The p-Menthane lactones

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

The p-Menthane lactones - Part 2

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Photo by permission of M. Roudintska - Art & Parfum

The other enantiomeric pairs of the p-menthane lactones (perhydro-3,6-dimethyl-2-benzo[b]furanones) are found in The p-Menthane lactones - Part 1. Related materials are found in Part 3

c

(3R,3aR,6R,7aR)-perhydro-3,6-dimethyl-2-benzo[b]furanone - no odor description given

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

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

Ref: 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 "2b1" is incorrectly listed as (3R,3aR,6R,7aS)-

c c

(3S,3aS,6S,7aS)-perhydro-3,6-dimethyl-2-benzo[b]furanone - coconut like

Odor Threshold = 0.000007 ng/l in air (Katja Buhr)

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

Ref: 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 "2a2" is incorrectly listed as (3S,3aS,6S,7aR)-

c

c

(3S,3aR,6R,7aR)-perhydro-3,6-dimethyl-2-benzo[b]furanone - coconut like

Odor Threshold = 30 ng/l in air (Katja Buhr)

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

Ref: 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 "2d1" is incorrectly listed as (3S,3aR,6R,7aS)-

c c

(3R,3aS,6S,7aS)-perhydro-3,6-dimethyl-2-benzo[b]furanone - coconut like

Odor Threshold = 0.0075 ng/l in air (Katja Buhr)

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

Ref: 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 "2c2" is incorrectly listed as (3R,3aS,6S,7aR)-

c

c

(3R,3aS,6R,7aS)-perhydro-3,6-dimethyl-2-benzo[b]furanone - coconut like

Odor Threshold = 7.5 ng/l in air (Katja Buhr)

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

Ref: 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 "2c1" is incorrectly listed as (3R,3aS,6R,7aR)-

c c

(3S,3aR,6S,7aR)-perhydro-3,6-dimethyl-2-benzo[b]furanone - no description given

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

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

Ref: 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 "2d2" is incorrectly listed as (3S,3aR,6S,7aS)-

c

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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