TryptopholCAS# 526-55-6 |
Quality Control & MSDS
3D structure
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Number of papers citing our products
| Cas No. | 526-55-6 | SDF | Download SDF |
| PubChem ID | 10685 | Appearance | Powder |
| Formula | C10H11NO | M.Wt | 161.2 |
| Type of Compound | Alkaloids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | 2-(1H-indol-3-yl)ethanol | ||
| SMILES | C1=CC=C2C(=C1)C(=CN2)CCO | ||
| Standard InChIKey | MBBOMCVGYCRMEA-UHFFFAOYSA-N | ||
| Standard InChI | InChI=1S/C10H11NO/c12-6-5-8-7-11-10-4-2-1-3-9(8)10/h1-4,7,11-12H,5-6H2 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Tryptophol is an aromatic alcohol found as a secondary product of alcoholic fermentation that induces sleep in humans. Tryptophol can inhibit the infection/replication of GVE2 by interacting with the host's Clp protease. Tryptophol can inhibit the proliferation of U937 cells by inducing apoptosis via a pathway involving caspase-8 followed by caspase-3. Tryptophol induces apoptosis through Death Receptor (DR) 5 and that the resistance of peripheral blood lymphocytes (PBL) to tryptophol-induced apoptosis might be due to competition from decoy receptor (DcR). |
| Targets | PARP | Caspase |
| In vitro | Tryptophol induces death receptor (DR) 5-mediated apoptosis in U937 cells.[Pubmed: 17690453]Biosci Biotechnol Biochem. 2007 Aug;71(8):2065-8.Tryptophol is a natural component isolated from vinegar produced from the boiled extract of black soybean. We have reported that Tryptophol induces apoptosis in U937 cells via activation of caspase-8 followed by caspase-3. Tryptophol, however, did not affect human peripheral blood lymphocytes (PBL). Genotoxicity of tryptophol in a battery of short-term assays on human white blood cells in vitro.[Pubmed: 18248512]Basic Clin Pharmacol Toxicol. 2008 May;102(5):443-52.
The effects of tryptophol on immune responses and it implications toward trypanosome-induced immunosuppression.[Pubmed: 776647]Experientia. 1976 May 15;32(5):645-7.
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| In vivo | Tryptophol, 5-hydroxytryptophol and 5-methoxytryptophol induced sleep in mice.[Reference: WebLink]Life Sci. 1970 Mar 15;9(6):323-9.
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| Kinase Assay | Isolation of tryptophol as an apoptosis-inducing component of vinegar produced from boiled extract of black soybean in human monoblastic leukemia U937 cells.[Pubmed: 17284845]Biosci Biotechnol Biochem. 2007 Feb;71(2):371-9.We isolated a novel apoptosis-inducing component, Tryptophol, from vinegar produced from boiled extract of black soybean (black soybean vinegar). |
Tryptophol Dilution Calculator
Tryptophol Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 6.2035 mL | 31.0174 mL | 62.0347 mL | 124.0695 mL | 155.0868 mL |
| 5 mM | 1.2407 mL | 6.2035 mL | 12.4069 mL | 24.8139 mL | 31.0174 mL |
| 10 mM | 0.6203 mL | 3.1017 mL | 6.2035 mL | 12.4069 mL | 15.5087 mL |
| 50 mM | 0.1241 mL | 0.6203 mL | 1.2407 mL | 2.4814 mL | 3.1017 mL |
| 100 mM | 0.062 mL | 0.3102 mL | 0.6203 mL | 1.2407 mL | 1.5509 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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The effects of tryptophol on immune responses and it implications toward trypanosome-induced immunosuppression.[Pubmed:776647]
Experientia. 1976 May 15;32(5):645-7.
Daily administration of Tryptophol to laboratory rodents resulted in significantly depressed antibody production of heterologous red blood cell challenge, did not alter cellular-mediated responses to oxazalone. These results suggest that trypanosome-produced Tryptophol may account for the immunodepression observed during trypanosomiasis.
