Brilliant blue FCF

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Brilliant blue FCF
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Names
IUPAC name
disodium;2-[[4-[ethyl-[(3-sulfonatophenyl)methyl]amino]phenyl]-[4-[ethyl-[(3-sulfonatophenyl)methyl]azaniumylidene]cyclohexa-2,5-dien-1-ylidene]methyl]benzenesulfonate
Other names
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  • FD&C Blue No.1
  • Acid blue 9
  • D&C Blue No. 4
  • Atracid Blue FG
  • Acilan Turquoise Blue AE
  • Aizen Brilliant Blue FCF
  • Alzen Food Blue No. 1
  • Erioglaucine
  • Eriosky blue
  • Patent Blue AR
  • Xylene Blue VSG
  • C.I. 42090
  • CI Food Blue 2
  • Basacid Blue 755
  • Sulfacid Brilliant Blue 5 J
  • Neolan Blue E-A
  • Brilliant Blue FD
  • Brilliant Blue Lake
  • Blue #1 Lake
  • Bucacid Azure Blue
Identifiers
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3D model (JSmol)
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  • InChI=1S/C37H36N2O9S3.2Na/c1-3-38(25-27-9-7-11-33(23-27)49(40,41)42)31-19-15-29(16-20-31)37(35-13-5-6-14-36(35)51(46,47)48)30-17-21-32(22-18-30)39(4-2)26-28-10-8-12-34(24-28)50(43,44)45;;/h5-24H,3-4,25-26H2,1-2H3,(H2-,40,41,42,43,44,45,46,47,48);;/q;2*+1/p-2 checkY
    Key: SGHZXLIDFTYFHQ-UHFFFAOYSA-L checkY
  • InChI=1/C37H36N2O9S3.2Na/c1-3-38(25-27-9-7-11-33(23-27)49(40,41)42)31-19-15-29(16-20-31)37(35-13-5-6-14-36(35)51(46,47)48)30-17-21-32(22-18-30)39(4-2)26-28-10-8-12-34(24-28)50(43,44)45;;/h5-24H,3-4,25-26H2,1-2H3,(H2-,40,41,42,43,44,45,46,47,48);;/q;2*+1/p-2
    Key: SGHZXLIDFTYFHQ-NUQVWONBAU
  • CCN(CC1=CC(=CC=C1)S(=O)(=O)[O-])C2=CC=C(C=C2)C(=C3C=CC(=[N+](CC)CC4=CC(=CC=C4)S(=O)(=O)[O-])C=C3)C5=CC=CC=C5S(=O)(=O)[O-].[Na+].[Na+]
Properties
C37H34N2Na2O9S3
Molar mass 792.85 g/mol
Melting point 283 °C (decomposes)
soluble
Hazards
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2
1
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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Brilliant blue FCF (Blue 1) is a synthetic organic compound used primarily as a blue colorant for processed foods, medications, dietary supplements, and cosmetics.[1] It is classified as a triarylmethane dye and is known under various names, such as FD&C Blue No. 1 or acid blue 9. It is denoted by E number E133 and has a color index of 42090. It has the appearance of a blue powder and is soluble in water and glycerol,[2] with a maximum absorption at about 628 nanometers.[3] It is one of the oldest FDA-approved color additives, having been permanently listed for use in food and ingested drugs in 1969. It is generally considered nontoxic and safe for consumption.[4][5][6]

Production

Brilliant blue FCF is a synthetic dye produced by the condensation of 2-formylbenzenesulfonic acid and the appropriate aniline followed by oxidation.[7] It can be combined with tartrazine (E102) to produce various shades of green.

It is usually a disodium salt. The diammonium salt has CAS number 2650-18-2.[8] Calcium and potassium salts are also permitted. It can also appear as an aluminium lake. The chemical formula is C37H34N2Na2O9S3.

Related dyes are C.I. acid green 3 (CAS#4680-78-8[9]) and acid green 9 (CAS#4857-81-2[10]). In these dyes, the 2-sulfonic acid group is replaced by H and Cl, respectively.[11]

Many attempts have been made to find similarly colored natural dyes that are as stable as brilliant blue FCF. Blue pigments must possess many chemical traits, including pi-bond conjugation, aromatic rings, heteroatoms and heteroatom groups, and ionic charges in order to absorb low energy red light. Most natural blue dyes are either unstable, blue only in alkaline conditions, or toxic; good candidates for further research into use as natural dyes include anthocyanin, trichotomine, and phycocyanin[12] derivatives.

File:Jolly Ranchers - blue and red (cropped).png
Blue and red Jolly Rancher candy. The blue color is brilliant blue FCF dye.

Applications

File:Vodka and Blue Curacao (with Brilliant Blue FCF).jpg
Vodka with Blue Curaçao syrup

Like many other color additives, the primary use of Blue No. 1 is to correct or enhance natural coloring or to give colorless compounds a vivid hue.[13]

In the United States, of the two approved blue food dyes (the other being Indigo carmine, or FD&C Blue #2), brilliant blue FCF is the more common of the two. As a blue color, brilliant blue FCF is often found in cotton candy, ice cream, canned processed peas, packet soups, bottled food colorings, icings, ice pops, blueberry flavored products, children's medications, dairy products, sweets[14] soft drinks, and drinks, especially the liqueur Blue Curaçao. It is also used in soaps, shampoos, mouthwash[15] and other hygiene and cosmetics applications.

