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Determination of Sudan I and a Newly Synthesized Sudan III Positional Isomer in the Color Additive D&C Red No. 17 Using High-Performance Liquid Chromatography

Determination of Sudan I and a Newly Synthesized Sudan III Positional Isomer in the Color Additive D&C Red No. 17 Using High-Performance Liquid Chromatography

Adrian Weisz, India C James, Christian J Tae, Clark D Ridge, Yoichiro Ito

Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2017 Nov;34(11):1831-1841.

PMID: 28665764

Abstract:

Specifications in the Code of Federal Regulations for the color additive D&C Red No. 17 (Colour Index 26100) limit the levels of two subsidiary colors, 1-(phenylazo)-2-naphthol (Sudan I) and 1-[[2-(phenylazo)phenyl]azo]-2-naphthalenol (Sudan III o-isomer), to 3% and 2%, respectively. The present work reports the development of a high-performance liquid chromatography (HPLC) method for the quantitative determination of these subsidiary colors. Since Sudan III o-isomer needed to be synthesized for use as a reference material, a two-step procedure was devised: (i) preparative-scale synthesis of the intermediate 2-aminoazobenzene (2AAB) and its purification by counter-current chromatography and (ii) diazotization of 2AAB and coupling with 2-naphthol. Characterization of the newly synthesized Sudan III o-isomer is also reported. Sudan I and Sudan III o-isomer were quantified by using five-point calibration curves with data points ranging from 0.108 to 3.240% and 0.077 to 2.227% by weight, respectively. The HPLC method is rapid (14 min for the total analysis cycle) and simple to implement. It was applied to the analysis of test portions from 25 batches of D&C Red No. 17 submitted to the U.S. Food and Drug Administration (USFDA) for certification, and it has recently been implemented by USFDA for routine batch certification of that color additive.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP1014689178	Sudan III-(naphthyl-d6)		1014689-17-8	Price

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