Mammalian blood odorant and chirality: synthesis and sensory evaluation by humans and mice of the racemate and enantiomers of trans-4,5-epoxy-(E)-2-decenal

Mori, Kenji; Osada, Kensuke; Amaike, Masayasu

doi:10.1016/j.tetasy.2015.06.011

Cited by 6 publications

(6 citation statements)

References 25 publications

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“…Human data represent the highest and the lowest individual detection treshold value reported in a given study. [1] Mori, Osada, & Amaike (2015), [2] Guth & Grosch (1990), [3] Buettner & Schieberle (2001).…”

Section: Resultsmentioning

confidence: 99%

“…Chemo-analytical studies of mammalian blood found one compound, trans -4,5-epoxy-(E)-2-decenal, to evoke a typical “metallic, blood-like” odor quality in humans (Rachamadugu, 2012). Subsequent studies reported that large carnivores such as Siberian tigers and African wild dogs are as attracted to this single volatile compound as they are to the odor of real blood (Nilsson et al., 2014), and that mice display avoidance responses not only when exposed to the odor of real blood (Lahger, 2016) but also when presented with the odor of this blood odor component alone (Mori, Osada, & Amaike, 2015). Thus, these studies suggest that the odor of trans -4,5-epoxy-(E)-2-decenal may indeed be perceived by both predator and prey species as “blood-like” and that it may act as a “key” or “character-impact” compound for the odor of blood (Dunkel et al., 2014).…”

Section: Introductionmentioning

confidence: 99%

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Olfactory Sensitivity for the Mammalian Blood Odor Component Trans-4,5-epoxy-(E)-2-decenal in CD-1 Mice

Sarrafchi

Laska

2016

Perception

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Using a conditioning paradigm and an automated olfactometer, we investigated the olfactory sensitivity of CD-1 mice for the mammalian blood odor component trans-4,5-epoxy-(E)-2-decenal. We found that two of the animals significantly discriminated concentrations down to 3.0 ppt (parts per trillion) from the solvent, and three animals even successfully detected dilutions as low as 0.3 ppt. Intraspecific comparisons between the olfactory detection thresholds obtained here with those obtained in earlier studies with other odorants show that mice are extraordinarily sensitive to this blood odor component. Interspecific comparisons of olfactory detection thresholds show that human subjects are even more sensitive to trans-4,5-epoxy-(E)-2-decenal than the mice tested here. Both intra- and inter-specific comparisons suggest that neither neuroanatomical properties such as the size of the olfactory epithelium, the total number of olfactory receptor neurons, or the size of olfactory brain structures, nor genetic properties such as the number of functional olfactory receptor genes or the proportion of functional relative to the total number of olfactory receptor genes allow us to reliably predict a species' olfactory sensitivity. In contrast, the results support the notion that the behavioral relevance of an odorant rather than neuroanatomical or genetic properties may determine a species' olfactory sensitivity.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Olfactory Sensitivity for the Mammalian Blood Odor Component Trans-4,5-epoxy-(E)-2-decenal in CD-1 Mice

Sarrafchi

Laska

2016

Perception

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“…(6R,7S,2E)-6,7-Epoxy-2-nonenal has been identified as a sex-aggregation pheromone of the red-necked longhorn beetle (Aromia bungii) [5] and its synthesis has been recently developed by Mori and co-workers [6,7]. (2E)-trans-4,5-Epoxy-2-decenal is present in mammalian blood and may be used by predators to track their prey [8,9]. A classical example of cis-epoxides with semiochemical activity is the chemical communication system of the gypsy moth (Lymantria dispar) and the nun moth (Lymantria monacha).…”

Section: Synthesis Of Disparlure and Monachalure Enantiomers From 23mentioning

confidence: 99%

Synthesis of disparlure and monachalure enantiomers from 2,3-butanediacetals

Drop¹,

Wojtasek²,

Frąckowiak-Wojtasek³

2020

Beilstein J. Org. Chem.

