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

The 2-methoxy-3-[1-methylpropyl]pyrazines

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Photo by permission of M. Roudintska - Art & Parfum

(-)-(R)-2-methoxy-3-[1-methylpropyl]pyrazine - a burdock like, green and earthy odor; Qualitatively, there is no significant difference between the organoleptic properties of the (S)-(+)-, (R)-(-) enantiomers or the racemate but the (-)-(R)-2-methoxy-3-[1-methylpropyl]pyrazine appears to have a somewhat more burdocklike aroma than its antipode.

Odor threshold = 0.01 ppb

Ref: Satoru Mihara, Hideki Masuda, Osamu Nishimura, and Hideki Tateba, Determination of the Enantiomeric Composition of 2-Met hoxy-3-(1'-methylpropyl) pyrazine from Galbanum Oil Using Achiral and Chiral Lanthanide Shift Reagents, J. Agric. Food Chem. 1990, 38, 465-467

(+)-(S)-2-methoxy-3-[1-methylpropyl]pyrazine - a burdock like, green and earthy odor

Odor threshold = 0.1 ppb

This is the natural isomer of Galbanum

Ref: Satoru Mihara, Hideki Masuda, Osamu Nishimura, and Hideki Tateba, Determination of the Enantiomeric Composition of 2-Met hoxy-3-(1'-methylpropyl) pyrazine from Galbanum Oil Using Achiral and Chiral Lanthanide Shift Reagents, J. Agric. Food Chem. 1990, 38, 465-467

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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