Indigo carmine

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Contents

Indigo carmine
Indigo carmine.svg
Indigo-carmine-3D-balls.png
Names
Preferred IUPAC name
Disodium [2(2′)E]-3,3′-dioxo-1,1′,3,3′-tetrahydro[2,2′-biindolylidene]-5,5′-disulfonate
Other names
  • indigotine
  • 5,5′-indigodisulfonic acid sodium salt
  • Brilliant Indigo
  • 4 G
  • C.I. Acid Blue 74
  • C.I. 73015
  • CI Food Blue 1
  • FD&C Blue 2
  • Sicovit Indigotin 85
  • E132
  • indigotindisulfonate sodium
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.011.572 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 212-728-8
E number E132 (colours)
KEGG
PubChem CID
UNII
  • InChI=1S/C16H10N2O8S2.2Na/c19-15-9-5-7(27(21,22)23)1-3-11(9)17-13(15)14-16(20)10-6-8(28(24,25)26)2-4-12(10)18-14;;/h1-6,17-18H,(H,21,22,23)(H,24,25,26);;/q;2*+1/p-2/b14-13+;; Yes check.svgY
    Key: KHLVKKOJDHCJMG-QDBORUFSSA-L Yes check.svgY
  • InChI=1/C16H10N2O8S2.2Na/c19-15-9-5-7(27(21,22)23)1-3-11(9)17-13(15)14-16(20)10-6-8(28(24,25)26)2-4-12(10)18-14;;/h1-6,17-18H,(H,21,22,23)(H,24,25,26);;/q;2*+1/p-2/b14-13+;;
    Key: KHLVKKOJDHCJMG-AKPRSONXBD
  • [Na+].[Na+].[O-]S(=O)(=O)c3cc4C(=O)\C(=C2\C(=O)c1cc(ccc1N2)S([O-])(=O)=O)Nc4cc3
Properties
C16H8N2Na2O8S2
Molar mass 466.36 g/mol
Appearancepurple solid
Melting point >300 °C (572 °F)
10 g/L (25 °C (77 °F))
Hazards
GHS labelling:
GHS-pictogram-exclam.svg [1]
Warning
H302 [1]
NFPA 704 (fire diamond)
NFPA 704.svgHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Pharmacology
V04CH02 ( WHO )
Legal status
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)
Indigotindisulfonate sodium
Clinical data
Trade names Bludigo
License data
Identifiers
E number E132 (colours) OOjs UI icon edit-ltr-progressive.svg
CompTox Dashboard (EPA)
ECHA InfoCard 100.011.572 OOjs UI icon edit-ltr-progressive.svg

Indigo carmine, or 5,5′-indigodisulfonic acid sodium salt, is an organic salt derived from indigo by aromatic sulfonation, which renders the compound soluble in water. Like indigo, it produces a blue color, and is used in food and other consumables, cosmetics, and as a medical contrast agent and staining agent; it also acts as a pH indicator. It is approved for human consumption in the United States and European Union. [3] [4] It has the E number E132, and is named Blue No. 2 by the US Federal Food, Drug, and Cosmetic Act.

Uses

Indigo Carmine(pH indicator)
below pH 11.4above pH 13.0
11.413.0
Experiment using indigo carmine as an indicator Indigokarmin.jpg
Experiment using indigo carmine as an indicator

Indigo carmine in a 0.2% aqueous solution is blue at pH 11.4 and yellow at 13.0. Indigo carmine is also a redox indicator, turning yellow upon reduction. Another use is as a dissolved ozone indicator [5] through the conversion to isatin-5-sulfonic acid. [5] This reaction has been shown not to be specific to ozone: it also detects superoxide, an important distinction in cell physiology. [6] It is also used as a dye in the manufacturing of capsules.

Medical uses

Container of indigotindisulfonate sodium for medical use. Indigo carmine.jpg
Container of indigotindisulfonate sodium for medical use.

