Synthesis and taste properties of sodium disubstituted phenylsulfamates. Structure-taste relationships for sweet and bitter/sweet sulfamates

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

doi:10.1016/0308-8146(93)90178-i

Cited by 15 publications

(15 citation statements)

References 18 publications

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“…N,N-Disulfo-1,4-phenylenediamine (2) was prepared by modification of reported methods [20,21] as a PPh 4 salt. 2 was oxidized by lead(IV) acetate according to the literature method [20].…”

Section: Resultsmentioning

confidence: 99%

A New BEDT-TTF-Based Organic Charge Transfer Salt with a New Anionic Strong Acceptor, N,N'-Disulfo-1,4-benzoquinonediimine

et al. 2012

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Abstract:A novel organic dianion, N,N'-Disulfo-1,4-benzoquinonediimine (1) has been prepared, which is a strong electron acceptor. The reduction potential of the PPh 4 salt indicates that 1 is a stronger acceptor than DDQ (2,3-dichloro-5,6-dicyano-1,4-benzoquinone). The dianionic acceptor provided a BEDT-TTF salt, (BEDT-TTF) 4 1· 3H 2 O, the structures and physical properties of which are reported.

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“…N,N-Disulfo-1,4-phenylenediamine (2) was prepared by modification of reported methods [20,21] as a PPh 4 salt. 2 was oxidized by lead(IV) acetate according to the literature method [20].…”

Section: Resultsmentioning

confidence: 99%

A New BEDT-TTF-Based Organic Charge Transfer Salt with a New Anionic Strong Acceptor, N,N'-Disulfo-1,4-benzoquinonediimine

et al. 2012

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“…Several Quantitative Structure-Taste Relationships (QSTRs) for predicting the sweetness of chemicals were proposed in the past years and are summarized in Table 1 . The earlier work included compounds such as perillartine and aniline derivatives (Iwamura, 1980 ; van der Wel et al, 1987 ), sweet and bitter aldoxime derivatives (Kier, 1980 ), perillartine derivatives, aspartyl dipeptides, and carbosulfamates (Takahashi et al, 1982 , 1984 ; Miyashita et al, 1986a , b ; Okuyama et al, 1988 ), as well as sulfamate derivatives (Spillane and McGlinchey, 1981 ; Spillane et al, 1983 , 1993 , 2000 , 2002 , 2003 , 2006 , 2009 ; Spillane and Sheahan, 1989 , 1991 ; Drew et al, 1998 ; Kelly et al, 2005 ). Moreover, two QSTR models to discriminate sweet, tasteless and bitter compounds have been proposed (Rojas et al, 2016a ).…”

Section: Introductionmentioning

confidence: 99%

A QSTR-Based Expert System to Predict Sweetness of Molecules

et al. 2017

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This work describes a novel approach based on advanced molecular similarity to predict the sweetness of chemicals. The proposed Quantitative Structure-Taste Relationship (QSTR) model is an expert system developed keeping in mind the five principles defined by the Organization for Economic Co-operation and Development (OECD) for the validation of (Q)SARs. The 649 sweet and non-sweet molecules were described by both conformation-independent extended-connectivity fingerprints (ECFPs) and molecular descriptors. In particular, the molecular similarity in the ECFPs space showed a clear association with molecular taste and it was exploited for model development. Molecules laying in the subspaces where the taste assignation was more difficult were modeled trough a consensus between linear and local approaches (Partial Least Squares-Discriminant Analysis and N-nearest-neighbor classifier). The expert system, which was thoroughly validated through a Monte Carlo procedure and an external set, gave satisfactory results in comparison with the state-of-the-art models. Moreover, the QSTR model can be leveraged into a greater understanding of the relationship between molecular structure and sweetness, and into the design of novel sweeteners.

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“…La medición experimental del gusto se realiza mediante panelistas entrenados y soluciones estándar dulces, amargas, ácidas y saladas. De esta manera, se asigna un gusto y su intensidad (cuando es posible) a cada compuesto (Spillane et al, 1993).…”

Section: Conclusionesunclassified

“…Para enfrentar estos inconvenientes, los químicos han desarrollado modelos matemáticos basados en la teoría QSAR/QSPR con la finalidad de predecir el dulzor de los compuestos y optimizar la síntesis los mismos. Además de los modelos QSAR previamente descritos para los gustos dulce-amargo, se han propuesto otros modelos que buscan discriminar entre compuestos dulces y no dulces de carbosulfamatos (Miyashita et al, 1986a;Okuyama et al, 1988) y otros derivados del sulfamato (Spillane & McGlinchey, 1981;Spillane & Sheahan, 1989;Spillane & Sheahan, 1991;Spillane et al, 1993;Spillane et al, 2000;Spillane et al, 2003;Spillane et al, 2009).…”

Section: Conclusionesunclassified

“…En la Tabla 5.12 se presentan los diversos modelos QSAR desarrollados para discriminar moléculas dulces y no dulces. En la mayoría de los casos estos modelos se han establecido mediante el uso de bases de datos con familias de compuestos homogéneas (Iwamura, 1980;Kier, 1980;Spillane & McGlinchey, 1981;Takahashi et al, 1982;Spillane et al, 1983;Takahashi et al, 1984;Miyashita et al, 1986a;Miyashita et al, 1986b;Okuyama et al, 1988;Spillane & Sheahan, 1989;Spillane & Sheahan, 1991;Spillane et al, 1993;Drew et al, 1998;Spillane et al, 2000;Spillane et al, 2002;Spillane et al, 2003;Spillane et al, 2009). Este hecho limita la generalización de tales modelos a diferentes tipos de compuestos, es decir, el dominio de aplicabilidad de los mismos es restringido.…”

Section: Si Las Distancias D D1 Y D D2 Son Menores Que Los Umbrales Deunclassified

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Estudio y aplicación de técnicas matemáticas de la teoría QSAR–QSPR en química analítica y química de los alimentos

Rojas¹

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Synthesis and taste properties of sodium disubstituted phenylsulfamates. Structure-taste relationships for sweet and bitter/sweet sulfamates

Cited by 15 publications

References 18 publications

A New BEDT-TTF-Based Organic Charge Transfer Salt with a New Anionic Strong Acceptor, N,N'-Disulfo-1,4-benzoquinonediimine

A New BEDT-TTF-Based Organic Charge Transfer Salt with a New Anionic Strong Acceptor, N,N'-Disulfo-1,4-benzoquinonediimine

A QSTR-Based Expert System to Predict Sweetness of Molecules

Estudio y aplicación de técnicas matemáticas de la teoría QSAR–QSPR en química analítica y química de los alimentos

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