Tartrazine

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Tartrazine
Names
IUPAC name
Trisodium 5-hydroxy-1-(4-sulfonatophenyl)-4-[(E)-(4-sulfonatophenyl)diazenyl]-1H-pyrazole-3-carboxylate
Other names
FD&C Yellow 5
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.016.091 Edit this at Wikidata
E number E102 (colours)
UNII
  • InChI=1S/C16H12N4O9S2.3Na/c21-15-13(18-17-9-1-5-11(6-2-9)30(24,25)26)14(16(22)23)19-20(15)10-3-7-12(8-4-10)31(27,28)29;;;/h1-8,21H,(H,22,23)(H,24,25,26)(H,27,28,29);;;/q;3*+1/p-3/b18-17+;;; checkY
    Key: YXHBBEQKMVAJOH-GLCFPVLVSA-K checkY
  • InChI=1/C16H12N4O9S2.3Na/c21-15-13(18-17-9-1-5-11(6-2-9)30(24,25)26)14(16(22)23)19-20(15)10-3-7-12(8-4-10)31(27,28)29;;;/h1-8,21H,(H,22,23)(H,24,25,26)(H,27,28,29);;;/q;3*+1/p-3/b18-17+;;;
    Key: YXHBBEQKMVAJOH-KAGMCZNHBW
  • [Na+].[Na+].[Na+].[O-]S(=O)(=O)c1ccc(cc1)/N=N/c3c(nn(c2ccc(cc2)S([O-])(=O)=O)c3O)C([O-])=O
Properties
C16H9N4Na3O9S2
Molar mass 534.36 g·mol−1
20 g/100 mL
Solubility 18 g/100 mL in glycerol, negligible in ethanol
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Tartrazine is a synthetic lemon yellow azo dye primarily used as a food coloring.[1][2][3][4] It is also known as E number E102, C.I. 19140, FD&C Yellow 5, Acid Yellow 23, Food Yellow 4, and trisodium 1-(4-sulfonatophenyl)-4-(4-sulfonatophenylazo)-5-pyrazolone-3-carboxylate).[5]

Tartrazine is a commonly used color all over the world, mainly for yellow, and can also be used with Brilliant Blue FCF (FD&C Blue 1, E133) or Green S (E142) to produce various green shades.

Products containing tartrazine

Foods

Many foods contain tartrazine in varying proportions, depending on the manufacturer or person preparing the food, although the recent trend is to avoid it or substitute a non-synthetic dyeing substance such as annatto, malt color, or beta carotene [citation needed] (see Sensitivities and intolerance, below).

When in food, tartrazine is typically labelled as “color”, “tartrazine”, or “E102”, depending on the jurisdiction, and the applicable labeling laws (see Regulation below).

Products containing tartrazine commonly include processed commercial foods that have an artificial yellow or green color, or that consumers expect to be brown or creamy looking. It has been frequently used in the bright yellow coloring of imitation “lemon” filling in baked goods. The following is a list of foods that may contain tartrazine:

Personal care and cosmetics products

A number of personal care and cosmetics products may contain tartrazine, usually labelled as CI 19140 or FD&C Yellow 5, including:

Medications

Various types of medications include tartrazine to give a yellow, orange or green hue to a liquid, capsule, pill, lotion, or gel, primarily for easy identification.[6] Types of pharmaceutical products that may contain tartrazine include vitamins, antacids, cold medications (including cough drops and throat lozenges), lotions and prescription drugs.

Most, if not all, medication data sheets are required to contain a list of all ingredients, including tartrazine. Some include tartrazine in the allergens alert section.

The Canadian Compendium of Pharmaceuticals and Specialties (CPS), a prescribing reference book for health professionals, mentions tartrazine as a potential allergy for each drug that contains tartrazine.

Other products

Other products, such as household cleaning products, paper plates, pet foods, crayons, inks for writing instruments, stamp dyes, face paints and envelope glues, may also contain tartrazine.

Chemistry

Tartrazine is water-soluble[7] and has a maximum absorbance in an aqueous solution at 425 nm.[8]

Like many azo dyes tartrazine is manufactured using petrochemicals as starting stock, and was formerly manufactured using chemicals derived from coal tar as the starting material.[9]

Potential health effects on humans

Sensitivity

Tartrazine appears to cause the most allergic and intolerance reactions of all the azo dyes, particularly among asthmatics and those with an aspirin intolerance.[10] Symptoms from tartrazine sensitivity can occur by either ingestion or cutaneous exposure to a substance containing tartrazine. Symptoms appear after periods of time ranging from minutes up to 14 hours.[11]

The prevalence of tartrazine intolerance is estimated at roughly 360,000 U.S. Citizens affected, less than 0.12% of the general population.[12] According to the FDA, tartrazine causes hives in fewer than 1 in 10,000 people, or 0.01%.[13]

It is not clear how many individuals are sensitive or intolerant to tartrazine, but the University of Guelph estimates that it is 1 to 10 out of every ten thousand people (0.01% to 0.1% of the population).[14] There is much controversy about whether tartrazine has ill effects on individuals who are not clearly intolerant.

