Amaranth (dye)

Amaranth (dye)

Names
IUPAC name Trisodium (4E)-3-oxo-4-[(4-sulfonato-1-naphthyl)hydrazono]naphthalene-2,7-disulfonate
Other names FD&C Red No. 2, E123, C.I. Food Red 9, Acid Red 27, Azorubin S, C.I. 16185
Identifiers
CAS Number	915-67-3 Y
3D model (Jmol)	Interactive image
ChemSpider	21169821 Y
ECHA InfoCard	100.011.839
E number	E123 (colours)
PubChem	6093196
UNII	37RBV3X49K Y
InChI InChI=1S/C20H14N2O10S3.3Na/c23-20-18(35(30,31)32)10-11-9-12(33(24,25)26)5-6-13(11)19(20)22-21-16-7-8-17(34(27,28)29)15-4-2-1-3-14(15)16;;;/h1-10,23H,(H,24,25,26)(H,27,28,29)(H,30,31,32);;;/q;3*+1/p-3 Y Key: WLDHEUZGFKACJH-UHFFFAOYSA-K Y InChI=1/C20H14N2O10S3.3Na/c23-20-18(35(30,31)32)10-11-9-12(33(24,25)26)5-6-13(11)19(20)22-21-16-7-8-17(34(27,28)29)15-4-2-1-3-14(15)16;;;/h1-10,23H,(H,24,25,26)(H,27,28,29)(H,30,31,32);;;/q;3*+1/p-3 Key: WLDHEUZGFKACJH-DFZHHIFOAW
SMILES [Na+].[Na+].[Na+].[O-]S(=O)(=O)c4ccc(N=Nc1c2ccc(cc2cc(c1O)S([O-])(=O)=O)S([O-])(=O)=O)c3ccccc34
Properties
Chemical formula	C20H11N2Na3O10S3
Molar mass	604.47305
Appearance	Dark red solid
Melting point	120 °C (248 °F; 393 K) (decomposes)
Hazards
R-phrases	R36/37/38
S-phrases	S36/37/39
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Amaranth, FD&C Red No. 2, E123, C.I. Food Red 9, Acid Red 27, Azorubin S, or C.I. 16185 is a dark red to purple 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.

Amaranth is an anionic dye. It can be applied to natural and synthetic fibers, leather, paper, and phenol-formaldehyde resins. As a food additive it has E number E123. Amaranth usually comes as a trisodium salt. It has the appearance of reddish-brown, dark red to purple water-soluble powder that decomposes at 120 °C without melting. Its water solution has absorption maximum at about 520 nm. Like all azo dyes, Amaranth was, during the middle of the 20th century, made from coal tar; modern synthetics are more likely to be made from petroleum byproducts.

Since 1976 Amaranth has been banned in the United States by the Food and Drug Administration (FDA) as a suspected carcinogen. Its use is still legal in some countries, notably in the United Kingdom where it is most commonly used to give Glacé cherries their distinctive color.

After an incident in 1954 involving FD&C Orange Number 1, the FDA retested food colors. In 1960 the FDA was given jurisdiction over color additives, limiting the amounts that could be added to foods and requiring producers of food color to ensure safety and proper labeling of colors. Permission to use food additives was given on a provisional basis, which could be withdrawn should safety issues arise. The FDA gave "generally recognized as safe" (GRAS) provisional status to substances already in use, and extended Red No. 2's provisional status 14 times.