Scarlet GN, or C.I. Food Red 2, FD&C Red No. 4, or C.I. 14815 is a red azo dye once used as a food dye. As a food additive, it has the E number E125. It is usually used as a disodium salt.
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| Names | |
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| Systematic IUPAC name
Disodium 3-[(2,4-Dimethyl-5-sulfonatophenyl)hydrazinylidene]-4-oxonaphthalene-1-sulfonate | |
Other names
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| Identifiers | |
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3D model (JSmol) |
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| ChemSpider |
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| ECHA InfoCard | 100.019.870 |
| EC Number |
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| E number | E125 (colours) |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C18H14N2Na2O7S2 | |
| Molar mass | 480.42 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Preparation
editTo synthesize Food Red 2, 2,4-dimethylaniline-6-sulfonic acid is diazotized with sodium nitrite and hydrochloric acid Diazotization.[1] The resulting diazonium salt is reacted with 5-hydroxynaphthalene-1-sulfonic acid via azo coupling.
Use
editOriginally, Food Red 2 was used as a food colorant. Under the designation E 125, Food Red 2 was approved as a food colorant in the EU by Directive 62/2645/EEC until the end of 1976.[2][3]
Food Red 2 is mainly used as a colorant in cosmetics (shampoos, bubble bath, liquid soaps).[4] It is approved in the EU by Regulation (EC) No. 1223/2009.[5] The colorant is also approved for cosmetics in South Africa, Turkey, and Thailand, whereas in Japan and the USA it may not be used in food, pharmaceuticals, or cosmetics.[4]
In the United States, it is not permitted for use in food or ingested drugs and may only be used in externally applied drugs and cosmetics, due to potential carcinogenic effects from ingesting it.[6][7][8] An exception was added in 1965 to allow its use in the coloring of maraschino cherries, which were considered mainly decorative and not a foodstuff.[9] This exception was repealed and the dye banned in the US on September 22, 1976 due to mounting safety concerns.[10] In the European Union, it is not permitted as a food additive.[11]
References
edit- ↑ Alfred Junghahn (1902), "Ueber die 1.3.4-Xylidin-5-sulfonsäure", Berichte der deutschen chemischen Gesellschaft, vol. 35, no. 3, pp. 3747–3767, doi:10.1002/cber.190203503208
- ↑ Aufgenommen durch die EU-Richtlinie 1962 2645.
- ↑ Gestrichen durch die EU-Richtlinie 1976 399.
- 1 2 Gisbert Otterstätter (2007), Färbung von Lebensmitteln, Arzneimitteln, Kosmetika (3 ed.), Hamburg: Behr’s Verlag, ISBN 978-3-89947-369-8
- ↑ EU-Verordnung 2009 1223, Anhang IV: Liste der in kosmetischen Mitteln zugelassene Farbstoffe, Laufende Nummer 20.
- ↑ 21 CFR 81.10
- ↑ 21 CFR 81.30
- ↑ 21 CFR 82.304
- ↑ Pavia, Donald L. (2005). Introduction to Organic Laboratory Techniques: A Small Scale Approach (2nd ed.). Thomson Brooks/Cole. pp. 387–389. ISBN 0534408338. Retrieved January 25, 2013.
- ↑ "F.D.I. Bans Use of Red No. 4 Dye And Carbon Black in Food Items". New York Times. September 23, 1976. Retrieved 20 February 2025.
- ↑ Current EU approved additives and their E Numbers, Food Standards Agency