1H-indol-3-ylmethanol

• ChemBase编号: 64722
• 分子式: C9H9NO
• 平均质量: 147.17386
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 1H-indol-3-ylmethanol
• IUPAC传统名: indole-3-carbinol
• 别名: 吲哚-3-甲醇; 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

登记号

• CAS号: 700-06-1
• EC号: 211-836-2
• MDL号: MFCD00005632
• Beilstein号: 121323
• PubChem SID: 162030461; 24896113
• PubChem CID: 3712
• CHEBI ID: 24814
• CHEMBL: 155625
• Chemspider ID: 3581
• 维基百科标题: Indole-3-carbinol

理论计算性质

• Acid pKa: 15.095989
• 质子受体: 1
• 质子供体: 2
• LogD (pH = 5.5): 1.304658
• LogD (pH = 7.4): 1.304658
• Log P: 1.304658
• 摩尔折射率: 43.9604 cm^3
• 极化性: 18.035147 Å^3
• 极化表面积: 36.02 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Dimethyl Sulfoxide; Methanol; Partially in cold water
• 外观: Off-white solid; White Solid
• 熔点: 96-99 °C; 96-99 °C(lit.); 96-99°C; 96-99°C

安全信息

• 保存条件: -20°C; 2-8°C; Amber Vial, -20°C Freezer, Under Inert Atmosphere
• 保存注意事项: 2-80C; IRRITANT; Irritant
• RTECS编号: NL9483000
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36/38; R36/38
• 安全公开号: 26-36; S26, S36
• TSCA收录: false; 否
• GHS危险品标识: GHS07
• GHS警示词: Warning
• NFPA704:
  

  0

  1

  0
• GHS危险声明: H315-H319
• GHS警示性声明: P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: 2-8°C

产品相关信息

• 纯度: 97%; 98%
• 成盐信息: Free Base

详细说明

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

参考文献

• 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):