• Home   /  
  • Archive by category "1"

Indigotine Synthesis Essay

IUPAC name

3,3′-dioxo-2,2′-bisindolyden-5,5′-disulfonic acid disodium salt

Other names

5,5′-indigodisulfonic acid sodium salt
Brilliant Indigo
4 G
C.I. Acid Blue 74
C.I. 73015
Food Blue 1
C Blue 2
Sicovit Indigotin 85


CAS Number

3D model (JSmol)

ECHA InfoCard100.011.572
E numberE132 (colours)




  • 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+;; Y
  • 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+;;



  • [Na+].[Na+].[O-]S(=O)(=O)c3cc4C(=O)\C(=C2\C(=O)c1cc(ccc1N2)S([O-])(=O)=O)Nc4cc3


Chemical formula

Molar mass466.36 g/mol
Appearancepurple solid
Melting point>300 °C (572 °F)

Solubility in water

10 g/L (25 °C (77 °F))
GHS pictograms[1]
GHS signal wordWarning

GHS hazard statements

NFPA 704

ATC code

V04CH02 (WHO)

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

N verify (what is YN ?)
Infobox references

Indigo carmine, or 5,5′-indigodisulfonic acid sodium salt, is an organic salt derived from indigo by sulfonation, which renders the compound soluble in water. It is approved for use as a food colorant in the U.S and E.U.,[2][3] It has the E numberE132. It is also a pH indicator.


Indigo Carmine(pH indicator)
below pH 11.4above pH 13.0

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[4] through the conversion to isatin-5-sulfonic acid.[4] This reaction has been shown not to be specific to ozone, however: it also detects superoxide, an important distinction in cell physiology.[5] It is also used as a dye in the manufacturing of capsules.

In obstetric surgery, indigo carmine solutions are sometimes employed to detect amniotic fluid leaks. In urologic surgery, intravenous injection of indigo carmine is often used to highlight portions of the urinary tract. The dye is filtered rapidly by the kidneys from the blood, and colors the urine blue. This enables structures of the urinary tract to be seen in the surgical field, and demonstrate if there is a leak. However, the dye can cause a potentially dangerous increase in blood pressure in some cases.[6]

See also[edit]


  1. ^ ab"Indigo carmine". Sigma Aldrich. Retrieved 10 March 2016. 
  2. ^Summary of Color Additives for Use in United States in Foods, Drugs, Cosmetics, and Medical Devices, United States Food and Drug Administration
  3. ^Current EU approved additives and their E Numbers, Food Standards Agency, 26 November 2010
  4. ^ abTakeuchi K, Ibusuki T (March 1989). "Quantitative determination of aqueous-phase ozone by chemiluminescence using indigo-5,5'-disulfonate". Anal. Chem. 61 (6): 619–23. doi:10.1021/ac00181a025. PMID 2729594. 
  5. ^Kettle AJ, Clark BM, Winterbourn CC (April 2004). "Superoxide converts indigo carmine to isatin sulfonic acid: implications for the hypothesis that neutrophils produce ozone". J. Biol. Chem. 279 (18): 18521–5. doi:10.1074/jbc.M400334200. PMID 14978029. 
  6. ^Craik, Johnathan Donaldson (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. Retrieved 18 October 2012. 

1. Burrows A. Palette of our palates: a brief history of food coloring and its regulation. Compr Rev Food Sci Food Saf. 2009;8:394–408. doi: 10.1111/j.1541-4337.2009.00089.x.[Cross Ref]

2. Nigg JT, Lewis K, Edinger T, Falk M. Meta-analysis of attention-deficit/hyperactivity disorder or attention-deficit/hyperactivity disorder symptoms, restriction diet, and synthetic food color additives. J Am Acad Child Adolesc Psychiatry. 2012;51:86–97. doi: 10.1016/j.jaac.2011.10.015.[PMC free article][PubMed][Cross Ref]

3. Feingold BF. Adverse reactions to food additives. Presented at: The American Medical Association Annual Meeting; June 24–28, 1973; Chicago, IL.

4. Feingold BF. Hyperkinesis and learning disabilities linked to artificial food flavors and colors. Am J Nurs. 1975;75:797–803.[PubMed]

5. Feingold BF. Hyperkinesis and learning disabilities linked to the ingestion of artificial food colors and flavors. J Learn Disabil. 1976;9:551–559. doi: 10.1177/002221947600900902.[Cross Ref]

6. Feingold BF. The role of diet in behaviour. Ecol Dis. 1982;1:153–165.[PubMed]

7. Feingold BF. Hyperkinesis and learning disabilities linked to the ingestion of artificial food colors and flavors. Speech to: American Academy of Pediatrics; November 8, 1977; New York, NY.

