Indigo carmine
{{Short description|Blue dye derived from indigo}}
{{About|the blue dye derived from indigo|the unrelated red dye|Carmine||Carmine (disambiguation)}}
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| ImageFile = Indigo carmine.svg
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| ImageFile1 =Indigo-carmine-3D-balls.png
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| PIN = Disodium [2(2′)E]-3,3′-dioxo-1,1′,3,3′-tetrahydro[2,2′-biindolylidene]-5,5′-disulfonate
| OtherNames = {{Unbulleted list|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}}
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| CASNo = 860-22-0
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| ChEBI = 31695
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| ChEMBL = 2105023
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| ChemSpiderID = 4447431
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| DrugBank = DB11577
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| DrugBank1 = DBSALT001752
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| EC_number = 212-728-8
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| KEGG = D01563
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| PubChem = 2723854
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| SMILES = [Na+].[Na+].[O-]S(=O)(=O)c3cc4C(=O)\C(=C2\C(=O)c1cc(ccc1N2)S([O-])(=O)=O)Nc4cc3
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| StdInChI = 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+;;
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| StdInChIKey = KHLVKKOJDHCJMG-QDBORUFSSA-L
| 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+;;
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| InChIKey = KHLVKKOJDHCJMG-AKPRSONXBD
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| UNII = D3741U8K7L
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|Section2={{Chembox Properties
| Formula = C16H8N2Na2O8S2
| MolarMass = 466.36 g/mol
| Appearance = purple solid
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| MeltingPt = >{{convert|300|C}}
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| Solubility = 10 g/L ({{convert|25|C}})
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|Section3={{Chembox Hazards
| GHSPictograms = {{GHS exclamation mark}}{{cite web|title=Indigo carmine|url=http://www.sigmaaldrich.com/MSDS/MSDS/DisplayMSDSPage.do?country=TH&language=en&productNumber=131164&brand=SIAL&PageToGoToURL=http%3A%2F%2Fwww.sigmaaldrich.com%2Fcatalog%2Fproduct%2Fsial%2F131164%3Flang%3Den|website=Sigma Aldrich|access-date=15 Feb 2022}}
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{{Infobox drug
| drug_name = Indigotindisulfonate sodium
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| tradename = Bludigo
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| DailyMedID = Indigotindisulfonate
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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.[https://www.fda.gov/ForIndustry/ColorAdditives/ColorAdditiveInventories/ucm115641.htm Summary of Color Additives for Use in United States in Foods, Drugs, Cosmetics, and Medical Devices], Food and Drug Administration[http://www.food.gov.uk/safereating/chemsafe/additivesbranch/enumberlist Current EU approved additives and their E Numbers], Food Standards Agency, 26 November 2010 It has the E number E132, and is named Blue No. 2 by the US Federal Food, Drug, and Cosmetic Act.
Uses
{{pH_indicator_template|indicator_name=Indigo Carmine|low_pH=11.4|high_pH=13.0|low_pH_color=blue|low_pH_text=white|high_pH_color=yellow}}
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{{cite journal | vauthors = Takeuchi K, Ibusuki T | title = Quantitative determination of aqueous-phase ozone by chemiluminescence using indigo-5,5'-disulfonate | journal = Analytical Chemistry | volume = 61 | issue = 6 | pages = 619–623 | date = March 1989 | pmid = 2729594 | doi = 10.1021/ac00181a025 }} through the conversion to isatin-5-sulfonic acid. This reaction has been shown not to be specific to ozone: it also detects superoxide, an important distinction in cell physiology.{{cite journal | vauthors = Kettle AJ, Clark BM, Winterbourn CC | title = Superoxide converts indigo carmine to isatin sulfonic acid: implications for the hypothesis that neutrophils produce ozone | journal = The Journal of Biological Chemistry | volume = 279 | issue = 18 | pages = 18521–18525 | date = April 2004 | pmid = 14978029 | doi = 10.1074/jbc.M400334200 | doi-access = free }} It is also used as a dye in the manufacturing of capsules.
= Medical uses =
Indigotindisulfonate sodium, sold under the brand name Bludigo, is used as a contrast agent during surgical procedures. It is indicated for use in cystoscopy in adults following urological and gynecological procedures.{{cite web | title = NDA APPROVAL: Bludigo (indigotindisulfonate sodium) injection | url = https://www.accessdata.fda.gov/drugsatfda_docs/appletter/2022/216264Orig1s000ltr.pdf | publisher = U.S. Food and Drug Administration }} {{PD-notice}} It was approved for medical use in the United States in July 2022.{{specify|Presumably means only this particular product?|date=August 2024}}
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.{{cite journal | vauthors = Craik JD, Khan D, Afifi R |title=The Safety of Intravenous Indigo Carmine to Assess Ureteric Patency During Transvaginal Uterosacral Suspension of the Vaginal Vault |journal=Journal of Pelvic Medicine & Surgery |date=January–February 2009 |volume=15 |issue=1 |pages=11–15 |doi=10.1097/SPV.0b013e3181986ace }}
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.{{cite journal | vauthors = Jang JY | title = The Past, Present, and Future of Image-Enhanced Endoscopy | journal = Clinical Endoscopy | volume = 48 | issue = 6 | pages = 466–475 | date = November 2015 | pmid = 26668791 | pmc = 4676674 | doi = 10.5946/ce.2015.48.6.466 | doi-access = free }}
= Food, pharmaceutical, cosmetic, and scientific uses =
Indigo carmine is one of the few blue food colorants. Others include the anthocyanidins and rare substances such as variagatic acid and popolohuanone.{{cite journal | vauthors = Newsome AG, Culver CA, van Breemen RB | title = Nature's palette: the search for natural blue colorants | journal = Journal of Agricultural and Food Chemistry | volume = 62 | issue = 28 | pages = 6498–6511 | date = July 2014 | pmid = 24930897 | doi = 10.1021/jf501419q }}
Safety and regulation
{{Missing information|article|legal status outside US/EU and most usages|date=August 2024}}
Indigo carmine 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.{{cite journal | vauthors = Amchova P, Kotolova H, Ruda-Kucerova J | title = Health safety issues of synthetic food colorants | journal = Regulatory Toxicology and Pharmacology | volume = 73 | issue = 3 | pages = 914–922 | date = December 2015 | pmid = 26404013 | doi = 10.1016/j.yrtph.2015.09.026 }}
References
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External links
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