Citrus Red 2

Citrus Red 2, Citrus Red No. 2, C.I. Solvent Red 80, or C.I. 12156 is an artificial dye. As a food dye, it has been permitted by the US Food and Drug Administration (FDA) since 1956 to color the skin of oranges.[1][2][3] Citrus Red 2 is listed by the International Agency for Research on Cancer (IARC) as a group 2B carcinogen, a substance "possibly carcinogenic to humans".[4]

Not to be confused with FD&C Red 2.
Citrus Red 2
Names
IUPAC name
1-(2,5-Dimethoxy-phenylazo)-naphthalen-2-ol
Other names
Citrus Red No. 2, C.I. Solvent Red 80, C.I. 12156, E121
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.026.162
E number E121 (colours)
KEGG
UNII
  • InChI=1S/C18H16N2O3/c1-22-13-8-10-17(23-2)15(11-13)19-20-18-14-6-4-3-5-12(14)7-9-16(18)21/h3-11,21H,1-2H3/b20-19+ checkY
    Key: GJUABKCEXOMRPQ-FMQUCBEESA-N checkY
  • InChI=1/C18H16N2O3/c1-22-13-8-10-17(23-2)15(11-13)19-20-18-14-6-4-3-5-12(14)7-9-16(18)21/h3-11,21H,1-2H3/b20-19+
    Key: GJUABKCEXOMRPQ-FMQUCBEEBN
  • COc3ccc(cc3/N=N/c1c2ccccc2ccc1O)OC
Properties
C18H16N2O3
Molar mass 308.337 g·mol−1
Appearance Orange to yellow solid or a dark red powder
Melting point 156 °C (313 °F; 429 K)
Insoluble
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamond
0
0
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Properties

Citrus Red 2 is an orange to yellow solid or a dark red powder with a melting point of 156 °C. It is not soluble in water, but is readily soluble in many organic solvents.

Use

In the United States, Citrus Red 2 is sometimes used to color oranges. It is only permitted to be used on the peel.[1] It is permitted when the fruit is intended to be eaten, but is not permitted when the fruit is intended or used for processing, for example to manufacture orange juice.[2] It is used on some oranges from the US state of Florida but is banned in the US states of California and Arizona.

References
  1. Anonymous. 1988. Florida Citrus Fruit Laws. Florida Statutes. 601.
  2. "Code of Federal Regulations: Title 21, Section 74.302". U.S. Food and Drug Administration. Retrieved 20 May 2014.
  3. Hall, David J (1989). "Peel Disorders of Florida Citrus as Related to Growing Area and Color-add formulations". Proc. Fla. State Hort. Soc. 102: 243–246.
  4. Agents Classified by the IARC Monographs Archived 2011-10-25 at the Wayback Machine, IARC
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