8. Feingold BF. Why Your Child is Hyperactive. New York: Random House; 1975.

9. Lipton MA, Mayo JP. Diet and hyperkinesis: an update. J Am Diet Assoc. 1983;83:132–134.[PubMed]

10. Mattes JA. The Feingold diet: a current reappraisal. J Learn Disabil. 1983;16:319–323. doi: 10.1177/002221948301600602.[PubMed][Cross Ref]

11. Feingold BF. A view from the other side. Speech to: Newspaper Food Editors and Writers Association; June 8, 1977; Milwaukee, WI.

12. Conners CK, Goyette CH, Southwick DA. Food additives and hyperkinesis: preliminary report of a double-blind crossover experiment. Psychopharmacol Bull. 1976;12:10–11.[PubMed]

13. Defined diets and childhood hyperactivity. NIH Consens Statement, 1982:4:1-11.

14. Kavale KA, Forness SR. Hyperactivity and diet treatment: a meta-analysis of the Feingold hypothesis. J Learn Disabil. 1983;16:324–330. doi: 10.1177/002221948301600604.[PubMed][Cross Ref]

15. Schab DW, Trinh NH. Do artificial food colors promote hyperactivity in children with hyperactive syndromes? A meta-analysis of double-blind placebo-controlled trials. J Dev Behav Pediatr. 2004;25:423–434. doi: 10.1097/00004703-200412000-00007.[PubMed][Cross Ref]

16. Stevens L, Kuczek T, Burgess JR, Hurt EA, Arnold LE. Dietary sensitivities and ADHD: 35 years of research. Clin Pediatr. 2011;50:279–293. doi: 10.1177/0009922810384728.[PubMed][Cross Ref]

17. Egger J, Carter CM, Graham PJ, Gumley D, Soothill JF. Controlled trial of oligoantigenic treatment in the hyperkinetic syndrome. Lancet. 1985;1:540–545. doi: 10.1016/S0140-6736(85)91206-1.[PubMed][Cross Ref]

18. Rowe KS, Rowe KJ. Synthetic food coloring and behavior: a dose response effect in a double-blind, placebo-controlled, repeated-measures study. J Pediatr. 1994;125:691–698. doi: 10.1016/S0022-3476(06)80164-2.[PubMed][Cross Ref]

19. Bateman B, Warner JO, Hutchinson E, et al. The effects of a double blind, placebo controlled, artificial food colourings and benzoate preservative challenge on hyperactivity in a general population sample of preschool children. Ach Dis Child. 2004;89:506–511. doi: 10.1136/adc.2003.031435.[PMC free article][PubMed][Cross Ref]

20. McCann D, Barrett A, Cooper A, et al. Food additives and hyperactive behavior in 3-year-old and 8/9-year-old children in the community: a randomised, double-blinded, placebo-controlled trial. Lancet. 2007;370:1560–1567. doi: 10.1016/S0140-6736(07)61306-3.[PubMed][Cross Ref]

21. Diagnostic and statistical manual of mental disorders, 4th ed. Washington, DC: American Psychiatric Association, 2000.

22. Regulation (EC) No 1333/2008 of the European Parliament and of the Council. In: Official Journal of the European Union. http://eur-lex.europa.eu/LexUriServ/LexUriServ.do?uri=OJ:L:2008:354:0016:0033:en:PDF.

23. Center for Science in the Public Interest, 2008. Petition to Ban the Use of Yellow 5 and Other Food Dyes, in the Interim to Require a Warning on Foods Containing These Dyes, to Correct the Information the Food and Drug Administration Gives to Consumers on the Impact of These Dyes on the Behavior of Some Children, and to Require Neurotoxicity Testing of New Food Additives and Food Colors. Available at: http://www.fda.gov/downloads/AdvisoryCommittees/CommitteesMeetingMaterials/FoodAdvisoryCommittee/UCM248005.pdf. Accessed April 6, 2012.

24. FDA/CFSAN Food Advisory Committee, 2011. Center for Food Safety and Applied Nutrition, March 30-31, 2011, Food Advisory Committee Meeting

25. Certified Color Additives and Childhood Hyperactivity, Food Advisory Charge and Questions. Available at: http://www.fda.gov/downloads/AdvisoryCommittees/CommitteesMeetingMaterials/FoodAdvisoryCommittee/UCM247999.pdf. Accessed May 19, 2012.25. FDA/CFSAN Food Advisory Committee, 2011. Background Document for the Food Advisory Committee: Certified Color Additives in Food and Possible Association with Attention Deficit Hyperactivity Disorder in Children March 30-31, 2011. Available at: http://www.fda.gov/downloads/AdvisoryCommittees/CommitteesMeetingMaterials/FoodAdvisoryCommittee/UCM248549.pdf. Accessed May 19, 2012.

26. FDA/CFSAN Food Advisory Committee, 2011. Overview and Evaluation of Proposed Association between Artificial Food Colors and Attention Deficit Hyperactivity Disorders (ADHD) and Problem Behaviors in Children. Interim Toxicology Review Memorandum, September 1, 2010, Attachment 4. Available at: http://www.fda.gov/downloads/AdvisoryCommittees/CommitteesMeetingMaterials/FoodAdvisoryCommittee/UCM248113.pdf. Accessed May 19, 2012.

