1H-indol-3-ylmethanol

• ChemBase ID: 64722
• Molecular Formular: C9H9NO
• Molecular Mass: 147.17386
• Monoisotopic Mass: 147.06841391
• SMILES: c1(c[nH]c2c1cccc2)CO
• Canonical SMILES: OCc1c[nH]c2c1cccc2
• InChI: InChI=1S/C9H9NO/c11-6-7-5-10-9-4-2-1-3-8(7)9/h1-5,10-11H,6H2
• InChIKey: IVYPNXXAYMYVSP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1H-indol-3-ylmethanol
• IUPAC Traditional name: indole-3-carbinol
• Synonyms: Indole-3-carbinol; 3-Indolemethanol; Indole-3-carbinol; 3-Hydroxymethylindole; 3-Indolemethanol; Indole-3-carbinol; 3-Indolylcarbinol; 1H-Indole-3-methanol; 3-Hydroxymethylindoll; Indole-3-methanol; I3C; Indol-3-yl-methanol; 3-Hydroxymethylindole; (1H-Indol-3-yl)-methanol; 3-(Hydroxymethyl)indole; 3-Indolemethanol; 吲哚-3-甲醇

Database IDs

• CAS Number: 700-06-1
• EC Number: 211-836-2
• MDL Number: MFCD00005632
• Beilstein Number: 121323
• PubChem SID: 24896113; 162030461
• PubChem CID: 3712
• CHEBI ID: 24814
• CHEMBL: 155625
• Chemspider ID: 3581
• Wikipedia Title: Indole-3-carbinol

CALCULATED PROPERTIES

• Acid pKa: 15.095989
• H Acceptors: 1
• H Donor: 2
• LogD (pH = 5.5): 1.304658
• LogD (pH = 7.4): 1.304658
• Log P: 1.304658
• Molar Refractivity: 43.9604 cm^3
• Polarizability: 18.035147 Å^3
• Polar Surface Area: 36.02 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dimethyl Sulfoxide; Methanol; Partially in cold water
• Apperance: Off-white solid; White Solid
• Melting Point: 96-99 °C; 96-99 °C(lit.); 96-99°C; 96-99°C

Safety Information

• Storage Condition: -20°C; 2-8°C; Amber Vial, -20°C Freezer, Under Inert Atmosphere
• Storage Warning: 2-80C; IRRITANT; Irritant
• RTECS: NL9483000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/38; R36/38
• Safety Statements: 26-36; S26, S36
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• NFPA704:
  

  0

  1

  0
• GHS Hazard statements: H315-H319
• GHS Precautionary statements: P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: 97%; 98%
• Salt Data: Free Base

DETAILS

MP Biomedicals - 02155025

(3-Indolemethanol) Off-white crystals.

MP Biomedicals - 05214564

MP Biomedicals Rare Chemical collection

Selleck Chemicals - S2313

Research Area: Metabolic Disease
Biological Activity:
Indole-3-carbinol is produced by the breakdown of the glucosinolate glucobrassicin, which can be found at relatively high levels in cruciferous vegetables. Dose-related decreases in tumor susceptibility due to Indole-3-carbinol (inferred by decreases in aflatoxin-DNA binding). Indole-3-carbinol induces a G1 growth arrest of human reproductive cancer cells. This is significant in the prevention and treatment of cancer, as the G1 phase of cell growth occurs early in the cell lifecycle, and, for most cells, is the major period of cell cycle during its lifespan. [1][2]

Sigma Aldrich - I7256

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.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. I7256.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - I578000

Inhibits cancinogenesis at the initiation stage. A metabolite of 3-methylindole

REFERENCES

• Hsu JC et al. Biochem Pharmacol. 2006 Dec 15;72(12):1714-23.
• Stresser, D.M., et al.: J. Biochem. Toxicol., 10, 191 (1995)
• Bailey, G.S., et al.: J. Natl. Cancer Inst., 78, 931 (1995)
• D’Agostino et. al. Drug Metabolism and Disp. 27: 2018 (2009)
• On treatment with acids, is converted to a stabilized cation 3-methylene-3H-indolium, which can undergo further reaction to give diindol-3-ylmethane. Moody's group have demonstrated a formal [3+2] cycloaddition of the cation to a variety of alkenes to give cyclopenta[b]indoles: J. Chem. Soc., Perkin 1, 1127 (1995):