Total avoidance is the most common way to deal with tartrazine sensitivity,[15] but progress has been made in reducing people’s tartrazine sensitivity in a study of people who are simultaneously sensitive to both aspirin and tartrazine.[16]

Asthma

A systematic review of the medical literature concluded that among patients with asthma, research has shown that exposure to tartrazine does not worsen symptoms and avoidance of tartrazine does not improve symptoms; however, "due to the paucity of evidence, it is not possible to provide firm conclusions as to the effects of tartrazine on asthma control".[17]

Regulation

Canada

Tartrazine is listed as a permitted food coloring in Canada.[18] The majority of pre-packaged foods are required to list all ingredients, including all food additives such as color; however section B.01.010 (3)(b) of the Regulations provide food manufacturers with the choice of declaring added color(s) by either their common name or simply as "colour".[19]

In February 2010, Health Canada consulted the public and manufacturers on their plans to change the labelling requirements. Health Canada felt that it might be prudent to require the identification of specific colors on food labels, to allow consumers to make better informed choices.[20] The results of the consultation supported increased transparency.[21] Some respondents proposed banning the use of synthetic food colors, however Health Canada found that existing scientific literature does not demonstrate that synthetic food coloring is unsafe in the general population; they are instead considering more transparent labelling to allow those with sensitivities to food color to make informed choices. The relevant proposed regulatory changes will be developed and published for consultation in Part I of the Canada Gazette,[22] the official newsletter of the Government of Canada.

United Kingdom and EU

The European Food Safety Authority allows for tartrazine to be used in processed cheese, canned or bottled fruit or vegetables, processed fish or fishery products, and wines and wine-based drinks.[23][24]

In response to concerns about the safety of certain food additives, the UK FSA commissioned a study by researchers at Southampton University of the effect of a mixture of six food dyes (Tartrazine, Allura Red, Ponceau 4R, Quinoline Yellow WS, Sunset Yellow 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.[25][26] The study found "a possible link between the consumption of these artificial colours and a sodium benzoate preservative and increased hyperactivity" in the children;[25][26] 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.[25]

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.[25][26] 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."[25][27]

United States

The United States requires the presence of tartrazine to be declared on food and drug products (21 CFR 74.1705 (revised April 2013), 21 CFR 201.20) and also color batches to be preapproved by the United States Food and Drug Administration (FDA).[13] As part of these regulations, the FDA requires that the Precautions section of prescription drug labels include the warning statement, "This product contains FD+C Yellow No. 5 (tartrazine) which may cause allergic-type reactions (including bronchial asthma) in certain susceptible persons. Although the overall incidence of FD+C Yellow No. 5 (tartrazine) sensitivity in the general population is low, it is frequently seen in patients who also have aspirin hypersensitivity."[28]

The FDA regularly seizes products if found to be containing undeclared tartrazine, declared but not FDA-tested, or labeled something other than FD&C yellow 5 or Yellow 5. Such products seized often include noodles.[29]

In 2010, the Center for Science in the Public Interest (CSPI) called for the FDA to ban Yellow 5.[30] The FDA reviewed the data, and did not ban it.[25]

Alternative coloring agents

Organic foods typically use beta carotene or curcumin (from turmeric) as an additive when a yellow color is wanted and annatto (E160b) might be used for non organic foods. Other alternatives include chlorophyll (green), beet powder (red or pink), cocoa powder (brown), paprika (brown) and saffron (orange).

