(4R,5R)-(+)-epoxy-(E)-2-decenal - Mori et al. (2015) report - Impressions of the odors of (+)- and (-)-isomers as 0.01% solution in triacetin (triacetylglycerol) were examined by flavorists at T. Hasegawa Co. Their responses were as follows: For (4R,5R)-(+)-epoxy-(E)-2-decenal - weak, metallic, green and oily. Both enantiomers showed similar odor quality, although they were different in odor intensity. Recognition threshold in water - 1.1 ppb Detection threshold in water - 0.62 ppb Daniher et al. (2002) report - At 0.02 ppb in water - no smell, no taste (weakest enantiomer) At 0.2 ppb in water - mild metallic smell and taste At 20 ppb in water - clear metallic and bean taste/smell "The profile in all the samples is similar, with the (-) isomer at least 3-5 times stronger than the (+/-) racemate, or 10 times stronger than the (+) isomer." Note - In 2012, Rachamadugu found that trans-4,5-epoxy-(E)-2-decenal evoked a typical "metallic, blood-like" odor quality in humans. In 2014, Nilsson et al. reported that trans-4,5-epoxy-(E)-2-decenal could be as efficient in eliciting behavioral responses among dogs and tigers as the odor of mammalian blood. Evaluation by Mori et al. indicated the racemate (±) made mice scared stiff at a dosage of approximately 1 mg, while the enantiomers were not significantly bioactive. Ref: Mori, Kenji, Kazumi Osada, and Masayasu Amaike. "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." Tetrahedron: Asymmetry 26.15 (2015): 861-867. Daniher, Andrew; Furrer, Stefan; Goeke, Andreas; Epoxydecenal isomers, United States Patent 6,335,047 (January 1, 2002) Rachamadugu SK (2012), Characterization of specific volatiles of blood with the potential as predator chemoattractants and as prey warning signals. M.Sc. thesis, Linköping University, Linköping, Sweden Nilsson S, Sjöberg J, Amundin M, Hartmann C, Buettner A, Laska M (2014), Behavioral Responses to Mammalian Blood Odor and a Blood Odor Component in Four Species of Large Carnivores. PLoS ONE 9(11): e112694. doi:10.1371/journal.pone.0112694

(4S,5S)-(-)-epoxy-(E)-2-decenal - Mori et al. (2015) report - Impressions of the odors of (+)- and (-)-isomers as 0.01% solution in triacetin (triacetylglycerol) were examined by flavorists at T. Hasegawa Co. Their responses were as follows: For (4S,5S)-(-)-epoxy-(E)-2-decenal - strong, metallic, oily, fatty and peely. Both enantiomers showed similar odor quality, although they were different in odor intensity. Recognition threshold in water - 0.047 ppb Detection threshold in water - 0.019 ppb Daniher et al. (2002) report - At 0.02 ppb in water - faint smell, mild metallic taste (strongest enantiomer) At 0.2 ppb in water - strong metallic smell/taste At 20 ppb in water - strong metallic and bean taste/smell "The profile in all the samples is similar, with the (-) isomer at least 3-5 times stronger than the (+/-) racemate, or 10 times stronger than the (+) isomer." Note - In 2012, Rachamadugu found that trans-4,5-epoxy-(E)-2-decenal evoked a typical "metallic, blood-like" odor quality in humans. In 2014, Nilsson et al. reported that trans-4,5-epoxy-(E)-2-decenal could be as efficient in eliciting behavioral responses among dogs and tigers as the odor of mammalian blood. Evaluation by Mori et al. indicated the racemate (±) made mice scared stiff at a dosage of approximately 1 mg, while the enantiomers were not significantly bioactive. Ref: Mori, Kenji, Kazumi Osada, and Masayasu Amaike. "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." Tetrahedron: Asymmetry 26.15 (2015): 861-867. Daniher, Andrew; Furrer, Stefan; Goeke, Andreas; Epoxydecenal isomers, United States Patent 6,335,047 (January 1, 2002) Rachamadugu SK (2012), Characterization of specific volatiles of blood with the potential as predator chemoattractants and as prey warning signals. M.Sc. thesis, Linköping University, Linköping, Sweden Nilsson S, Sjöberg J, Amundin M, Hartmann C, Buettner A, Laska M (2014), Behavioral Responses to Mammalian Blood Odor and a Blood Odor Component in Four Species of Large Carnivores. PLoS ONE 9(11): e112694. doi:10.1371/journal.pone.0112694

Ionones, Irones, Damascones & Structurally Related Odorants

Acyclics (Alcohols, Esters, Acids, Aldehydes)

Lactones

Sesquiterpenoid Related Odorants