Indole-3-carbinol

Chembox new
ImageFile = Indole-3-carbinol.png ImageSize =
IUPACName = 1H-indol-3-ylmethanol
OtherNames = Indole-3-carbinol, 3-Indolylcarbinol, 1H-Indole-3-methanol, 3-Hydroxymethylindole, 3-Indolemethanol, Indole-3-methanol, I3C
Section1 = Chembox Identifiers
CASNo = 700-06-1
EINECS = 211-836-2
PubChem = 3712
SMILES = C1=CC=C2C(=C1)C(=CN2)CO
InChI = 1/C9H9NO/c11-6-7-5-10-9- 4-2-1-3-8(7)9/h1-5,10-11H,6H2
RTECS = NL9483000
ChEBI = 24814
Section2 = Chembox Properties
Formula = C₉H₉NO
MolarMass = 147.18 g/mol
Appearance = Off-white solid
Density =
MeltingPt = 96 - 99 °C
BoilingPt =
Solubility = Partially in cold water
Section3 = Chembox Hazards
EUClass = Irritating (Xi)
MainHazards =
FlashPt =
Autoignition =
NFPA-H = 1
NFPA-F = 0
NFPA-R = 0
NFPA-O =
RPhrases = R36/38
SPhrases = S26, S36

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 benefitscite journal
journal = Pharmacological research
volume = 55
issue = 3
year = 2007
pages = 224–236
title = Cruciferous vegetables and human cancer risk: epidemiologic evidence and mechanistic basis.
last = Dashwood
first = RH, et al
url =
format =
accessdate =
doi = 10.1016/j.phrs.2007.01.009 Entrez Pubmed|17317210] .

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.cite journal
journal = Carcinogenesis, Jan;
volume = 10
issue = 1
year = 1989
pages = 175–181
title = Quantitative inter-relationships between aflatoxin B1 carcinogen dose, indole-3-carbinol anti-carcinogen dose, target organ DNA adduction and final tumor response.
last = Dashwood
first = RH, et al
url =
format =
accessdate =
doi = 10.1093/carcin/10.1.175
pmid = 2491968 Entrez Pubmed|2491968]

In 2006, Hsu et al proved that indole-3-carbinol induces a G1 growth arrest of human reproductive cancer cells.cite journal
journal = Biochem Pharmacol., Dec 15;
volume = 72
issue = 12
year = 2006
pages = 1714–23
title = Indole-3-carbinol mediated cell cycle arrest of LNCaP human prostate cancer cells requires the induced production of activated p53 tumor suppressor protein.
last = Hsu
first = JC, et al
url =
format =
accessdate =
doi = 10.1016/j.bcp.2006.08.012 Entrez Pubmed|16970927] 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).cite journal| journal = Journal of Cerebral Blood Flow & Metabolism| volume = 19| issue = | year = 1999| pages = 1263–1269| title = Neuroprotection by Estrogens in a Mouse Model of Focal Cerebral Ischemia and in Cultured Neurons: Evidence for a Receptor-Independent Antioxidative Mechanism| last = Culmsee| first = Carsten| url = http://www.nature.com/jcbfm/journal/v19/n11/full/9590625a.html| format = | accessdate =| doi = 10.1097/00004647-199911000-00011 ] [cite web|url=http://www.sfn.org/index.cfm?pagename=brainBriefings_estrogensInfluenceOnTheBrain|title=Society for Neuroscience, "Estrogen's Influence on the Brain"]

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

External links

* [http://www.chemblink.com/products/700-06-1.htm Data at chemblink.com]
* [http://www.sciencelab.com/xMSDS-Indole_3_carbinol-9924365 MSDS at sciencelab.com]