Linalool Oxide Research Articles

Simultaneous distillation‐solvent extraction gas chromatography‐mass spectrometry analysis of Tokaj Muscat Yellow wines

In the present study, simultaneous distillation-solvent extraction conditions were optimized for the extraction of organic compounds from naturally sweet Tokaj wines. Solvent selection, optimization of phase ratio, time of extraction, and addition of modifier were studied. The volatile organic compounds profile of Slovak Tokaj Muscat Yellow wine was characterized using simultaneous distillation-solvent extraction gas chromatography-mass spectrometry. Identified volatile organic compounds belonged to terpenes, esters, higher alcohols, volatile acids, lactones, and furanoids. At optimized simultaneous distillation-solvent extraction conditions, analytical parameters such as linearity (R2 > 0.98), repeatability (from 3.33% to 10.39%), quantitation, and detection limits for selected compounds (ethyl hexanoate, geraniol, linalool oxide, α-terpineol, 1-octanol, geranyl acetate, nerol, benzyl alcohol, benzaldehyde, 1,2-dihydrolinalool, 4-terpineol, and diethyl succinate) were estimated.

Inhalation of low-dose basil (Ocimum basilicum) essential oil improved cardiovascular health and plasma lipid markers in high fat diet-induced obese rats.

This study investigated the antiobesogenic effects of the inhalation of volatile compounds derived from basil essential oil (BEO) in high fat diet-induced obese rats. A total of 47 volatile compounds were identified in BEO using gas chromatography-mass spectrometry. Major volatile compounds identified by olfactory testing include linalool oxide, linalool, 1-menthene, and carvone. White adipose tissue significantly decreased in the rats that inhaled 0.3% BEO (more than +10%) compared to the control. Plasma marker analysis showed increased high-density lipoprotein-cholesterol (ca. double fold) and decreased low-density lipoprotein-cholesterol (more than -30%) levels in inhaled 1% BEO group compared to the control. Leptin significantly decreased in the 0.3 and 1% BEO groups (more than -70 and -85%, respectively). Last, systolic blood pressure at week 12 was significantly lower in inhaled 1% BEO group (more than -15%) compared to the control. The results of this study suggest that BEO inhalation may be effective in managing plasma lipid markers (cholesterols and leptin) and possibly metabolic disorders such as obesity. Practical Application: Changes in metabolic health markers, which are effected by inhalation of volatiles in basil (Ocimum basilicum) essential oil, will provide physiological variations in vivo to the public. In this study, the opposite effects were identified between 0.3% and 1% inhalation, respectively. Therefore, our findings will provide optimized and useful guidance for inhalation of basil essential oil.

Understanding the aroma diversity of Dancong tea (Camellia sinensis) from the floral and honey odors: Relationship between volatile compounds and sensory characteristics by chemometrics

Dancong is a Chinese oolong tea famous for its aroma diversity. However, this diversity in characteristic is challenging to be clarified in either sensory or chemical aspects. In this study, the aromas from Dancong teas were characterized based on the typical odors of “floral” and “honey”. The volatile compounds underlying the odors were investigated through chemometrics. Seventy Dancong teas of various categories were collected to approximate the diversity in aroma. According to the sensory evaluation, the floral or honey odor was detected in every sample. For volatile characterization, 57 compounds were identified by gas chromatography-mass spectrometry (GC-MS) coupled with headspace-solid phase microextraction (HS-SPME) across samples. The difference in floral and honey odors was related to volatile variation among the teas, as both the odor-based classification and the volatile-based unsupervised learning analyses yielded consistent sample clustering patterns. Nine volatiles were identified as putative markers for the odor difference, where indole, (E)-nerolidol, 2-phenylacetonitrile, and γ-caprolactone accounted for the floral odor predominance, while hexyl 2-methylbutanoate, (Z)-3-hexenyl pentanoate, (Z)-linalool oxide (pyranoid), (E)-linalool oxide (furanoid), and (Z)-linalool oxide (furanoid) contributed to the honey odor perception. These results point to a volatile-endorsed categorization framework based on the floral and honey odors that can assist in Dancong aroma quality control.

