Quinoline Yellow WS

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Contents

Quinoline Yellow WS [1]
Quinoline Yellow WS.svg
Names
IUPAC name
Sodium 2-(1,3-dioxoindan-2-yl)quinolinedisulfonate
Other names
  • C.I. Acid Yellow 3
  • Food Yellow 13
  • D&C Yellow No. 10
  • Acid yellow 3
  • Quinidine Yellow KT
  • Japan Yellow 203
  • Lemon Yellow ZN 3
  • C.I. 47005
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.116.526 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 305-897-5
E number E104 (colours)
PubChem CID
UNII
  • 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 Yes check.svgY
    Key: FZUOVNMHEAPVBW-UHFFFAOYSA-L Yes check.svgY
  • InChI=1/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
    Key: FZUOVNMHEAPVBW-NUQVWONBAX
  • [Na+].[Na+].[O-]S(=O)(=O)c1cc(cc2ccc(nc12)C4C(=O)c3ccccc3C4=O)S([O-])(=O)=O
Properties
C18H13NO5/8/11S1/2/3Na1/2/3
Molar mass 477.38 g/mol
AppearanceGreenish yellow powder
Melting point 150 °C (302 °F; 423 K) (decomposes)
Soluble [2]
Acidity (pKa)1.8
Hazards [3]
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H302
P264, P270, P301+P312, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Quinoline Yellow WS is a mixture of organic compounds derived from the dye Quinoline Yellow SS (spirit soluble). Owing to the presence of sulfonate groups, the WS dyes are water-soluble (WS). It is a mixture of disulfonates (principally), monosulfonates and trisulfonates of 2-(2-quinolyl)indan-1,3-dione with a maximum absorption wavelength of 416 nm. [4] p. 119

Uses

Quinoline Yellow is used as a greenish yellow food additive in certain countries, designated in Europe as the E number E104. [5] In the EU and Australia, Quinoline Yellow is permitted in beverages and is used in foods, like sauces, decorations, and coatings; Quinoline Yellow is not listed as a permitted food additive in Canada or the US, where it is permitted in medicines and cosmetics and is known as D&C Yellow 10. [6] :461 The Codex Alimentarius does not list it. [6] :461

Health effects

Quinoline Yellow WS has not been associated with any significant long-term toxicity, is not genotoxic or carcinogenic and there is no evidence of adverse effects on reproduction or development. [6] Food colorants in general have been the subject of much scrutiny for their effect on health. [7]

Possible cause of hyperactivity

Since the 1970s and the well-publicized advocacy of Benjamin Feingold, there has been public concern that food colorings may cause ADHD-like behavior in children. [8] These concerns have led the U.S. FDA and other food safety authorities to regularly review the scientific literature, and led the UK FSA to commission a study by researchers at the University of Southampton to assess the effect of a mixture of six food dyes (Tartrazine, Allura Red, Ponceau 4R, Quinoline Yellow WS, Sunset Yellow FCF and Carmoisine (dubbed the "Southampton 6")) and sodium benzoate (a preservative) on children in the general population, who consumed them in beverages; the study published in 2007. [8] [9] The study found "a possible link between the consumption of these artificial colours and a sodium benzoate preservative and increased hyperactivity" in the children; [8] [9] the advisory committee to the FSA that evaluated the study also determined that because of study limitations, the results could not be extrapolated to the general population, and further testing was recommended". [8]

The European regulatory community, with a stronger emphasis on the precautionary principle, required labelling and temporarily reduced the acceptable daily intake (ADI) for the food colorings; the UK FSA called for voluntary withdrawal of the colorings by food manufacturers. [8] [9] However, in 2009 the EFSA re-evaluated the data at hand and determined that "the available scientific evidence does not substantiate a link between the color additives and behavioral effects". [8] [10] On the basis of other evidence the EFSA also reduced the acceptable daily intake (ADI) from 10 to 0.5 mg/kg. [10]

The US FDA did not make changes following the publication of the Southampton study, but following a citizen petition filed by the Center for Science in the Public Interest in 2008, requesting the FDA ban several food additives, the FDA commenced a review of the available evidence, and still made no changes. [8]

No evidence supports broad claims that food coloring causes food intolerance and ADHD-like behavior in children. [11] :452 It is possible that certain food coloring may act as a trigger in those who are genetically predisposed, but the evidence is weak. [8] [12]

Related Research Articles

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<span class="mw-page-title-main">Food coloring</span> Substance used to color food or drink

Food coloring, color additive or colorant is any dye, pigment, or substance that imparts color when it is added to food or beverages. Colorants can be supplied as liquids, powders, gels, or pastes. Food coloring is commonly used in commercial products and in domestic cooking.

Carmine – also called cochineal, cochineal extract, crimson lake, or carmine lake – is a pigment of a bright-red color obtained from the aluminium complex derived from carminic acid. Specific code names for the pigment include natural red 4, C.I. 75470, or E120. Carmine is also a general term for a particularly deep-red color.

<span class="mw-page-title-main">Annatto</span> Orange-red condiment and food coloring derived from the seeds of the achiote tree

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<span class="mw-page-title-main">Tartrazine</span> Chemical compound

Tartrazine is a synthetic lemon yellow azo dye primarily used as a food coloring. It is also known as E number E102, C.I. 19140, FD&C Yellow 5, Yellow 5 Lake, Acid Yellow 23, Food Yellow 4, and trisodium 1-(4-sulfonatophenyl)-4-(4-sulfonatophenylazo)-5-pyrazolone-3-carboxylate.

