Sunset Yellow FCF

Sunset Yellow FCF
IUPAC name Disodium 6-hydroxy-5-[(4-sulfophenyl)azo]-2-naphthalenesulfonate
Other names Orange Yellow S; FD&C Yellow 6; C.I. 15985; E110
Identifiers
CAS number	2783-94-0 Y
PubChem	6093232
ChemSpider	11431290 Y
UNII	H77VEI93A8 Y
KEGG	C19531 Y
Jmol-3D images	Image 1
SMILES [Na+].[Na+].[O-]S(=O)(=O)c1ccc(cc1)/N=N/c2c3ccc(cc3ccc2O)S([O-])(=O)=O
InChI InChI=1S/C16H12N2O7S2.2Na/c19-15-8-1-10-9-13(27(23,24)25)6-7-14(10)16(15)18-17-11-2-4-12(5-3-11)26(20,21)22;;/h1-9,19H,(H,20,21,22)(H,23,24,25);;/q;2*+1/p-2/b18-17+;; Y Key: OIQPTROHQCGFEF-QIKYXUGXSA-L Y InChI=1/C16H12N2O7S2.2Na/c19-15-8-1-10-9-13(27(23,24)25)6-7-14(10)16(15)18-17-11-2-4-12(5-3-11)26(20,21)22;;/h1-9,19H,(H,20,21,22)(H,23,24,25);;/q;2*+1/p-2/b18-17+;; Key: OIQPTROHQCGFEF-JLAJEUQUBH
Properties
Molecular formula	C16H10N2Na2O7S2
Molar mass	452.37 g mol−1
Melting point	300 °C, 573 K, 572 °F
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Sunset Yellow FCF (also known as Orange Yellow S, FD&C Yellow 6 or C.I. 15985) is a synthetic yellow azo dye, manufactured from aromatic hydrocarbons from petroleum. When added to foods, it is denoted by E Number E110.^[1] Although there are reports it can induce an allergic reaction, this is not confirmed by scientific research.^[2]

Uses

Sunset Yellow is useful in fermented foods which must be heat treated. It may be found in orange sodas, marzipan, Swiss rolls, apricot jam, citrus marmalade, lemon curd, sweets, beverage mix and packet soups, margarine, custard powders, packaged lemon gelatin desserts, energy drinks such as Lucozade, breadcrumbs, snack chips such as Doritos, packaged instant noodles, cheese sauce mixes and powdered marinades, bottled yellow and green food colouring, ice creams, pharmaceutical pills and prescription medicines, over-the-counter medicines (especially children's medicines) cake decorations and icings, squashes, and other products with artificial yellow, orange or red colours.

Sunset Yellow is often used in conjunction with E123, amaranth, to produce a brown colouring in both chocolates and caramel.^{[citation needed]}

At high concentrations, Sunset Yellow in solution with water undergoes a phase change from an isotropic liquid to a nematic liquid crystal. This occurs between 0.8 M and 0.9 M at room temperature.

Possible health effects

Sunset Yellow is a sulfonated version of Sudan I, a possible carcinogen,^{[citation needed]} which is frequently present in it as an impurity. Sunset Yellow itself may be responsible for causing an allergic reaction in people with an aspirin intolerance,^[3] resulting in various symptoms, including gastric upset, diarrhea, vomiting, nettle rash (urticaria), swelling of the skin (angioedema) and migraines.^[4] The colouring has also been linked to hyperactivity in young children.^[5]

The following additives were tested in the research:^[5]

• Sunset yellow (E110) (FD&C Yellow #6) - colouring found in squashes
• Carmoisine (E122) - red colouring in jellies
• Tartrazine (E102) (FD&C Yellow #5) - yellow colouring
• Ponceau 4R (E124) - red colouring
• Sodium benzoate (E211) - preservative
• Quinoline yellow (E104) - food colouring
• Allura red AC (E129) (FD&C Red #40) - orange/red food dye

Regulation

As a result of these potential health issues, there have been calls for the withdrawal of Sunset Yellow from food use.

On 6 September 2007, the British Food Standards Agency revised advice on certain artificial food additives, including E110. The report said, "This has been a major study investigating an important area of research. The results suggest that consumption of certain mixtures of artificial food colours and sodium benzoate preservative are associated with increases in hyperactive behaviour in children.