Brilliant blue FCF is extensively used as a water tracer agent.[16] Due to its ability to retain color for long periods of time, brilliant blue FCF outperforms other dye tracers. Additionally, brilliant blue FCF has a low toxicity level that is favorable for the environment. However, brilliant blue FCF has different impacts on varying soils. Brilliant blue FCF is attracted to and sorbed in acidic soils due to its large size and ionic charge. Soil composition and flow velocity also affect the level of sorption of brilliant blue FCF.[17]

Brilliant blue FCF dye within beverages items—such as soda—can be used in the blue bottle experiment. In such foods, both the dye and reducing agents are incorporated in the same solution. When the solution is blue, oxygen is present. On the addition of NaOH, a reaction occurs that removes the oxygen, turning the solution clear. The dye turns back to blue once it is reoxidized by swirling the solution, incorporating oxygen from the air as an oxidizing agent.[18]

History

Brilliant Blue FCF was first synthesized in the early 20th century as part of the development of synthetic dyes derived from coal tar and aniline compounds.[19] It gained regulatory prominence in the United States when it was among the first synthetic colorants certified for food use under the Federal Food, Drug, and Cosmetic Act of 1938.[19] In 1969, following a safety review prompted by concerns over certain synthetic colorants, Brilliant Blue FCF was one of the few dyes permanently approved by the U.S. Food and Drug Administration for use in food, drugs, and cosmetics.[20] Its vivid hue, water solubility, chemical stability, and low toxicity contributed to its widespread use.[21] Despite ongoing interest in natural blue alternatives, Brilliant Blue FCF continues to be widely used in commercial products.

Health and safety

File:Blue smarties.JPG
In the United Kingdom, Smarties chocolates were colored with brilliant blue FCF (top) until 2008, later being replaced with a natural spirulina coloring (bottom).

When applied to the tongue or to shaven skin, brilliant blue FCF can be absorbed directly into the bloodstream.[22] However, in experiments with rodents, it was found that it is poorly absorbed from the gastrointestinal tract, and 95% of the ingested dye can be found in the feces. [23]

Due to its nontoxic properties, brilliant blue FCF has been used as a biological stain. When dissolved in an acidic medium, this dye has been used to stain cell walls, bacteria, and fungal cells. The dye does not inhibit the growth of any of these species.[24]

For similar reasons, brilliant blue FCF is also being utilized in hemostatic medical devices, most notably the Hemopatch—designed to be placed on bleeding tissues and coagulate the blood. A low concentration of brilliant blue FCF is placed on the backside of the Hemopatch at 1 cm increments, allowing surgeons to cut precisely and indicate the side of the Hemopatch that is an active hemostatic agent for correct placement.[25]

Brilliant blue FCF is an approved food colorant and pharmacologically inactive substance for drug formulations in the EU and the United States. It is also legal in other countries. In a 1979 clinical trial of patients with perennial asthma, brilliant blue FCF, tested alongside two other non-azobenzene dyes (Erythrosine & Indigotin), was found to have no effect on pulmonary function in 42 of 43 participants.[26] This indicates that brilliant blue FCF is highly unlikely to cause allergic reactions in individuals with pre-existing moderate asthma. But, a case study of a 55-year-old man in 1996 reporting occupational asthma when exposed to Indigotine (a derivative of Indigotin) at work found reduced pulmonary function could be recapitulated under laboratory conditions upon exposure;[27] suggesting that there may be some people sensitive to non-azobenzene dyes or just Indigotin particularly. In 2003, the U.S. FDA issued a public health advisory to warn health care providers of the potential toxicity of this synthetic dye in enteral feeding solutions.[28] The following legal limits apply in the EU (E 133) and other countries: 150–300 mg/kg depending on the type of food. Safety limit for foods and drugs: 0.1 mg/day per kg body weight.[29] The acceptable daily intake for brilliant blue FCF is 6 mg/kg.

