EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

indole-3-carbinol
methanol, indol-3-yl-

Supplier Sponsors

CAS Number: 700-06-1Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:211-836-2
FDA UNII:C11E72455F
Nikkaji Web:J193.059A
Beilstein Number:0121323
MDL:MFCD00005632
XlogP3:1.10 (est)
Molecular Weight:147.17693000
Formula:C9 H9 N O
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome or firefox)
Category:pharmaceuticals / chemical synthisis
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 360.60 °C. @ 760.00 mm Hg (est)
Flash Point: 341.00 °F. TCC ( 171.90 °C. ) (est)
logP (o/w): 1.366 (est)
Soluble in:
 water, 8339 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
AIDP
Indole-3-Carbinol I3C 98% min.
BOC Sciences
For experimental / research use only.
3-Hydroxymethylindole >98%
Odor: characteristic
Use: Indole-3-carbinol downregulates cell cycle-related proteins (CDK4, CDK6, cyclin D1 and pRb)
BST Tianjin Co.
Indole-3-methanol
Changsha Organic Herb
Broccoli Extract
Maypro Industries
Indole-3-carbinol
Penta International
INDOLE-3-CARBINOL
Risun Ingredients
Indole-3-carbinol 99%min
Sabinsa Corporation
Indole-3-carbinol
Sigma-Aldrich: Sigma
For experimental / research use only.
Indole-3-carbinol
TCI AMERICA
For experimental / research use only.
3-Indolemethanol >95.0%(N)
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
subcutaneous-rat LDLo 500 mg/kg
BEHAVIORAL: COMA
Food and Cosmetics Toxicology. Vol. 18, Pg. 159, 1980.

Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category: pharmaceuticals / chemical synthisis
Recommendation for indole-3-carbinol usage levels up to:
 not for fragrance use.
 
Recommendation for indole-3-carbinol flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
ClinicalTrials.gov:search
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
Env. Mutagen Info. Center:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :3712
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
1H-indol-3-ylmethanol
Chemidplus:0000700061
RTECS:NL9483000 for cas# 700-06-1
 
References:
 1H-indol-3-ylmethanol
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):3712
Pubchem (sid):134976802
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2009
(IUPAC):Atomic Weights of the Elements 2009 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
HMDB (The Human Metabolome Database):HMDB05785
FooDB:FDB000939
Export Tariff Code:2933.99.8290
MedlinePlusSupp:View
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
RSC Learn Chemistry:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 broccoli asparagus broccoli leaf
Search Trop Picture
 brussel sprout shoot
Search Trop Picture
 cabbage leaf
Search Trop Picture
 
Synonyms:
3-hydroxymethyl indole
3-(hydroxymethyl)-1H-indole
3-(hydroxymethyl)indole
3-hydroxymethylindole
1H-indol-3-yl-methanol
(1H-indol-3-yl)-methanol
(1H-indol-3-yl)methanol
 indol-3-ylmethan-1-ol
1H-indol-3-ylmethanol
3-indole carbinol
3-indole methanol
 indole-3-carbidol
 indole-3-methanol
1H-indole-3-methanol
3-indolemethanol
3-indolylcarbinol
 methanol, indol-3-yl-
 

Articles:

