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

The Methyl 2-methylbutyrates

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Photo by permission of M. Roudintska - Art & Parfum

Methyl (R)-(-)-2-methylbutanoate - fruity, dairy (Boelens et. al.)

= Methyl (R)-(-)-2-methylbutyrate

Flavor perception threshold = 5 ppb in water (Amano et. al)

Odor perception threshold (nasal) for racemic Methyl 2-methylbutanoate: 0.4 ppb in water (Blank et. al)

Odor perception threshold (retronasal) for racemic Methyl 2-methylbutanoate: 0.2 ppb in water (Blank et. al)

On the basis of the Odor perception threshold (nasal) for racemic and the (S)-enantiomer, we calculate that the Odor perception threshold (nasal) for Methyl (R)-(-)-2-methylbutanoate would be about ~0.5 ppb

Ref: Mans H. Boelens, Harrie Boelens & Leo J. van Gemert, Perfumer & Flavorist, Vol. 18, No. 6, 1-15, 1993 and references therein; Imre Blank, Alina Sen & Werner Grosch (1992), Sensory study on the character-impact flavour compounds of dill herb (Anethum graveolens L.), Food Chem., 43, 337-343; Akira Amano, Kazuhiko Tokoro, Kenichi Uchiumi, United States Patent 5496580, Method for improving flavor of food or drink (March 5, 1996)

Methyl (S)-(+)-2-methylbutanoate - fruity, apple-like (Boelens et. al.); fruity Blank et. al)

Odor perception threshold (nasal): 0.3 ppb in water (Blank et. al)

Flavor perception threshold = 5 ppb in water (Amano et. al)

= Methyl (S)-(+)-2-methylbutyrate

Ref: Mans H. Boelens, Harrie Boelens & Leo J. van Gemert, Perfumer & Flavorist, Vol. 18, No. 6, 1-15, 1993 and references therein; Imre Blank, Alina Sen & Werner Grosch (1992), Sensory study on the character-impact flavour compounds of dill herb (Anethum graveolens L.), Food Chem., 43, 337-343; Akira Amano, Kazuhiko Tokoro, Kenichi Uchiumi, United States Patent 5496580, Method for improving flavor of food or drink (March 5, 1996)

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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