Tartrazine

Tartrazine
IUPAC name Trisodium (4E)-5-oxo-1-(4-sulfonatophenyl)-4-[(4-sulfonatophenyl)hydrazono]-3-pyrazolecarboxylate [citation needed]
Other names FD&C Yellow 5
Identifiers
CAS number	1934-21-0 Y
PubChem	6321403
ChemSpider	10606981 Y
UNII	I753WB2F1M Y
Jmol-3D images	{{#if:[Na+].[Na+].[Na+].[O-]S(=O)(=O)c1ccc(cc1)/N=N/c3c(nn(c2ccc(cc2)S([O-])(=O)=O)c3O)C([O-])=O|Image 1
SMILES [Na+].[Na+].[Na+].[O-]S(=O)(=O)c1ccc(cc1)/N=N/c3c(nn(c2ccc(cc2)S([O-])(=O)=O)c3O)C([O-])=O
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
Properties
Molecular formula	C16H9N4Na3O9S2
Molar mass	534.3 g/mol
Hazards
NFPA 704	1 2 0
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Tartrazine is a synthetic lemon yellow azo dye primarily used as a food coloring.^[1][2] 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).^[3]

Tartrazine is a synthetic organic chemical.^[4][5] It is water soluble^[6] and has a maximum absorbance in an aqueous solution at 427±2 nm.^[7]

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 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 ^{[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. 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) and pureed fruit.

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.

Sensitivities and intolerance

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]

A variety of immunologic responses have been attributed to tartrazine ingestion, including anxiety, migraine,^[9] clinical depression, blurred vision, itching, general weakness, heatwaves, feeling of suffocation, purple skin patches, and sleep disturbance.^[10]

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.^{[citation needed]} In children, asthma attacks and hives have been claimed, as well as supposed links to thyroid tumors and chromosomal damage.^{[citation needed]}. A study has shown that a mixture of Tartrazine (E102), Poncea u 4R (E124), Sunset Yellow FCF (E110), Carmoisine (E122) and sodium benzoate does cause hyperactivity in children tested.^[11][12] However, due to the high polarity of the compound, it is unlikely to cross the blood-brain barrier to produce a psychopharmacological effect, and actual dietary intake of tartrazine is unlikely to produce any adverse effects in humans.^[13]

A study has indicated that exclusion of tartrazine among Asthma patients would benefit those with proven sensitivity to it, but no evidence that it had an effect on most people with Asthma. ^[14]

The mechanism of sensitivity is obscure and has been called pseudoallergic.^{[citation needed]} The prevalence of tartrazine intolerance is estimated at roughly 360,000 Americans affected, less than 0.12% of the general population.^[15] According to the FDA, tartrazine causes hives in fewer than 1 in 10,000 people, or 0.01%.^[16]

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.^[10]

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,^[17] 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.^[18]

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, an 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:

• Sunset yellow (E110) (FD&C Yellow #6) - Coloring found in squashes
• Carmoisine (E122) - Red coloring in jellies
• Tartrazine (E102) (FD&C Yellow #5) - Yellow coloring
• Ponceau 4R (E124) - Red coloring
• Sodium benzoate (E211) - Preservative
• Quinoline yellow (E104) - Food coloring
• Allura red AC (E129) (FD&C Red #40) - Orange / red food dye^[19]

On April 10, 2008, the Food Standards Agency called for a voluntary removal of the colors (but not sodium benzoate) by 2009.^[20] 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.^[21]

UK ministers have agreed that the six colorings will be phased out by 2009.^[22]

Research in mammals

• Tartrazine has a noticeable effect on the behavior of young mice.^[13][23]

• Tartrazine inflamed the stomach lining (increased the number of lymphocytes and eosinophils) of rats when given in the diet for a prolonged time.^[24]

• Tartrazine was found to adversely affect and alter biochemical markers in vital organs, e.g., liver and kidney, of rats, not only at higher doses, but also at low doses.^[25]

Regulation

Canada

Tartrazine is listed as a permitted food coloring in Table III of section B.16.100 of the Food and Drug Regulations. 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".

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.^[26] The results of the consultation supported increased transparency. 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, the official newsletter of the Government of Canada.

Europe

The use of tartrazine was banned in Norway,^[27] and was also banned in Austria^[27] and Germany until the ban was overturned by a European Union directive.^[28] The United Kingdom's Food Standards Agency in April 2008 called for a voluntary phase-out of tartrazine, along with five other colorings, because research it funded suggested a link with hyperactivity in children. They also require any product with tartrazine or five other artificial colorings to have a warning that reads "may have an adverse effect on activity and attention in children".^{[29] [30]}

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.

United States

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.^[16] 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 noodles.^[31] Despite being a synthetic dye, tartrazine may be legally included in organic foods, because the USDA allows processed foods to be certified organic if they are 95% organic by weight.^[32] 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."^[33]

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.^[34][35]

References

External links

• Color Additives Information (Food and Drug Administration)
• Petition to the FDA to delist Yellow #5 (Food and Drug Administration)
• MSDS for Tartrazine (MSDS)
• Some more details, other common names
• Reuters report on EU discussion of Food Additives ban