FD&C YELLOW #6 lake or E110 or Sunset Yellow FCF is an azo dye, a class of commercial organic dyes.
The name describes the structure of the molecule.
- FD&C indicates that the color has been approved by the United States Food and Drug Administration (FDA) for use in foods, drugs, and cosmetics. (1986)
- Yellow No. 6 refers to a particular yellow color.
- Lake indicates that the color has been combined with a substance (often a calcium or aluminum salt) to make it water-insoluble, often used in products that are not meant to dissolve immediately in water.
Description of raw materials used in production.
- The raw materials for the production of FD&C Yellow No. 6 include petroleum derivatives and other chemicals that undergo various chemical reactions to produce the dye.
Step-by-step summary of industrial production process.
- Synthesis of Sulfanilic Acid. The first step involves synthesizing sulfanilic acid from aniline and sulfuric acid.
- Diazotization Coupling. The sulfanilic acid is then converted into a diazonium salt, which is coupled with a compound called 2-naphthol.
- Isolation and Purification. The formed dye is isolated, purified, and then converted into its sodium salt form to make it water-soluble.
- Drying. The dye is then dried and ground into a fine powder.
Form and color. It is generally comes as an orange/reddish powder and, when dissolved, produces a yellow/orange hue in solution.
Commercial applications.
This dye is widely used in various food, cosmetic, and pharmaceutical products to impart a yellow/orange hue. It is used in beverages, candies, ice cream, drugs, and many other products.
Safety
The problem associated with azo dyes (monoazo or diazo) is photocatalytic degradation (1) leading to eventual oxidation and subsequent formation of impurities such as aromatic amines (2) some of which have carcinogenic activity.
It is used in:
- biocides (e.g. disinfectants, pest control products)
- fertilisers
- cosmetics
- personal care products
- inks and toners
- air care products
- textile treatment products
- dyes
- paper chemicals
Molecular Formula: C16H10N2Na2O7S2
Molecular Weight: 452.363 g/mol
UNII: H77VEI93A8
CAS: 2783-94-0 1325-37-7 15790-07-5 1342-61-6 12707-27-6
EC Number: 220-491-7 239-888-1 215-393-6
PubChem Substance ID 24870256
MDL number MFCD00036437
Colour Index Number 15985
References_____________________________________________________________________
(1) Li M, He W, Liu Y, Wu H, Wamer WG, Lo YM, Yin JJ. FD&C Yellow No. 5 (tartrazine) degradation via reactive oxygen species triggered by TiO2 and Au/TiO2 nanoparticles exposed to simulated sunlight. J Agric Food Chem. 2014 Dec 10;62(49):12052-60. doi: 10.1021/jf5045052. Epub 2014 Nov 24. PMID: 25393426.
Abstract. When exposed to light, TiO2 nanoparticles (NPs) become photoactivated and create electron/hole pairs as well as reactive oxygen species (ROS). We examined the ROS production and degradation of a widely used azo dye, FD&C Yellow No. 5 (tartrazine), triggered by photoactivated TiO2 NPs. Degradation was found to follow pseudo-first order reaction kinetics where the rate constant increased with TiO2 NP concentration. Depositing Au on the surface of TiO2 largely enhanced electron transfer and ROS generation, which consequently accelerated dye degradation. Alkaline conditions promoted ROS generation and dye degradation. Results from electron spin resonance spin-trap spectroscopy suggested that at pH 7.4, both hydroxyl radical (•OH) and singlet oxygen ((1)O2) were responsible for dye discoloration, whereas at pH 5, the consumption of (1)O2 became dominant. Implications for dye degradation in foods and other consumer products that contain both TiO2 and FD&C Yellow No. 5 as ingredients are discussed.
(2) Belai N, White SR. Determination of Unsulfonated Aromatic Amines in FD&C Yellow No. 5 and FD&C Yellow No. 6 by Liquid Chromatography-Triple Quadrupole Mass Spectrometry. J AOAC Int. 2019 Mar 1;102(2):580-589. doi: 10.5740/jaoacint.18-0165.
Abstract. Background: This paper describes a simple and sensitive ultra-HPLC-triple quadrupole MS (LC-MS/MS) method for the determination of six unsulfonated aromatic amines in the color additives FD&C Yellow No. 5 (Y5) and FD&C Yellow No. 6 (Y6). The six amines determined by this method are aniline (ANL), benzidine (BNZ), 4-aminobiphenyl (4ABP), 4-aminoazobenzene (4AAB), 2-aminobiphenyl (2ABP), and 4-aminobenzonitrile (4ABN). Objective: This method is intended for use in batch certification of the color additives by the U.S. Food and Drug Administration (FDA) to ensure that each lot meets published specifications for coloring foods, drugs, and cosmetics. Methods: A modified quick, easy, cheap, effective, rugged, and safe (QuEChERS) procedure is used for extraction of the amines. Quantitative determination was performed in electrospray positive ionization and multiple-reaction monitoring modes. Results: Validation of the method demonstrated overall recovery of 101-115% and precision of 1.74-9.78% for all analytes. Excellent regression coefficients were obtained, with values >0.999. Conclusions: The validated method was successfully used for the analyses of 30 Y5 and Y6 samples and provided results that are consistent with results from the current method used by FDA, with greater sensitivity and low matrix effects. Highlights: The validation results demonstrate that the new LC-MS/MS method is applicable for use in routine batch certification.