Determination of Terpenes in Traditional Chinese Medicine (TCM) by Comprehensive Two-Dimensional Gas Chromatography – Mass Spectrometry (GC × GC) Coupled to High-Resolution Quadrupole Time-of-Flight Mass Spectrometry (QTOFMS) with Orthogonal Partial Least Squares – Discrimination Analysis (OPLS-DA)

With a variety of pharmacological effects, the genus Elsholtzia and Mosla of Lamiaceae contain volatile components, including monoterpenes, sesquiterpenes, and their oxygenated derivatives that are widely used in traditional Chinese medicine (TCM). In this work, the volatile terpenes were studied by a more efficient technique based on headspace solid-phase micro-extraction (HS-SPME) combined with comprehensive two-dimensional gas chromatography and quadrupole time-of-flight mass spectrometry (GC × GC-QTOFMS). A total of 91 terpenes consisting of 7 monoterpenes, 34 monoterpene oxides, 39 sesquiterpenes, and 11 sesquiterpene oxides were identified. From the retention time, 4,8,8-trimethyl-2-methylene-4-vinylbicyclo[5.2.0] nonane was identified to be the dominant volatile component in E. blanda, M. chinensis for the first time with 8% prevalence, but further verification is needed. 10 volatile terpenes, including 2-isopropyl-5-methyl-3- cyclohexen-1-one, isoegomaketone, α-muurolene, linalool oxide, ethyl2-(5-methyl- 5-vinyltetrahydrofuran-2-yl)propan-2-ylcarbonate, perilla ketone, elsholtzia ketone, alloaromadendrene oxide, artemisia ketone, longifolene-(V4) were identified by multivariate orthogonal partial least-squares discrimination analysis (OPLS-DA). Because these terpenes have significant pharmacological effects, such as anti-anxiety, anti-oxidation, anti-bacteria, and anti-virus properties, the identification of these terpenes may result in new information related to their pharmacological activities.

Volatile organic compounds released by wheat as a result of striped shieldbug feeding and insect behaviour

AbstractThe most popular plant protection method is chemical; however, this is often connected with repeated treatments. Therefore, eco‐friendly strategies need to be investigated. A good alternative is to use the natural repellent properties of plants. The aims of this study were to determine how adult striped shieldbugs (Aelia acuminata L.) feeding on spring wheat plants affect the emission of volatile organic compounds (VOCs) and to determine the reaction of these insects to synthetic blends of VOCs. Using GC/MS for VOC analysis, we find that Aelia acuminata L. (1 or 2 adult pairs) significantly induced VOC emissions from wheat plants. In comparison with controls, larger amounts of (Z)‐3‐hexenal, (E)‐2‐hexenal, (Z)‐3‐hexen‐1‐ol, (E)‐2‐hexen‐1‐ol, β‐pinene, β‐myrcene, (Z)‐3‐hexen‐1‐yl acetate, 1‐hexyl acetate, 4‐heptanone, (Z)‐ocimene, linalool, linalool oxide, benzyl acetate, methyl salicylate, indole, β‐caryophyllene and (E)‐β‐farnesene were released as a result of the biotic stress, with two pairs of insects causing a significantly stronger plant reaction. On the basis of the VOCs identified and their emitted concentrations for two pairs of feeding adult striped shieldbugs, two blends of VOCs were prepared in three concentrations: blend I—(Z)‐3‐hexenal, (E)‐2‐hexenal, (Z)‐3‐hexen‐1‐ol, (E)‐2‐hexen‐1‐ol, (Z)‐3‐hexen‐1‐yl acetate and 1‐hexyl acetate, and blend II—(Z)‐ocimene, linalool, benzyl acetate, methyl salicylate, β‐caryophyllene and (E)‐β‐farnesene. Using an olfactometer (Y‐tube) to study insect behaviour, it was found that the male striped shieldbugs were not attracted to any of the blends at any concentration. Female shieldbugs were attracted to blend I at concentration 1. As for the remaining concentrations of both blends, females and males were repelled, with the higher the concentration the stronger the insect reaction.

Characterizations of botanical attractant of Halyomorpha halys and selection of relevant deorphanization candidates via computational approach

Halyomorpha halys has been recognized as a global cross-border pest species. Along with well-established pheromone trapping approaches, there have been many attempts to utilize botanical odorant baits for field monitoring. Due to sensitivity, ecological friendliness, and cost-effectiveness for large-scale implementation, the selection of botanical volatiles as luring ingredients and/or synergists for H. halys is needed. In the current work, botanical volatiles were tested by olfactometer and electrophysiological tests. Results showed that linalool oxide was a potential candidate for application as a behavioral modifying chemical. It drove remarkable attractiveness toward H. halys adults in Y-tube assays, as well as eliciting robust electroantennographic responsiveness towards antennae. A computational pipeline was carried out to screen olfactory proteins related to the reception of linalool oxide. Simulated docking activities of four H. halys odorant receptors and two odorant binding proteins to linalool oxide and nerolidol were performed. Results showed that all tested olfactory genes were likely to be involved in plant volatile-sensing pathways, and they tuned broadly to tested components. The current work provides insights into the later development of field demonstration strategies using linalool oxide and its molecular targets.

