The p-Menthane lactones

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

The p-Menthane lactones - Part 1

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Photo by permission of M. Roudintska - Art & Parfum

There are 8 enantiomeric pairs of the p-menthane lactones (perhydro-3,6-dimethyl-2-benzo[b]furanones); any pair for which at least one odor description is given is included & in Part 2. Related materials are found in The p-Menthane lactones - Part 3

(+)-(3R,3aS,6R,7aR)-perhydro-3,6-dimethyl-2-benzo[b]furanone - very powerful coumarinic odor notes, sweet with a caramel type character (Gaudin); also described as coconut like by GC-O (Katja Buhr)

Odor Threshold = >100 ng/l in air (Katja Buhr)

= (3R,3aS,6R,7aR)-3,6-Dimethyl-3a,4,5,6,7a-hexahydro-2(3H)-benzofuranone

Ref: Gaudin, Jean-Marc, Use of furanones as perfuming ingredients, United States Patent 5,464,824, November 7, 1995; Jean-Marc Gaudin, Synthesis and Organoleptic Properties of p-Menthane Lactones, Tetrahedron, Volume 56, Issue 27 , 30 June 2000, Pages 4769-4776; Katja Buhr, Untersuchungen zu Struktur-Geruchsbeziehungen von Lactonen, Ph.D. Thesis, Universität Wuppertal, Munich (2006), pp. 48-61; Note - in Buhr's thesis the absolute configuration for the structure (shown here) designated as "2g1" is incorrectly listed as (3R,3aS,6R,7aS)-

(-)-(3S,3aR,6S,7aS)-perhydro-3,6-dimethyl-2-benzo[b]furanone (87% pure) - Odor: butyric, rancid, coumarinic, lactonic, sulfury, powerful.

Odor Threshold = >100 ng/l in air (Katja Buhr)

= (3S,3aR,6S,7aS)-3,6-Dimethyl-3a,4,5,6,7a-hexahydro-2(3H)-benzofuranone

Ref: Gaudin, Jean-Marc, Use of furanones as perfuming ingredients, United States Patent 5,464,824, November 7, 1995; Jean-Marc Gaudin, Synthesis and Organoleptic Properties of p-Menthane Lactones, Tetrahedron, Volume 56, Issue 27 , 30 June 2000, Pages 4769-4776; Katja Buhr, Untersuchungen zu Struktur-Geruchsbeziehungen von Lactonen, Ph.D. Thesis, Universität Wuppertal, Munich (2006), pp. 48-61; Note - in Buhr's thesis the absolute configuration for the structure (shown here) designated as "2h2" is incorrectly listed as (3S,3aR,6S,7aR)-

(-)-(3S,3aS,6R,7aS)-perhydro-3,6-dimethyl-2-benzo[b]furanone (98% pure) - coumarinic, lactonic, cold tobacco side (Gaudin); also described as coconut like by GC-O (Katja Buhr)

Odor Threshold = 0.000001 ng/l in air (Katja Buhr)

= (3S,3aS,6R,7aS)-3,6-Dimethyl-3a,4,5,6,7a-hexahydro-2(3H)-benzofuranone

Ref: Gaudin, Jean-Marc, Use of furanones as perfuming ingredients, United States Patent 5,464,824, November 7, 1995; Jean-Marc Gaudin, Synthesis and Organoleptic Properties of p-Menthane Lactones, Tetrahedron, Volume 56, Issue 27 , 30 June 2000, Pages 4769-4776; Katja Buhr, Untersuchungen zu Struktur-Geruchsbeziehungen von Lactonen, Ph.D. Thesis, Universität Wuppertal, Munich (2006), pp. 48-61; Note - in Buhr's thesis the absolute configuration for the structure (shown here) designated as "2a1" is incorrectly listed as (3S,3aS,6R,7aR)-

(+)-(3R,3aR,6S,7aR)-perhydro-3,6-dimethyl-2-benzo[b]furanone - coumarinic, hay, earthy, lactonic (Gaudin)
Odor Threshold = >100 ng/l in air (Katja Buhr)

= (3R,3aR,6S,7aR)-3,6-Dimethyl-3a,4,5,6,7a-hexahydro-2(3H)-benzofuranone

Ref: Gaudin, Jean-Marc, Use of furanones as perfuming ingredients, United States Patent 5,464,824, November 7, 1995; Jean-Marc Gaudin, Synthesis and Organoleptic Properties of p-Menthane Lactones, Tetrahedron, Volume 56, Issue 27 , 30 June 2000, Pages 4769-4776; Katja Buhr, Untersuchungen zu Struktur-Geruchsbeziehungen von Lactonen, Ph.D. Thesis, Universität Wuppertal, Munich (2006), pp. 48-61; Note - in Buhr's thesis the absolute configuration for the structure (shown here) designated as "2b2" is incorrectly listed as (3R,3aR,6R,7aR)-

(-)-(3R,3aR,6R,7aS)-perhydro-3,6-dimethyl-2-benzo[b]furanone - coumarinic, flouve, hay, sulfur, rubbery (Gaudin); also described as coconut like by GC-O (Katja Buhr)
Odor Threshold = 0.4 ng/l in air (Katja Buhr)

= (3R,3aR,6R,7aS)-3,6-Dimethyl-3a,4,5,6,7a-hexahydro-2(3H)-benzofuranone

Ref: Gaudin, Jean-Marc, Use of furanones as perfuming ingredients, United States Patent 5,464,824, November 7, 1995; Jean-Marc Gaudin, Synthesis and Organoleptic Properties of p-Menthane Lactones, Tetrahedron, Volume 56, Issue 27 , 30 June 2000, Pages 4769-4776; Katja Buhr, Untersuchungen zu Struktur-Geruchsbeziehungen von Lactonen, Ph.D. Thesis, Universität Wuppertal, Munich (2006), pp. 48-61; Note - in Buhr's thesis the absolute configuration for the structure (shown here) designated as "2f1" is incorrectly listed as (3R,3aR,6R,7aR)-

