Brilliant blue FCF: Difference between revisions

Brilliant blue FCF
Names
	IUPAC name ethyl - [4 - [ [4 - [ethyl -[(3 - sulfophenyl) methyl] amino] phenyl] - (2 - sulfophenyl) methylidene] - 1 - cyclohexa - 2, 5 - dienylidene] - [(3 - sulfophenyl) methyl] azanium
	Other names FD&C Blue No.1; Acid Blue 9; D&C Blue No. 4; Alzen Food Blue No. 1; Atracid Blue FG; Erioglaucine; Eriosky blue; Patent Blue AR; Xylene Blue VSG; C.I. 42090
Identifiers
CAS Number	3844-45-9 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL423337;
ChemSpider	18556 ;
ECHA InfoCard	100.021.219
E number	E133 (colours)
PubChem CID	19700;
UNII	H3R47K3TBD ;
CompTox Dashboard (EPA)	DTXSID2020189 ;
	InChI 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 Key: SGHZXLIDFTYFHQ-UHFFFAOYSA-L ; 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;
	SMILES [Na+].[Na+].[O-]S(=O)(=O)c1cccc(c1)CN(c2ccc(cc2)/C(=C\4/C=C\C(=[N+](\CC)Cc3cccc(c3)S([O-])(=O)=O)/C=C/4)c5ccccc5S([O-])(=O)=O)CC;
Properties
Chemical formula	C37H34N2Na2O9S3
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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Revision as of 10:20, 18 December 2012

Brilliant Blue FCF (Blue 1), also known under commercial names, is a colorant for foods and other substances to induce a color change. It is denoted by E number E133 and has a color index of 42090. It has the appearance of a reddish-blue powder. It is soluble in water, and the solution has a maximum absorption at about 628 nanometer.

Chemistry

It is a synthetic dye produced using aromatic hydrocarbons from petroleum.^[1] 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. Calcium and potassium salts are also permitted. It can also appear as an aluminium lake. The chemical formation is C₃₇H₃₄N₂Na₂O₉S₃. The dye is poorly absorbed from the gastro-intestinal tract and 95% of the ingested dye can be found in the feces. It also reacts with certain bile pigments to form green feces.^{[citation needed]}

Applications

As a blue color, Brilliant Blue FCF is often found in ice cream, canned processed peas, packet soups, bottled food colorings, icings, ice pops, blue raspberry flavored products, dairy products, sweets^[2] and drinks, especially the liqueur blue curacao. It is also used in soaps, shampoos, mouthwash^[3] and other hygiene and cosmetics applications. In soil science, Brilliant Blue is applied in tracing studies to visualize infiltration and water distribution in the soil.

Health and safety

Brilliant Blue FCF has previously been banned in Austria, Belgium, Denmark, France, Germany, Greece, Italy, Spain, Sweden, and Switzerland among others ^[4] but has been certified as a safe food additive in the EU and is today legal in most of the countries. It has the capacity for inducing an allergic reaction in individuals with pre-existing moderate asthma.^[5] In the United States production exceeds 1 million pounds annually, and daily consumption is around 16 mg per person.^{[citation needed]}

Biomedical research

Scientists who were investigating the use of compounds to lessen the severity of inflammation following spinal cord injury had previously tested a compound called OxATP to block a key ATP receptor in spinal neurons. However, OxATP has toxic side effects and must be injected directly into the spinal cord; in searching for alternatives they noted that Brilliant Blue FCF has a similar structure. This led them to test a related dye, Brilliant Blue G, also known as Coomassie Brilliant Blue in rats, which improved recovery from spinal cord injury.^[6]

