Indole-3-carbinol

Base Information

• Chemical Name: Indole-3-carbinol
• CAS No.: 700-06-1
• Molecular Formula: C9H9NO
• Molecular Weight: 147.177
• Hs Code.: 29339900
• European Community (EC) Number: 211-836-2
• NSC Number: 525801
• UNII: C11E72455F
• DSSTox Substance ID: DTXSID7031458
• Nikkaji Number: J193.059A
• Wikipedia: Indole-3-carbinol
• Wikidata: Q1770257
• NCI Thesaurus Code: C1135
• Pharos Ligand ID: M4UPL6GDXD32
• Metabolomics Workbench ID: 38756
• ChEMBL ID: CHEMBL155625
• Mol file: 700-06-1.mol

Synonyms:1H-indole-3-methanol;3-hydroxymethylindole;I3C cpd;indole-3-carbinol;indole-3-methanol

Chemical Property of Indole-3-carbinol

Chemical Property:

• Appearance/Colour: Off-white powder
• Melting Point: 96-99 °C(lit.)
• Refractive Index: 1.5670 (estimate)
• Boiling Point: 360.6 °C at 760 mmHg
• PKA: 15.10±0.10(Predicted)
• Flash Point: 171.9 °C
• PSA: 36.02000
• Density: 1.272 g/cm³
• LogP: 1.66020
• Storage Temp.: 2-8°C
• Solubility.: soluble in Methanol
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 147.068413911
• Heavy Atom Count: 11
• Complexity: 138

Purity/Quality:

99%, ^*data from raw suppliers

Indole-3-carbinol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=CN2)CO
• Recent ClinicalTrials: Trial of Indole-3-Carbinol and Silibinin
• Sources: Indole-3-carbinol (I3C) is a bioactive phytochemical found abundantly in cruciferous vegetables such as broccoli, cabbage, green peas, cauliflower, and Brussels sprouts.^[1]
• Categories and Type: I3C is classified as a bioactive phytochemical and belongs to the group of indole compounds.
• Uses: Indole-3-carbinol (I3C) has been studied for its potential in preventing and treating various chronic diseases, including inflammation, obesity, diabetes, cardiovascular disease, cancer, hypertension, neurodegenerative diseases, and osteoporosis. I3C and its metabolite 3,3′-diindolylmethane (DIM) have shown promise as cancer chemopreventive agents in preclinical models and clinical trials.^[2]
• Mechanism of Action: I3C and its metabolites alter multiple signaling pathways controlling cellular events such as oxidation, inflammation, proliferation, differentiation, apoptosis, angiogenesis, and immunity. DIM, a metabolite of I3C, is particularly involved in modulating aryl hydrocarbon receptor (AHR) signaling.^[3]
• Production Methods: I3C is naturally occurring and is produced when raw cruciferous vegetables are consumed or processed. It can also be obtained through extraction and purification processes for use in dietary supplements or pharmaceuticals.
• References: [1] Indole-3-Carbinol: Occurrence, Health-Beneficial Properties, and Cellular/Molecular Mechanisms; DOI 10.1146/annurev-food-060721-025531; [2] Biomedical application of Indole-3-carbinol: A mini-review; DOI 10.1016/j.phytol.2020.09.024; [3] Indoles Derived From Glucobrassicin: Cancer Chemoprevention by Indole-3-Carbinol and 3,3'-Diindolylmethane; DOI 10.3389/fnut.2021.734334

Technology Process of Indole-3-carbinol

There total 32 articles about Indole-3-carbinol 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: 100.0%

Indole-3-carboxaldehyde (487-89-8,1228547-52-1) → indole-3-carbinol (700-06-1)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃; for 1h;

DOI:10.1002/chem.201503355

Reference yield: 100.0%

indole (120-72-9) + formaldehyd (50-00-0,30525-89-4,61233-19-0) → indole-3-carbinol (700-06-1)

Guidance literature:

With sodium methylate; for 8h; Heating;

DOI:10.1007/BF00772147

Reference yield: 84.0%

3-methoxycarbonylindole (942-24-5) → indole-3-carbinol (700-06-1)

Guidance literature:

3-methoxycarbonylindole; With pentadec-3-en-2-one; trimethylsilyl trifluoromethanesulfonate; triphenylphosphine; In dichloromethane; at -78 - 0 ℃; for 1h; Inert atmosphere;

With diisobutylaluminium hydride; In hexane; dichloromethane; at -78 ℃; Inert atmosphere;

With potassium carbonate; In methanol; hexane; dichloromethane; at 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/ol501463p

upstream raw materials:

1,3,5-Trioxan

indole

methanol

sodium methylate

Downstream raw materials:

N-morpholinyl-3-indolylmethylamine

indole-3-acetonitrile

3-((4-(N,N-Dimethylamino)phenyl)methyl)-indole

1H-indole-3-carboxylic acid

Refernces

• 1、 Panahi, Farhad,Haghighi, Fatemeh,Khalafi-Nezhad, Ali. "Reduction of Aldehydes with Formic acid in Ethanol using Immobilized Iridium Nanoparticles on a Triazine-phosphanimine Polymeric Organic Support". . . Retrieved 2020/07/06.
• 2、 Zhang,Xu,Wang,Kang. "Efficient Synthesis and Biological Activity of Novel Indole Derivatives as VEGFR-2 Tyrosine Kinase Inhibitors". . p. 3006 - 3016. Retrieved 2018/02/21.