catalyzed reactions of citral and seem to provide an explanation for the appearance of p,α‐dimethylstyrene in other citral‐containing essential oils of the Rutaceae citrus plants.

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“…However, thermal-diffusivity values for distilled and centrifuged lime essential oils are clearly different since their relative deviation is approximately 7.5 %. This difference can be related to a variation in chemical composition of these essential oils related with the extraction processes [14][15][16], which is evident in the chromatographic analysis (Table 4). In distilled lime essential oil, the terpene β-pinene swap in isomers; it is chemically transformed in other terpenes and swaps by hydration to alcohols such as α-terpineol, β-terpineol, γ -terpineol, terpinen-1-ol, terpinen-4-ol, and 1,4-cineol.…”

Section: Resultsmentioning

confidence: 99%

Thermal-Diffusivity Measurements of Mexican Citrus Essential Oils Using Photoacoustic Methodology in the Transmission Configuration

López‐Muñoz¹,

González

López³

et al. 2011

Int J Thermophys

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Photoacoustic methodology in the transmission configuration (PMTC) was used to study the thermophysical properties and their relation with the composition in Mexican citrus essential oils providing the viability of using photothermal techniques for quality control and for authentication of oils and their adulteration. Linear relations for the amplitude (on a semi-log scale) and phase, as functions of the sample's thickness, for the PMTC was obtained through a theoretical model fit to the experimental data for thermal-diffusivity measurements in Mexican orange, pink grapefruit, mandarin, lime type A, centrifuged essential oils, and Mexican distilled lime essential oil. Gas chromatography for distilled lime essential oil and centrifuged lime essential oil type A is reported to complement the study. Experimental results showed close thermal-diffusivity values between Mexican citrus essential oils obtained by centrifugation, but a significant difference of this physical property for distilled lime oil and the corresponding value obtained by centrifugation, which is due to their different chemical compositions involved with the extraction processes.

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An Investigation of the Chemical Constituents of Distilled Lime Oil (Citrus Medica, L., Var. Acida, Brandis) (Citrus Aurantifolia, Swingle)^*

Cited by 16 publications

References 0 publications

Comparative Study of the Chemical Profiles of the Essential Oils of Ripe and Rotten Fruits of Citrus Aurantifolia Swingle

Comparative Study of the Chemical Profiles of the Essential Oils of Ripe and Rotten Fruits of Citrus Aurantifolia Swingle

The Mechanism of Formation of p,α‐Dimethylstyrene in the Essential Oil of Distilled Lime (Citrus Aurantifolia)

Thermal-Diffusivity Measurements of Mexican Citrus Essential Oils Using Photoacoustic Methodology in the Transmission Configuration

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An Investigation of the Chemical Constituents of Distilled Lime Oil (Citrus Medica, L., Var. Acida, Brandis) (Citrus Aurantifolia, Swingle)*

Cited by 16 publications

References 0 publications

Comparative Study of the Chemical Profiles of the Essential Oils of Ripe and Rotten Fruits of Citrus Aurantifolia Swingle

Comparative Study of the Chemical Profiles of the Essential Oils of Ripe and Rotten Fruits of Citrus Aurantifolia Swingle

The Mechanism of Formation of p,α‐Dimethylstyrene in the Essential Oil of Distilled Lime (Citrus Aurantifolia)

Thermal-Diffusivity Measurements of Mexican Citrus Essential Oils Using Photoacoustic Methodology in the Transmission Configuration

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An Investigation of the Chemical Constituents of Distilled Lime Oil (Citrus Medica, L., Var. Acida, Brandis) (Citrus Aurantifolia, Swingle)^*