<span class="mw-page-title-main">Sunset yellow FCF</span> Chemical compound used as colorant

Sunset yellow FCF is a petroleum-derived orange azo dye with a pH-dependent maximum absorption at about 480 nm at pH 1 and 443 nm at pH 13, with a shoulder at 500 nm. When added to foods sold in the United States, it is known as FD&C Yellow 6; when sold in Europe, it is denoted by E Number E110.

<span class="mw-page-title-main">Sodium benzoate</span> Chemical compound

Sodium benzoate also known as benzoate of soda is the sodium salt of benzoic acid, widely used as a food preservative (with an E number of E211) and a pickling agent. It appears as a white crystalline chemical with the formula C6H5COONa.

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<span class="mw-page-title-main">Brilliant blue FCF</span> Chemical compound

Brilliant blue FCF is a synthetic organic compound used primarily as a blue colorant for processed foods, medications, dietary supplements, and cosmetics. It is classified as a triarylmethane dye and is known under various names, such as FD&C Blue No. 1 or acid blue 9. It is denoted by E number E133 and has a color index of 42090. It has the appearance of a blue powder and is soluble in water and glycerol, with a maximum absorption at about 628 nanometers. It is one of the oldest FDA-approved color additives and is generally considered nontoxic and safe.

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<span class="mw-page-title-main">Ponceau 4R</span> Chemical compound

Ponceau 4R is a synthetic colourant that may be used as a food colouring. It is denoted by E Number E124. Its chemical name is 1-(4-sulfo-1-napthylazo)-2-napthol-6,8-disulfonic acid, trisodium salt. Ponceau is the generic name for a family of azo dyes.

<span class="mw-page-title-main">Allura Red AC</span> Chemical compound

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<span class="mw-page-title-main">Sodium bisulfite</span> Chemical compound

Sodium bisulfite (or sodium bisulphite, sodium hydrogen sulfite) is a chemical mixture with the approximate chemical formula NaHSO3. Sodium bisulfite in fact is not a real compound, but a mixture of salts that dissolve in water to give solutions composed of sodium and bisulfite ions. It appears in form of white or yellowish-white crystals with an odor of sulfur dioxide. Regardless of its ill-defined nature, sodium bisulfite is used in many different industries such as a food additive with E number E222 in the food industry, a reducing agent in the cosmetic industry, and a decomposer of residual hypochlorite used in the bleaching industry.

References

  1. "QUINOLINE YELLOW WS (C.I. ACID YELLOW 3)" . Retrieved 30 June 2023.
  2. Additives FAO [ dead link ]
  3. "Quinoline Yellow for microscopy (Hist.), mixture of mono- and disulfonic acid sodium salt". Sigma Aldrich.
  4. Joint FAO/WHO Expert Committee on Food Additives (1991). Guide to specifications for general notices: general analytical techniques, identification tests, test solutions, and other reference materials (Rev. 2 [= ed. 1991] ed.). Rome: Food and Agriculture Organization of the United Nations. ISBN   9789251029916.
  5. "Current EU approved additives and their E Numbers", Food Standards Agency website, retrieved 15 Dec 2011
  6. 1 2 3 Abbey J, et at. Colorants. pp 459-465 in Encyclopedia of Food Safety, Vol 2: Hazards and Diseases. Eds, Motarjemi Y et al. Academic Press, 2013. ISBN   9780123786135
  7. Amchova, Petra; Kotolova, Hana; Ruda-Kucerova, Jana "Health safety issues of synthetic food colorants" Regulatory Toxicology and Pharmacology (2015), 73(3), 914-922. doi : 10.1016/j.yrtph.2015.09.026
  8. 1 2 3 4 5 6 7 8 FDA. Background Document for the Food Advisory Committee: Certified Color Additives in Food and Possible Association with Attention Deficit Hyperactivity Disorder in Children: March 30-31, 2011
  9. 1 2 3 Sarah Chapman of Chapman Technologies on behalf of Food Standards Agency in Scotland. March 2011 [Guidelines on approaches to the replacement of Tartrazine, Allura Red, Ponceau 4R, Quinoline Yellow, Sunset Yellow and Carmoisine in food and beverages]
  10. 1 2 EFSA Panel on Food Additives and Nutrient Sources added to Food (ANS (November 2009). "Scientific Opinion on the re-evaluation of Quinoline Yellow (E 104) as a food additive". EFSA Journal. 7 (11): 1329. doi: 10.2903/j.efsa.2009.1329 .
  11. Tomaska LD and Brooke-Taylor, S. Food Additives - General pp 449-454 in Encyclopedia of Food Safety, Vol 2: Hazards and Diseases. Eds, Motarjemi Y et al. Academic Press, 2013. ISBN   9780123786135
  12. Millichap JG, Yee MM (February 2012). "The diet factor in attention-deficit/hyperactivity disorder". Pediatrics. 129 (2): 330–337. doi:10.1542/peds.2011-2199. PMID   22232312. S2CID   14925322.