Myths

Rumors began circulating about tartrazine in the 1990s regarding a link to its consumption (specifically its use in Mountain Dew) and adverse effects on male potency, testicle and penis size, and sperm count. There are no documented cases supporting the claim tartrazine will shrink a penis or cause it to stop growing.[31][32]

Although tartrazine is one of various food colors said to cause food intolerance and ADHD-like behavior in children, evidence for this claim is lacking.[33]: 452  It is possible that certain food colorings may act as a trigger in those who are genetically predisposed, but the evidence is weak.[25][34]

References

  1. ^ Food Standards Australia New Zealand. "Food Additives- Numerical List". Archived from the original on June 25, 2009. Retrieved 2 December 2009. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  2. ^ Current EU approved additives and their E Numbers, Food Standards Agency website, retrieved 15 Dec 2011
  3. ^ "Food Dyes". Center for Science in the Public Interest. Retrieved 8 March 2013.
  4. ^ "What is Food Coloring Made Of?". WiseGeek. Retrieved 8 March 2013.
  5. ^ "Acid Yellow 23". ChemBlink, an online database of chemicals from around the world.
  6. ^ "Tartrazine". drugs.com.
  7. ^ http://siri.org/msds/f2/ccd/ccdqw.html
  8. ^ Jain, Rajeev; Bhargava, Meenakshi; Sharma, Nidhi (2003). "Electrochemical Studies on a Pharmaceutical Azo Dye: Tartrazine". Industrial & Engineering Chemistry Research. 42 (2): 243–247. doi:10.1021/ie020228q.
  9. ^ Nutrition, Center for Food Safety and Applied. "Color Additives: FDA's Regulatory Process and Historical Perspectives". FDA.
  10. ^ "E102 Tartrazine, FD&C yellow No.5". UK Food Guide. Retrieved 2007-11-30.
  11. ^ Alvarez Cuesta E, Alcover Sánchez R, Sainz Martín T, Anaya Turrientes M, García Rodríguez D (Jan–Feb 1981). "[Pharmaceutical preparations which contain tartrazine]". Allergol Immunopathol (Madr). 9 (1): 45–54.
  12. ^ Elhkim MO, Héraud F, Bemrah N, et al. (April 2007). "New considerations regarding the risk assessment on Tartrazine: An update toxicological assessment, intolerance reactions and maximum theoretical daily intake in France". Regulatory Toxicology and Pharmacology. 47 (3): 308–316. doi:10.1016/j.yrtph.2006.11.004. PMID 17218045.
  13. ^ a b "Does FD&C Yellow No. 5 cause any allergic reactions?". United States Food and Drug Administration. Archived from the original on 2007-10-09. Retrieved 2007-10-20.
  14. ^ Food Science | Educating Food Leaders for over 100 years
  15. ^ Dipalma JR (November 1990). "Tartrazine sensitivity". American Family Physician. 42 (5): 1347–50. PMID 2239641.
  16. ^ Michel O, Naeije N, Bracamonte M, Duchateau J, Sergysels R (May 1984). "Decreased sensitivity to tartrazine after aspirin desensitization in an asthmatic patient intolerant to both aspirin and tartrazine". Annals of Allergy. 52 (5): 368–70. PMID 6721262.
  17. ^ Ardern KD, Ram FS (2014-01-24). "Tartrazine exclusion for allergic asthma". Cochrane Database Syst Rev (4): CD000460. doi:10.1002/14651858.CD000460. PMID 11687081.
  18. ^ Table III of section B.16.100, Food and Drug Regulations
  19. ^ section B.01.010 (3)(b)
  20. ^ "Health Canada Proposal to Improve Food Colour Labelling Requirements". Health Canada. Retrieved 15 June 2012.
  21. ^ Health Canada reviews comments received on the proposed changes to current food colour labelling regulations for prepackaged foods
  22. ^ Canada Gazette
  23. ^ further details can be found on the EFSA food additives database page on tartrazine
  24. ^ FOODS
  25. ^ a b c d e f g 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
  26. ^ a b c 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]
  27. ^ EFSA Panel on Food Additives and Nutrient Sources added to Food (ANS) (November 2009). "Scientific Opinion on the re-evaluation Tartrazine (E 102)". EFSA Journal. 7 (11): 1331–1382. doi:10.2903/j.efsa.2009.1331. The Panel concludes that the present dataset does not give reason to revise the ADI of 7.5 mg/kg bw/day.
  28. ^ CFR - Code of Federal Regulations Title 21
  29. ^ ORA (May 2, 2013). "Import Alert 45-02". fda.gov. Retrieved May 5, 2013.
  30. ^ "Group urges ban of 3 common dyes". CNN. 2010-06-30. Retrieved 2010-07-01.
  31. ^ "Re: DOES YELLOW 5 LOWER SPERM COUNT". Madsci.org. Retrieved 2012-11-10.
  32. ^ "Mountain Dew Shrinks Testicles". snopes.com. Retrieved 2012-11-10.
  33. ^ 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
  34. ^ 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.

External links

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