Citrus Red 2

Not to be confused with FD&C 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]

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
CAS Number	6358-53-8 Y
3D model (JSmol)	Interactive image
ChemSpider	16735746 Y
ECHA InfoCard	100.026.162
E number	E121 (colours)
KEGG	C19214 Y
PubChem CID	9570225
UNII	2QE5Y68984 Y
CompTox Dashboard (EPA)	DTXSID6024838
InChI 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+ Y Key: GJUABKCEXOMRPQ-FMQUCBEESA-N Y 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
SMILES COc3ccc(cc3/N=N/c1c2ccccc2ccc1O)OC
Properties
Chemical formula	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)
Solubility in water	Insoluble
Hazards
NFPA 704 (fire diamond)	0 0 0
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

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]

References

1. Anonymous. 1988. Florida Citrus Fruit Laws. Florida Statutes. 601. ^{[full citation needed]}
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