Tartrazine

Tartrazine

Names
IUPAC name Trisodium (4E)-5-oxo-1-(4-sulfonatophenyl)-4-[(4-sulfonatophenyl)hydrazono]-3-pyrazolecarboxylate
Other names FD&C Yellow 5
Identifiers
CAS Number	1934-21-0 Y
ChemSpider	10606981 Y
Jmol interactive 3D	Image
PubChem	6321403
UNII	I753WB2F1M Y
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+;;; Y Key: YXHBBEQKMVAJOH-GLCFPVLVSA-K Y 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 [Na+].[Na+].[Na+].[O-]S(=O)(=O)c1ccc(cc1)/N=N/c3c(nn(c2ccc(cc2)S([O-])(=O)=O)c3O)C([O-])=O
Properties
Chemical formula	C16H9N4Na3O9S2
Molar mass	534.36 g·mol−1
Hazards
NFPA 704	1 2 0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

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 betacarotene (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:

• Desserts and sweets: ice cream, ice pops and popsicles, confectionery and hard candy (such as gummy bears, Peeps marshmallow treats, etc.), cotton candy, instant puddings and gelatin (such as Jell-O), cake mixes, pastries (such as Pillsbury pastries), custard powder, marzipan, biscuits and cookies.

• Beverages: soft drinks (such as Mountain Dew), energy and sports drinks, powdered drink mixes (such as Kool-Aid), fruit cordials, and flavored/mixed alcoholic beverages.

• Snacks: flavored corn chips (such as Doritos, nachos, etc.), chewing gum, popcorn (both microwave and cinema-popped), and potato chips.

• Condiments and spreads: jam, jelly (including mint jelly), marmalade, mustard, horseradish, pickles (and other products containing pickles such as tartar sauce and dill pickle dip), and processed sauces.

• Other processed foods: cereal (such as corn flakes, muesli, etc.), instant or "cube" soups), rices (like paella, risotto, etc.), noodles (such as some varieties of Kraft Dinner), pureed fruit and pickled peppers, bright-green-colored seaweed salad.

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:

• Liquid and bar soaps, green hand sanitizer, moisturizers and lotions, mouth washes, perfumes, toothpastes, and shampoos, conditioners and other hair products.

• Cosmetics, such as eyeshadow, blush, face powder and foundation, lipstick, etc. - even those that are primarily pink or purple. (Usually make-up manufacturers use one label for all shades in a product line, placing the phrase "may contain" ahead of all colors that are used in that line, not necessarily that specific shade.)

• Nail polish, nail polish remover, temporary tattoos, and tanning lotions.

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. 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.

Chemical properties

Tartrazine is water-soluble^[6] and has a maximum absorbance in an aqueous solution at 425 nm.^[7]

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.^[8] 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 to 6 to 14 hours.^[9]

The prevalence of tartrazine intolerance is estimated at roughly 360,000 Americans affected, less than 0.12% of the general population.^[10] According to the FDA, tartrazine causes hives in fewer than 1 in 10,000 people, or 0.01%.^[11]

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).^[12] 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,^[13] 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.^[14]

Asthma

People with asthma who have a proven sensitivity to tartrazine benefit from avoiding it, but there is no evidence that eliminating tartrazine has an effect on most people with asthma.^[15]

Regulation

Canada

Tartrazine is listed as a permitted food coloring in Canada.^[16] 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".^[17]

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.^[18] The results of the consultation supported increased transparency.^[19] 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,^[20] 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.^[21][22]

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.^[23][24] The study found "a possible link between the consumption of these artificial colours and a sodium benzoate preservative and increased hyperactivity" in the children;^[23][24] 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.^[23]

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.^[23][24] 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."^[23][25]

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).^[11] As part of these regulations, the U.S. Food and Drug Administration (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."^[26]

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.^[27]

In 2010, the Center for Science in the Public Interest (CSPI) called for the FDA to ban Yellow 5.^[28] The FDA reviewed the data, and did not ban it.^[23]

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 man's penis or cause it to stop growing.^[29][30]

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.^[31]:452 It is possible that certain food colorings may act as a trigger in those who are genetically predisposed, but the evidence is weak.^[23][32]

References

External links

• Color Additives Information (Food and Drug Administration)
• Petition to the FDA to delist Yellow #5 (Food and Drug Administration)
• "Scientific Opinion on the re-evaluation Tartrazine (E 102) / EFSA Panel on Food Additives and Nutrient Sources added to Food (ANS), EFSA Journal 2009; 7(11):1331" (PDF). European Food Safety Authority (EFSA), Parma, Italy. Retrieved 2015-10-25. 
• MSDS for Tartrazine (MSDS)
• Some more details, other common names
• Reuters report on EU discussion of Food Additives ban