Correlations between odour activity and the structural modifications of acrylates

Bauer, Patrick; Denk, Philipp; Fuss, Julia Maria; Lorber, Katja; Ortner, Eva; Buettner, Andrea

doi:10.1007/s00216-019-01936-6

Cited by 6 publications

(7 citation statements)

References 31 publications

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“…2. The findings for 1-alken-3-one and n-alkyl acrylates correlate well with the OT values found in previous studies [4,18].…”

Section: Odour Thresholds In Airsupporting

confidence: 91%

“…Within set 1, short-chained acrylates, namely ethyl acrylate and propyl acrylate, showed a geranium-like, lighter gaslike, and garlic-like odour, which correlated well with the findings of a previous study in which such representatives have been described as "lighter gas-like, glue-like, garliclike" and "lighter gas-like, sulphurous" [4]. Further elongation of the carbon chain initially brought about a mushroomlike and geranium-like odour and finally led to the fruity and soapy nuances.…”

Section: Odour Qualities Of 1-alkyl Acrylates and 1-alken-3-onessupporting

confidence: 87%

Section: Introductionmentioning

confidence: 56%

“…With regard to the unexpected smell effects, our previous studies revealed that butyl acrylate and 1-octen-3-one elicit highly comparable odour impressions to the panellists [4,12,13,18]. However, we found that the odour threshold of 1-octen-3-one is up to 100 times lower than of its acrylic homologue butyl acrylate [4,18]. Due to their apparent comparable molecular structure, one might postulate that both substances interact with the same or similar receptors; striking is their similarity regarding the α,β-unsaturated carbonyl function as well as the corresponding alkyl-moiety and, accordingly, coinciding chain length of both substances.…”

Section: Introductionmentioning

confidence: 99%

“…In these studies, butyl acrylate showed a mushroom-like and geranium leaf-like odour that influenced the scent of acrylic paints. It has been shown that most of the acrylates used for industrial purposes revealed a low odour threshold value (OT) with ethyl acrylate showing the lowest OT among the n-alkyl acrylate series [4].…”

Section: Introductionmentioning

confidence: 99%

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Influence of elongation and desaturation on chemosensory properties in acrylates and their corresponding 1-alken-3-ones

Bauer

Ortner²,

Buettner³

2022

Anal Bioanal Chem

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Acrylates as well as 1-alken-3-ones are both known to be odour active substances but are generally identified in different materials. Nonetheless, butyl acrylate and 1-octen-3-one were both found to elicit a similar mushroom-like odour in previous studies. This led to the question of whether acrylates and enones with the same overall chain length generally elicited similar odours and whether they had similar odour thresholds. Overall, most of the investigated substances showed a mushroom-like, geranium-like or fruity odour. In contrast, short chained substances elicited garlic-like, lighter gas-like or glue-like, odour qualities, suggesting a correlation between the odour quality and the overall chain length. The results showed that only between the analogue structures butyl acrylate and 1-octen-3-one as well as hexyl acrylate and 1-decen-3-one could similar odour qualities be observed. All investigated substances showed low odour threshold values in air between 0.0032 ng/lair (1-hexen-3-one) and 55 ng/lair (1-dodecen-3-one). Overall, 1-alken-3-ones revealed a higher dependency on the chain length when compared to their respective acrylates. The introduction of a second terminal double bond led to a decrease of OT values in case of the acrylates and to an increase in case of the ketones that neither contained a second terminal double bond nor a double bond located close to the carbonyl group. Despite their structural similarities, the results suggest that both substance classes are perceived in a different manner and are therefore likely to be recognized by different types of receptors or are related to different activation patterns in multi-receptor stimulation processes. Graphical abstract

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“…2. The findings for 1-alken-3-one and n-alkyl acrylates correlate well with the OT values found in previous studies [4,18].…”

Section: Odour Thresholds In Airsupporting

confidence: 91%

Section: Odour Qualities Of 1-alkyl Acrylates and 1-alken-3-onessupporting

confidence: 87%