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Preparative separation and identification of novel subsidiary colors of the color additive D&C Red No. 33 (Acid Red 33) using spiral high-speed counter-current chromatography.

ABSTRACT: Three low-level subsidiary color impurities (A, B, and C) often present in batches of the color additive D&C Red No. 33 (R33, Acid Red 33, Colour Index No. 17200) were separated from a portion of R33 by spiral high-speed counter-current chromatography (HSCCC). The separation involved use of a very polar solvent system, 1-BuOH/5mM aq. (NH4)2SO4. Addition of ammonium sulfate to the lower phase forced partition of the components into the upper phase, thereby eliminating the need to add a hydrophobic counterion as was previously required for separations of components from sulfonated dyes. The very polar solvent system used would not have been retained in a conventional multi-layer coil HSCCC instrument, but the spiral configuration enabled retention of the stationary phase, and thus, the separation was possible. A 1g portion of R33 enriched in A, B, and C was separated using the upper phase of the solvent system as the mobile phase. The retention of the stationary phase was 38.1%, and the separation resulted in 4.8 mg of A of >90% purity, 18.3mg of B of >85% purity, and 91 mg of C of 65-72% purity. A second separation of a portion of the C mixture resulted in 7 mg of C of >94% purity. The separated impurities were identified by high-resolution mass spectrometry and NMR spectroscopic techniques as follows: 5-amino-3-biphenyl-3-ylazo-4-hydroxy-naphthalene-2,7-disulfonic acid, A; 5-amino-4-hydroxy-6-phenyl-3-phenylazo-naphthalene-2,7-disulfonic acid, B; and 5-amino-4-hydroxy-3,6-bis-phenylazo-naphthalene-2,7-disulfonic acid, C. The isomers A and B are compounds reported for the first time. Application of the spiral HSCCC method resulted in the additional benefit of yielding 930 mg of the main component of R33, 5-amino-4-hydroxy-3-phenylazo-naphthalene-2,7-disulfonic acid, of >97% purity.

SUBMITTER: Weisz A

PROVIDER: S-EPMC4305482 | biostudies-literature | 2015 Feb

REPOSITORIES: biostudies-literature

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Preparative separation and identification of novel subsidiary colors of the color additive D&C Red No. 33 (Acid Red 33) using spiral high-speed counter-current chromatography.

Weisz Adrian A Ridge Clark D CD Mazzola Eugene P EP Ito Yoichiro Y

Journal of chromatography. A 20150103

Three low-level subsidiary color impurities (A, B, and C) often present in batches of the color additive D&C Red No. 33 (R33, Acid Red 33, Colour Index No. 17200) were separated from a portion of R33 by spiral high-speed counter-current chromatography (HSCCC). The separation involved use of a very polar solvent system, 1-BuOH/5mM aq. (NH4)2SO4. Addition of ammonium sulfate to the lower phase forced partition of the components into the upper phase, thereby eliminating the need to add a hydrophobi ...[more]

PMID: 25591404

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Project description:It is estimated that inherited red-green color deficiency, which involves both the protan and deutan deficiency types, is common in men. For red-green defective observers, some reddish colors appear desaturated and brownish, unlike those seen by normal observers. Despite its prevalence, few studies have investigated the effects that red-green color deficiency has on the psychological properties of colors (color emotions). The current study investigated the influence of red-green color deficiency on the following six color emotions: cleanliness, freshness, hardness, preference, warmth, and weight. Specifically, this study aimed to: (1) reveal differences between normal and red-green defective observers in rating patterns of six color emotions; (2) examine differences in color emotions related to the three cardinal channels in human color vision; and (3) explore relationships between color emotions and color naming behavior. Thirteen men and 10 women with normal vision and 13 men who were red-green defective performed both a color naming task and an emotion rating task with 32 colors from the Berkeley Color Project (BCP). Results revealed noticeable differences in the cleanliness and hardness ratings between the normal vision observers, particularly in women, and red-green defective observers, which appeared mainly for colors in the orange to cyan range, and in the preference and warmth ratings for colors with cyan and purple hues. Similarly, naming errors also mainly occurred in the cyan colors. A regression analysis that included the three cone-contrasts (i.e., red-green, blue-yellow, and luminance) as predictors significantly accounted for variability in color emotion ratings for the red-green defective observers as much as the normal individuals. Expressly, for warmth ratings, the weight of the red-green opponent channel was significantly lower in color defective observers than in normal participants. In addition, the analyses for individual warmth ratings in the red-green defective group revealed that luminance cone-contrast was a significant predictor in most red-green-defective individuals. Together, these results suggest that red-green defective observers tend to rely on the blue-yellow channel and luminance to compensate for the weak sensitivity of long- and medium-wavelength (L-M) cone-contrasts, when rating color warmth.

Dataset Information

Preparative separation and identification of novel subsidiary colors of the color additive D&C Red No. 33 (Acid Red 33) using spiral high-speed counter-current chromatography.

Publications

Preparative separation and identification of novel subsidiary colors of the color additive D&C Red No. 33 (Acid Red 33) using spiral high-speed counter-current chromatography.

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