Alteration of Phenolic and Volatile Compounds of Tea Leaf Extract by Tyrosinase and β-Glucosidase during Preparation of Ready-to-Drink Tea on Farm.

The manufacturing of ready-to-drink black tea was through a long process, up to 14-18 hours. There was an alternative way to produce RTD black tea directly on the farm to reduce time production and improve the quality of black tea using exogenous enzymes, i.e., tyrosinase and β-glucosidase. Tyrosinase was investigated for the ability to improve the color of tea extract by oxidize the phenolic content of green tea leaves to theaflavin and thearubigin, and β-glucosidase can enhance the volatile compounds by hydrolyze glycosidic bonds in tea leaves. Incubation of tea leaf extract with tyrosinase produces a high content of theaflavin and good color of tea extract but lowered the antioxidant activity. According to the TF/TR ratio values, tyrosinase treated tea leaf extract was in the best quality tea range. The use of β-glucosidase showed an increase in the proportion of good volatile compounds of linalool, linalool oxide, methyl salicylate, and β-damascenone.

The Effects of Preharvest Mild Shading on the Quality and Production of Essential Oil from Kaffir Lime Leaves (Citrus hystrix)

Kaffir lime (Citrus hystrix DC) is a less popular citrus species commonly used as a food spice and a source of essential oil. Early studies report the success of preharvest mild shading to increase leaf yield, although there is still limited information on the effect of preharvest shading on the quality of essential oil produced. The aim of this current study is to evaluate the effect of preharvest mild shading factors on the yield, physical characteristics, and metabolite fingerprinting of kaffir lime leaves essential oil (KLLEO). One-year-old kaffir lime trees were sampled in two preharvest treatments, i.e., open sun and mild shading (24% light reduction) at Pasir Kuda experimental field, Bogor, Indonesia. Statistical analysis showed that there was no significant effect of preharvest treatment on yield and physical characteristics (color, specific gravity, and refractive index) of KLLEO. In contrast, there was a metabolite fingerprinting variation of KLLEO as an effect of mild shading. The relative percentage of bergamol, citronellol, caryophyllene oxide, citronellic acid, isopulegol, isopulegyl formate, limonene, linalool, and linalool oxide was increased by mild shading. On the other hand, the main metabolite (citronellal) was significantly reduced by about 10% in shading treatment, as compared to the open-sun ones.

Characterization of key aroma compounds and relationship between aroma compounds and sensory attributes in different aroma types of Fu brick tea

Aroma is one of the most important sensory properties of tea. Floral-fungal aroma type, ripe-fungal aroma type and fresh-fungal aroma type were the main aroma types of Fu brick tea by QDA. A total of 112 volatile compounds were identified and quantified in tea samples by HS-SPME/GC-MS analysis. Ten voaltiles in floral-fungal aroma type, eleven voaltiles in ripe-fungal aroma type, and eighteen voaltiles in fresh-fungal aroma type were identified as key aroma compounds for the aroma characteristics formation in three aroma types of Fu brick tea. In addition, PLS analysis revealed that 3,4-dehydro-β-ionone, dihydro-β-ionone, (+)-carotol and linalool oxide Ⅱ were the key contributors to the 'floral and fruity' attribute, α-terpineol contributed to 'woody' and 'stale' attributes, and thirteen aroma compounds related to 'green' attribute. Taken together, these findings will provide new insights into the formation mechanism of different aroma characteristics in Fu brick tea.

Effect of the Seasonal Climatic Variations on the Accumulation of Fruit Volatiles in Four Grape Varieties Under the Double Cropping System.