27. FDA Food Advisory Committee, 2011. Quick Minutes: Food Advisory Committee Meeting March 30-31, 2011. Available at: http://www.fda.gov/advisorycommittees/committeesmeetingmaterials/foodadvisorycommittee/ucm250901.htm. Accessed 19 May, 2012.

28. Weiss B. Synthetic food colors and neurobehavioral hazards: the view from environmental health research. Environ Health Perspect. 2012;120:1–5. doi: 10.1289/ehp.1103827.[PMC free article][PubMed][Cross Ref]

29. Diagnostic and statistical manual of mental disorders, 4th ed., text revision. Washington, DC: American Psychiatric Association, 2000.

30. Arnold LE, Bozzolo H, Amato A, et al. Acetyl-l-carnitine (ALC) in attention-deficit/hyperactivity disorder (ADHD): a multi-site placebo-controlled pilot trial. J Child Adolesc Psychopharmacol. 1997;17:791–801. doi: 10.1089/cap.2007.018.[PubMed][Cross Ref]

31. World Health Organization. ICD-10: International statistical classification of diseases and related health problems, 10th revised ed. New York, NY, 2008.

32. Santosh PJ, Taylor E, Swanson J, et al. Reanalysis of the multimodal treatment study of attention-deficit/hyperactivity disorder (ADHD) based on ICD-10 criteria for hyperkinetic disorder (HD) Clin Neurosci Res. 2005;5:307–314. doi: 10.1016/j.cnr.2005.09.010.[Cross Ref]

33. Diagnostic and statistical manual of mental disorders, 3rd ed. Washington, DC: American Psychiatric Association, 1980.

34. Chobanian AV, Bakris GL, Black HR, et al. Seventh report of the joint national committee on prevention, detection, evaluation, and treatment of high blood pressure. Hypertension. 2003;42:1206–1252. doi: 10.1161/01.HYP.0000107251.49515.c2.[PubMed][Cross Ref]

35. Pelham WE, Fabiano GA, Massetti Evidence-based assessment of attention deficit hyperactivity disorder in children and adolescents. J. Clin Child Adol Psychol. 2005;34:449–476. doi: 10.1207/s15374424jccp3403_5.[PubMed][Cross Ref]

36. Farone SV, Perlis RH, Doyle AE, et al. Molecular genetics of attention-deficit/hyperactivity disorder. Biol Psychiatry. 2005;57:1313–1323. doi: 10.1016/j.biopsych.2004.11.024.[PubMed][Cross Ref]

37. Pearce N. Epidemiology in a changing world: variation, causation, and ubiquitous risk factors. I J Epidemiol. 2011;40:503–512.[PubMed]

38. Wender PH. The minimal brain dysfunction syndrome. Ann Rev Med. 1975;26:45–62. doi: 10.1146/annurev.me.26.020175.000401.[PubMed][Cross Ref]

39. Akinbami LJ, Xiang L, Pastor PN, Reuben CA. Attention deficit hyperactivity disorder among children aged 5-17 years in the United States, 1998-2009. NCHS Data Brief 2011;70:xx. [PubMed]

40. Burde B, Choate MS. Early asymptomatic lead exposure and development at school age. Pediatrics. 1975;87:638–642. doi: 10.1016/S0022-3476(75)80845-6.[PubMed][Cross Ref]

41. Fergusson DM, Horwood LJ, Lynskey MT. Early dentine lead levels and subsequent cognitive and behavioural development. J Child Psychol Psychiat. 1993;34:215–227. doi: 10.1111/j.1469-7610.1993.tb00980.x.[PubMed][Cross Ref]

42. Bouchard MF, Bellinger DC, Wright RO, Weisskopf MG. Attention-deficit/hyperactivity disorder and urinary metabolites of organophosphate pesticides. Pediatrics. 2010;125:1270–1277. doi: 10.1542/peds.2009-3058.[PMC free article][PubMed][Cross Ref]

43. Marks AR, Harley K, Bradman A, et al. Organiophosphate pesticide exposure and attention in young Mexican-American children: The CHAMACOS study. Environ Health Perspect. 2010;118:1768–1774. doi: 10.1289/ehp.1002056.[PMC free article][PubMed][Cross Ref]

44. Sagiv SK, Thurston SW, Bellinger DC, et al. Prenatal organochlorine exposure and behaviors associated with attention deficit hyperactivity disorder in school-aged children. Am J Epidemiol. 2010;171:593–601. doi: 10.1093/aje/kwp427.[PMC free article][PubMed]

One thought on “Indigotine Synthesis Essay

Leave a comment

L'indirizzo email non verrà pubblicato. I campi obbligatori sono contrassegnati *