The 3-Butylhexahydrophthalides

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

You must have Java installed to view the molecular visualization on this page
Photo by permission of M. Roudintska - Art & Parfum

(3S,3aS,7aR)-3-Butylhexahydrophthalide - sweet, warm, heavy, slightly medicinal (by GC-O); also described as “sweet and sickly”

GC - Odor Threshold = 0.13 ng

Also known as: (3S,3aS,7aR)-3-butylhexahydro-2-benzofuran-1(3H)-one

Of the the two enantiomers shown here, only the odorless 3R,3aR,7aS isomer is found in celery, celeriac, and fennel.

Ref: Bartschat, D.; Wust, M.; Hanssum, H.; Mosandl, A. Stereoisomeric flavor compounds LXXVII: 3-Butylhexahydrophthalides: Simultaneous enantioselective analysis, structure elucidation, and sensorial properties of the stereoisomers; J. High Resolut. Chromatogr. 1997, 20, 251-256; Dietmar Bartschat, Thomas Beck, and Armin Mosandl, Stereoisomeric Flavor Compounds. 79. Simultaneous Enantioselective Analysis of 3-Butylphthalide and 3-Butylhexahydrophthalide Stereoisomers in Celery, Celeriac, and Fennel, J. Agric. Food Chem. 1997, 45, 4554-4557

(3R,3aR,7aS)-3-Butylhexahydrophthalide - odorless by GC-O at 125 ng

Odor Threshold = >125 ng

Also known as: (3R,3aR,7aS)-3-butylhexahydro-2-benzofuran-1(3H)-one

Of the the two enantiomers shown here, only the odorless 3R,3aR,7aS isomer is found in celery, celeriac, and fennel.

Ref: Bartschat, D.; Wust, M.; Hanssum, H.; Mosandl, A. Stereoisomeric flavor compounds LXXVII: 3-Butylhexahydrophthalides: Simultaneous enantioselective analysis, structure elucidation, and sensorial properties of the stereoisomers; J. High Resolut. Chromatogr. 1997, 20, 251-256; Dietmar Bartschat, Thomas Beck, and Armin Mosandl, Stereoisomeric Flavor Compounds. 79. Simultaneous Enantioselective Analysis of 3-Butylphthalide and 3-Butylhexahydrophthalide Stereoisomers in Celery, Celeriac, and Fennel, J. Agric. Food Chem. 1997, 45, 4554-4557; See also Glesni MacLeod and Jennifer M. Ames, Volatile components of celery and celeriac, Phytochemistry, Volume 28, Issue 7, 1989, Pages 1817-1824

(3S,3aR,7aS)-3-Butylhexahydrophthalide - odorless by GC-O at 125 ng

GC - Odor Threshold = >125 ng

Also known as: (3S,3aR,7aS)-3-butylhexahydro-2-benzofuran-1(3H)-one

Of the the two enantiomers shown here, only the odorless 3S,3aR,7aS isomer is found in celery and celeriac.

Ref: Bartschat, D.; Wust, M.; Hanssum, H.; Mosandl, A. Stereoisomeric flavor compounds LXXVII: 3-Butylhexahydrophthalides: Simultaneous enantioselective analysis, structure elucidation, and sensorial properties of the stereoisomers; J. High Resolut. Chromatogr. 1997, 20, 251-256; Dietmar Bartschat, Thomas Beck, and Armin Mosandl, Stereoisomeric Flavor Compounds. 79. Simultaneous Enantioselective Analysis of 3-Butylphthalide and 3-Butylhexahydrophthalide Stereoisomers in Celery, Celeriac, and Fennel, J. Agric. Food Chem. 1997, 45, 4554-4557

(3R,3aS,7aR)-3-Butylhexahydrophthalide - odorless by GC-O at 125 ng

GC - Odor Threshold = >125 ng

Also known as: (3R,3aS,7aR)-3-butylhexahydro-2-benzofuran-1(3H)-one

Of the the two enantiomers shown here, only the odorless 3S,3aR,7aS isomer is found in celery and celeriac.