(+)-(3S,3aS,6S,7aR)-Perhydro-3,6-dimethyl-2-benzo[b]furanone - described as coconut like by GC-O (Katja Buhr)
Odor Threshold = 0.5 ng/l in air (Katja Buhr)

(3S,3aS,6S,7aR)-3,6-Dimethyl-3a,4,5,6,7a-hexahydro-2(3H)-benzofuranon

Ref: Gaudin, Jean-Marc, Use of furanones as perfuming ingredients, United States Patent 5,464,824, November 7, 1995; Jean-Marc Gaudin, Synthesis and Organoleptic Properties of p-Menthane Lactones, Tetrahedron, Volume 56, Issue 27 , 30 June 2000, Pages 4769-4776; Katja Buhr, Untersuchungen zu Struktur-Geruchsbeziehungen von Lactonen, Ph.D. Thesis, Universität Wuppertal, Munich (2006), pp. 48-61; Note - in Buhr's thesis the absolute configuration for the structure (shown here) designated as "2e2" is incorrectly listed as (3S,3aS,6S,7aS)-

(+)-(3S,3aS,6R,7aR)-perhydro-3,6-dimethyl-2-benzo[b]furanone - tonka, beans, hay, flouve type characters are best represented whose coumarinic character is more marked in the bottom note than in the top note, and is accompanied of a metallic side (Gaudin); also described as coconut like by GC-O (Katja Buhr)
Odor Threshold = 0.15 ng/l in air (Katja Buhr)

= (3S,3aS,6R,7aR)-3,6-Dimethyl-3a,4,5,6,7a-hexahydro-2(3H)-benzofuranone

Ref: Gaudin, Jean-Marc, Use of furanones as perfuming ingredients, United States Patent 5,464,824, November 7, 1995; Jean-Marc Gaudin, Synthesis and Organoleptic Properties of p-Menthane Lactones, Tetrahedron, Volume 56, Issue 27 , 30 June 2000, Pages 4769-4776; Katja Buhr, Untersuchungen zu Struktur-Geruchsbeziehungen von Lactonen, Ph.D. Thesis, Universität Wuppertal, Munich (2006), pp. 48-61; Note - in Buhr's thesis the absolute configuration for the structure (shown here) designated as "2e1" is incorrectly listed as (3S,3aS,6R,7aS)-

(-)-(3R,3aR,6S,7aS)-perhydro-3,6-dimethyl-2-benzo[b]furanone - description not given (Gaudin); described as coconut like by GC-O (Katja Buhr)
Odor Threshold = 0.003 ng/l in air (Katja Buhr)

= (3R,3aR,6S,7aS)-3,6-Dimethyl-3a,4,5,6,7a-hexahydro-2(3H)-benzofuranone

Ref: Gaudin, Jean-Marc, Use of furanones as perfuming ingredients, United States Patent 5,464,824, November 7, 1995; Jean-Marc Gaudin, Synthesis and Organoleptic Properties of p-Menthane Lactones, Tetrahedron, Volume 56, Issue 27 , 30 June 2000, Pages 4769-4776; Katja Buhr, Untersuchungen zu Struktur-Geruchsbeziehungen von Lactonen, Ph.D. Thesis, Universität Wuppertal, Munich (2006), pp. 48-61; Note - in Buhr's thesis the absolute configuration for the structure (shown here) designated as "2f2" is incorrectly listed as (3R,3aR,6S,7aR)-

(-)-(3S,3aR,6R,7aS)-perhydro-3,6-dimethyl-2-benzo[b]furanone - coumarinic, flouve, hay, vaguely sulphury odor.
Odor Threshold = >100 ng/l in air (Katja Buhr)

= (3S,3aR,6R,7aS)-3,6-Dimethyl-3a,4,5,6,7a-hexahydro-2(3H)-benzofuranone

Ref: Gaudin, Jean-Marc, Use of furanones as perfuming ingredients, United States Patent 5,464,824, November 7, 1995; Jean-Marc Gaudin, Synthesis and Organoleptic Properties of p-Menthane Lactones, Tetrahedron, Volume 56, Issue 27 , 30 June 2000, Pages 4769-4776; Katja Buhr, Untersuchungen zu Struktur-Geruchsbeziehungen von Lactonen, Ph.D. Thesis, Universität Wuppertal, Munich (2006), pp. 48-61; Note - in Buhr's thesis the absolute configuration for the structure (shown here) designated as "2h1" is incorrectly listed as (3S,3aR,6R,7aR)-

(+)-(3R,3aS,6S,7aR)-perhydro-3,6-dimethyl-2-benzo[b]furanone - description not given
Odor Threshold = >100 ng/l in air (Katja Buhr)

= (3R,3aS,6S,7aR)-3,6-Dimethyl-3a,4,5,6,7a-hexahydro-2(3H)-benzofuranone

Ref: Gaudin, Jean-Marc, Use of furanones as perfuming ingredients, United States Patent 5,464,824, November 7, 1995; Jean-Marc Gaudin, Synthesis and Organoleptic Properties of p-Menthane Lactones, Tetrahedron, Volume 56, Issue 27 , 30 June 2000, Pages 4769-4776; Katja Buhr, Untersuchungen zu Struktur-Geruchsbeziehungen von Lactonen, Ph.D. Thesis, Universität Wuppertal, Munich (2006), pp. 48-61; Note - in Buhr's thesis the absolute configuration for the structure (shown here) designated as "2g2" is incorrectly listed as (3R,3aS,6S,7aS)-

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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