700-06-1 Usage
Description
Indole-3-carbinol, also known as I3C, is a novel secondary plant metabolite found in cruciferous vegetables such as cabbage, cauliflower, and Brussels sprouts. It is an indolyl alcohol with a hydroxymethyl group at position 3, which contributes to its potential health benefits. Indole-3-carbinol is an off-white powder that is soluble in organic solvents like benzene, ethanol, DMSO, and dimethyl formamide (DMF). However, it is an unstable compound that rapidly oligomerizes in acidic environments, such as the stomach.
Uses
Used in Cancer Prevention:
Indole-3-carbinol is used as a cancer prevention agent, particularly for breast, cervical, and colon cancers. It acts as an inhibitor of Amyloid-beta deposition and inhibits carcinogenesis at the initiation stage, making it a promising candidate for cancer prevention.
Used in Encapsulation for Anti-cancerogenic Studies:
Indole-3-carbinol has been encapsulated with poly-lactic-co-glycolic acid (PLGA) to study its in-vitro anti-cancerogenic effects on various cancer cell lines, including breast adenocarcinoma epithelial (MCF7), colon adenocarcinoma epithelial (Caco2), and prostate carcinoma epithelial (PC3) cells.
Used as a Cytochrome P4501A (CYP1A) Inducer:
Indole-3-carbinol is also used as a CYP1A inducer, which plays a role in the metabolism of various substances in the body.
Used in Pharmaceutical Applications:
Indole-3-carbinol, being produced by members of the Cruciferae family, particularly the Brassica genus, has potential applications in the pharmaceutical industry due to its anticancer properties and ability to induce CYP1A.
Preparation
Using indole, phosphorus oxychloride and N,N-dimethylformamide as raw materials, indole-3-carbaldehyde was synthesized by Vilsmeier-Haack reaction with a yield of 87.1%.
Synthesis Reference(s)
Canadian Journal of Chemistry, 31, p. 775, 1953 DOI: 10.1139/v53-106The Journal of Organic Chemistry, 61, p. 1493, 1996 DOI: 10.1021/jo951219c
Biochem/physiol Actions
Inhibits cancinogenesis at the initiation stage. Has be shown to inhibit carcinogenesis in several animal species, but it enhances tumor incidence if administered at a post-initiation stage. Found in cruciferous vegetables.
Anticancer Research
I3C is a bioactive compound majorly found in Brassica vegetables including broccoli,cauliflower, and collard greens. I3C and its derivative diindolylmethane (DIM)have been investigated for cancer prevention and treatment of breast, prostate, andovarian cancers. I3C partially modulates the tyrosine kinase/PI3K/Akt signalingpathway which leads to the prevention of lung adenocarcinoma which is induced byusing tobacco carcinogen in A/J mice. DIM transduces signaling via aryl hydrocarbon(Ah) receptor, NF-κB/Wnt/Akt/mTOR signaling pathways, cell cycle arrest,modulated cytochrome P450 enzymes, and altered angiogenetic and invasive,metastatic, and epigenetic behavior of cancer cells. Combination of DIM and I3Cinduces Nrf2-mediated phase II drug metabolizing genes (GSTm2, UGT1A1, andNQO1) and antioxidant genes (HO-1, SOD-1) (Weng et al. 2008; 2012).
Check Digit Verification of cas no
The CAS Registry Mumber 700-06-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 7,0 and 0 respectively; the second part has 2 digits, 0 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 700-06:
(5*7)+(4*0)+(3*0)+(2*0)+(1*6)=41
41 % 10 = 1
So 700-06-1 is a valid CAS Registry Number.
InChI:InChI=1/C9H9NO/c11-6-7-5-10-9-4-2-1-3-8(7)9/h1-5,10-11H,6H2
700-06-1Relevant articles and documents
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Clerin,Bruice
, p. 5571 (1974)
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Chemoselective transfer hydrogenation of aromatic and heterocyclic aldehydes by green chemically prepared cobalt oxide nanoparticles
Krishnaveni,Lakshmi,Kaveri,Kadirvelu
, (2020/09/16)
A new surfactant (quercetin) assisted hydrothermal method is used for the preparation of phase pure cobalt oxide (Co3O4) nanoparticles (Nps). The quercetin acted well as surfactant in producing size controlled Nps. The produced Nps were extensively characterized by various techniques to reveal its chemical composition, structure, morphology, size and thermal behavior. The main objective of the study is to employ the prepared material as heterogeneous catalyst for hydrogenation of therapeutically important aldehydes. The capability of the catalyst is appear to be good, since the yield of alcohols from structurally different aldehydes is adequate with short period of time. Also the catalyst is recyclable, stable, no need of addition of ligands for activation and environmentally benign.
Development of indole sulfonamides as cannabinoid receptor negative allosteric modulators
Greig, Iain R.,Baillie, Gemma L.,Abdelrahman, Mostafa,Trembleau, Laurent,Ross, Ruth A.
, p. 4403 - 4407 (2016/08/25)
Existing CB1 negative allosteric modulators (NAMs) fall into a limited range of structural classes. In spite of the theoretical potential of CB1 NAMs, published in vivo studies have generally not been able to demonstrate the expected therapeutically-relevant CB1-mediated effects. Thus, a greater range of molecular tools are required to allow definitive elucidation of the effects of CB1 allosteric modulation. In this study, we show a novel series of indole sulfonamides. Compounds 5e and 6c (ABD1075) had potencies of 4 and 3?nM respectively, and showed good oral exposure and CNS penetration, making them highly versatile tools for investigating the therapeutic potential of allosteric modulation of the cannabinoid system.