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2,3-Butanediacetal derivatives were used for the stereoselective synthesis of unsymmetrically substituted cis-epoxides. The procedure was applied for the preparation of both enantiomers of disparlure and monachalure, the components of the sex pheromones of the gypsy moth (Lymantria dispar) and the nun moth (Lymantria monacha) using methyl (2S,3R,5R,6R)-3-ethylsulfanylcarbonyl-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane-2-carboxylate as the starting material.

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“…However, whereas mammalian predators such as tigers and wild dogs were found to be attracted by this blood odor component, the mouse, a prey species, avoided it. The only other study so far that assessed behavioral responses of mice to trans-4,5-epoxy-(E)-2-decenal reported that inbred C57BL/6J mice displayed freezing when exposed to this odorant [32]. Although this finding is in line with the present study, it should be mentioned that the method employed by Mori et al [32] included an unphysiologically high concentration of the blood odor component and a test arena lacking an escape room or an alternative compartment which may have contributed to the freezing response which was the only behavioral measure recorded.…”

Section: Behavioral Response To the Blood Odor Componentmentioning

confidence: 99%

“…The only other study so far that assessed behavioral responses of mice to trans-4,5-epoxy-(E)-2-decenal reported that inbred C57BL/6J mice displayed freezing when exposed to this odorant [32]. Although this finding is in line with the present study, it should be mentioned that the method employed by Mori et al [32] included an unphysiologically high concentration of the blood odor component and a test arena lacking an escape room or an alternative compartment which may have contributed to the freezing response which was the only behavioral measure recorded. The present study, in contrast, exposed the mice to a concentration of trans-4,5-epoxy-(E)-2-decenal which was only a factor of 100 above the olfactory detection threshold of mice [22] and thus much closer to the concentration that is found in mammalian blood.…”

Section: Behavioral Response To the Blood Odor Componentmentioning

confidence: 99%

Behavioral responses of CD-1 mice to conspecific and heterospecific blood odors and to a blood odor component

Lahger

Laska

2018

Physiology & Behavior

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The odor of blood may have both aversive and attractive properties for mammals, depending on the species of the odor donor and the species perceiving the odor. To better understand the informational content of blood odor for a prey species we assessed behavioral responses of male CD-1 mice (n=60) to the odor of blood of same-sex and opposite-sex conspecifics, of a natural predator of mice (cat), and of a herbivore (horse) and an omnivore (human) non-predator of mice. Further, we assessed their behavior towards the mammalian blood odor component trans-4,5-epoxy-(E)-2-decenal which recent studies have shown to be as attractive to mammalian predators as the odor of real blood. A two-compartment test arena was used to record approach/avoidance behavior when the animals were presented with an odor in one compartment and a blank control in the other compartment. We found that both conspecific and heterospecific blood odors elicited significant avoidance behavior in the mice whereas a control odor (n-pentyl acetate) did not. The blood odor component trans-4,5-epoxy-(E)-2-decenal was also significantly avoided and thus appears to play an important role in the perception of mammalian blood odor in this prey species. These results support the notion that mammalian blood odor contains an olfactory warning signal which elicits an adaptive behavioral avoidance response in a prey species, the mouse. Our finding that the mice avoided the mammalian blood odor component trans-4,5-epoxy-(E)-2-decenal to the same degree as the odor of real blood suggests that this volatile compound might be (part of) this warning signal.

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Mammalian blood odorant and chirality: synthesis and sensory evaluation by humans and mice of the racemate and enantiomers of trans-4,5-epoxy-(E)-2-decenal

Cited by 6 publications

References 25 publications

Olfactory Sensitivity for the Mammalian Blood Odor Component Trans-4,5-epoxy-(E)-2-decenal in CD-1 Mice

Olfactory Sensitivity for the Mammalian Blood Odor Component Trans-4,5-epoxy-(E)-2-decenal in CD-1 Mice

Synthesis of disparlure and monachalure enantiomers from 2,3-butanediacetals

Behavioral responses of CD-1 mice to conspecific and heterospecific blood odors and to a blood odor component

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