Indigo carmine

Base Information

• Chemical Name: Indigo carmine
• CAS No.: 860-22-0
• Molecular Formula: C16H10N2Na2O8S2
• Molecular Weight: 466.36
• Hs Code.: 32041200
• European Community (EC) Number: 212-728-8
• UNII: D3741U8K7L
• DSSTox Substance ID: DTXSID1020190
• Nikkaji Number: J428.520D,J3.340E
• Wikipedia: Indigo_carmine
• Wikidata: Q410120
• NCI Thesaurus Code: C83799,C71675
• RXCUI: 227312
• ChEMBL ID: CHEMBL2105023
• Mol file: 860-22-0.mol

Synonyms:(delta-2,2'-biindole)-3,3'-dione;2-(1,3-Dihydro-3-oxo-5-sulpho-2H-indol-2-ylidene)-3- oxoindoline-5-sulphonic acid;Carmine, Indigo;D and C Blue NO. 6;FD and C Blue No. 2;indigo;Indigo Blue;Indigo Blue, Soluble;Indigo Carmine;Indigo Disulfonate;indigotin;Indigotindisulfonate;Indigotindisulfonate Sodium;Indigotindisulfonic Acid;Soluble Indigo Blue

Chemical Property of Indigo carmine

Chemical Property:

• Appearance/Colour: purple powder
• Melting Point: >300 °C
• Refractive Index: n20/D 1.335
• PSA: 189.36000
• Density: 1.01 g/mL at 20 °C
• LogP: 3.06060
• Storage Temp.: Store below +30°C.
• Sensitive.: Light Sensitive
• Solubility.: 1g/l
• Water Solubility.: 1 g/100 mL (25 ºC)
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 1
• Exact Mass: 465.95174613
• Heavy Atom Count: 30
• Complexity: 877

Purity/Quality:

99%, ^*data from raw suppliers

Indigo carmine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn; Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 22-24/25-36/37/39-27-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Dyes -> Other Dyes
• Canonical SMILES: C1=CC2=C(C=C1S(=O)(=O)[O-])C(=C(N2)C3=NC4=C(C3=O)C=C(C=C4)S(=O)(=O)[O-])O.[Na+].[Na+]
• Recent ClinicalTrials: Comparative Efficacy of Water & Indigo Carmine vs. Water or Air Method on Adenoma Detection Rate (ADR) - a Randomized Controlled Trial (RCT)
• Recent EU Clinical Trials: Chromoendoscopy versus conventional endoscopy in Patients with polyposis syndrome
• Recent NIPH Clinical Trials: The usefulness of AIM in colonoscopy
• Description: Indigo carmine is indigotindisulfonate sodium, a marker dye used during cystoscopy and ureteral catheterization. (1) Indigo carmine is also used in endoscopic procedures, lymph node and vessel delineation, and for tumor localization. Indigo carmine is an unapproved drug without FDA approved labeling. (2) There is no single dye that can replace indigo carmine. Choice of alternative agent will depend on type of procedure and physician discretion, as well as product availability. Indigo Carmine (IC) is the most common chemical dye for clothes dyeing, which is considered as a refractory molecule since it is required a rather strong chemical treatment for its elimination from the water waste. The presence of this dye in residuals causes notorious change of water color and smell even in very low concentration. Moreover, if some of this water reaches natural streams it can be toxic for aquatic living entities due to the formation of toxic compounds such as aromatic amines.
• Uses: Colorant for nylon, surgical sutures, foods and ingested drugs. As a reagent for functional kidney tests, for detection of nitrates, chlorates and in testing milk. Indigo Carmine (FD&C Blue #2) is a colorant. It has poor ph stability in that after 1 week at ph 3 and 5 it will appreciably fade, at ph 7 considerably fade, and at ph 8 fade completely. It is the least soluble of all food colors, with a solubility of 1.6 g in 100 ml of water at 25°c. Complete fading occurs in alkalis such as 10% sodium carbonate and 10% sodium hydroxide, with fading also occurring in 10% sugar systems. It has very poor light stability and oxidation stability, and moderate stability to heat; it has a deep blue hue with poor tinctorial strength. It is the only food color that has good resistance to reducing agents, but has very poor compatibility with food components. The major use is in pet food, but it is also used in candies, confections, and baked goods. The common name is indigotine. 5,5’Indigodisulfonic Acid Disodium Salt is a food additive that is widely used in the market. 5,5’Indigodisulfonic Acid Disodium Salt was also used as a dye for cationic cotton fabrics.

Technology Process of Indigo carmine

There total 3 articles about Indigo carmine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 60.0%

indigo (64784-13-0,482-89-3,141901-19-1,12626-73-2) → indigo carmine (860-22-0)

Guidance literature:

With sulfuric acid; at 25 - 30 ℃; for 1h;

Reference yield:

indigo-5,5'-disulfonic acid (483-20-5) → indigo carmine (860-22-0)

Guidance literature:

With sodium hydroxide; In water; acetone; pH=6.5 - 9;

Reference yield:

indole (120-72-9) → indigo carmine (860-22-0)

Guidance literature:

Multi-step reaction with 3 steps

1: molybdenum hexacarbonyl; acetic acid / tert-butyl alcohol / 7 h / 80 - 86 °C

2: sulfuric acid / 2 h / 90 - 105 °C

3: sodium hydroxide / water; acetone / pH 6.5 - 9

With sulfuric acid; acetic acid; sodium hydroxide; molybdenum hexacarbonyl; In water; acetone; tert-butyl alcohol;

upstream raw materials:

indole

indigo-5,5'-disulfonic acid

indigo

Downstream raw materials:

isatin-5-monosulphonic acid

malic acid

anthranilic acid

tartaric acid

Refernces

• 1、 -. "AN IMPROVED PROCESS FOR THE PREPARATION OF INDIGO CARMINE". . . Retrieved 2017/06/27.