γ-Dithiolactones - Analytical and Sensory Characteristics

Beck, Thomas L.; Mosandl, Armin

doi:10.1002/(sici)1521-4168(19990701)22:7<421::aid-jhrc421>3.0.co;2-r

Cited by 5 publications

(1 citation statement)

References 7 publications

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“…The very downfield 13 C NMR shift of the quaternary CX carbon (δ 247.5–248.1) was consistent with the γ-dithiolactone moiety −SC(S)CH–, as these signals in γ-thiolactone −SC(O)CH– or γ-thionolactone −OC(S)CH– functional groups typically appear around δ 209 or 222, respectively. − Furthermore, the IR spectrum of 3 contained a broad band around 3350 cm –1 attributable to the −OH group, whose presence was also indicated by an intense ion with m / z 145 (i.e., [M + H] + – 18) in the MS/MS spectrum (see the Supporting Information). The UV absorption maximum of 3 (309 nm) was also in perfect accordance with values reported in the literature for γ-dithiolactones (analogous γ-thio- and γ-thionolactones exhibit UV absorption maxima at around 235 and 250 nm, respectively) …”

Section: Resultsmentioning

confidence: 73%

Isoalliin-Derived Thiolanes Formed in Homogenized Onion

Štefanová

Zápal

Moos

et al. 2019

J. Agric. Food Chem.

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Several families of 3,4-dimethylthiolane-based compounds spontaneously formed upon cutting of onion (Allium cepa) were studied. We report the isolation of the first known example of a naturally occurring dithiolactone, 5-hydroxy-3,4dimethylthiolane-2-thione (cepadithiolactone A, C 6 H 10 OS 2 ). Furthermore, on the basis of conceivable spectroscopic evidence (MS, NMR, IR), we could disprove the structure previously proposed for onionin A (C 9 H 16 O 2 S 2 ), which is shown to be in fact (E)-3,4-dimethyl-5-(1-propenylsulfinyl)thiolane-2-ol. The identification of hitherto unknown methyl and propyl homologues of onionin A (dubbed onionins B and C, respectively) is also reported. Furthermore, the existence of the methyl and propyl homologues of cepathiolanes A (C 9 H 16 O 2 S 3 ), trivially named cepathiolanes B and C, respectively, has been newly revealed. The organoleptic properties of these 3,4-dimethylthiolanes and their role in the formation of the pink discoloration of processed onion were also evaluated.

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Section: Resultsmentioning

confidence: 73%

Isoalliin-Derived Thiolanes Formed in Homogenized Onion

Štefanová

Zápal

Moos

et al. 2019

J. Agric. Food Chem.

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Syntheses and olfactory characteristics of flavouring and perfuming lactone thiono-analogues

et al. 2005

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Thionation of several γ γ γ γ γ-, δ δ δ δ δ-and ε ε ε ε ε-lactones widely used in flavours and fragrances was carried out using three different synthetic procedures. γ γ γ γ γ -Thionolactones were synthesized via a microwave-assisted procedure, whereas δ δ δ δ δ-and ε ε ε ε ε-thionolactones were prepared using Lawesson's reagent or the P 4 S 10 -HMDO combination under standard conditions. The synthesized compounds were submitted to an olfactory evaluation: γ γ γ γ γ -thionolactones offered a large variety of odours related to saffron, mushrooms and fruits, while δ δ δ δ δ-thionolactones presented a strong character of sulphur with a poor variety of olfactory notes. cis-Jasmone thionolactone, 6-amylthionopyrone, and menthone thionolactone presented very interesting notes of blackcurrant, Tagetes minuta and celery, respectively.

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Cepathiolactols and Cepathiolactones─Two Newly Discovered Families of Organosulfur Compounds Formed in Cut Onion

Štefanová,

Bittnerová,

Moos

et al. 2024

J. Agric. Food Chem.

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Isolation and structural characterization of two large families of organosulfur compounds spontaneously formed upon cutting of onion (Allium cepa) were carried out. The structures of these hitherto unknown species, trivially named cepathiolactols and cepathiolactones, were established based on NMR, MS, and IR data. It was found that cepathiolactols (C x H y OS 3 and C x H y O 2 S 4 ; x = 7−12, y = 14−24) are 3,4-dimethyl-γ-thiolactols bearing various side chains linked via a disulfanyl moiety at position C-5. On the other hand, cepathiolactones were shown to be 3,4-dimethyl-γ-thiolactones structurally analogous to cepathiolactols. Sensory properties of cepathiolactols were also evaluated, along with testing their ability to participate in the formation of pink discoloration of processed onion.

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γ-Dithiolactones - Analytical and Sensory Characteristics

Cited by 5 publications

References 7 publications

Isoalliin-Derived Thiolanes Formed in Homogenized Onion

Isoalliin-Derived Thiolanes Formed in Homogenized Onion

Syntheses and olfactory characteristics of flavouring and perfuming lactone thiono-analogues

Cepathiolactols and Cepathiolactones─Two Newly Discovered Families of Organosulfur Compounds Formed in Cut Onion

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