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CI 47005
"Descrizione"
by Ark90 (12431 pt)
2023-Jul-10 11:52

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Quinoline Yellow or D&C Yellow No. 10 is a chemical azo compound, derived from quinophthalone, a dye used in a variety of industries: 

  • Food
  • Cosmetics. Nail polishes, cold soaps, liquid detergents.
  • Pharmaceuticals. Tablets
  • Textile. Fabrics
  • Plastic
  • etc

The synthesis process takes place in different steps:

  • Preparation of the diazonium salt. An aromatic amine is treated with nitrous acid (usually generated in situ from sodium nitrite and a strong acid) to form a diazonium salt. This reaction typically takes place in an aqueous and acidic environment and at low temperatures to stabilise the diazonium group.
  • Coupling reaction. The diazonium salt is then reacted with a phenol or aniline in a basic or slightly acidic solution to form the azo dye. 
  • Isolation and purification. The resulting dye is isolated, usually by filtration, and then purified, often by recrystallisation.

What it is for and where

Labeled with the number E104 in the list of European food color additives and internationally known as CI 47005.

It is also used to add color to non-food producing animal feed at a maximum dose of 500 mg/kg of feed.

Cosmetics

It is a restricted ingredient as IV/82 a Relevant Item in the Annexes of the European Cosmetics Regulation 1223/2009. Ingredient or substance at risk: 1H-Indene-1,3(2H)-dione, 2-(2-quinolinyl)-, sulfonated, sodium salts

Safety

Regulatory data on the genotoxicity and/or mutagenicity of this compound are still controversial. This study finds that, even with in vitro testing, this dye could cause harmful effects in humans if it is metabolized or absorbed through the skin (1).

Quinoline yellow studies

Typical optimum characteristics of the commercial colour Chinoline Yellow

Colour Index n47005
Food colour n.Yellow 13
F.D. & C. No.Yellow 10
Volatile matter (chloride and sulfate) Max30%
Solubility in water at 20°C120g/l
Combined ether extract. Max0.20%
Insoluble in water. Max0.20%
ClassXanthene
Light stability4
Stability at 100°C4
Alkali stability4
Subsidiary dyes. Max1.50%
Intermediate dyes. Max0.50%
Lead<10ppm
Arsenic<3ppm
Mercury<1ppm
Heavy Metals<20ppm




  • Molecular Formula : C18H9NNa2O8S2
  • Molecular Weight : 477.369 g/mol
  • CAS : 100208-62-6    8004-92-0
  • EC Number 616-849-0
  • UNII  0QYP77F82G
  • InChI=1S/C18H11NO8S2.2Na/c20-17-11-3-1-2-4-12(11)18(21)15(17)13-6-5-9-7-10(28(22,23)24)8-14(16(9)19-13)29(25,26)27;;/h1-8,15H,(H,22,23,24)(H,25,26,27);;/q;2*+1/p-2
  • InChl Key      FZUOVNMHEAPVBW-UHFFFAOYSA-L
  • SMILES  C1=CC=C2C(=C1)C(=O)C(C2=O)C3=NC4=C(C=C(C=C4C=C3)S(=O)(=O)[O-])S(=O)(=O)[O-].[Na+].[Na+]
  • IUPAC  disodium;2-(1,3-dioxoinden-2-yl)quinoline-6,8-disulfonate
  • DSSTox Substance ID  DTXSID0041721     DTXSID70873122
  • NACRES  NA.47

Synonyms 

  • CI 47005
  • E104
  • Acid Yellow 3
  • Yellow 13
  • Yellow 10
  • Lemon Yellow ZN 3
  • Quinoline Yellow S
  • Quinoline yellow WS
  • Sodium 2-(1,3-dioxo-2,3-dihydro-1H-inden-2-yl)quinoline-6,8-disulfonate
  • 2-(2-Quinolyl)-1,3-indandione disulfonic acid disodium salt
  • dipotassium 2-(1,3-dioxo-2H-inden-2-yl)quinoline-6,8-disulfonate
  • disodium 2-(1,3-dioxo-2H-inden-2-yl)quinoline-6,8-disulfonate
  • 2-(1,3-Dioxoindan-2-yl)quinoline-6,8-bis(sulfonic acid sodium) salt
  • disodium 2-(1,3-dioxo-2,3-dihydro-1h-inden-2-yl)-6,8-quinolinedisulfonate
  • disodium 2-(1,3-dioxo-2,3-dihydro-1H-inden-2-yl)quinoline-6,8-disulfonate

References______________________________________________________________

(1) Chequer FM, Venâncio Vde P, de Souza Prado MR, Campos da Silva e Cunha Junior LR, Lizier TM, Zanoni MV, Rodríguez Burbano R, Bianchi ML, Antunes LM. The cosmetic dye quinoline yellow causes DNA damage in vitro. Mutat Res Genet Toxicol Environ Mutagen. 2015 Jan 1;777:54-61. doi: 10.1016/j.mrgentox.2014.11.003.

Macioszek VK, Kononowicz AK. The evaluation of the genotoxicity of two commonly used food colors: Quinoline Yellow (E 104) and Brilliant Black BN (E 151). Cell Mol Biol Lett. 2004;9(1):107-22.


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