Erythrosine

Erythrosine
Names
IUPAC name
2-(6-Hydroxy-2,4,5,7-tetraiodo-3-oxo-xanthen-9-yl)benzoic acid
Identifiers
16423-68-0 YesY
3D model (Jmol) Interactive image
ChEMBL ChEMBL1332616 N
ChemSpider 3144 YesY
ECHA InfoCard 100.036.779
E number E127 (colours)
PubChem 3259
UNII 8TL7LH93FM N
Properties
C20H6I4Na2O5
Molar mass 879.86 g/mol
Melting point 142 to 144 °C (288 to 291 °F; 415 to 417 K)[1]
Hazards
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
1
2
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Erythrosine, also known as Red No. 3, is an organoiodine compound, specifically a derivative of fluorone. It is cherry-pink synthetic, primarily used for food coloring.[2] It is the disodium salt of 2,4,5,7-tetraiodofluorescein. Its maximum absorbance is at 530 nm[3] in an aqueous solution, and it is subject to photodegradation.

Uses

It is used as a:

Erythrosine is commonly used in sweets such as some candies and popsicles, and even more widely used in cake-decorating gels. It is also used to color pistachio shells.[8][9] As a food additive, it has the E number E127.

Health effects

As a result of efforts begun in the 1970s, in 1990 the U.S. FDA had instituted a partial ban on erythrosine, citing research that high doses have been found to cause cancer in rats.[10] In June 2008, the Center for Science in the Public Interest (CSPI) petitioned the FDA for a complete ban on erythrosine in the United States.[11]

A series of toxicology tests combined with a review of other reported studies concluded that erythrosine is non-genotoxic and the above-mentioned increase in tumors is caused by a non-genotoxic mechanism.[12]

A 1990 study concluded that "chronic erythrosine ingestion may promote thyroid tumor formation in rats via chronic stimulation of the thyroid by TSH." [13]

Regulation and prevalence

While commonly used in many countries of the world, erythrosine is less commonly used in the United States (the second least used after Fast Green FCF) because Allura Red AC (Red #40) is generally used instead. However, Allura Red AC is banned in many European countries because it is an azo dye.[14] Erythrosine can be used in colored food and ingested drugs in the USA without any restriction, however, its use is banned in cosmetics and external drugs.[15] The lake variant is also banned from use in the United States.

Synonyms

Erythrosine B; Erythrosin B; Acid Red 51; C.I. 45430; FD & C Red No.3; E127; 2',4',5',7'-Tetraiodo-3',6'-dihydroxy-spiro[3H-isobenzofuran-1,9'-xanthen]-3-one disodium salt; Tetraiodofluorescein Sodium Salt; Calcoid Erythrosine N; 2,4,5,7-Tetraiodo-3,6-dihydroxyxanthene-9-spiro-1'-3H-isobenzofuran-3'-one disodium salt; 2',4',5',7'-Tetraiodofluorescein, disodium salt; C.I.Food Red 14; Aizen Erythrosine; Tetraiodifluorescein, disodium salt; Spiro[isobenzofuran- 1(3H),9'-[9H]xanthen]-3-one, 3',6'-dihydroxy-2',4',5',7'-tetraiodo-, disodium salt.[16][17]

Classification

It is listed under the following number systems:

References

  1. ↑ http://www.chemicalbook.com/ChemicalProductProperty_US_CB0393696.aspx
  2. ↑ Phyllis A. Lyday "Iodine and Iodine Compounds" in Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim
  3. ↑ Food Color Additives
  4. ↑ "Genotoxic and mutagenic effects of erythrosine B, a xanthene food dye, on HepG2 cells". Food and Chemical Toxicology. 50 (10): 3447–3451. October 2012 – via science direct.
  5. ↑ Gurr, Edward (2012). Synthetic Dyes in Biology, Medicine And Chemistry. elsevier. pp. 197, 198.
  6. 1 2 Dictionary of Analytical Reagents. Crc Press. 1993. p. 474.
  7. ↑ "Erythrosine is a potential photosensitizer for the photodynamic therapy of oral plaque biofilms". Journal of Antimicrobal Chemotherapy. 57 (4). January 16, 2006.
  8. ↑ Food Product Design Article
  9. ↑ Blue Diamond Ultra Premium Blend Mixed Nuts, distributed by Diamond Foods, Inc. Stockton, CA
  10. ↑ FDA: Red Dye's Reluctant Regulator; Partial Ban Points to Limitations of 30-Year-Old Delaney Clause, The Washington Post, February 7, 1990
  11. ↑ FDA Urged To Ban Some Food Dyes, CBS News, June 3, 2008
  12. ↑ Lin, George H. Y.; Brusick, David J. (1986). "Mutagenicity studies on FD&C Red No.3". Mutagenesis. 1 (4): 253–259. doi:10.1093/mutage/1.4.253. PMID 2457780.
  13. ↑ Jennings, A. S.; Schwartz S. L.; Balter N. J.; Gardner D; Witorsch R. J. (May 1990). "Effects of oral erythrosine (2',4',5',7'-tetraiodofluorescein) on the pituitary-thyroid axis in rats.". Toxicology and Applied Pharmacology. 103 (3): 549–56. doi:10.1016/0041-008x(90)90327-q. PMID 2160137.
  14. ↑ European Ban on Certain Azo Dyes
  15. ↑ "Color Additive Status List". Food & Drug Administration. December 2015. Retrieved May 16, 2016.
  16. ↑ Erythrosin B, University of South Carolina
  17. ↑ Erythrosine, chemicalland21.com
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