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

The Terpinen-4-ols

(4-Terpineols)

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Photo by permission of M. Roudintska - Art & Parfum

(4S)-(-)-terpinen-4-ol - musty, dusty ( odor evaluation by GC-olfactometry by Nishimura); In the stronger smelling (4R)-(-)-menthen-4-ol, an intense herbal-green odor and a pronounced earthy note dominate the flowery tonality (from Delay & Ohloff).

Also known as (4S)-(-)-4-terpineol

Ref: Osamu Nishimura, Enantiomer separation of the characteristic odorants in Japanese fresh rhizomes of Zingiber officinale Roscoe (ginger) using multidimensional GC system and confirmation of the odour character of each enantiomer by GC-olfactometry, Flavour & Fragrance Journal, 16, 13-18 (2001); M. Volkan Kisakürek, Edgar Heilbronner, Highlights of Chemistry: As Mirrored in Helvetica Chimica Acta, Wiley-VCH - Publisher, 1994, p. 367 from François Delay, Günther Ohloff, Synthesis of (R)- and (S)-p-Mentha-1,8-dien-4-ols from (R)-Limonene, Helvetica Chimica Acta, Volume 62, Issue 7, Date: 31 October 1979, Pages: 2168-2173

(4R)-(+)-terpinen-4-ol - musty ( odor evaluation by GC-olfactometry by Nishimura); commercially available (+)-menthen-4-ol is known to have a warm, peppery, mildly earthy, musty-woody odor of moderate tenacity. The earthy-musty notes are pleasantly green. Its flowery character resembles that of alpha-terpineol (from Delay & Ohloff).

Also known as (4R)-(+)-4-terpineol and (+)-menthen-4-ol

Ref: Osamu Nishimura, Enantiomer separation of the characteristic odorants in Japanese fresh rhizomes of Zingiber officinale Roscoe (ginger) using multidimensional GC system and confirmation of the odour character of each enantiomer by GC-olfactometry, Flavour & Fragrance Journal, 16, 13-18 (2001); M. Volkan Kisakürek, Edgar Heilbronner, Highlights of Chemistry: As Mirrored in Helvetica Chimica Acta, Wiley-VCH - Publisher, 1994, p. 367 from François Delay, Günther Ohloff, Synthesis of (R)- and (S)-p-Mentha-1,8-dien-4-ols from (R)-Limonene, Helvetica Chimica Acta, Volume 62, Issue 7, Date: 31 October 1979, Pages: 2168-2173

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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Copyright 2001 - Leffingwell & Associates