References

^ El Ali, Bassam M.; Bassam El Ali; Ali, Mohammad Farahat (2005). Handbook of industrial chemistry: organic chemicals. New York: McGraw-Hill. ISBN 0-07-141037-6.{{cite book}}: CS1 maint: multiple names: authors list (link)
^ Nestle Aero packet ingredients listing barcode: 7613031579334
^ "LISTERINE Antiseptic Mouthwash, SMART RINSE, WHITENING, ADVANCED, Fluoride Rinse, and Tartar Protection Products". Listerine.com. Retrieved 2009-07-31.
^ Official Journal of the European Union L 295. The European Commission. 12 November 2011.
^ J. Allergy Clin. Immunol.; VOL 64 ISS Jul 1979, P32-37, (REF 25)
^ Peng, Weiguo (July 28, 2009). "Systemic administration of an antagonist of the ATP-sensitive receptor P2X7 improves recovery after spinal cord injury". Proceedings of the National Academy of Sciences of the United States of America. 106 (30): 12489–12493. doi:10.1073/pnas.0902531106. PMC 2718350. PMID 19666625. Retrieved 1 April 2010. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)

W. H. Hansen (1966). "Chronic toxicity of two food colors, Brilliant Blue FCF and Indigotine". Toxicology and Applied Pharmacology. 8 (1): 29–36. doi:10.1016/0041-008X(66)90097-4. PMID 5950860. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
J. F. Borzelleca (1990). "Lifetime toxicity/carcinogenicity studies of FD & C blue No. 1 (Brilliant blue FCF) in rats and mice". Food and Chemical Toxicology. 28 (4): 221–235. doi:10.1016/0278-6915(90)90034-K. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
J. P. Brown (1980). "Synthesis of ¹⁴C-labelled FD & C blue no. 1 (brilliant blue FCF) and its intestinal absorption and metabolic fate in rats". Food and Cosmetics Toxicology. 18 (1): 1–5. doi:10.1016/0015-6264(80)90002-4. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)

External links

[isbn0-07-141037-6-1] El Ali, Bassam M.; Bassam El Ali; Ali, Mohammad Farahat (2005). Handbook of industrial chemistry: organic chemicals. New York: McGraw-Hill. ISBN 0-07-141037-6.{{cite book}}: CS1 maint: multiple names: authors list (link)

[2] Nestle Aero packet ingredients listing barcode: 7613031579334

[3] "LISTERINE Antiseptic Mouthwash, SMART RINSE, WHITENING, ADVANCED, Fluoride Rinse, and Tartar Protection Products". Listerine.com. Retrieved 2009-07-31.

[4] Official Journal of the European Union L 295. The European Commission. 12 November 2011.

[5] J. Allergy Clin. Immunol.; VOL 64 ISS Jul 1979, P32-37, (REF 25)

[6] Peng, Weiguo (July 28, 2009). "Systemic administration of an antagonist of the ATP-sensitive receptor P2X7 improves recovery after spinal cord injury". Proceedings of the National Academy of Sciences of the United States of America. 106 (30): 12489–12493. doi:10.1073/pnas.0902531106. PMC 2718350. PMID 19666625. Retrieved 1 April 2010. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)

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 | verifiedrevid = 444217443
 | ImageFile = Brilliant Blue FCF.png
-|IUPACName= <small>ethyl - [4 - [ [4 - [ethyl -[(3 - sulfophenyl) methyl] amino] phenyl] - (2 - sulfophenyl) methylidene] - 1 - cyclohexa - 2, 5 - dienylidene] - [(3 - sulfophenyl) methyl] azanium</small>
+|IUPACName= ethyl - [4 - [ [4 - [ethyl -[(3 - sulfophenyl) methyl] amino] phenyl] - (2 - sulfophenyl) methylidene] - 1 - cyclohexa - 2, 5 - dienylidene] - [(3 - sulfophenyl) methyl] azanium
 | OtherNames = [[Federal Food, Drug, and Cosmetic Act|FD&C]] Blue No.1<br/>Acid Blue 9<br/>D&C Blue No. 4<br/>Alzen Food Blue No. 1<br/>Atracid Blue FG<br/>Erioglaucine<br/>Eriosky blue<br/>Patent Blue AR<br/>Xylene Blue VSG<br/>[[Color Index|C.I.]] 42090
 | Section1 = {{Chembox Identifiers