The double cropping system has been widely applied in many subtropical viticultural regions. In the 2-year study of 2014–2015, four grape varieties were selected to analyze their fruit volatile compounds in four consecutive seasons in the Guangxi region of South China, which had a typical subtropical humid monsoon climate. Results showed that berries of winter seasons had higher concentrations of terpenes, norisoprenoids, and C6/C9 compounds in “Riesling,” “Victoria,” and “Muscat Hamburg” grapes in both of the two vintages. However, in the “Cabernet Sauvignon” grapes, only the berries of the 2014 winter season had higher terpene concentrations, but lower norisoprenoid concentrations than those of the corresponding summer season. The Pearson correlation analysis showed the high temperature was the main climate factor that affected volatile compounds between the summer and winter seasons. Hexanal, γ-terpinene, terpinen-4-ol, cis-furan linalool oxide, and trans-pyran linalool oxide were all negatively correlated with the high-temperature hours in all of the four varieties. Transcriptome analysis showed that the upregulated VviDXSs, VviPSYs, and VviCCDs expressions might contribute to the accumulations of terpenes or norisoprenoids in the winter berries of these varieties. Our results provided insights into how climate parameters affected grape volatiles under the double cropping system, which might improve the understanding of the grape berries in response to the climate changes accompanied by extreme weather conditions in the future.

Identification of volatile compounds correlated with consumer acceptability of strawberry preserves: Untargeted GC–MS analysis

Volatile compounds that impact the acceptability of strawberry preserves were investigated by untargeted GC–MS flavoromics analysis. Chemical profiles for fifteen strawberry preserves were modeled against consumer liking scores by orthogonal partial least squares (OPLS) with good fit (R2Y = 0.998) and predictive ability (Q2 = 0.853). Ten highly predictive compounds were selected, nine of which were identified, and eight of which were quantified using tandem mass spectrometry. Sensory recombination difference testing revealed that the addition of predictive compounds to an average-liked preserve at levels found in the most-liked preserve induced a perceptible difference to frequent consumers of strawberry jams. One of the highly predictive compounds was identified (MS and synthesis) as a novel linalool oxide product 2-methyl-2-vinyl-tetrahydrofuran with a fruity, herbal-minty, piney aroma and a low odor threshold value.

Urinary Volatomic Expression Pattern: Paving the Way for Identification of Potential Candidate Biosignatures for Lung Cancer.

The urinary volatomic profiling of Indian cohorts composed of 28 lung cancer (LC) patients and 27 healthy subjects (control group, CTRL) was established using headspace solid phase microextraction technique combined with gas chromatography mass spectrometry methodology as a powerful approach to identify urinary volatile organic metabolites (uVOMs) to discriminate among LC patients from CTRL. Overall, 147 VOMs of several chemistries were identified in the intervention groups—including naphthalene derivatives, phenols, and organosulphurs—augmented in the LC group. In contrast, benzene and terpenic derivatives were found to be more prevalent in the CTRL group. The volatomic data obtained were processed using advanced statistical analysis, namely partial least square discriminative analysis (PLS-DA), support vector machine (SVM), random forest (RF), and multilayer perceptron (MLP) methods. This resulted in the identification of nine uVOMs with a higher potential to discriminate LC patients from CTRL subjects. These were furan, o-cymene, furfural, linalool oxide, viridiflorene, 2-bromo-phenol, tricyclazole, 4-methyl-phenol, and 1-(4-hydroxy-3,5-di-tert-butylphenyl)-2-methyl-3-morpholinopropan-1-one. The metabolic pathway analysis of the data obtained identified several altered biochemical pathways in LC mainly affecting glycolysis/gluconeogenesis, pyruvate metabolism, and fatty acid biosynthesis. Moreover, acetate and octanoic, decanoic, and dodecanoic fatty acids were identified as the key metabolites responsible for such deregulation. Furthermore, studies involving larger cohorts of LC patients would allow us to consolidate the data obtained and challenge the potential of the uVOMs as candidate biomarkers for LC.

Enhanced and specific epoxidation activity of P450 BM3 mutants for the production of high value terpene derivatives.

Terpenes are natural molecules of valuable interest for different industrial applications. Cytochromes P450 enzymes can functionalize terpenoids to form high value oxidized derivatives in a green and sustainable manner, representing a valid alternative to chemical catalysis. In this work, an enhanced and specific epoxidation activity of cytochrome P450 BM3 mutants was found for the terpenes geraniol and linalool. This is the first report showing the epoxidation of linalool by P450 BM3 and its mutant A2 (Asp251Gly/Gln307His) with the formation of valuable oxide derivatives, highlighting the relevance of this enzymes for industrial applications.

