Synthesis and taste properties of sodium monosubstituted phenylsulfamates

William J. Spillane; Caroline A. Ryder; Maryanne Sheahan

doi:10.1016/0308-8146(94)90193-7

Synthesis and taste properties of sodium monosubstituted phenylsulfamates

William J. Spillane
, Caroline A. Ryder
, Maryanne Sheahan

Cellular & Molecular Medicine

University of Galway

Research output: Contribution to a Journal (Peer & Non Peer) › Article › peer-review

10 Citations (Scopus)

Abstract

Thirty-four monosubstituted ortho-, meta- and para-phenylsulfamates have been synthesized, characterized and tasted. The compounds (as sodium salts) display all four primary tastes often in combination. Some structure-sweet taste relationships have been derived using measurements made with CPK models and using Hammett sigma values for the various substituents. For the 14 meta-substituted compounds (including five previously made) those having x (the length of the aromatic portion including the substituent) in the range 5·82 ± 0·12 A ̊ and V_CPK (= x.y.z) ≤ 295 A ̊³ displayed some sweetness, this being much more pronounced and exclusive for those compounds with V_CPK ≤ 170 A ̊³. All the sweet meta-compounds had σ_m in the range -0·07 to + 0·56. The ortho-compounds that showed some sweet component in their taste generally had σ_o in the range -0·30 to + 0·81 and the para-compounds nine of which had a sweet aftertaste had σ_p in the range -0·27 to + 0·66.

Original language	English
Pages (from-to)	405-411
Number of pages	7
Journal	Food Chemistry
Volume	51
Issue number	4
DOIs	https://doi.org/10.1016/0308-8146(94)90193-7
Publication status	Published - 1994

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title = "Synthesis and taste properties of sodium monosubstituted phenylsulfamates",

abstract = "Thirty-four monosubstituted ortho-, meta- and para-phenylsulfamates have been synthesized, characterized and tasted. The compounds (as sodium salts) display all four primary tastes often in combination. Some structure-sweet taste relationships have been derived using measurements made with CPK models and using Hammett sigma values for the various substituents. For the 14 meta-substituted compounds (including five previously made) those having x (the length of the aromatic portion including the substituent) in the range 5·82 ± 0·12 A ̊ and VCPK (= x.y.z) ≤ 295 A ̊3 displayed some sweetness, this being much more pronounced and exclusive for those compounds with VCPK ≤ 170 A ̊3. All the sweet meta-compounds had σm in the range -0·07 to + 0·56. The ortho-compounds that showed some sweet component in their taste generally had σo in the range -0·30 to + 0·81 and the para-compounds nine of which had a sweet aftertaste had σp in the range -0·27 to + 0·66.",

author = "Spillane, \{William J.\} and Ryder, \{Caroline A.\} and Maryanne Sheahan",

year = "1994",

doi = "10.1016/0308-8146(94)90193-7",

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pages = "405--411",

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number = "4",

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TY - JOUR

T1 - Synthesis and taste properties of sodium monosubstituted phenylsulfamates

AU - Spillane, William J.

AU - Ryder, Caroline A.

AU - Sheahan, Maryanne

PY - 1994

Y1 - 1994

N2 - Thirty-four monosubstituted ortho-, meta- and para-phenylsulfamates have been synthesized, characterized and tasted. The compounds (as sodium salts) display all four primary tastes often in combination. Some structure-sweet taste relationships have been derived using measurements made with CPK models and using Hammett sigma values for the various substituents. For the 14 meta-substituted compounds (including five previously made) those having x (the length of the aromatic portion including the substituent) in the range 5·82 ± 0·12 A ̊ and VCPK (= x.y.z) ≤ 295 A ̊3 displayed some sweetness, this being much more pronounced and exclusive for those compounds with VCPK ≤ 170 A ̊3. All the sweet meta-compounds had σm in the range -0·07 to + 0·56. The ortho-compounds that showed some sweet component in their taste generally had σo in the range -0·30 to + 0·81 and the para-compounds nine of which had a sweet aftertaste had σp in the range -0·27 to + 0·66.

AB - Thirty-four monosubstituted ortho-, meta- and para-phenylsulfamates have been synthesized, characterized and tasted. The compounds (as sodium salts) display all four primary tastes often in combination. Some structure-sweet taste relationships have been derived using measurements made with CPK models and using Hammett sigma values for the various substituents. For the 14 meta-substituted compounds (including five previously made) those having x (the length of the aromatic portion including the substituent) in the range 5·82 ± 0·12 A ̊ and VCPK (= x.y.z) ≤ 295 A ̊3 displayed some sweetness, this being much more pronounced and exclusive for those compounds with VCPK ≤ 170 A ̊3. All the sweet meta-compounds had σm in the range -0·07 to + 0·56. The ortho-compounds that showed some sweet component in their taste generally had σo in the range -0·30 to + 0·81 and the para-compounds nine of which had a sweet aftertaste had σp in the range -0·27 to + 0·66.

UR - https://www.scopus.com/pages/publications/0027960975

U2 - 10.1016/0308-8146(94)90193-7

DO - 10.1016/0308-8146(94)90193-7

M3 - Article

SN - 0308-8146

VL - 51

SP - 405

EP - 411

JO - Food Chemistry

JF - Food Chemistry

IS - 4

ER -

Synthesis and taste properties of sodium monosubstituted phenylsulfamates

Abstract

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