Isolation of tryptophol as an apoptosis-inducing component of vinegar produced from boiled extract of black soybean in human monoblastic leukemia U937 cells.[Pubmed:17284845]
Biosci Biotechnol Biochem. 2007 Feb;71(2):371-9. Epub 2007 Feb 7.
We isolated a novel apoptosis-inducing component, Tryptophol, from vinegar produced from boiled extract of black soybean (black soybean vinegar). Compound-6 purified from an ethyl acetate extract of black soybean vinegar using high performance liquid chromatography (HPLC) induced fragmentation of DNA and the development of apoptotic bodies (characteristic physiological features of apoptosis) in U937 cells. By analysis of chemical structure, this active compound was identified as Tryptophol. Tryptophol induced apoptosis involving caspase-8 and -3 activation, followed by cleavage of poly (ADP-ribose) polymerase (PARP), as shown by measurement of enzyme activity and immunoblot analysis. The cell viability of normal lymphocytes separated from human blood was less affected by Tryptophol, and fragmentation of DNA was not induced in normal lymphocytes. These results indicate that Tryptophol isolated from black soybean vinegar inhibited the proliferation of U937 cells by inducing apoptosis via a pathway involving caspase-8 followed by caspase-3, without affecting normal lymphocytes.
Tryptophol induces death receptor (DR) 5-mediated apoptosis in U937 cells.[Pubmed:17690453]
Biosci Biotechnol Biochem. 2007 Aug;71(8):2065-8.
Tryptophol is a natural component isolated from vinegar produced from the boiled extract of black soybean. We have reported that Tryptophol induces apoptosis in U937 cells via activation of caspase-8 followed by caspase-3. Tryptophol, however, did not affect human peripheral blood lymphocytes (PBL). In this study, we found that Tryptophol enhances formation of a death-inducing signaling complex including death receptor (DR) 5. Cell viability and induction of apoptosis by Tryptophol was reduced by transfection with decoy receptor (DcR) 1. These results indicate that Tryptophol induces apoptosis through DR5 and that the resistance of PBL to Tryptophol-induced apoptosis might be due to competition from DcR1.
Genotoxicity of tryptophol in a battery of short-term assays on human white blood cells in vitro.[Pubmed:18248512]
Basic Clin Pharmacol Toxicol. 2008 May;102(5):443-52.
The genotoxic effects of Tryptophol (indole-3-ethanol), an aromatic alcohol and known secondary metabolite of the opportunistic yeast Candida albicans and other Candida spp., were studied using a battery of short-term assays on human white blood cells in vitro. The concentration range of Tryptophol tested was 0.25 mM to 2.00 mM. Lymphocyte viability and induction of apoptosis/necrosis were studied by simultaneous use of a fluorescent assay with ethidium bromide and acridine orange. Levels of primary DNA damage and dynamics of DNA repair were evaluated using the alkaline comet assay while the levels and nature of residual DNA damage were assessed by the analysis of structural chromosome aberrations, the sister chromatid exchange test and the cytokinesis-block micronucleus assay. The results obtained suggest cytotoxic, cytostatic and genotoxic effects of the Tryptophol treatment in vitro that were mainly dose-dependent. The type and the extent of DNA lesions detected in Tryptophol-treated samples indicate the possibility that observed damage is mediated by highly reactive aldehyde metabolite and/or free radicals produced by treatment. The results show that mortality of lymphocytes in Tryptophol-treated samples was primarily caused by apoptosis. The generation of additional DNA strand breaks and cytogenetic consequences (chromosome aberrations, sister chromatid exchanges and micronuclei), as observed in this study, sustain the possibility that Tryptophol toxicity is mediated by the formation of DNA cross-links and aldehyde-protein adducts. In conclusion, this preliminary study elucidates only a part of Tryptophol toxicity to human cells. Because current evidence is not sufficient to obtain information relevant for human risk assessment, further in vitro and in vivo studies are essential in order to clarify remaining issues, especially to elucidate the exact mechanisms and nature of the damage produced following treatment as well to estimate possible interindividual variability in genotoxic responses to the chemical.