PubMed:Effects of chemopreventive natural products on non-homologous end-joining DNA double-strand break repair.
PubMed:Isatis canescens is a rich source of glucobrassicin and other health-promoting compounds.
PubMed:Molecular approaches toward targeted cancer prevention with some food plants and their products: inflammatory and other signal pathways.
PubMed:Urinary 3,3'-diindolylmethane: a biomarker of glucobrassicin exposure and indole-3-carbinol uptake in humans.
PubMed:Natural indoles, indole-3-carbinol and 3,3'-diindolymethane, inhibit T cell activation by staphylococcal enterotoxin B through epigenetic regulation involving HDAC expression.
PubMed:Effects of brussels sprouts and their phytochemical components on oxidative stress-induced neuronal damages in PC12 cells and ICR mice.
PubMed:Contamination of deconjugation enzymes derived from Helix pomatia with the plant bioactive compounds 3,3'-diindolylmethane, 5-methoxypsoralen, and 8-methoxypsoralen.
PubMed:Indole-3-carbinol protects against pressure overload induced cardiac remodeling via activating AMPK-α.
PubMed:Indole-3-carbinol inhibits LPS-induced inflammatory response by blocking TRIF-dependent signaling pathway in macrophages.
PubMed:Encapsulation of indole-3-carbinol and 3,3'-diindolylmethane in zein/carboxymethyl chitosan nanoparticles with controlled release property and improved stability.
PubMed:Involvement of SIRT1-AMPK signaling in the protective action of indole-3-carbinol against hepatic steatosis in mice fed a high-fat diet.
PubMed:I3C and ICZ inhibit migration by suppressing the EMT process and FAK expression in breast cancer cells.
PubMed:Antiangiogenic activity of indole-3-carbinol in endothelial cells stimulated with activated macrophages.
PubMed:Indole-3-carbinol directly targets SIRT1 to inhibit adipocyte differentiation.
PubMed:In vitro suppression of growth of murine WEHI-3 leukemia cells and in vivo promotion of phagocytosis in a leukemia mice model by indole-3-carbinol.
PubMed:Indole-3-carbinol prevents diet-induced obesity through modulation of multiple genes related to adipogenesis, thermogenesis or inflammation in the visceral adipose tissue of mice.
PubMed:3,3'-Diindolylmethane induces G1 arrest and apoptosis in human acute T-cell lymphoblastic leukemia cells.
PubMed:Effect of the pasteurization process on the contents of ascorbigen, indole-3-carbinol, indole-3-acetonitrile, and 3,3'-diindolylmethane in fermented cabbage.
PubMed:LC-MS/MS quantification of sulforaphane and indole-3-carbinol metabolites in human plasma and urine after dietary intake of selenium-fortified broccoli.
PubMed:3,3'-Diindolylmethane but not indole-3-carbinol activates Nrf2 and induces Nrf2 target gene expression in cultured murine fibroblasts.
PubMed:3,3'-Diindolylmethane inhibits prostate cancer development in the transgenic adenocarcinoma mouse prostate model.
PubMed:Effects of lycopene, indole-3-carbinol, and luteolin on nitric oxide production and iNOS expression are organ-specific in rats.
PubMed:Cancer prevention with natural compounds.
PubMed:Chemopreventive properties of indole-3-carbinol, diindolylmethane and other constituents of cardamom against carcinogenesis.
PubMed:Effect of 4-methoxyindole-3-carbinol on the proliferation of colon cancer cells in vitro, when treated alone or in combination with indole-3-carbinol.
PubMed:Indole-3-carbinol induces apoptosis through p53 and activation of caspase-8 pathway in lung cancer A549 cells.
PubMed:Antiangiogenic effects of indole-3-carbinol and 3,3'-diindolylmethane are associated with their differential regulation of ERK1/2 and Akt in tube-forming HUVEC.
PubMed:Dietary chemopreventive phytochemicals: too little or too much?
PubMed:Sulforaphane but not ascorbigen, indole-3-carbinole and ascorbic acid activates the transcription factor Nrf2 and induces phase-2 and antioxidant enzymes in human keratinocytes in culture.
