Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Indigo carmine: Difference between pages

{{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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| 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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| KEGG = D01563

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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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| 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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| Formula = C₁₆H₈N₂Na₂O₈S₂

| MolarMass = 466.36 g/mol

| Appearance = purple solid

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| Solubility = 10 g/L ({{convert|25|C}})

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| GHSPictograms = {{GHS exclamation mark}}<ref name=sigma>{{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}}</ref>

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| Legal_US_comment = <ref name="Bludigo FDA label">{{cite web | title=Bludigo- indigotindisulfonate sodium injection | website=DailyMed | date=7 November 2022 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=73f246c4-b127-452e-856f-134b56cb8870 | access-date=21 January 2023}}</ref>

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{{Infobox drug

| drug_name = Indigotindisulfonate sodium

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| tradename = Bludigo

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'''Indigo carmine''', or '''5,5′-indigodisulfonic acid sodium salt''', is an [[wikt:organic salt#English|organic salt]] derived from [[Indigo dye|indigo]] by [[aromatic sulfonation]], which renders the compound soluble in water. Like indigo, it [[Blue#Colourants|produces a blue color]], and is used in [[food colorant|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.<ref name="FDA colors">[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]]</ref><ref name=FSAlist>[http://www.food.gov.uk/safereating/chemsafe/additivesbranch/enumberlist Current EU approved additives and their E Numbers], [[Food Standards Agency]], 26 November 2010</ref> 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}}

[[File:Индигокармин.jpg|thumb|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<ref name="pmid2729594">{{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 }}</ref> through the conversion to isatin-5-sulfonic acid.<ref name="pmid2729594" /> This reaction has been shown not to be specific to ozone: it also detects [[superoxide]], an important distinction in cell physiology.<ref name="pmid14978029">{{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 }}</ref> It is also used as a dye in the manufacturing of [[Capsule (pharmacy)|capsules]].

=== Medical uses ===

[[File:Indigo carmine.jpg|thumb|Container of indigotindisulfonate sodium for medical use.]]

'''Indigotindisulfonate sodium''', sold under the brand name '''Bludigo''', is used as a [[contrast agent]] during surgical procedures.<ref name="Bludigo FDA label" /> It is [[indicated]] for use in [[cystoscopy]] in adults following [[urological]] and [[gynecological]] procedures.<ref name="Bludigo FDA label" /><ref name="FDA approval letter">{{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}}</ref> It was approved for medical use in the United States in July 2022.{{specify|Presumably means only this particular product?|date=August 2024}}<ref name="Bludigo FDA label" /><ref name="FDA approval letter" />

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.<ref>{{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 }}</ref>

Indigo carmine [[staining|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 tumor|benign]] and [[malignant]] lesions and growths on mucosal surfaces of the body.<ref>{{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 }}</ref>

=== 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]].<ref>{{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 }}</ref>

==Safety and regulation==

{{Missing information|article|legal status outside US/EU and most usages|date=August 2024}}

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.<ref>{{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 }}</ref>

== References ==

{{reflist}}

== External links ==

{{Diagnostic agents}}

{{Portal bar | Medicine}}

{{DEFAULTSORT:Indigo Carmine}}

[[Category:PH indicators]]

[[Category:Sulfonates]]

[[Category:Organic sodium salts]]

[[Category:Indoles]]

[[Category:Enones]]

[[Category:Food colorings]]

[[Category:Redox indicators]]

[[Category:E-number additives]]

[[Category:Acid dyes]]