Tartrazine
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Tartrazine is a synthetic lemon yellow azo dye primarily used as a
food coloring Food coloring, color additive or colorant is any dye, pigment, or substance that imparts color when it is added to food or beverages. Colorants can be supplied as liquids, powders, gels, or pastes. Food coloring is commonly used in commercia ...
. It is also known as
E number E numbers, short for Europe numbers, are codes for substances used as food additives, including those found naturally in many foods, such as vitamin C, for use within the European Union (EU) and European Free Trade Association (EFTA). Commonly ...
E102, C.I. 19140, FD&C Yellow 5, Yellow 5
Lake A lake is often a naturally occurring, relatively large and fixed body of water on or near the Earth's surface. It is localized in a basin or interconnected basins surrounded by dry land. Lakes lie completely on land and are separate from ...
, Acid Yellow 23, Food Yellow 4, and trisodium 1-(4-sulfonatophenyl)-4-(4-sulfonatophenylazo)-5-pyrazolone-3-carboxylate. Tartrazine is a commonly used coloring agent 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. It serves as a dye for wool and silks, a colorant in food, drugs and cosmetics and an adsorption-elution indicator for chloride estimations in biochemistry.


History

Tartrazine was discovered in 1884 by Swiss chemist Johann Heinrich Ziegler, who developed the yellow azo dye in the laboratories of the Bindschedler'sche Fabrik für chemische Industrie in
Basel Basel ( ; ), also known as Basle ( ), ; ; ; . is a city in northwestern Switzerland on the river Rhine (at the transition from the High Rhine, High to the Upper Rhine). Basel is Switzerland's List of cities in Switzerland, third-most-populo ...
( CIBA). This was patented and produced in Germany by
BASF BASF SE (), an initialism of its original name , is a European Multinational corporation, multinational company and the List of largest chemical producers, largest chemical producer in the world. Its headquarters are located in Ludwigshafen, Ge ...
in 1885 (DRP 34294). The process was first presented in 1887 in '' Chemische Berichte'', the journal of the German Chemical Society. Although the structure proposed by Ziegler was not confirmed, he was able to develop an alternative synthesis of tartrazine based on the idea that a hydrazone is the tautomeric form of an
azo compound Azo compounds are organic compounds bearing the functional group diazenyl (, in which R and R′ can be either aryl or alkyl groups). IUPAC defines azo compounds as: "Derivatives of diazene (diimide), , wherein both hydrogens are substituted ...
(azo-hydrazo tautomerism). This production process was patented in 1893 (British Patent 5693).