PubMed:3,3'-diindolylmethane attenuates colonic inflammation and tumorigenesis in mice.
PubMed:Effect of boiling on the content of ascorbigen, indole-3-carbinol, indole-3-acetonitrile, and 3,3'-diindolylmethane in fermented cabbage.
PubMed:Ascorbigen: chemistry, occurrence, and biologic properties.
PubMed:Indole-3-carbinol inhibits Sp1-induced matrix metalloproteinase-2 expression to attenuate migration and invasion of breast cancer cells.
PubMed:Mechanism of decreased susceptibility for Gram-negative bacteria and synergistic effect with ampicillin of indole-3-carbinol.
PubMed:Inhibitory effects of a dietary phytochemical 3,3'-diindolylmethane on the phenobarbital-induced hepatic CYP mRNA expression and CYP-catalyzed reactions in female rats.
PubMed:Indole-3-carbinol (I3C) exhibits inhibitory and preventive effects on prostate tumors in mice.
PubMed:Protective effects of isothiocyanates alone or in combination with vitamin C towards N-nitrosodibutylamine or N-nitrosopiperidine-induced oxidative DNA damage in the single-cell gel electrophoresis (SCGE)/HepG2 assay.
PubMed:Renal vascular and tubulointerstitial inflammation and proliferation in Cyp1a1-Ren2 transgenic rats with inducible ANG II-dependent malignant hypertension.
PubMed:Quantitative combination effects between sulforaphane and 3,3'-diindolylmethane on proliferation of human colon cancer cells in vitro.
PubMed:Phytochemicals induce breast cancer resistance protein in Caco-2 cells and enhance the transport of benzo[a]pyrene-3-sulfate.
PubMed:Can indole-3-carbinol-induced changes in cervical intraepithelial neoplasia be extrapolated to other food components?
PubMed:Role of antioxidants in prophylaxis and therapy: A pharmaceutical perspective.
PubMed:Molecular targets of dietary agents for prevention and therapy of cancer.
PubMed:Estrogen receptor alpha as a target for indole-3-carbinol.
PubMed:In vivo relevance of two critical levels for NAD(P)H:quinone oxidoreductase (NQO1)-mediated cellular protection against electrophile toxicity found in vitro.
PubMed:Effects of indole-3-carbinol and phenethyl isothiocyanate on colon carcinogenesis induced by azoxymethane in rats.
PubMed:Inhibition of cell proliferation and in vitro markers of angiogenesis by indole-3-carbinol, a major indole metabolite present in cruciferous vegetables.
PubMed:Induction of phase-1 metabolizing enzymes by oltipraz, flavone and indole-3-carbinol enhance the formation and transport of benzo[a]pyrene sulfate conjugates in intestinal Caco-2 cells.
PubMed:Targets for indole-3-carbinol in cancer prevention.
PubMed:Effects of dietary chemopreventive phytochemicals on P-glycoprotein function.
PubMed:Chemopreventive effect of indole-3-carbinol on induction of preneoplastic altered hepatic foci.
PubMed:Clinical trials in cancer prevention: current results and perspectives for the future.
PubMed:Profiling glucosinolates, flavonoids, alkaloids, and other secondary metabolites in tissues of Azima tetracantha L. (Salvadoraceae).
PubMed:Induction of apoptosis in a non-small cell human lung cancer cell line by isothiocyanates is associated with P53 and P21.
PubMed:Induction of apoptosis in human prostate cancer cell line, PC3, by 3,3'-diindolylmethane through the mitochondrial pathway.
PubMed:Lack of an inducible effect of dietary soy isoflavones on the mRNA abundance of hepatic cytochrome P-450 isozymes in rats.
PubMed:The disposition and metabolism of 2-amino-3-methylimidazo-[4,5-f]quinoline in the F344 rat at high versus low doses of indole-3-carbinol.
PubMed:Indole-3-carbinol and 3,3'-diindolylmethane induce apoptosis in human prostate cancer cells.
PubMed:Chemoprevention of colon cancer by Korean food plant components.
PubMed:Convenient synthesis of 5,6,11,12,17,18- hexahydrocyclononal[1,2-b:4,5-b':7,8-b'']triindole, a novel phytoestrogen.
PubMed:Lack of chemoprevention of indole-3-carbinol in N-methyl-N-nitrosourea-induced mammary carcinogenesis in rats.
