Names | |
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IUPAC name Trisodium 5-hydroxy-1-(4-sulfonatophenyl)-4-[(E)-(4-sulfonatophenyl)diazenyl]-1H-pyrazole-3-carboxylate | |
Other names
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Identifiers | |
3D model (JSmol) | |
ChemSpider | |
ECHA InfoCard | 100.016.091 |
E number | E102 (colours) |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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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) | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
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, Yellow 5 Lake, Acid Yellow 23, Food Yellow 4, and trisodium 1-(4-sulfonatophenyl)-4-(4-sulfonatophenylazo)-5-pyrazolone-3-carboxylate. [5]
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.
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 (CIBA). This was patented and produced in Germany by BASF in 1885 (DRP 34294). The process was first presented in 1887 in Chemische Berichte , the journal of the German Chemical Society. [6] 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-hydrazo tautomerism). This production process was patented in 1893 (British Patent 5693). [7] [8]
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 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:[ citation needed ]
A number of personal care and cosmetics products may contain tartrazine, usually labelled as CI 19140 or FD&C Yellow 5, including:
Various medications include tartrazine to give a yellow, orange or green hue to a liquid, capsule, pill, lotion, or gel, primarily for easy identification. [9] 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, 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.
Tartrazine is water-soluble [10] and has a maximum absorbance in an aqueous solution at 425 nm. [11] It is one of the oldest known members of the pyrazolone family of dyes. [12]
The prevalence of tartrazine intolerance is estimated at 360,000 U.S. Citizens affected, less than 0.12% of the general population. [13] According to the FDA, tartrazine causes hives in fewer than 1 in 10,000 people, or 0.01%. [14]
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). [15]
Tartrazine has been suspected of exacerbating asthma, but medical evidence does not confirm this. [16]
Tartrazine is one of various food colors said to cause food intolerance and ADHD-like behavior in children. [17] 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. [18] [19]
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. [20] [21] The rumors likely began as the result of an in vitro study showing an effect on estrogen receptors; however this effect was disproven in later in vivo 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. [22]
Tartrazine is listed as a permitted food coloring in Canada. [23] 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". [24]
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. [25] The results of the consultation supported increased transparency. [26] 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, [27] the official newsletter of the Government of Canada.
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). [14] 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]
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. [30] [31]
The European regulatory community, with a stronger[ compared to? ] 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. [18] 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." [18] [32]
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. [33]
Yellow tartrazine (E102) was banned in Austria [34] and Germany, before European Parliament and Council Directive 94/36/EC lifted the ban.
Yellow tartrazine (E102) is banned in Norway (not an E.U. member.) [35] [36]
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. [18] The study found "a possible link between the consumption of these artificial colours and a sodium benzoate preservative and increased hyperactivity" in the children; [18] [37] 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. [18]
In 2008 Scotland asked for Scottish food producers voluntarily stop using these food dyes. [37] A 2010 study found that one third of food producers were still using at least one of the Southampton Six. [38]
Tartrazine has been used as a biocompatible photoblocker for generating transparent hydrogels with complex inner structures. [39]
Food additives are substances added to food to preserve flavor or enhance taste, appearance, or other sensory qualities. Some additives have been used for centuries as part of an effort to preserve food, for example vinegar (pickling), salt (salting), smoke (smoking), sugar (crystallization), etc. This allows for longer-lasting foods such as bacon, sweets or wines. With the advent of ultra-processed foods in the second half of the twentieth century, many additives have been introduced, of both natural and artificial origin. Food additives also include substances that may be introduced to food indirectly in the manufacturing process, through packaging, or during storage or transport.
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 commercial products and in domestic cooking.
Quinoline Yellow WS is a mixture of organic compounds derived from the dye Quinoline Yellow SS. Owing to the presence of sulfonate groups, the WS dyes are water-soluble (WS). It is a mixture of disulfonates (principally), monosulfonates and trisulfonates of 2-(2-quinolyl)indan-1,3-dione with a maximum absorption wavelength of 416 nm.p. 119
Carmine – also called cochineal, cochineal extract, crimson lake, or carmine lake – is a pigment of a bright-red color obtained from the aluminium complex derived from carminic acid. Specific code names for the pigment include natural red 4, C.I. 75470, or E120. Carmine is also a general term for a particularly deep-red color.
Annatto is an orange-red condiment and food coloring derived from the seeds of the achiote tree, native to tropical parts of the Americas. It is often used to impart a yellow to red-orange color to foods, but sometimes also for its flavor and aroma. Its scent is described as "slightly peppery with a hint of nutmeg" and flavor as "slightly nutty, sweet and peppery".
Sunset yellow FCF is a petroleum-derived orange 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. When added to foods sold in the United States, it is known as FD&C Yellow 6; when sold in Europe, it is denoted by E Number E110.
Astaxanthin is a keto-carotenoid within a group of chemical compounds known as carotenones or terpenes. Astaxanthin is a metabolite of zeaxanthin and canthaxanthin, containing both hydroxyl and ketone functional groups.
