3,3'-Diindolylmethane
3,3'-Diindolylmethane
CAS: 1968-05-4
Molecular Formula: C17H14N2
3,3'-Diindolylmethane - Names and Identifiers
| Name | 3,3'-Diindolylmethane |
| Synonyms | DIM Arundine Plant Indole Diindoylmethane Di(1H-indol-3-yl) 3,3'Diindolemethane 3,3-Diindolylmethane 3,3-Methylenediindole 3,3'-DIINDOLYLMETHANE 3,3'-Diindolylmethane 3,3'-METHYLENEDIINDOLE 3,3'-Methylenebisindole 3,3'-METHYLENEBISINDOLE 3,3'-Diindolylmethane(DIM) 3,3'-METHYLENEBIS-1H-INDOLE 3,3'-methanediylbis(1H-indole) |
| CAS | 1968-05-4 |
| EINECS | 100-201-5 |
| InChI | InChI=1/C17H14N2/c1-3-7-16-14(5-1)12(10-18-16)9-13-11-19-17-8-4-2-6-15(13)17/h1-8,10-11,18-19H,9H2 |
3,3'-Diindolylmethane - Physico-chemical Properties
| Molecular Formula | C17H14N2 |
| Molar Mass | 246.31 |
| Density | 1.271±0.06 g/cm3(Predicted) |
| Melting Point | 167 °C |
| Boling Point | 230 °C(Press: 0.01 Torr) |
| Flash Point | 232.5°C |
| Solubility | Chloroform (Sparingly), Methanol (Slightly) |
| Vapor Presure | 8.07E-10mmHg at 25°C |
| Appearance | Powder |
| Color | White to Pale Beige |
| pKa | 16.91±0.30(Predicted) |
| Storage Condition | 2-8°C |
| Refractive Index | 1.765 |
| MDL | MFCD00195766 |
| Use | An antineoplastic agent that activates Chk 2 and cytochrome p450 |
| In vitro study | DIM is an effective radioprotector and reliever, acting by stimulating ATM-driven DDR-like responses and NF-κB survival signals. DIM can inhibit the invasion, angiogenesis, proliferation and induce apoptosis of tumor cells by regulating signaling pathways, such as AKT, NF-κB and foxo3. It can also inhibit estrogen-induced gene expression and cause endoplasmic reticulum stress. DIM can alter estrogen metabolism and antagonize estrogen and androgen receptor activity. |
| In vivo study | After multiple doses of DIM, it effectively resists whole-body radiation. In in vivo tests, DIM has a radioprotective or mitigating effect. In normal tissues, DIM activates ATM. DIM can be administered to mice by oral gavage (250 mg/kg) with high bioavailability and no acute toxicity. |
3,3'-Diindolylmethane - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| WGK Germany | 3 |
| RTECS | NM0332000 |
| HS Code | 29349990 |
| Hazard Class | IRRITANT |
3,3'-Diindolylmethane - Reference Information
| introduction | 3,3 '-diindole methane (3,3'-Diindolylmethane) is white to white crystalline powder, soluble in methanol, ethyl acetate, dichloromethane and other organic solvents. |
| application | 3,3 '-diindole methane widely exists in natural plants of cruciferous family. it has important biological and pharmacological activities and is widely used in the fields of medicine and health products. |
| preparation | place indole (1.17g,10mmol),CTAB(50% mol) and oxalic acid (50% mol) in a 25ml single-mouth round bottom flask, add 5ml of deionized water, stir fully for 5 minutes, and then add formaldehyde aqueous solution (0.38g solution, 5mmol formaldehyde) dropwise. Reaction at room temperature for 3 hours, stop the reaction. The reaction solution was extracted three times with 15ml ethyl acetate, and the organic phase was collected and dried with anhydrous Na2SO4 for 5 hours. The solvent was removed under reduced pressure and recrystallized with a mixed solution of methanol and water (methanol/H2O = 10/1) to obtain a white solid 3,3 '-diindole methane with a 85% yield. |
| Biological activity | 3,3 '-Diindolylmethane(DIM) is the main digestion product of indole-3-carbinol, and indole-3-carbinol is a potential anti-cancer substance in cruciferous vegetables. 3,3 '-Diindolylmethane(DIM) is a purely strong antagonist of androgen receptor (AR). |
| Target | Value |
| Use | Pharmaceutical intermediates; can be found in natural phytochemicals belonging to cruciferous plants, acid-catalyzed reaction products, indole -3-methanol; It has the function of anti-tumor agent; this derivative, under relatively high concentration conditions, can directly accelerate the apoptosis of human cancer cells, and can also sensitize TRAIL to induce the apoptosis of human cancer cells; DIM induces a G1 cell loop inhibition, which is expressed in human breast cancer MCF-7 cells through mechanism and inclusion. DIM is a powerful inhibitor of mitochondrial H -ATPase. As a new plant growth promoter, the function of DIM and its derivatives has been applied to eco-friendly systematic research |
Last Update：2024-04-10 22:29:15
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