Products containing tartrazine


Foods

Many foods contain tartrazine in various proportions, depending on the manufacturer or person preparing the food. When in food, tartrazine is typically labelled as "color", "tartrazine", or "E102", depending on the jurisdiction, and the applicable labeling laws (see
Regulation Regulation is the management of complex systems according to a set of rules and trends. In systems theory, these types of rules exist in various fields of biology and society, but the term has slightly different meanings according to context. Fo ...
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 confectionery:
ice cream Ice cream is a frozen dessert typically made from milk or cream that has been flavoured with a sweetener, either sugar or an alternative, and a spice, such as Chocolate, cocoa or vanilla, or with fruit, such as strawberries or peaches. Food ...
, ice pops and popsicles,
confectionery Confectionery is the Art (skill), art of making confections, or sweet foods. Confections are items that are rich in sugar and carbohydrates, although exact definitions are difficult. In general, however, confections are divided into two bro ...
and hard candy (such as gummy bears, marshmallows, etc.), cotton candy, instant puddings and gelatin,
cake Cake is a flour confection usually made from flour, sugar, and other ingredients and is usually baked. In their oldest forms, cakes were modifications of bread, but cakes now cover a wide range of preparations that can be simple or elabor ...
mixes, pastries, custard powder, marzipan,
biscuits A biscuit is a Flour, flour-based baked food item. Biscuits are typically hard, flat, and Unleavened bread, unleavened. They are usually sweet and may be made with sugar, chocolate, icing (food), icing, jam, ginger, or cinnamon. They can also ...
, and cookies. * Beverages: soft drinks, energy and sports drinks, powdered drink mixes, fruit cordials, and flavored/mixed alcoholic beverages. * Snacks: flavored corn chips (such as nachos, etc.),
chewing gum Chewing gum is a soft, cohesive substance designed to be chewed without being swallowed. Modern chewing gum is composed of gum base, sweeteners, softeners/plasticizers, flavors, colors, and, typically, a hard or powdered polyol coating. Its tex ...
,
popcorn Popcorn (also called popped corn, popcorns, or pop-corn) is a variety of corn kernel which expands and puffs up when heated. The term also refers to the snack food produced by the expansion. It is one of the oldest snacks, with evidence of p ...
(both microwave and cinema-popped), and potato chips. * Condiments and spreads: jam, jelly (including mint jelly), marmalade, mustard,
horseradish Horseradish (''Armoracia rusticana'', syn. ''Cochlearia armoracia'') is a perennial plant of the family Brassicaceae (which also includes Mustard plant, mustard, wasabi, broccoli, cabbage, and radish). It is a root vegetable, cultivated and us ...
, pickles (and other products containing pickles such as tartar sauce and dill pickle dip), and processed sauces. * Other processed foods:
cereal A cereal is a grass cultivated for its edible grain. Cereals are the world's largest crops, and are therefore staple foods. They include rice, wheat, rye, oats, barley, millet, and maize ( Corn). Edible grains from other plant families, ...
(such as
corn flakes Corn flakes, or cornflakes, are a breakfast cereal made from toasting flakes of corn (maize). Originally invented as a Breakfast, breakfast food to counter indigestion, it has become a popular food item in the American cuisine, American diet and ...
,
muesli Muesli ( ) is a cold Swiss cuisine, Swiss breakfast dish, the primary ingredient of which is rolled oats. Traditionally, it is set to soak in water overnight ("overnight oats") and eaten the next morning with fresh fruit, nuts, lemon juice, and ...
, etc.), instant or "cube" soups,
rice Rice is a cereal grain and in its Domestication, domesticated form is the staple food of over half of the world's population, particularly in Asia and Africa. Rice is the seed of the grass species ''Oryza sativa'' (Asian rice)—or, much l ...
s (like
paella Paella (, , , , ; ) is a rice dish originally from the Valencian Community. ''Paella'' is regarded as one of the community's identifying symbols. It is one of the best-known dishes in Spanish cuisine. The dish takes its name from the wide, sha ...
, risotto, etc.), noodles, 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
soap Soap is a salt (chemistry), salt of a fatty acid (sometimes other carboxylic acids) used for cleaning and lubricating products as well as other applications. In a domestic setting, soaps, specifically "toilet soaps", are surfactants usually u ...
s, green hand sanitizer,
moisturizer A moisturizer, or emollient, is a Cosmetics, cosmetic preparation used for protecting, moisturizing, and lubricating the Human skin, skin. These functions are normally performed by Sebaceous gland, sebum produced by healthy skin. The word "emollie ...
s and
lotion Lotion is a low-viscosity topical preparation intended for application to the skin. By contrast, creams and gels have higher viscosity, typically due to lower water content. Lotions are applied to external skin with bare hands, a brush, a clea ...
s, mouth washes,
perfumes Perfume (, ) is a mixture of fragrance, fragrant essential oils or aroma compounds (fragrances), Fixative (perfumery), fixatives and solvents, usually in liquid form, used to give the human body, animals, food, objects, and living-spaces an agre ...
, 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 (also known as nail varnish in British English or nail enamel) is a lacquer that can be applied to the human Nail (anatomy), fingernails or toenails to decorate and protect the nail plates. The formula has been revised repeatedly t ...
, nail polish remover, temporary tattoos, and tanning lotions.


Medications

Various 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 Vitamins are organic molecules (or a set of closely related molecules called vitamers) that are essential to an organism in small quantities for proper metabolic function. Essential nutrients cannot be synthesized in the organism in suff ...
, antacids, cold medications (including cough drops and
throat lozenge A throat lozenge (also known as a cough drop, sore throat sweet, troche, cachou, pastille or cough sweet) is a small, typically medicated tablet intended to be dissolved slowly in the mouth to temporarily stop coughs, lubricate, and soothe irri ...
s), 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, envelope glues, and deodorants, may also contain tartrazine.


Chemistry

Tartrazine is water-soluble and has a maximum absorbance in an aqueous solution at 425 nm. It is one of the oldest known members of the
pyrazolone Pyrazolone is 5-membered heterocycle containing two adjacent nitrogen atoms. It can be viewed as a derivative of pyrazole possessing an additional ketone, carbonyl (C=O) group. Compounds containing this functional group are useful commercially in ...
family of dyes.


