Enantiomeric Distribution Of Linalool Research Articles

Chemical Compositions of Commercial Essential Oils From Coriandrum sativum Fruits and Aerial Parts

Coriander and cilantro, the fruit and herb of Coriandrum sativum, are popular additives in various cuisines worldwide. The essential oils derived from coriander and cilantro are also popular and have shown some remarkable biological properties and health benefits. In this report, we have analyzed the essential oil compositions of 19 commercial coriander and 28 commercial cilantro essential oil samples by gas chromatography–mass spectrometry (GC–MS) techniques. In addition, 5 coriander and 4 cilantro commercial essential oil samples were analyzed by chiral GC–MS. Commercial coriander essential oil is dominated by linalool (62.2%-76.7%) with lesser quantities of α-pinene (0.3%-11.4%), γ-terpinene (0.6%-11.6%), and camphor (0.0%-5.5%). Commercial cilantro essential oil is composed largely of (2 E)-decenal (16.0%-46.6%), linalool (11.8%-29.8%), (2 E)-decen-1-ol (0.0%-24.7%), decanal (5.2%-18.7%), (2 E)-dodecenal (4.1%-8.7%), and 1-decanol (0.0%-9.5%). The enantiomeric distribution of linalool was 87% (+)-linalool:13% (−)-linalool in both coriander and cilantro essential oils, while α-pinene was 93% (+):7% (−) in coriander, 90% (+):10% (−) in cilantro; and (+)-camphor:(−)-camphor was 13%:87% in both essential oils. Chiral GC–MS analysis was able to detect an adulterated coriander essential oil sample. The data provided in this study serves to establish a baseline for future evaluations of these essential oils as well as a screen for authenticity or adulteration.

Linalool enantiomeric distribution in rosewood-reminiscent populations in Central Amazon

ABSTRACTThe enantiomeric distribution of linalool can strongly impact the fragrance of essential oils, thereby affecting the usage criteria of linalool for the perfumery industry. The enantiomers 3R-(−)-linalool and 3S-(+)-linalool present distinctive aromas; the former is woody, floral and lavender-like, while the latter is sweet, herb-like and citric. The aim of this research was to investigate variations in the enantiomeric distribution of linalool in oils extracted from the leaves and branches of 54 samples from rosewood (Aniba rosaeodora Ducke) trees in natural populations in the Brazilian Amazon. The essential oil was obtained by hydrodistillation, and the analysis of enantiomer composition was performed using chiral gas chromatography. The ratio 3R-(−)-linalool:3S-(+)-linalool varied between 5:95 and 44:56 in the samples. The enantiomeric distribution was not significantly different between oils from leaves across different collection sites but was significantly different between leaves and branches, indicating that these plant organs have distinct olfactory properties.

Analysis and stereodifferentiation of linalool in Theobroma cacao and cocoa products using enantioselective multidimensional gas chromatography

Contents and enantiomeric distributions of linalool (3,7-dimethyl-1,6-octadien-3-ol) were investigated in raw and roasted cocoa beans (seeds of Theobroma cacao) of defined origin as well as in commercial products, such as cocoa powders or chocolates. The stereodifferentiation of linalool was achieved by enantioselective multidimensional gas chromatography using heptakis (2,3-di-O-methyl-6-O-tert-butyldimethylsilyl)-β-cyclodextrin as chiral stationary phase. Simultaneous steam distillation–extraction at pH 7 allowed sample preparation without racemization of linalool. Cocoa beans contain linalool primarily as (S)-enantiomer. Model experiments and analyses of commercial products such as cocoa powders and chocolates revealed that technological procedures employed in the manufacturing of cocoa products do not result in significant changes of the original enantiomeric distribution of linalool.

Characteristic volatile components of Japanese sour citrus fruits: Yuzu, Sudachi and Kabosu

ABSTRACTThe volatile components of both the peel and juice of three major Japanese sour citrus cultivars with pleasant flavour, Yuzu (Citrus junos Sieb. ex Tanaka), Sudachi (Citrus sudachi Hort. ex Shirai) and Kabosu (Citrus sphaerocarpa Hort. ex Tanaka) were investigated using the solvent assisted flavour evaporation technique after solvent extraction. Limonene was the most abundant monoterpene hydrocarbon in all the extracts, followed by γ‐terpinene and β‐phellandrene in Yuzu and Sudachi and by myrcene in Kabosu. Mintsulfide was newly identified in juice extracts from Yuzu and Kabosu. Among the oxygenated components of these extracts, linalool was the most abundant in both the peel and juice of Yuzu and the peel of Sudachi, while both the peel and juice of Kabosu revealed the presence of high quantity of saturated aliphatic aldehydes. Wine lactone and rose oxide were identified in all the extracts, which have not been previously reported to occur in these citrus cultivars. The odour‐active components of each oxygenated fraction were revealed by aroma extract dilution analysis. Linalool, trans‐4,5‐epoxy‐(2E)‐decenal and wine lactone showed relatively high flavour dilution factors in the peel and juice of these citrus cultivars. The enantiomeric distribution of linalool, cis‐rose oxide, β‐citronellol and wine lactone was determined using a multi‐dimensional chiral gas chromatography–mass spectrometry. With regard to linalool, the (R)‐enantiomer was predominant in Yuzu and the (S)‐enantiomer in Sudachi and Kabosu. Copyright © 2012 John Wiley & Sons, Ltd.

Characteristic Volatile Components of Kabosu (Citrus sphaerocarpa Hort. ex Tanaka)

The volatile components of both peel and juice of Japanese citrus, Kabosu (Citrus sphaerocarpa Hort. ex Tanaka) were investigated using SAFE (Solvent Assisted Flavor Evaporation) technique after solvent extraction. In this study, wine lactone, rose oxide, (2E)-4,5-epoxy-2-decenal, mintsulfide, and indole were newly identified from Kabosu. AEDA (Aroma Extract Dilution Analysis) of the oxygenated fraction of the peel extract showed high FD (Flavor Dilution) factors for linalool, (2E)-4,5-epoxy-2-decenal, octanal, (4Z)-decenal, beta-citronellol, geraniol, and wine lactone, while wine lactone, linalool, eugenol, geraniol, and (2E)-4,5-epoxy-2-decenal from the juice extract. The enantiomeric distribution of linalool, cis-rose oxide, beta-citronellol, and wine lactone were also determined using a multidimensional chiral GC/MS.

Enantiomeric Distribution of Linalool, Linalyl Acetate and Camphor in Bulgarian Lavender Oil

The enantiomeric distribution of linalool, linalyl acetate and camphor in Bulgarian lavender oils was determined by multidimensional GC/MS.