Principles and some techniques of high-resolution headspace analysis

Dravnieks, Andrew; O’Donnell, Anne E.

doi:10.1021/jf60178a002

Cited by 85 publications

(31 citation statements)

References 2 publications

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“…Still, we can only Figure 4. Selected lowest-energy conformers (PM3) of (2ЈЈE)-cyclopropanecarboxylic acid 2Ј-methyl-2Ј-(1ЈЈ,2ЈЈ,4ЈЈ-trimethylpent-2ЈЈ-enyloxy)propyl ester (19) speculate about the active conformer of these highly flexible musk odorants.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis and Odor of Aliphatic Musks: Discovery of a New Class of Odorants

Kraft

Eichenberger

2004

Eur J Org Chem

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To find new aliphatic musks, we synthesized the propionates (12), and of hydroxyacetic acid 1-(5Ј,5Ј-dimethylcyclohex-1Ј-enyl)ethyl ester (13) starting from 1-(3Ј,3Ј-dimethylcyclohex-1Ј-enyl)-ethanone (5) and 1-ethynyl-3,3-dimethylcyclohexanol (9). We found that the 3,3-dimethylcyclohexenyl derivatives 8 (odor threshold 0.2 ng/air) and 12 (odor threshold 0.6 ng/air) are superior musk odorants, and, thus, we constructed 1,2,4-trimethylpent-2-enyloxy analogues as seco versions. The synthesis of the esters 17−26 commenced with a Wittig−Horner− Emmons reaction of isobutyric aldehyde (14),

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Section: Resultsmentioning

confidence: 99%

“…The odor thresholds were determined by GC-olfactometry. [18,19] Different dilutions of the sample substance were injected into a gas chromatograph in descending order of concentration until the panelist fails to detect the respective substance at the sniffing port. The panelist smells in blind and presses a button on perceiving an odor.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Odor of Aliphatic Musks: Discovery of a New Class of Odorants

Kraft

Eichenberger

2004

Eur J Org Chem

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“…or purum grade) from Fluka without further purification. The odor thresholds were determined by GC-olfactometry: [23,24] Different dilutions of the sample substance were injected into a gas chromatograph in descending order of concentration until the panelist failed to detect the respective substance at the sniffing port. The panelist smelled in blind and pressed a button on perceiveing an odor.…”

Section: Methodsmentioning

confidence: 99%

Conception, Characterization and Correlation of New Marine Odorants

Kraft

Eichenberger

2003

Eur J Org Chem

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Via a synthetic sequence consisting of PPA‐mediated Friedel−Crafts acylation of veratrol (8), Clemmensen reduction, demethylation with TMSI, Williamson ether synthesis employing 3‐chloro‐2‐(chloromethyl)prop‐1‐ene and in‐situ ruthenium tetroxide oxidation, numerous substituted benzo[b][1,4]dioxepinones 15−27 and 2,3‐dihydro‐1H‐5,9‐dioxacyclohepta[f]indenones 7, 13 and 14 were prepared to study their odor−structure correlation. In the course of these studies, we discovered the extremely powerful new marine odorant 7‐(3′‐methylbutyl)benzo[b][1,4]dioxepin‐3‐one (16). On the basis of the measured odor threshold data, an olfactophore model was constructed that rationalizes the observed odor intensities, and indicates an aliphatic hydrophobe at a distance of 6.3 Å from the centre of the aromatic‐ring binding site. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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“…This issue was addressed by using humidified air as a make-up carrier gas to deliver the odorants to the human assessors [22]. In modern odour ports, volatiles are typically carried to the nose in a stream of heated and humidified air (50 -75% relative humidity (RH)).…”

Section: Gc-o Hardwarementioning

confidence: 99%

Gas chromatography-olfactometry

2006

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ReviewGas chromatography-olfactometry GC-olfactometry (GC-O) refers to the use of human assessors as a sensitive and selective detector for odour-active compounds. The aim of this technique is to determine the odour activity of volatile compounds in a sample extract, and assign a relative importance to each compound. Methods can be classified into three types: detection frequency, dilution to threshold and direct intensity. Dilution to threshold methods measure the potency of odour-active compounds by using a series of extract dilutions, whereas detection frequency and direct-intensity methods measure odouractive compound intensity, or relative importance, in a single concentrated extract. Factors that should be considered to improve the value of GC-O analysis are the extraction method, GC instrument conditions, including the design and operation of the odour port, methods of recording GC-O data and controlling the potential for human assessor bias using experimental design and a trained panel. Considerable emphasis is placed on the requirement for multidimensional GC analysis, and on best practice when using human assessors.

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Principles and some techniques of high-resolution headspace analysis

Cited by 85 publications

References 2 publications

Synthesis and Odor of Aliphatic Musks: Discovery of a New Class of Odorants

Synthesis and Odor of Aliphatic Musks: Discovery of a New Class of Odorants

Conception, Characterization and Correlation of New Marine Odorants

Gas chromatography-olfactometry

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