PubMed:Plant-derived biomolecules in fermented cabbage.
PubMed:Development of a multi-organ rat model for evaluating chemopreventive agents: efficacy of indole-3-carbinol-. Certain health supplements may cause both carcinogenic and anticarcinogenic effects.
PubMed:Development of a multi-organ rat model for evaluating chemopreventive agents: efficacy of indole-3-carbinol.
PubMed:Effect of nutritional indoles on activity of xenobiotic metabolism enzymes and T-2 toxicity in rats.
PubMed:Risk reduction for DDT toxicity and carcinogenesis through dietary modification.
PubMed:Post-initiation treatment of Indole-3-carbinol did not suppress N-methyl-N-nitrosourea induced mammary carcinogenesis in rats.
PubMed:Effects of indole-3-carbinol on immune responses, aberrant crypt foci, and colonic crypt cell proliferation in rats.
PubMed:Soy isoflavonoid aglycons genistein and daidzein Do not increase the cytochrome P-450 content of the liver microsomes of mice.
PubMed:[Indole derivatives in vegetables of the family Cruciferae].
PubMed:Progress in cancer chemoprevention: development of diet-derived chemopreventive agents.
PubMed:Dietary indole-3-carbinol alters immune functions in rats.
PubMed:Indole-3-carbinol as a chemopreventive agent in 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) carcinogenesis: inhibition of PhIP-DNA adduct formation, acceleration of PhIP metabolism, and induction of cytochrome P450 in female F344 rats.
PubMed:Induction of apoptosis in MCF-7 cells by indole-3-carbinol is independent of p53 and bax.
PubMed:Effect of some indole derivatives on xenobiotic metabolism and xenobiotic-induced toxicity in cultured rat liver slices.
PubMed:An expressional system of human cytochrome P-450 CYP1A1 gene transcription.
PubMed:Modulation of drug-metabolising enzyme expression by condensation products of indole-3-ylcarbinol, an inducer in cruciferous vegetables.
PubMed:1. The chemistry and pharmacology of indole-3-carbinol (indole-3-methanol) and 3-(methoxymethyl)indole. [Part II].
PubMed:Effects of dietary anticarcinogens on rat gastrointestinal glutathione S-transferase theta 1-1 levels.
PubMed:Prevention of cyclophosphamide-induced micronucleus formation in mouse bone marrow by indole-3-carbinol.
PubMed:1 - 1. The chemistry and pharmacology of indole-3-carbinol (indole-3-methanol) and 3-(methoxymethyl)indole. [Part I].
PubMed:Induction of rat pancreatic glutathione S-transferase and quinone reductase activities by a mixture of glucosinolate breakdown derivatives found in Brussels sprouts.
PubMed:Development validation and problems with the toxic equivalency factor approach for risk assessment of dioxins and related compounds.
PubMed:Assessment of mutagenic potential of propoxur and its modulation by indole-3-carbinol.
PubMed:Long term dietary indole-3-carbinol inhibits diethylnitrosamine-initiated hepatocarcinogenesis in the infant mouse model.
PubMed:Chemoprotection against the formation of colon DNA adducts from the food-borne carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in the rat.
PubMed:3,3'-Diindolylmethane induces apoptosis in human cancer cells.
PubMed:Mechanisms of indole-3-carbinol (I3C) anticarcinogenesis: inhibition of aflatoxin B1-DNA adduction and mutagenesis by I3C acid condensation products.
PubMed:Induction of hepatic CYP1A by indole-3-carbinol in protection against aflatoxin B1 hepatocarcinogenesis in rainbow trout.
PubMed:Mechanisms of tumor modulation by indole-3-carbinol. Disposition and excretion in male Fischer 344 rats.
PubMed:The anticarcinogen 3,3'-diindolylmethane is an inhibitor of cytochrome P-450.
PubMed:Bioactive organosulfur phytochemicals in Brassica oleracea vegetables--a review.
PubMed:Regulation of hepatic cytochrome P4501A by indole-3-carbinol: transient induction with continuous feeding in rainbow trout.
