Chirality & Odour Perception
John C. Leffingwell, Ph.D.

The 2-methyl-N-(2'-methylbutylidene)butan-1-amines

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Photo by permission of M. Roudintska - Art & Parfum

(2S)-2-methyl-N-((2'S)-2'-methylbutylidene)butan-1-amine - Light, metallic, oily character.Seafood (internal organs of shrimp) with sweet butter-like and esteric scent.

= N-[(2S)-2-methylbutyl]-N-[(2'S)-2'-methylbutylidene]amine

Ref: Toru Tachihara, Susumu Ishizaki, Yoshiko Kurobayashi, Hiroshi Tamura, Youichi Ikemoto, Atsushi Onuma, Keisuke Yoshikawa, Tetsuya Yanai, Takeshi Kitahara; Synthesis and Odor Evaluation of Stereoisomers of Imine Derivatives in Roasted Spotted Shrimp, Helv. Chim. Acta 2003, 86, No. 2, 274-279

(2R)-2-methyl-N-((2'R)-2'-methylbutylidene)butan-1-amine - Mild, sweet, fruity, slightly phenolic element, including the peel of mango, apple, citrus.

= N-[(2R)-2-methylbutyl]-N-[(2'R)-2'-methylbutylidene]amine

Ref: Toru Tachihara, Susumu Ishizaki, Yoshiko Kurobayashi, Hiroshi Tamura, Youichi Ikemoto, Atsushi Onuma, Keisuke Yoshikawa, Tetsuya Yanai, Takeshi Kitahara; Synthesis and Odor Evaluation of Stereoisomers of Imine Derivatives in Roasted Spotted Shrimp, Helv. Chim. Acta 2003, 86, No. 2, 274-279

(2S)-2-methyl-N-((2'R)-2'-methylbutylidene)butan-1-amine - Metallic, slightly heavy, cocoa-like odor with esteric, fruity element. Sweeter odor than the (2S,2'S)-stereoisomer. Image of burned fish, shrimp.

= N-[(2S)-2-methylbutyl]-N-[(2'R)-2-methylbutylidene]amine

Ref: Toru Tachihara, Susumu Ishizaki, Yoshiko Kurobayashi, Hiroshi Tamura, Youichi Ikemoto, Atsushi Onuma, Keisuke Yoshikawa, Tetsuya Yanai, Takeshi Kitahara; Synthesis and Odor Evaluation of Stereoisomers of Imine Derivatives in Roasted Spotted Shrimp, Helv. Chim. Acta 2003, 86, No. 2, 274-279

(2R)-2-methyl-N-((2'S)-2'-methylbutylidene)butan-1-amine - Seafood, including fish odor wuth phenolic, esteric, fruity element.

= N-[(2R)-2-methylbutyl]-N-[(2'S)-2-methylbutylidene]amine

Ref: Toru Tachihara, Susumu Ishizaki, Yoshiko Kurobayashi, Hiroshi Tamura, Youichi Ikemoto, Atsushi Onuma, Keisuke Yoshikawa, Tetsuya Yanai, Takeshi Kitahara; Synthesis and Odor Evaluation of Stereoisomers of Imine Derivatives in Roasted Spotted Shrimp, Helv. Chim. Acta 2003, 86, No. 2, 274-279

Cyclic Terpenoid Odorants

Bicyclic Terpenoid Odorants

Acyclic Terpenoid Odorants

Ionones, Irones, Damascones & Structurally Related Odorants

Acyclics (Alcohols, Esters, Acids, Aldehydes)

Lactones

Sesquiterpenoid Related Odorants

Steroid Urine Type Odorants

Sandalwood Type Odorants

Musk Odorants

Miscellaneous

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