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

The Menthols

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Photo by permission of M. Roudintska - Art & Parfum

 

(1S,3S,4R)-(+)-menthol - fresh, some cooling, sweet-minty with musty, bitter, phenolic and herbaceous notes

Taste Threshold = 300 ppb

Cooling Threshold = 3000 ppb

Ref: Leffingwell, J.C. & R.E. Shackelford, Laevo-Menthol - Syntheses and organoleptic properties, Cosmetics and Perfumery, 89(6), 69-89, 1974; Hopp, R., Menthol: its origins, chemistry, physiology and toxicological properties, Rec. Adv. Tobacco Science, Vol. 19, 3-46 (1993); Enberger, R. and R. Hopp, Synthesis and sensory charachteristics on menthol enantiomers and their derivitives for the use of nature-identical peppermint oils., Topics in Flavor Research, R.G. Berger, S. Nitz and P. Schrier, Editors, H. Eichorn, Marzling, Germany, pp. 201-218 (1988).

 

(1R,3R,4S)-(-)-menthol - very cooling, fresh, sweet, minty

Taste Threshold = 400 ppb

Cooling Threshold = 800 ppb

Ref: Leffingwell, J.C. & R.E. Shackelford, Laevo-Menthol - Syntheses and organoleptic properties, Cosmetics and Perfumery, 89(6), 69-89, 1974; Hopp, R., Menthol: its origins, chemistry, physiology and toxicological properties, Rec. Adv. Tobacco Science, Vol. 19, 3-46 (1993); Enberger, R. and R. Hopp, Synthesis and sensory charachteristics on menthol enantiomers and their derivitives for the use of nature-identical peppermint oils., Topics in Flavor Research, R.G. Berger, S. Nitz and P. Schrier, Editors, H. Eichorn, Marzling, Germany, pp. 201-218 (1988).

(1S,3R,4R)-(-)-neomenthol - minty, musty, fresh, earthy-camphoraceous, some cooling

Taste Threshold = 600 ppb

Cooling Threshold = 25000 ppb

Ref: Leffingwell, J.C. & R.E. Shackelford, Laevo-Menthol - Syntheses and organoleptic properties, Cosmetics and Perfumery, 89(6), 69-89, 1974; Hopp, R., Menthol: its origins, chemistry, physiology and toxicological properties, Rec. Adv. Tobacco Science, Vol. 19, 3-46 (1993); Enberger, R. and R. Hopp, Synthesis and sensory charachteristics on menthol enantiomers and their derivitives for the use of nature-identical peppermint oils., Topics in Flavor Research, R.G. Berger, S. Nitz and P. Schrier, Editors, H. Eichorn, Marzling, Germany, pp. 201-218 (1988).

(1R,3S,4S)-(+)-neomenthol - sweet, musty, fresh, some cooling, minty

Taste Threshold = 500 ppb

Cooling Threshold = 2500 ppb

Ref: Leffingwell, J.C. & R.E. Shackelford, Laevo-Menthol - Syntheses and organoleptic properties, Cosmetics and Perfumery, 89(6), 69-89, 1974; Hopp, R., Menthol: its origins, chemistry, physiology and toxicological properties, Rec. Adv. Tobacco Science, Vol. 19, 3-46 (1993); Enberger, R. and R. Hopp, Synthesis and sensory charachteristics on menthol enantiomers and their derivitives for the use of nature-identical peppermint oils., Topics in Flavor Research, R.G. Berger, S. Nitz and P. Schrier, Editors, H. Eichorn, Marzling, Germany, pp. 201-218 (1988).

(1S,3R,4S)-(-)-isomenthol - musty, sweet, herbaceous, earthy-camphoraceous, hay, slight cooling

Taste Threshold = 600 ppb

Cooling Threshold = 30000 ppb

Ref: Leffingwell, J.C. & R.E. Shackelford, Laevo-Menthol - Syntheses and organoleptic properties, Cosmetics and Perfumery, 89(6), 69-89, 1974; Hopp, R., Menthol: its origins, chemistry, physiology and toxicological properties, Rec. Adv. Tobacco Science, Vol. 19, 3-46 (1993); Enberger, R. and R. Hopp, Synthesis and sensory charachteristics on menthol enantiomers and their derivitives for the use of nature-identical peppermint oils., Topics in Flavor Research, R.G. Berger, S. Nitz and P. Schrier, Editors, H. Eichorn, Marzling, Germany, pp. 201-218 (1988).

(1R,3S,4R)-(+)-isomenthol - musty, woody, fresh-carrot-minty, earthy-camphoraceous, slight cooling

Taste Threshold = 700 ppb

Cooling Threshold = 7000 ppb

Ref: Leffingwell, J.C. & R.E. Shackelford, Laevo-Menthol - Syntheses and organoleptic properties, Cosmetics and Perfumery, 89(6), 69-89, 1974; Hopp, R., Menthol: its origins, chemistry, physiology and toxicological properties, Rec. Adv. Tobacco Science, Vol. 19, 3-46 (1993); Enberger, R. and R. Hopp, Synthesis and sensory charachteristics on menthol enantiomers and their derivitives for the use of nature-identical peppermint oils., Topics in Flavor Research, R.G. Berger, S. Nitz and P. Schrier, Editors, H. Eichorn, Marzling, Germany, pp. 201-218 (1988).

 (1S,3S,4S)-(-)-neoisomenthol - musty, earthy-camphoraceous, sweet, minty, woody, slight cooling

Taste Threshold = 1000 ppb

Cooling Threshold = 6000 ppb

Ref: Leffingwell, J.C. & R.E. Shackelford, Laevo-Menthol - Syntheses and organoleptic properties, Cosmetics and Perfumery, 89(6), 69-89, 1974; Hopp, R., Menthol: its origins, chemistry, physiology and toxicological properties, Rec. Adv. Tobacco Science, Vol. 19, 3-46 (1993); Enberger, R. and R. Hopp, Synthesis and sensory charachteristics on menthol enantiomers and their derivitives for the use of nature-identical peppermint oils., Topics in Flavor Research, R.G. Berger, S. Nitz and P. Schrier, Editors, H. Eichorn, Marzling, Germany, pp. 201-218 (1988).

(1R,3R,4R)-(+)-neoisomenthol - musty, earthy-camphoraceous, woody, carrot, herbaceous, minty, very little cooling

Taste Threshold = 200 ppb

Cooling Threshold = >25000 ppb

Ref: Leffingwell, J.C. & R.E. Shackelford, Laevo-Menthol - Syntheses and organoleptic properties, Cosmetics and Perfumery, 89(6), 69-89, 1974; Hopp, R., Menthol: its origins, chemistry, physiology and toxicological properties, Rec. Adv. Tobacco Science, Vol. 19, 3-46 (1993); Enberger, R. and R. Hopp, Synthesis and sensory charachteristics on menthol enantiomers and their derivitives for the use of nature-identical peppermint oils., Topics in Flavor Research, R.G. Berger, S. Nitz and P. Schrier, Editors, H. Eichorn, Marzling, Germany, pp. 201-218 (1988).

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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