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Tartrazine

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Tartrazine
Names
IUPAC name Trisodium (4E)-5-oxo-1-(4-sulfonatophenyl)-4--3-pyrazolecarboxylate
Other names FD&C Yellow 5
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.016.091 Edit this at Wikidata
E number E102 (colours)
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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+;;;Key: YXHBBEQKMVAJOH-GLCFPVLVSA-K
  • 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
SMILES
  • ...S(=O)(=O)c1ccc(cc1)/N=N/c3c(nn(c2ccc(cc2)S()(=O)=O)c3O)C()=O
Properties
Chemical formula C16H9N4Na3O9S2
Molar mass 534.3 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound
For the Sonic the Hedgehog character, see E-102 Gamma
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Tartrazine (otherwise known as E number E102, C.I. 19140, or FD&C Yellow 5) is a synthetic lemon yellow azo dye used as a food coloring. It is water soluble and has a maximum absorbance in an aqueous solution at 427±2 nm.

Tartrazine is a commonly used color all over the world, mainly for yellow, but 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 the cook in charge, although nowadays the trend is to avoid it or substitute a non-synthetic dyeing substance such as annatto, malt color, or betacarotene (see Sensitivities & Intolerance, below).

Products including tartrazine commonly include confectionery, cotton candy, soft drinks (Mountain Dew), energy drinks, instant puddings, flavored corn chips (Doritos, nachos, etc.), cereals (corn flakes, muesli, etc.), cake mixes, pastries, custard powder, yellow popcorn, soups (particularly instant or "cube" soups), sauces, some rices (like paella, risotto, etc.), powdered drink mixes, sports drinks, ice cream, ice pops, candy, Gummy Bears Peeps marshmallow treats, chewing gum, marzipan, jam, jelly (particularly mint jelly), gelatins, marmalade, mustard, horseradish, yogurt, noodles such as Kraft Dinner, pickles and other pickled products such as tartar sauce and dill pickle dip, certain brands of fruit squash, fruit cordial, potato chips, biscuits, and many convenience foods together with glycerin, lemon and honey products.

Nonfood products

Soaps, cosmetics, shampoos and other hair products, moisturizers, crayons, hand sanitizer, nail polish, inks for writing instruments and stamp dyes also may use it.

Medications

Vitamins, antacids, medicinal capsules and certain prescription drugs.

Sensitivities and intolerance

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Tartrazine appears to cause the most allergic and intolerance reactions of all the azo dyes, particularly among asthmatics and those with an aspirin intolerance. Symptoms from tartrazine sensitivity can occur by either ingestion or cutaneous exposure to a substance containing tartrazine.

A variety of immunologic responses have been attributed to tartrazine ingestion, including anxiety, migraines, clinical depression, blurred vision, itching, general weakness, heatwaves, feeling of suffocation, purple skin patches, and sleep disturbance.

Certain people who are exposed to the dye experience symptoms of tartrazine sensitivity even at extremely small doses, some for periods up to 72 hours after exposure. In children, asthma attacks and hives have been claimed, as well as supposed links to thyroid tumors, chromosomal damage, and hyperactivity.


The mechanism of sensitivity is obscure and has been called pseudoallergic. The prevalence of tartrazine intolerance is estimated at roughly 360,000 Americans affected, about 0.12% of the general population. According to the FDA, tartrazine causes hives in fewer than 1 in 10,000 people, or 0.01%.

A 1994 study at the University of Melbourne suggested that children previously identified as hyperactive may exhibit an increase in irritability, restlessness, and sleep disturbance after ingesting tartrazine.

It is not clear to what extent these problems can be specifically linked to tartrazine in affected individuals. The existence of a sensitivity reaction is well-known, but the existence of more extreme effects remain controversial. The incidence of tartrazine intolerance is fairly low as indicated above, and 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, 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.

Research in mammals

  • Tartrazine has a noticeable effect on the behavior of young mice.
  • Tartrazine inflamed the stomach lining (increased the number of lymphocytes and eosinophils) of rats when given in the diet for a prolonged time.
  • Tartrazine adversely affects and alters biochemical markers in vital organs, e.g., liver and kidney, not only at higher doses, but also at low doses.

Possible health effects

On September 6, 2007, the British Food Standards Agency revised advice on certain artificial food additives, including tartrazine.

Professor Jim Stevenson from Southampton University, and author of 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."

The following additives were tested in the research:

On April 10, 2008, the Food Standards Agency called for a voluntary removal of the colors (but not sodium benzoate) by 2009. In addition, it recommended that there should be action to phase them out in food and drink in the European Union (EU) over a specified period.

UK ministers have agreed that the six colorings will be phased out by 2009.

Regulation

Because of the problem of tartrazine intolerance, the United States requires the presence of tartrazine to be declared on food and drug products (21 CFR 74.1705, 21 CFR 201.20) and also the color batch used to be preapproved by the FDA. The FDA regularly seizes products if found to be containing undeclared tartrazine, declared but not tested by them, or if labeled other than FD&C yellow 5 or Yellow 5. Such products seized often include Chinese "egg noodles". On June 30, 2010, the Center for Science in the Public Interest (CSPI) called for the FDA to ban Yellow 5. Executive Director Michael Jacobson 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."