Indigotindisulfonate sodium, sold under the brand name Bludigo, is used as a contrast agent during surgical procedures. [2] It is indicated for use in cystoscopy in adults following urological and gynecological procedures. [2] [7] It was approved for medical use in the United States in July 2022.[ specify ] [2] [7]

In obstetric surgery, it may be used to detect amniotic fluid leaks. In urologic surgery, intravenous indigo carmine can be used to highlight portions of the urinary tract. The dye is filtered rapidly by the kidneys from the blood, and colors the urine blue. However, the dye can cause a potentially dangerous acute increase in blood pressure in some cases. [8]

Indigo carmine stain is not absorbed into cells, so it is applied to tissues to enhance the visibility of mucosa. This leads to its use for examination and diagnosis of benign and malignant lesions and growths on mucosal surfaces of the body. [9]

Food, pharmaceutical, cosmetic, and scientific uses

Indigo carmine is one of the few blue food colorants. Others include the anthocyanidins and rare entites such as variagatic acid and popolohuanone. [10]

Safety and regulation

Indigo carmin shows "genotoxicity, developmental toxicity or modifications of haematological parameters in chronic toxicity studies". Only at 17 mg/kg of body weight per day were effects on testes observed. [11]

Related Research Articles

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<span class="mw-page-title-main">Indigo dye</span> Chemical compound, food additive and dye

Indigo dye is an organic compound with a distinctive blue color. Indigo is a natural dye extracted from the leaves of some plants of the Indigofera genus, in particular Indigofera tinctoria. Dye-bearing Indigofera plants were commonly grown and used throughout the world, particularly in Asia, with the production of indigo dyestuff economically important due to the historical rarity of other blue dyestuffs.

<span class="mw-page-title-main">Food coloring</span> Substance used to color food or drink

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<span class="mw-page-title-main">Methylene blue</span> Blue dye also used as a medication

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<span class="mw-page-title-main">Sulfonic acid</span> Organic compounds with the structure R−S(=O)2−OH

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<span class="mw-page-title-main">Brilliant blue FCF</span> Chemical compound

Brilliant blue FCF is a synthetic organic compound used primarily as a blue colorant for processed foods, medications, dietary supplements, and cosmetics. 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, with a maximum absorption at about 628 nanometers. It is one of the oldest FDA-approved color additives and is generally considered nontoxic and safe.

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References

  1. 1 2 "Indigo carmine". Sigma Aldrich. Retrieved 15 Feb 2022.
  2. 1 2 3 4 "Bludigo- indigotindisulfonate sodium injection". DailyMed. 7 November 2022. Retrieved 21 January 2023.
  3. Summary of Color Additives for Use in United States in Foods, Drugs, Cosmetics, and Medical Devices, Food and Drug Administration
  4. Current EU approved additives and their E Numbers, Food Standards Agency, 26 November 2010
  5. 1 2 Takeuchi K, Ibusuki T (March 1989). "Quantitative determination of aqueous-phase ozone by chemiluminescence using indigo-5,5'-disulfonate". Analytical Chemistry. 61 (6): 619–623. doi:10.1021/ac00181a025. PMID   2729594.
  6. Kettle AJ, Clark BM, Winterbourn CC (April 2004). "Superoxide converts indigo carmine to isatin sulfonic acid: implications for the hypothesis that neutrophils produce ozone". The Journal of Biological Chemistry. 279 (18): 18521–18525. doi: 10.1074/jbc.M400334200 . PMID   14978029.
  7. 1 2 "NDA APPROVAL: Bludigo (indigotindisulfonate sodium) injection" (PDF). U.S. Food and Drug Administration.PD-icon.svg This article incorporates text from this source, which is in the public domain .
  8. Craik JD, Khan D, Afifi R (January–February 2009). "The Safety of Intravenous Indigo Carmine to Assess Ureteric Patency During Transvaginal Uterosacral Suspension of the Vaginal Vault". Journal of Pelvic Medicine & Surgery. 15 (1): 11–15. doi:10.1097/SPV.0b013e3181986ace.
  9. Jang JY (November 2015). "The Past, Present, and Future of Image-Enhanced Endoscopy". Clinical Endoscopy. 48 (6): 466–475. doi: 10.5946/ce.2015.48.6.466 . PMC   4676674 . PMID   26668791.
  10. Newsome AG, Culver CA, van Breemen RB (July 2014). "Nature's palette: the search for natural blue colorants". Journal of Agricultural and Food Chemistry. 62 (28): 6498–6511. doi:10.1021/jf501419q. PMID   24930897.
  11. Amchova P, Kotolova H, Ruda-Kucerova J (December 2015). "Health safety issues of synthetic food colorants". Regulatory Toxicology and Pharmacology. 73 (3): 914–922. doi:10.1016/j.yrtph.2015.09.026. PMID   26404013.