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

The p-Menthane lactones - Part 3

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Photo by permission of M. Roudintska - Art & Parfum

Enantiomeric pairs of the p-menthane lactones (perhydro-3,6-dimethyl-2-benzo[b]furanones) are found in The p-Menthane lactones - Part 1 & Part 2

 

(+)-(3aS,6R,7aR)-perhydro-6-methyl-3-methylene-2-benzo[b]furanone - coumarinic, lactonic, tonka, daffodil, very powerful.; perhydro-6-methyl-3-methylene-2-benzo[b]furanone possesses a very powerful odor of the coumarinic, fat, lactonic type, with a balsamic bottom note reminiscent of the odor of daffodil. This is an odor note which is very close to that of coumarin and which is best represented in (+)-(3aS,6R,7aR)-perhydro-6-methyl-3-methylene-2-benzo[b ]furanone, a preferred compound of the invention

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

 

(-)-(3aR,6S,7aS)-perhydro-6-methyl-3-methylene-2-benzo[b]furanone - Not available

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

(3aS,6R,7aS)-perhydro-6-methyl-3-methylene-2-benzo[b]furanone - coumarinic, lactonic, tonka

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

(3aR,6S,7aR)-perhydro-6-methyl-3-methylene-2-benzo[b]furanone - not available

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

(+)-(6R)-3(RS)-3,6-dimethyl-4,5,6,7-tetrahydro-1-benzofuran-2(3H)-one - it develops a phenolic/coumarin-like odour, making it a useful alternative to coumarin. It also has a completely original, minty odoriferous note much appreciated by perfumers

Ref: Frerot, Eric; & Bagnoud, Alain; Method for preparing a gamma-unsaturated beta-lactone and use thereof as an aromatic and flavouring ingredient, United States Patent Application 20020098271, July 25, 2002

(-)-(6S)-3(RS)-3,6-dimethyl-4,5,6,7-tetrahydro-1-benzofuran-2(3H)-one - not available

 

(-)-(3aS,6R,7aS)-perhydro-3,3,6-trimethyl-2-benzo[b]furanone - lactonic, fruity, coumarinic

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

(+)-(3aR,6S,7aR)-perhydro-3,3,6-trimethyl-2-benzo[b]furanone - not available

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

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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