Canthaxanthin is a keto-carotenoid pigment widely distributed in nature. Carotenoids belong to a larger class of phytochemicals known as terpenoids. The chemical formula of canthaxanthin is C40H52O2. It was first isolated in edible mushrooms. It has also been found in green algae, bacteria, crustaceans, and bioaccumulates in fish such as carp, golden grey mullet, seabream and trush wrasse.
The United States Federal Food, Drug, and Cosmetic Act is a set of laws passed by the United States Congress in 1938 giving authority to the U.S. Food and Drug Administration (FDA) to oversee the safety of food, drugs, medical devices, and cosmetics. The FDA's principal representative with members of congress during its drafting was Charles W. Crawford. A principal author of this law was Royal S. Copeland, a three-term U.S. senator from New York. In 1968, the Electronic Product Radiation Control provisions were added to the FD&C. Also in that year the FDA formed the Drug Efficacy Study Implementation (DESI) to incorporate into FD&C regulations the recommendations from a National Academy of Sciences investigation of effectiveness of previously marketed drugs. The act has been amended many times, most recently to add requirements about bioterrorism preparations.
Sunless tanning, also known as UV filled tanning, self tanning, spray tanning, or fake tanning, refers to the effect of a suntan without exposure to the Sun. Sunless tanning involves the use of oral agents (carotenids), or creams, lotions or sprays applied to the skin. Skin-applied products may be skin-reactive agents or temporary bronzers (colorants).
Brilliant blue FCF is a synthetic organic compound used primarily as a blue colorant for processed foods, medications, dietary supplements, and cosmetics. It is classified as a triarylmethane dye and is known under various names, such as FD&C Blue No. 1 or acid blue 9. It is denoted by E number E133 and has a color index of 42090. It has the appearance of a blue powder and is soluble in water and glycerol, with a maximum absorption at about 628 nanometers. It is one of the oldest FDA-approved color additives and is generally considered nontoxic and safe.
Erythrosine, also known as Red No. 3, is an organoiodine compound, specifically a derivative of fluorone. It is a pink dye which is primarily used for food coloring. It is the disodium salt of 2,4,5,7-tetraiodofluorescein. Its maximum absorbance is at 530 nm in an aqueous solution, and it is subject to photodegradation.
Ponceau 4R is a synthetic colourant that may be used as a food colouring. It is denoted by E Number E124. Its chemical name is 1-(4-sulfo-1-napthylazo)-2-napthol-6,8-disulfonic acid, trisodium salt. Ponceau is the generic name for a family of azo dyes.
Allura Red AC, also known as FD&C Red 40 or E129, is a red azo dye commonly used in food. It was developed in 1971 by the Allied Chemical Corporation, who gave the substance its name.
Azorubine is an azo dye consisting of two naphthalene subunits. It is a red solid. It is mainly used in foods that are heat-treated after fermentation. It has E number E122.
Amaranth, FD&C Red No. 2, E123, C.I. Food Red 9, Acid Red 27, Azorubin S, or C.I. 16185 is a modified red azo dye used as a food dye and to color cosmetics. The name was taken from amaranth grain, a plant distinguished by its red color and edible protein-rich seeds.
The Feingold diet is an elimination diet initially devised by Benjamin Feingold following research in the 1970s that appeared to link food additives with hyperactivity; by eliminating these additives and various foods the diet was supposed to alleviate the condition.
Caramel color or caramel coloring is a water-soluble food coloring. It is made by heat treatment of carbohydrates (sugars), in general in the presence of acids, alkalis, or salts, in a process called caramelization. It is more fully oxidized than caramel candy, and has an odor of burnt sugar and a somewhat bitter taste. Its color ranges from pale yellow to amber to dark brown.
Cosmetics ingredients come from a variety of sources but, unlike the ingredients of food, are often not considered by most consumers. Cosmetics often use vibrant colors that are derived from a wide variety of sources, ranging from crushed insects to rust.
Numerous governmental and non-governmental organizations have criticized the U. S. Food and Drug Administration for alleged excessive and/or insufficient regulation. The U.S. Food and Drug Administration (FDA) is an agency of the United States Department of Health and Human Services and is responsible for the safety regulation of most types of foods, dietary supplements, drugs, vaccines, biological medical products, blood products, medical devices, radiation-emitting devices, veterinary products, and cosmetics. The FDA also enforces section 361 of the Public Health Service Act and the associated regulations, including sanitation requirements on interstate travel as well as specific rules for control of disease on products ranging from animals sold as pets to donations of human blood and tissue.
Importantly, all the studies reporting potential reproductive risks used high doses, which cannot be ingested from food sources. Tartrazine does not seem to exert any reproductive toxicity under the current ADI.
The Panel concludes that the present dataset does not give reason to revise the ADI of 7.5 mg/kg bw/day.