Odor Differences between Enantiomeric Isomers

Russell, G.; Hills, J. I.

doi:10.1126/science.172.3987.1043

Cited by 104 publications

(46 citation statements)

References 3 publications

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“…Concerning the other chiral compounds, carvone is one of the well-known examples for a clear difference in smell between the two enantiomers (Russell and Hills, 1971). In the GC-O analyses of the samples, odor qualities for carvone were described as neither clearly caraway-nor spearmint-like, but rather a mixture of both with a tendency towards one or the other.…”

Section: Stereochemical and Sensory Aspects Of Odorant Constituentsmentioning

confidence: 98%

Identification of odorants in frankincense (Boswellia sacra Flueck.) by aroma extract dilution analysis and two-dimensional gas chromatography–mass spectrometry/olfactometry

Niebler

Buettner

2015

Phytochemistry

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Section: Stereochemical and Sensory Aspects Of Odorant Constituentsmentioning

confidence: 98%

Identification of odorants in frankincense (Boswellia sacra Flueck.) by aroma extract dilution analysis and two-dimensional gas chromatography–mass spectrometry/olfactometry

Niebler

Buettner

2015

Phytochemistry

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“…In addition, structurally diverse molecules can elicit indistinguishable odors, while similar molecules, such as stereoisomers, can yield distinct odors (e.g., R(–)-carvone smells like spearmint, but S()-carvone smells like caraway). 141,142 To date, the type of odor elicited by a volatile compound cannot be reliably predicted by the structure of the molecule. 143 …”

Section: Smellmentioning

confidence: 99%

Genetics of Taste and Smell

Reed

Knaapila

2010

Progress in Molecular Biology and Translational Science

218

118

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Eating is dangerous. While food contains nutrients and calories that animals need to produce heat and energy, it may also contain harmful parasites, bacteria, or chemicals. To guide food selection, the senses of taste and smell have evolved to alert us to the bitter taste of poisons and the sour taste and off-putting smell of spoiled foods. These sensory systems help people and animals to eat defensively, and they provide the brake that helps them avoid ingesting foods that are harmful. But choices about which foods to eat are motivated by more than avoiding the bad; they are also motivated by seeking the good, such as fat and sugar. However, just as not everyone is equally capable of sensing toxins in food, not everyone is equally enthusiastic about consuming high-fat, high-sugar foods. Genetic studies in humans and experimental animals strongly suggest that the liking of sugar and fat is influenced by genotype; likewise, the abilities to detect bitterness and the malodors of rotting food are highly variable among individuals. Understanding the exact genes and genetic differences that affect food intake may provide important clues in obesity treatment by allowing caregivers to tailor dietary recommendations to the chemosensory landscape of each person.

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“…Reputed differences in quality were sometimes questioned as attributable to the presence of impurities. In 1971, three independent investigations using the enantiomers R(-) and S(+)-carvone showed conclusively that enantiomers can have different odor qualities (25,30,36). These studies and more recent work on odor thresholds for enantiomers of carvone and α-ionone (32) suggest the existence of olfactory receptors with chiral selectivity.…”

Section: Procedurementioning

confidence: 97%

Trigeminal and Olfactory Chemosensory Impact of Selected Terpenes

Cometto‐Muñiz

Cain

Abraham

et al. 1998

Pharmacology Biochemistry and Behavior

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COMETTO-MUÑIZ, J. E., W. S. CAIN, M. H. ABRAHAM AND R. KUMARSINGH. Trigeminal and olfactory chemosensory impact of selected terpenes. PHARMACOL BIOCHEM BEHAV. In Experiment 1, four normosmics and four anosmics (3 congenital, 1 idiopathic) provided odor and nasal pungency thresholds, respectively, for the following terpenes: ∆ 3 -carene, p-cymene, linalool, 1,8-cineole, and geraniol, plus the structurally-related compound cumene. Additionally, all subjects provided nasal localization (i.e., right/left) and eye irritation thresholds. Trigeminally-mediated thresholds (i.e., nasal pungency, nasal localization, and eye irritation) lay about three orders of magnitude above odor thresholds -which ranged between 0.1 and 1.7 ppm. The results implied uniform chemesthetic sensitivity across tasks and sites of impact. In Experiment 2, normosmics and anosmics provided odor and nasal pungency thresholds, respectively, for three pairs of isomeric terpenes: α-and γ-terpinene, α-and ß-pinene, and R(+)-and S(-)-limonene.Odor thresholds ranged between 1.4 and 19 ppm -that is, about an order of magnitude higher than those of the previous terpenes -with no substantial differences between odor thresholds of members of a pair. Regarding chemesthetic impact, only α-terpinene evoked nasal pungency. The overall outcome suggests comparable trigeminal chemosensitivity between nose and eyes and between normosmics and anosmics, as shown before for homologous n-alcohols. It also lends support to a previously-derived solvation model of the chemesthetic potency of airborne substances, and indicates the likely importance of certain molecular-size restrictions for effective trigeminal impact.

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Odor Differences between Enantiomeric Isomers

Cited by 104 publications

References 3 publications

Identification of odorants in frankincense (Boswellia sacra Flueck.) by aroma extract dilution analysis and two-dimensional gas chromatography–mass spectrometry/olfactometry

Identification of odorants in frankincense (Boswellia sacra Flueck.) by aroma extract dilution analysis and two-dimensional gas chromatography–mass spectrometry/olfactometry

Genetics of Taste and Smell

Trigeminal and Olfactory Chemosensory Impact of Selected Terpenes

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