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07-SEPTEMBER-2008 03:17:44 - Indole-3-carbinol Indole-3-carbinol IUPAC name 1H-indol-3-ylmethanol Other names Indole-3-carbinol, 3-Indolylcarbinol, 1H-Indole-3-methanol, 3-Hydroxymethylindole, 3-Indolemethanol, Indole-3-methanol, I3C Identifiers CAS number 700-06-1 PubChem 3712 EINECS number 211-836-2 ChEBI 24814 RTECS number NL9483000 SMILES C1=CC=C2C=C1C=CN2CO InChI 1/C9H9NO/c11-6-7-5-10-9- 4-2-1-3-879/h1-5,10-11H,6H2 Properties Molecular formula C9H9NO Molar mass 147.18 g/mol Appearance Off-white solid Melting point 96 - 99 °C Solubility in water Partially in cold water Hazards EU classification Irritating Xi NFPA 704 0 1 0 R-phrases R36/38 S-phrases S26, S36 Except where noted otherwise, data are given for materials in their standard state at 25 °C, 100 kPa Infobox references Indole-3-carbinol C9H9NO is produced by the breakdown of the glucosinolate glucobrassicin which can be found at relatively high levels in cruciferous vegetables. Indole-3-carbinol is the subject of on-going biomedical research into its possible anticarcinogenic, antioxidant, and anti-atherogenic effects. Research on indole-3-carbinol has been conducted primarily using laboratory animals and cultured cells. Limited and inconclusive human studies have been reported. A recent review of the biomedical research literature found that, evidence of an inverse association between cruciferous vegetable intake and breast or prostate cancer in humans is limited and inconsistent and larger randomized controlled trials are needed to determine if supplemental indole-3-carbinol has health benefits1. Contents 1 Indole-3-carbinol and cancer 2 Dietary sources 3 References 4 Footnotes 5 External links Indole-3-carbinol and cancer Investigation of mechanisms by which consumption of indole-3-carbinol might influence cancer incidence focus on its ability to alter estrogen metabolism and other cellular effects. Controlled studies have been performed on such animals as rats, mice, and rainbow trout, introducing various controlled levels of carcinogens, and levels of Indole-3-carbinol into their daily diet. Results showed dose-related decreases in tumor susceptibility due to Indole-3-carbinol inferred by decreases in aflatoxin-DNA binding. The first direct evidence of pure anti-initiating activity by a natural anticarcinogen indole-3-carbinol found in human diet was claimed by Dashwood, et al, in 1989.2 In 2006, Hsu et al proved that indole-3-carbinol induces a G1 growth arrest of human reproductive cancer cells.3 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. The G1 phase is marked by synthesis of various enzymes that are required in the next S phase, including those needed for DNA replication. It should be noted that indiscriminant overuse of indole-3-carbinol supplements in hopes of preventing cancer may be unwise, as hormone balance should be tested via simple blood test before regular consumption. Such caution is advised due to its effect on estrogen levels estrogen has a significant impact on brain function.45 Dietary sources Indole-3-carbinol occurs naturally in cruciferous vegetables such as cabbage, broccoli, brussels sprouts, and kale. It is also widely available in supplement form. References Michnovicz JJ, Bradlow HL. Induction of estradiol metabolism by dietary indole-3-carbinol in humans. J Natl Cancer Inst. 1990; 82:947-950. Entrez PubMed 2342128 Morgan DO. 2007 The Cell Cycle: Principles of Control. New Science Press: London Footnotes ^ Dashwood, RH, et al 2007. Cruciferous vegetables and human cancer risk: epidemiologic evidence and mechanistic basis.. Pharmacological research 55 3: 224-236. doi:10.1016/j.phrs.2007.01.009. Entrez PubMed 17317210 ^ Dashwood, RH, et al 1989. Quantitative inter-relationships between aflatoxin B1 carcinogen dose, indole-3-carbinol anti-carcinogen dose, target organ DNA adduction and final tumor response.. Carcinogenesis, Jan; 10 1: 175-181. doi:10.1093/carcin/10.1.175. PMID 2491968. Entrez PubMed 2491968 ^ Hsu, JC, et al 2006. Indole-3-carbinol mediated cell cycle arrest of LNCaP human prostate cancer cells requires the induced production of activated p53 tumor suppressor protein.. Biochem Pharmacol., Dec 15; 72 12: 1714-23. doi:10.1016/j.bcp.2006.08.012. Entrez PubMed 16970927 ^ Culmsee, Carsten 1999. Neuroprotection by Estrogens in a Mouse Model of Focal Cerebral Ischemia and in Cultured Neurons: Evidence for a Receptor-Independent Antioxidative Mechanism. Journal of Cerebral Blood Flow Metabolism 19: 1263-1269. doi:10.1097/00004647-199911000-00011. ^ Society for Neuroscience, Estrogen's Influence on the Brain. External links Data at chemblink.com MSDS at sciencelab.com Retrieved from http://en..org/wiki/Indole-3-carbinol Categories: Indoles | Alcohols Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page This page was last modified on 25 July 2008, at 22:01
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