See also

References

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  1. ^ Page Module:Citation/CS1/styles.css has no content."FD&C Blue 1 (Brilliant Blue)". International Association of Color Manufacturers. Archived from the original on 2019-05-06. Retrieved 2019-05-06.
  2. ^ Page Module:Citation/CS1/styles.css has no content."FD&C Blue No. 1: Brilliant Blue FCF Food Dye". culinarylore.com. 2015-08-04. Retrieved 2019-06-03.
  3. ^ Page Module:Citation/CS1/styles.css has no content.Al-Shehri AS, Zaheer Z, Alsudairi AM, Kosa SA (October 2021). "Photo-oxidative Decolorization of Brilliant Blue with AgNPs as an Activator in the Presence of K2S2O8 and NaBH4". ACS Omega. 6 (41): 27510–27526. doi:10.1021/acsomega.1c04501. PMC 8529662. PMID 34693172.
  4. ^ Page Module:Citation/CS1/styles.css has no content.Barrows JN, Lipman AL, Bailey CJ (2017-11-03). "Color Additives History". U.S. Food and Drug Administration. Retrieved 2025-02-14.
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  7. ^ Page Module:Citation/CS1/styles.css has no content.El Ali, Bassam M.; Bassam El Ali; Ali, Mohammad Farahat (2005). Handbook of industrial chemistry: organic chemicals. New York: McGraw-Hill. ISBN 978-0-07-141037-3.
  8. ^ Page Module:Citation/CS1/styles.css has no content."Acid Blue 9". CAS Common Chemistry.
  9. ^ Page Module:Citation/CS1/styles.css has no content."Acid Green". CAS Common Chemistry.
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  11. ^ Page Module:Citation/CS1/styles.css has no content.Gessner T, Mayer U (2002). "Triarylmethane and Diarylmethane Dyes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a27_179. ISBN 3-527-30673-0.
  12. ^ Page Module:Citation/CS1/styles.css has no content.Roda-Serrat, Maria Cinta; Christensen, Knud Villy; El-Houri, Rime Bahij; Fretté, Xavier; Christensen, Lars Porskjær (2018). "Fast cleavage of phycocyanobilin from phycocyanin for use in food colouring" (PDF). Food Chemistry. 240: 655–661. doi:10.1016/j.foodchem.2017.07.149. PMID 28946325.
  13. ^ Page Module:Citation/CS1/styles.css has no content.Nutrition, Center for Food Safety and Applied (2019-04-14). "Overview of Food Ingredients, Additives & Colors". FDA.[dead link]
  14. ^ Nestle Aero packet ingredients listing barcode: 7613031579334
  15. ^ Page Module:Citation/CS1/styles.css has no content."LISTERINE Antiseptic Mouthwash, Smart Rinse, Whitening, Advanced, Fluoride Rinse, and Tartar Protection Products". Listerine.com. Archived from the original on 2011-01-02. Retrieved 2009-07-31.
  16. ^ Page Module:Citation/CS1/styles.css has no content.Flury M, Flühler H (1994). "Brilliant Blue FCF as a Dye Tracer for Solute Transport Studies—A Toxicological Overview". Journal of Environmental Quality. 23 (5): 1108–1112. Bibcode:1994JEnvQ..23.1108F. doi:10.2134/jeq1994.00472425002300050037x. PMID 34872226.
  17. ^ Page Module:Citation/CS1/styles.css has no content.Allaire SE, Roulier S, Cessna AJ (2009-11-15). "Quantifying preferential flow in soils: A review of different techniques". Journal of Hydrology. 378 (1): 179–204. Bibcode:2009JHyd..378..179A. doi:10.1016/j.jhydrol.2009.08.013.
  18. ^ Page Module:Citation/CS1/styles.css has no content.Staiger FA, Peterson JP, Campbell DJ (2015-10-13). "Variations on the "Blue-Bottle" Demonstration Using Food Items That Contain FD&C Blue #1". Journal of Chemical Education. 92 (10): 1684–1686. Bibcode:2015JChEd..92.1684S. doi:10.1021/acs.jchemed.5b00190.
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  22. ^ Page Module:Citation/CS1/styles.css has no content.Lucová M, Hojerová J, Pažoureková S, Klimová Z (February 2013). "Absorption of triphenylmethane dyes Brilliant Blue and Patent Blue through intact skin, shaven skin and lingual mucosa from daily life products". Food and Chemical Toxicology. 52: 19–27. doi:10.1016/j.fct.2012.10.027. PMID 23127598. porcine tongue dorsum was exposed to human saliva with 15,000 ng/cm2 of dye for 20 min. 24-h diffusion resulted in 34 ng/cm2 of BB and 86 ng/cm2 of PB which can be directly absorbed into the blood system.
  23. ^ Page Module:Citation/CS1/styles.css has no content.Phillips, J. C.; Mendis, D.; Eason, C. T.; Gangolli, S. D. (1980). "The metabolic disposition of 14C-labelled Green S and Brilliant Blue FCF in the rat, mouse and guinea-pig". Food and Cosmetics Toxicology. 18 (1): 7–13. doi:10.1016/0015-6264(80)90003-6. ISSN 0015-6264. PMID 7372213.
  24. ^ Page Module:Citation/CS1/styles.css has no content.Chau HW, Goh YK, Si BC, Vujanovic V (August 2011). "An innovative brilliant blue FCF method for fluorescent staining of fungi and bacteria". Biotechnic & Histochemistry. 86 (4): 280–7. doi:10.3109/10520295.2010.492733. PMID 20560873. S2CID 37175297.
  25. ^ Page Module:Citation/CS1/styles.css has no content.Lewis KM, Kuntze CE, Gulle H (2015-12-22). "Control of bleeding in surgical procedures: critical appraisal of HEMOPATCH (Sealing Hemostat)". Medical Devices: Evidence and Research. 9: 1–10. doi:10.2147/mder.s90591. PMC 4694675. PMID 26730213.
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Further reading

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