Potential health effects on humans


Food intolerance, sensitivity, and allergies

The prevalence of tartrazine
intolerance Intolerance may refer to: * Hypersensitivity or intolerance, undesirable reactions produced by the immune system * ''Intolerance'' (film), a 1916 film by D. W. Griffith * ''Intolerance'' (album), the first solo album from Grant Hart, formerly ...
is estimated at 360,000 U.S. Citizens affected, less than 0.12% of the general population. According to the FDA, tartrazine causes
hives Hives, also known as urticaria, is a kind of skin rash with red or flesh-colored, raised, itchy bumps. Hives may burn or sting. The patches of rash may appear on different body parts, with variable duration from minutes to days, and typically ...
in fewer than 1 in 10,000 people, or 0.01%. It is not clear how many individuals are sensitive or intolerant to tartrazine, but the
University of Guelph The University of Guelph (abbreviated U of G) is a comprehensive Public university, public research university in Guelph, Ontario, Canada. It was established in 1964 after the amalgamation of Ontario Agricultural College (1874), the MacDonald I ...
estimates that it is 1 to 10 out of every ten thousand people (0.01% to 0.1% of the population).


Asthma

Tartrazine has been suspected of exacerbating
asthma Asthma is a common long-term inflammatory disease of the airways of the lungs. It is characterized by variable and recurring symptoms, reversible airflow obstruction, and easily triggered bronchospasms. Symptoms include episodes of wh ...
, but medical evidence does not confirm this.


Food intolerance and ADHD-like behavior

Tartrazine is one of various food colors said to cause food intolerance and ADHD-like behavior in children. It is possible that certain food colorings may act as a trigger in those who are genetically predisposed, but the evidence for this effect is weak.


Reproductive

Rumors began circulating about tartrazine in the 1990s regarding a link to its consumption (specifically its use in Mountain Dew) and alleged adverse effects on male erectile function, testicle and penis size, and sperm count. The rumors likely began as the result of an ''
in vitro ''In vitro'' (meaning ''in glass'', or ''in the glass'') Research, studies are performed with Cell (biology), cells or biological molecules outside their normal biological context. Colloquially called "test-tube experiments", these studies in ...
'' study showing an effect on estrogen receptors; however this effect was disproven in later ''
in vivo Studies that are ''in vivo'' (Latin for "within the living"; often not italicized in English) are those in which the effects of various biological entities are tested on whole, living organisms or cells, usually animals, including humans, an ...
'' studies. Tartrazine may have a reproductive effect at extremely high dosages, however it has no reproductive effect at the levels found in one food product.


Regulation


North America


Canada

Tartrazine is listed as a permitted food coloring in Canada. 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". The maximum permitted level of tartazine is 300 ppm.


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 The United States Food and Drug Administration (FDA or US FDA) is a List of United States federal agencies, federal agency of the United States Department of Health and Human Services, Department of Health and Human Services. The FDA is respo ...
(FDA). 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." 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.


Europe


European Union

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. The European regulatory community 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. 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." Tartrazine is among six artificial colors for which the European Union requires products that contain them to be marked with the statement ''May have an adverse effect on activity and attention in children''.


Austria and Germany

Yellow tartrazine (E102) was banned in Austria and Germany, before European Parliament and Council Directive 94/36/EC lifted the ban.


Norway

Yellow tartrazine (E102) was also banned in Norway several years ago, but the ban was likewise lifted due to the implementation of EU directive 94/36/EC. (Norway is not an E.U. member state, but has signed up to follow most EU regulations via the EEA agreement.)


United Kingdom

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 Sunset yellow FCF (also known as orange yellow S, or C.I. 15985) is a petroleum-derived orange Azo compound, azo dye with a pH-dependent maximum absorption at about 480 nm at pH 1 and 443 nm at pH 13, with a shoulder at 500 nm. Wh ...
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. The study found "a possible link between the consumption of these artificial colours and a sodium benzoate preservative and increased hyperactivity" in the children;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
/ref> 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. In 2008 Scotland asked for Scottish food producers voluntarily stop using these food dyes. A 2010 study found that one third of food producers were still using at least one of the Southampton Six.


Other uses


3D printing

Tartrazine has been used as a biocompatible photoblocker for generating transparent hydrogels with complex inner structures.


See also

* Sunset yellow FCF, also known as Yellow 6


References


External links


Color Additives Information, 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, European Food Safety Authority
{{Authority control Azo dyes Food colorings Organic sodium salts Benzenesulfonates Pyrazoles Salts of carboxylic acids E-number additives Acid dyes