(3S,3aS,7aR)-Wine lactone - intense sweet and coconut-like (coumarinic); this is the naturally occurring enantiomer Odor threshold = 0.00001-0.00004 ng/l in air = (3S,3aS,7aR)-3,6-dimethyl-3a,4,5,7a-tetrahydro-1-benzofuran-2(3H)-one Ref: Guth, Helmut, Determination of the Configuration of Wine Lactone, Helv. Chim. Acta 1996, 79: 6 1559-1571; Katja Buhr, Untersuchungen zu Struktur-Geruchsbeziehungen von Lactonen, Ph.D. Thesis, Universität Wuppertal, Munich (2006), pp. 48-61; Elisabetta Brenna, Claudio Fuganti and Stefano Serra, Enantioselective perception of chiral odorants, Tetrahedron: Asymmetry, 14, 1–42 (2003)

(3R,3aR,7aS)-Wine lactone - description not available Odor threshold = >1000 ng/l in air = (3R,3aR,7aS)-3,6-dimethyl-3a,4,5,7a-tetrahydro-1-benzofuran-2(3H)-one Ref: Guth, Helmut, Determination of the Configuration of Wine Lactone, Helv. Chim. Acta 1996, 79: 6 1559-1571; Katja Buhr, Untersuchungen zu Struktur-Geruchsbeziehungen von Lactonen, Ph.D. Thesis, Universität Wuppertal, Munich (2006), pp. 48-61; Elisabetta Brenna, Claudio Fuganti and Stefano Serra, Enantioselective perception of chiral odorants, Tetrahedron: Asymmetry, 14, 1–42 (2003)

(3S,3aR,7aR)-Wine lactone - described as coconut like by GC-O (Katja Buhr) Odor threshold = 0.05 - 0.2 ng/l in air = (3S,3aR,7aR)-3,6-dimethyl-3a,4,5,7a-tetrahydro-1-benzofuran-2(3H)-one Ref: Guth, Helmut, Determination of the Configuration of Wine Lactone, Helv. Chim. Acta 1996, 79: 6 1559-1571; Katja Buhr, Untersuchungen zu Struktur-Geruchsbeziehungen von Lactonen, Ph.D. Thesis, Universität Wuppertal, Munich (2006), pp. 48-61; Elisabetta Brenna, Claudio Fuganti and Stefano Serra, Enantioselective perception of chiral odorants, Tetrahedron: Asymmetry, 14, 1–42 (2003)

(3R,3aS,7aR)-Wine lactone - described as coconut like by GC-O (Katja Buhr)

Odor threshold = >1000 ng/l in air; also reported as 0.25 ng/l in air (Katja Buhr)

= (3R,3aS,7aR)-3,6-dimethyl-3a,4,5,7a-tetrahydro-1-benzofuran-2(3H)-one

Ref: Guth, Helmut, Determination of the Configuration of Wine Lactone, Helv. Chim. Acta 1996, 79: 6 1559-1571; Katja Buhr, Untersuchungen zu Struktur-Geruchsbeziehungen von Lactonen, Ph.D. Thesis, Universität Wuppertal, Munich (2006), pp. 48-61; Elisabetta Brenna, Claudio Fuganti and Stefano Serra, Enantioselective perception of chiral odorants, Tetrahedron: Asymmetry, 14, 1–42 (2003)

(3S,3aR,7aS)-Wine lactone - described as coconut like by GC-O (Katja Buhr)

Odor threshold = 80-160 ng/l in air

= (3S,3aR,7aS)-3,6-dimethyl-3a,4,5,7a-tetrahydro-1-benzofuran-2(3H)-one

Ref: Guth, Helmut, Determination of the Configuration of Wine Lactone, Helv. Chim. Acta 1996, 79: 6 1559-1571; Katja Buhr, Untersuchungen zu Struktur-Geruchsbeziehungen von Lactonen, Ph.D. Thesis, Universität Wuppertal, Munich (2006), pp. 48-61; Elisabetta Brenna, Claudio Fuganti and Stefano Serra, Enantioselective perception of chiral odorants, Tetrahedron: Asymmetry, 14, 1–42 (2003)

(3S,3aS,7aS)-Wine lactone - described as coconut like by GC-O (Katja Buhr)

Odor threshold = 0.007-0.014 ng/l in air

= (3S,3aS,7aS)-3,6-dimethyl-3a,4,5,7a-tetrahydro-1-benzofuran-2(3H)-one

Ref: Guth, Helmut, Determination of the Configuration of Wine Lactone, Helv. Chim. Acta 1996, 79: 6 1559-1571; Katja Buhr, Untersuchungen zu Struktur-Geruchsbeziehungen von Lactonen, Ph.D. Thesis, Universität Wuppertal, Munich (2006), pp. 48-61; Elisabetta Brenna, Claudio Fuganti and Stefano Serra, Enantioselective perception of chiral odorants, Tetrahedron: Asymmetry, 14, 1–42 (2003)

(3R,3aR,7aR)-Wine lactone - described as coconut like by GC-O (Katja Buhr)

Odor threshold = 14-28 ng/l in air

= (3R,3aR,7aR)-3,6-dimethyl-3a,4,5,7a-tetrahydro-1-benzofuran-2(3H)-one

Ref: Guth, Helmut, Determination of the Configuration of Wine Lactone, Helv. Chim. Acta 1996, 79: 6 1559-1571; Katja Buhr, Untersuchungen zu Struktur-Geruchsbeziehungen von Lactonen, Ph.D. Thesis, Universität Wuppertal, Munich (2006), pp. 48-61; Elisabetta Brenna, Claudio Fuganti and Stefano Serra, Enantioselective perception of chiral odorants, Tetrahedron: Asymmetry, 14, 1–42 (2003)

Ionones, Irones, Damascones & Structurally Related Odorants

Acyclics (Alcohols, Esters, Acids, Aldehydes)

Lactones

Sesquiterpenoid Related Odorants