"However, parents should not think that simply taking these additives out of food will prevent hyperactive disorders. We know that many other influences are at work but this at least is one a child can avoid."^[6]

On 10 April 2008, the Foods Standard Agency called for a voluntary removal of the colours (but not sodium benzoate) by 2009.^[7] In addition, it recommended there should be action to phase them out in food and drink in the European Union (EU) over a specified period.^[8]

Sunset Yellow is banned in Norway and Finland.^[9]

In 2008, a proposed EU deal specified that food and drinks containing any of six artificial colourings that may be linked to hyperactive behaviour in children will have to carry warnings, including Sunset Yellow. The requirement would apply to imports, as well as those made in the EU.^[10] Hundreds of products containing the colourings are expected to disappear from shops in the period 2008-2010 following the Food Standards Agency's (FSA) call for a voluntary ban on their use in food products.^[10] UK ministers have agreed that the six colourings will be phased out by 2009.^{[11][dated info]}

EFSA decided in 2009 to lower the acceptable daily intake (ADI) for Sunset Yellow FCF from 2.5 mg/kg to 1.0 mg/kg bodyweight per day^{[citation needed]}. Impurities in production may leave unsulphonated aromatic amines in concentrations of 100 mg/kg which may be associated with carcinogenicity.^{[citation needed]} Also a study found that mixtures of four synthetic colours plus the preservative sodium benzoate (E211) cause increased hyperactivity in humans. Sensitivity reactions may occur when Sunset Yellow FCF is mixed with other synthetic colours.^[5]

Also, the EFSA panel noted the JECFA limit for lead is ≤ 2 mg/kg, whereas the EC specification is ≤ 10 mg/kg. The colour additive can also increase the intake of aluminium beyond the tolerable weekly intake (TWI) of 1 mg/kg/week. Therefore, the limit for aluminum may become adjusted to accommodate for this.^[12]

On June 30, 2010, the Center for Science in the Public Interest (CSPI) called for the FDA to ban Yellow 6. The CSPI said, "These synthetic chemicals do absolutely nothing to improve the nutritional quality or safety of foods, but trigger behavior problems in children and, possibly, cancer in anybody."^[13]

On September 9, 2011 the European Union announced that they would be reducing the maximum permitted concentration of sunset yellow (in drinks) from 50mg/L to 20mg/L. The proposed change to be adopted by the end of the year. ^[14]

References

1. ^ Wood, Roger M. (2004). Analytical methods for food additives. Boca Raton: CRC Press. ISBN 1-85573-722-1. 
2. ^ Middleton, Elliott; N. Franklin Adkinson; John Yunginger; William Busse; Bruce Bochner; Stephen Holgate (2003). Middleton's allergy principles & practice. St. Louis: Mosby. ISBN 0-323-01425-9. 
3. ^ Ibero M, Eseverri JL, Barroso C, Botey J (1982). "Dyes, preservatives and salicylates in the induction of food intolerance and/or hypersensitivity in children". Allergol Immunopathol (Madr) 10 (4): 263–8. PMID 6295125. 
4. ^ Schultz-Ehrenburg U, Gilde O (1987). "[Results of studies in chronic urticaria with special reference to nutritional factors]" (in German). Z. Hautkr.. 62 Suppl 1: 88–95. PMID 3442085. 
5. ^ ^{a b c} McCann D, Barrett A, Cooper A, et al. (November 2007). "Food additives and hyperactive behaviour in 3-year-old and 8/9-year-old children in the community: a randomised, double-blinded, placebo-controlled trial". Lancet 370 (9598): 1560–7. doi:10.1016/S0140-6736(07)61306-3. PMID 17825405. 
6. ^ BBC Parents warned of additives link 6 September 2007
7. ^ BBC Europe-wide food colour ban call 10 April 2008
8. ^ FSA Board discusses colours advice 10 April 2008
9. ^ "Food additives". CBC News. 29 September 2008. http://www.cbc.ca/news/background/foodsafety/additives.html. 
10. ^ ^{a b} Meikle, James (11 August 2008). "EU plans warning labels on artificial colours". London: The Guardian. http://www.guardian.co.uk/lifeandstyle/2008/aug/11/foodanddrink.foodsafety. Retrieved 2008-09-08. 
11. ^ BBC Ministers agree food colour ban 12 November 2008
12. ^ "EFSA ::. Scientific Opinion on the re-evaluation of Sunset Yellow FCF (E 110) as a food additive". http://www.efsa.europa.eu/EFSA/efsa_locale-1178620753812_1211903029580.htm.  091113 efsa.europa.eu
13. ^ "Group urges ban of 3 common dyes". CNN. 2010-06-30. http://pagingdrgupta.blogs.cnn.com/2010/06/30/food-dyes-a-health-risk/. Retrieved 2010-07-01. 
14. ^ "Irn Bru unaffected by change in colouring rules.". BBC. 2011-09-09. http://www.bbc.co.uk/news/uk-scotland-scotland-business-14857275.