Amaranth (dye)

Amaranth
Names
IUPAC name
Trisodium (4E)-3-oxo-4-[(4-sulfonate-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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.011.839
EC Number
  • 213-022-2
E number E123 (colours)
KEGG
UNII
  • 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
  • [Na+].[Na+].[Na+].[O-]S(=O)(=O)c4ccc(N=Nc1c2ccc(cc2cc(c1O)S([O-])(=O)=O)S([O-])(=O)=O)c3ccccc34
Properties
C20H11N2Na3O10S3
Molar mass 604.47305
Appearance Dark red solid
Melting point 120 °C (248 °F; 393 K) (decomposes)
Hazards
GHS labelling:
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (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 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.

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 an absorption maximum of 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 dye 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.