Citrus Red 2
{{Distinguish|FD&C Red 2}}
{{Globalise|date=February 2016}}
{{chembox
| verifiedrevid = 433355550
| ImageFile = Citrus Red 2.png
| ImageFile1 = Citrus Red 2 ball-and-stick.png
| IUPACName = 1-(2,5-Dimethoxy-phenylazo)-naphthalen-2-ol
| OtherNames = {{Unbulleted list|Citrus Red No. 2|C.I. Solvent Red 80|C.I. 12156|E121}}
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 16735746
| 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+
| InChIKey = GJUABKCEXOMRPQ-FMQUCBEEBN
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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+
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = GJUABKCEXOMRPQ-FMQUCBEESA-N
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 6358-53-8
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 2QE5Y68984
| PubChem = 9570225
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C19214
| SMILES = COc3ccc(cc3/N=N/c1c2ccccc2ccc1O)OC
}}
|Section2={{Chembox Properties
| C=18 | H=16 | N=2 | O=3
| Appearance = Orange to yellow solid or a dark red powder
| Density =
| MeltingPtC = 156
| BoilingPt =
| Solubility = Insoluble
}}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
| NFPA-H = 0
| NFPA-F = 0
| NFPA-R = 0
}}
}}
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.{{Cite web |title=21 CFR 74.302 -- Citrus Red No. 2. |url=https://www.ecfr.gov/current/title-21/chapter-I/subchapter-A/part-74/subpart-A/section-74.302 |access-date=2025-05-05 |website=www.ecfr.gov |language=en}} 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".[http://monographs.iarc.fr/ENG/Classification/ClassificationsGroupOrder.pdf Agents Classified by the IARC Monographs] {{Webarchive|url=https://web.archive.org/web/20111025122327/http://monographs.iarc.fr/ENG/Classification/ClassificationsGroupOrder.pdf |date=2011-10-25 }}, IARC
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 has sometimes been used to color orange peels, subject to a limit of 2 milligrams per kilogram of oranges. It is permitted when the fruit is intended to be eaten, but not when the fruit is intended for processing; for example, to manufacture orange juice.
On April 22, 2025, the FDA announced plans to phase out synthetic food dyes by the end of 2026. This decision, led by FDA Commissioner Martin Makary, was driven by growing concerns over the potential health risks associated with synthetic food dyes. As part of this phase-out, the FDA revealed its intention to revoke approval for Citrus Red 2, along with another restricted-use dye, Orange B.{{Cite web |last=Choi |first=Joseph |date=2025-04-22 |title=FDA announces plans to phase out petroleum-based food dyes |url=https://thehill.com/policy/healthcare/5261583-fda-phases-out-petroleum-food-dyes/ |access-date=2025-04-24 |website=The Hill}}