Aroma effects of critical volatile compounds during thermophilic bacteria pile-fermentation in dark tea using gas chromatography mass spectrometry and odor activity value

Thermophilic bacteria play an important role in aroma formation during pile-fermentation process of dark tea. With the aim to reveal the impact of thermophilic bacteria on volatile compounds in dark tea, Bacillus licheniformis (thermophilic bacteria) were inoculated into sun-dried green tea for spontaneous fermentation. In this study, headspace solid phase microextraction combined to gas chromatography mass spectrometry (HS-SPME-GC-MS), odor activity value (OAV), principal component analysis (PCA) and orthogonal partial least squares discrimination analysis (OPLS-DA) were employed to investigated the characteristics of volatile compounds during thermophilic bacteria pile-fermentation. According to HS-SPME-GC-MS, a total of 64 volatile compounds were identified. PCA revealed that tea samples could be clearly discriminated from each other. Furthermore, sulcatone, hexanoic acid, linalool, 2-methyl-trans-decalin, myrtenal, and α-ionone were found to play an important role in discrimination of tea samples, based on OPLS-DA. In addition, the OAV could effectively characterize the aroma contribution of volatile compounds during thermophilic bacteria pile-fermentation, and (Z)-linalool oxide (furanoid), α-ionone, (E)-2-nonenal, and linalool were the critical volatile compounds of aroma quality in dark tea. This study provides insight into volatile compounds characteristics during thermophilic bacteria pile-fermentation in dark tea.

Chemical Composition and Lipoxygenase Inhibitory Activity of the Essential Oil of Alstonia Angustiloba

This study was aimed to investigate the chemica l compositions and lipoxygenase inhibitory activity of the essential oil from Alstonia angustiloba growing in Malaysia. The essential oils were obtained by hydrodistillation and fully characterized by gas chromatography and gas chromatography-mass spectrometry. Analysis of the A. angustiloba essential oil resulted in the identification of twenty-five chemical components, attributed 90.8% of the total oil. The most abundant components of A. angustiloba oil were linalool (21.2%), 1,8-cineole (16.8%), α-terpineol (9.5%), terpinene-4-ol (8.5%), β-caryophyllene (6.2%), and caryophyllene oxide (5.2%). The essential oil displayed moderate activity towards lipoxygenase activity with IC50 value of 45.8 μg/mL.

Antitermitic and antifungal properties of enantiopure linalool and furanoid linalool oxide confirmed in Lindera umbellata var. membranacea

In this study, antitermitic and antifungal activities of enantiopure linalool and linalool oxide (furanoid) in L. umbellata var. membranacea were evaluated with their racemates. Results of chiral analysis showed that linalool oxide in leaves dominated by (R)-linalool and in twigs dominated by (S)-linalool were (2R,5R)-trans- and (2R,5S)-cis-linalool oxide and (2S,5S)-trans- and (2S,5R)-cis-linalool oxide, respectively. All rac-, (R)-, and (S)-linalool at highest concentration showed termiticidal and antifeedant activities against Reticulitermes speratus. Antitermitic activities of linalool oxides differed depending on their stereostructures, and (2R,5R)-trans-linalool oxide showed the strongest termiticidal activity. (S)-linalool showed significantly stronger antifungal activity than that of rac- and (R)-linalool against Penicillium citrinum and Chaetomium globosum. Racemate of trans- and cis-linalool oxide showed potent activity against P. citrinum, Rhizopus oryzae, and C. globosum; however, the activity decreased in isolated pure enantiomers. These results suggest that linalool and linalool oxide exhibit different antitermitic and antifungal properties.

Aroma effects of key volatile compounds in Keemun black tea at different grades: HS-SPME-GC-MS, sensory evaluation, and chemometrics

The present study aimed to explore the relationship between the grade and the characteristic aroma in Keemun black tea (KBT). Headspace solid-phase microextraction (HS-SPME), gas chromatography-mass spectrometry (GC-MS), sensory evaluation, and chemometrics were employed to determine the changes in the flavor evolution of KBT at grade. The results showed that a total of 110 volatile components were identified. Linalool and linalool oxide were dominant. The orthogonal partial least squares discriminant analysis (OPLS-DA) combined with relative odor activity value (rOAV > 0.1) revealed that 11 volatile components were the key volatile compounds of KBT, such as benzeneacetaldehyde (rOAV: 3.43–5.96) and methyl salicylate (rOAV: 2.15 – 2.50). Furthermore, the partial least squares (PLS) model indicated that geraniol, linalool, and methyl salicylate benefited from the reservation of floral flavor of Keemun aroma characteristic of KBT. The findings presented in this thesis add to our understanding of KBT at different grades.

