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

The 3-Mercapto-3-methylhexan-1-ols

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Photo by permission of M. Roudintska - Art & Parfum

(3S)-(-)-3-mercapto-3-methylhexan-1-ol - The (S)-isomer exhibits herbaceous, agrestic and green notes (Acuna, et. al.). The (S)-3-mercapto-3-methyl-hexan-1-ol is useful to enhance the flavor properties of food products, especially the meaty, boiled meat character of meat products the cooked vegetable and meaty notes of soup products.

Also described as sweat and onion-like (Troccaz, et. al); also described by Hasegawa et. al. as having a strong meaty, fruity note wth a charachteristic sulfury odor

Ref: Acuna, Gonzalo; Gautschi, Markus); Kumli, Frank; Schmid, Joachim; Zsindely, Janos; Mercapto-alkanol flavor compounds, United States Patent 6,610,346, August 26, 2003; Myriam Troccaz, Christian Starkenmann, Yvan Niclass, Matthijs van de Waal, Anthony J. Clark, 3-Methyl-3-sulfanylhexan-1-ol as a Major Descriptor for the Human Axilla-Sweat Odour Profile, Chemistry & Biodiversity, Volume 1, Issue 7 , Pages 1022 - 1035 (2004); Yoshihiro Hasegawa, Masayuki Yabuki, Masamoto Matsukane, Identification of New Odoriferous Compounds in Human Axillary Sweat, Chemistry & Biodiversity, Volume 1, Issue 12, Date: December 2004, Pages: 2042-2050

(3R)-(+)-3-mercapto-3-methylhexan-1-ol - The (R)-isomer can be described as grapefruit/passion fruit, black currant and onion-like (Acuna, et. al.). The (R)-3-mercapto-3-methyl-hexan-1-ol is useful to enhance the typical natural, fruity character of exotic fruit flavors.

Also described as fruity and grapefruit-like (Troccaz, et. al); also described by Hasegawa et. al. as having a green fruity note

Ref: Acuna, Gonzalo; Gautschi, Markus); Kumli, Frank; Schmid, Joachim; Zsindely, Janos; Mercapto-alkanol flavor compounds, United States Patent 6,610,346, August 26, 2003; Myriam Troccaz, Christian Starkenmann, Yvan Niclass, Matthijs van de Waal, Anthony J. Clark, 3-Methyl-3-sulfanylhexan-1-ol as a Major Descriptor for the Human Axilla-Sweat Odour Profile, Chemistry & Biodiversity, Volume 1, Issue 7 , Pages 1022 - 1035 (2004); Yoshihiro Hasegawa, Masayuki Yabuki, Masamoto Matsukane, Identification of New Odoriferous Compounds in Human Axillary Sweat, Chemistry & Biodiversity, Volume 1, Issue 12, Date: December 2004, Pages: 2042-2050

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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