Ref: Bartschat, D.; Wust, M.; Hanssum, H.; Mosandl, A. Stereoisomeric flavor compounds LXXVII: 3-Butylhexahydrophthalides: Simultaneous enantioselective analysis, structure elucidation, and sensorial properties of the stereoisomers; J. High Resolut. Chromatogr. 1997, 20, 251-256; Dietmar Bartschat, Thomas Beck, and Armin Mosandl, Stereoisomeric Flavor Compounds. 79. Simultaneous Enantioselective Analysis of 3-Butylphthalide and 3-Butylhexahydrophthalide Stereoisomers in Celery, Celeriac, and Fennel, J. Agric. Food Chem. 1997, 45, 4554-4557

(3S,3aR,7aR)-3-Butylhexahydrophthalide - reminiscent of dry celery leaves by GC-O; also described as “celery, fruity"

GC - Odor Threshold = 25 ng

Also known as: (3S,3aR,7aR)-3-butylhexahydro-2-benzofuran-1(3H)-one

Ref: Bartschat, D.; Wust, M.; Hanssum, H.; Mosandl, A. Stereoisomeric flavor compounds LXXVII: 3-Butylhexahydrophthalides: Simultaneous enantioselective analysis, structure elucidation, and sensorial properties of the stereoisomers; J. High Resolut. Chromatogr. 1997, 20, 251-256; Dietmar Bartschat, Thomas Beck, and Armin Mosandl, Stereoisomeric Flavor Compounds. 79. Simultaneous Enantioselective Analysis of 3-Butylphthalide and 3-Butylhexahydrophthalide Stereoisomers in Celery, Celeriac, and Fennel, J. Agric. Food Chem. 1997, 45, 4554-4557

(3R,3aS,7aS)-3-Butylhexahydrophthalide - herbaceous, like celery by GC-O; also described as “celery, fruity"

GC - Odor Threshold = >12.5 ng

Also known as: (3R,3aS,7aS)-3-butylhexahydro-2-benzofuran-1(3H)-one

Ref: Bartschat, D.; Wust, M.; Hanssum, H.; Mosandl, A. Stereoisomeric flavor compounds LXXVII: 3-Butylhexahydrophthalides: Simultaneous enantioselective analysis, structure elucidation, and sensorial properties of the stereoisomers; J. High Resolut. Chromatogr. 1997, 20, 251-256; Dietmar Bartschat, Thomas Beck, and Armin Mosandl, Stereoisomeric Flavor Compounds. 79. Simultaneous Enantioselective Analysis of 3-Butylphthalide and 3-Butylhexahydrophthalide Stereoisomers in Celery, Celeriac, and Fennel, J. Agric. Food Chem. 1997, 45, 4554-4557

(3S,3aS,7aS) -3-Butylhexahydrophthalide - herbaceous, like celery by GC-O; also described as “celery, fruity"

GC - Odor Threshold = 25 ng

Also known as: (3S,3aS,7aS)-3-butylhexahydro-2-benzofuran-1(3H)-one

Ref: Bartschat, D.; Wust, M.; Hanssum, H.; Mosandl, A. Stereoisomeric flavor compounds LXXVII: 3-Butylhexahydrophthalides: Simultaneous enantioselective analysis, structure elucidation, and sensorial properties of the stereoisomers; J. High Resolut. Chromatogr. 1997, 20, 251-256; Dietmar Bartschat, Thomas Beck, and Armin Mosandl, Stereoisomeric Flavor Compounds. 79. Simultaneous Enantioselective Analysis of 3-Butylphthalide and 3-Butylhexahydrophthalide Stereoisomers in Celery, Celeriac, and Fennel, J. Agric. Food Chem. 1997, 45, 4554-4557

(3R,3aR,7aR)-3-Butylhexahydrophthalide - odorless by GC-O at 125 ng

GC - Odor Threshold = >125 ng

Also known as: (3R,3aR,7aR)-3-butylhexahydro-2-benzofuran-1(3H)-one

Ref: Bartschat, D.; Wust, M.; Hanssum, H.; Mosandl, A. Stereoisomeric flavor compounds LXXVII: 3-Butylhexahydrophthalides: Simultaneous enantioselective analysis, structure elucidation, and sensorial properties of the stereoisomers; J. High Resolut. Chromatogr. 1997, 20, 251-256; Dietmar Bartschat, Thomas Beck, and Armin Mosandl, Stereoisomeric Flavor Compounds. 79. Simultaneous Enantioselective Analysis of 3-Butylphthalide and 3-Butylhexahydrophthalide Stereoisomers in Celery, Celeriac, and Fennel, J. Agric. Food Chem. 1997, 45, 4554-4557

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

HOME