Effects of Berry Thinning on the Physicochemical, Aromatic, and Sensory Properties of Shine Muscat Grapes

The effects of the level of berry thinning (30% and 50% berry removal) on the quality and sensory properties of Shine Muscat grapes were investigated. As berry thinning increased, the total soluble solids content increased and titratable acidity decreased. Berry thinning increased berry size and cluster weight but caused no change in individual berry weight. Phenolic concentrations as measured by total phenolic, proanthocyanidin, and polymeric tannin concentrations tended to increase with an increase in berry thinning. Gas chromatographic analysis indicated that C6-compounds were the significant constituents of volatile alcohols and aldehydes; linalool was the most abundant monoterpene. Odor activity analysis indicated that (E)-2-hexen-1-ol, (E)-2-hexenal, 1-hexanal, (Z)-3-hexenal, (E)-β-damascenone, linalool, and (E)-linalool oxide were active odorants. Berry thinning increased the accumulation of linalool contributing to high sensory flavor scores in thinned berries. Furthermore, its oxidized derivative-linalool oxide-contributed to enhancing the Muscat flavor. In conclusion, berry thinning induced compositional changes in Shine Muscat grape berries by accelerating the ripening rate, contribution to improved sensory properties.

Ameliorative effects of ribes rubrum oil against gastric ulcers caused by indomethacin in experimental models

The objective of this study was to assess the anti-inflammatory effects of ribes rubrum oil at three different doses (5, 10 and 15 ml/kg b.w/day) in adult male albino rats with indomethacin-induced stomach ulcers (IND). Forty rats (135 ± 5 g) categorized into 5 groups (n = 8), for 45 days. Group (1) normal control, thirty-two rats were gavaged IND as single oral dose (30 mg/Kg b.w) resulted in gastric ulcer, then distributed to four groups, group (2) IND-intoxicated control, Groups 3, 4 and 5 were administrated ribes rubrum oil at levels of (5, 10 & 15 ml/kg b.w) respectively. Administrated levels of ribes rubrum oil found to have remarkable elevation in food conversion efficiency in experimental rats, gastric juice pH, in compared to the drunken control group, gastric prostaglandin E2 and gastric cytochrome P450 reductase levels were lower. The levels of pro-inflammatory cytokines NO, TNF-, and IL-1 were dramatically reduced, which was related with an increase in blood hemoglobin (Hb), packed cell volume (PCV), and red blood cells (RBCs)in ulcerogenic rats compared to intoxicated control. Data showed that, the main components of ribes rubrum oil are β-Pinene, γ-linolenic and Linalool oxide levels (25.9%, 23.10% and 10.5%, respectively) for their antioxidant activity. Findings showed that administrate ribes rubrum oil at dose 15 ml/kg followed by 10 ml/kg had the best results against ulcerogenic rats. In conclusion, the outcomes are consistent with the concept that ribes rubrum oil had a gastroprotective and antisecretory effects against gastric ulcer that may be attributed to the antioxidant properties of the oil that ameliorates the damage occur in gastric of rats.

A Practical Laboratory-Scale Synthesis of All Eight Stereoisomeric Forms of Terpene Linalool Oxide

In this work, we describe a user-friendly procedure for the preparation of all the isomeric forms of the terpene linalool oxide. The presented method is based on the transformation of the linalool enantiomers into the corresponding diastereoisomeric mixtures of the two furanoid oxides and two pyranoid oxides. Taking advantage of the different steric hindrance of the hydroxyl functional groups, the pyranoid forms were separated as a diastereoisomeric mixtures of their benzoate esters. Conversely, the cis- and trans-furanoid isomers were transformed in the corresponding acetates, which were directly separated by chromatography. The hydrolysis of the latter esters afforded cis- and trans-furanoid linalool oxides whereas the same reaction performed on the benzoates mixture afforded a separable mixture of cis- and trans-pyranoid linalool oxide. Overall, the method features, as a unique mandatory requirement, the availability of both linalool enantiomers, and can be conveniently performed from a milligram to a multigram scale.