The use of tartrazine was banned in Norway, and was also banned in Austria and Germany until the ban was overturned by a European Union directive. The United Kingdom's Food Standards Agency in April 2008 called for a voluntary phase-out of tartrazine, along with five other colorings, due to a reported link with hyperactivity in children.

Organic foods typically use beta carotene as an additive when a yellow color is wanted and annatto(E160b) might be used for nonorganic foods.

Myths

Rumors began circulating about tartrazine in the 1990s regarding a link to its consumption 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 man's penis or cause it to stop growing.

References

  1. Food Standards Australia New Zealand. "Food Additives- Numerical List". Retrieved 2 December 2009. {{cite web}}: Cite has empty unknown parameter: |coauthors= (help)
  2. "Current EU approved additives and their E Numbers", Food Standards Agency website, retrieved 15 Dec 2011
  3. http://siri.org/msds/f2/ccd/ccdqw.html
  4. Jain, Rajeev; Bhargava, Meenakshi; Sharma, Nidhi (2003). "Electrochemical Studies on a Pharmaceutical Azo Dye: Tartrazine". Industrial & Engineering Chemistry Research. 42 (2): 243. doi:10.1021/ie020228q.
  5. "E102 Tartrazine, FD&C yellow No.5". UK Food Guide. Retrieved 2007-11-30.
  6. ^ Rowe KS, Rowe KJ (1994). "Synthetic food coloring and behavior: a dose response effect in a double-blind, placebo-controlled, repeated-measures study". The Journal of Pediatrics. 125 (5 Pt 1): 691–8. doi:10.1016/S0022-3476(06)80164-2. PMID 7965420. {{cite journal}}: Unknown parameter |month= ignored (help)
  7. Donna McCann; et al. (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". The Lancet. 370 (9598): 1560–1567. doi:10.1016/S0140-6736(07)61306-3. PMID 17825405. {{cite journal}}: Explicit use of et al. in: |author= (help)
  8. EFSA: Assessment of the results of the study by McCann et al. (2007) on the effect of some colours and sodium benzoate on children’s behaviour. The EFSA Journal (2008) 660, 1-53.
  9. Elhkim MO, Héraud F, Bemrah N; et al. (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): 308–16. doi:10.1016/j.yrtph.2006.11.004. PMID 17218045. {{cite journal}}: Explicit use of et al. in: |author= (help); Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  10. ^ "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.
  11. Dipalma JR (1990). "Tartrazine sensitivity". American Family Physician. 42 (5): 1347–50. PMID 2239641. {{cite journal}}: Unknown parameter |month= ignored (help)
  12. Michel O, Naeije N, Bracamonte M, Duchateau J, Sergysels R (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. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  13. Tanaka T, Takahashi O, Oishi S, Ogata A (2008). "Effects of tartrazine on exploratory behavior in a three-generation toxicity study in mice". Reproductive Toxicology. 26 (2): 156–63. doi:10.1016/j.reprotox.2008.07.001. PMID 18687399. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  14. Tanaka T (2006). "Reproductive and neurobehavioural toxicity study of tartrazine administered to mice in the diet". Food and Chemical Toxicology. 44 (2): 179–87. doi:10.1016/j.fct.2005.06.011. PMID 16087284. {{cite journal}}: Unknown parameter |month= ignored (help)
  15. Moutinho IL, Bertges LC, Assis RV (2007). "Prolonged use of the food dye tartrazine (FD&C yellow no 5) and its effects on the gastric mucosa of Wistar rats". Brazilian Journal of Biology. 67 (1): 141–5. doi:10.1590/S1519-69842007000100019. PMID 17505761. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  16. Amin KA, Abdel Hameid H 2nd, Abd Elsttar AH (2010). "Effect of food azo dyes tartrazine and carmoisine on biochemical parameters related to renal, hepatic function and oxidative stress biomarkers in young male rats". Food Chem Toxicol. 48 (10): 2994–9. doi:10.1016/j.fct.2010.07.039. PMID 20678534. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link) CS1 maint: numeric names: authors list (link)
  17. "Parents warned of additives link". BBC News. 2007-09-06. Retrieved 2009-04-15.
  18. BBC Europe-wide food colour ban call April 10, 2008
  19. FSA Board discusses colours advice April 10, 2008
  20. BBC Ministers agree food colour ban November 12, 2008
  21. ORA. "IMPORT ALERT IA4502". Fda.gov. Retrieved 2009-04-15.
  22. "Group urges ban of 3 common dyes". CNN. 2010-06-30. Retrieved 2010-07-01.
  23. ^ "CBC News In Depth: Food Safety". CBC.ca. September 29, 2008 (last updated). Retrieved 6 November 2011. {{cite web}}: Check date values in: |date= (help)
  24. EFSA Panel on Food Additives and Nutrient Sources added to Food (ANS) (2009). European Food Safety Authority (ed.). "Scientific Opinion on the re-evaluation Tartrazine (E 102)" (PDF). EFSA Journal. 7 (11). European Food Safety Authority: 1331–1382. doi:10.2903/j.efsa.2009.1331. Retrieved 2011-10-09. The Panel concludes that the present dataset does not give reason to revise the ADI of 7.5 mg/kg bw/day. {{cite journal}}: Unknown parameter |month= ignored (help)
  25. "Europe-wide food colour ban call". BBC News. April 10, 2008.

External links

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