PubMed:Effect of the plant compound indole-3-carbinol on hepatic cholesterol homoeostasis.
PubMed:Metabolic activation of the food mutagen 3-amino-1,4-dimethyl-5H-pyrido-[4,3-b]indole (Trp-P-1) in endothelial cells of cytochrome P-450-induced mice.
PubMed:Indole-3-carbinol induces a rat liver glutathione transferase subunit (Yc2) with high activity toward aflatoxin B1 exo-epoxide. Association with reduced levels of hepatic aflatoxin-DNA adducts in vivo.
PubMed:Indole-3-carbinol and beta-naphthoflavone induction of aflatoxin B1 metabolism and cytochromes P-450 associated with bioactivation and detoxication of aflatoxin B1 in the rat.
PubMed:Effects of indole-3-carbinol on biotransformation enzymes in the rat: in vivo changes in liver and small intestinal mucosa in comparison with primary hepatocyte cultures.
PubMed:Chemoprotective and hepatic enzyme induction properties of indole and indenoindole antioxidants in rats.
PubMed:Intrinsic acute toxicity and hepatic enzyme inducing properties of the chemoprotectants indole-3-carbinol and 5,10-dihydroindeno[1,2-b]indole in mice.
PubMed:Modulation of mycotoxin and nitrosamine carcinogenesis by indole-3-carbinol: quantitative analysis of inhibition versus promotion.
PubMed:Modification of carcinogen metabolism by indolylic autolysis products of Brassica oleraceae.
PubMed:Natural pesticides and bioactive components in foods.
PubMed:Natural chemicals, synthetic chemicals, risk assessment, and cancer.
PubMed:Combined in vivo DNA binding and tumor dose-response studies to investigate the molecular dosimetry concept.
PubMed:Tumor dose-response studies with aflatoxin B1 and the ambivalent modulator indole-3-carbinol: inhibitory versus promotional potency.
PubMed:Mechanisms of anti-carcinogenesis by indole-3-carbinol. Studies of enzyme induction, electrophile-scavenging, and inhibition of aflatoxin B1 activation.
PubMed:The stability of the nitrosated products of indole, indole-3-acetonitrile, indole-3-carbinol and 4-chloroindole.
PubMed:In vivo disposition of the natural anti-carcinogen indole-3-carbinol after po administration to rainbow trout.
PubMed:Metaplastic pancreatic cells in liver tumors induced by diethylnitrosamine.
PubMed:Quantitative inter-relationships between aflatoxin B1 carcinogen dose, indole-3-carbinol anti-carcinogen dose, target organ DNA adduction and final tumor response.
PubMed:Modulation of diethylnitrosamine-induced hepatocarcinogenesis and O6-ethylguanine formation in rainbow trout by indole-3-carbinol, beta-naphthoflavone, and Aroclor 1254.
PubMed:Detoxification of isothiocyanate allelochemicals by glutathione transferase in three lepidopterous species.
PubMed:Mechanisms of anti-carcinogenesis by indole-3-carbinol: detailed in vivo DNA binding dose-response studies after dietary administration with aflatoxin B1.
PubMed:The significance of glutathione conjugation for aflatoxin B1 metabolism in rainbow trout and coho salmon.
PubMed:Differential induction of mixed-function oxidase (MFO) activity in rat liver and intestine by diets containing processed cabbage: correlation with cabbage levels of glucosinolates and glucosinolate hydrolysis products.
PubMed:Synthesis of N1-nitroso-3-nitromethylindole: a nonvolatile N-nitroso compound isolated from the nitrosation of the alkaloid gramine.
PubMed:Dietary influences on rat hepatic and intestinal DT-diaphorase activity.
PubMed:Occurrence and detection of natural mutagens and modifying factors in food products.
PubMed:Effect of dietary indole-3-carbinol on intestinal and hepatic monooxygenase, glutathione S-transferase and epoxide hydrolase activities in the rat.
PubMed:Effect of micronutrients, antioxidants and related compounds on the mutagenicity of 3,2'-dimethyl-4-aminobiphenyl, a colon and breast carcinogen.
PubMed:Protection by indole-3-carbinol against covalent binding of benzo[a]pyrene metabolites to mouse liver DNA and protein.
PubMed:Effect of dietary indole-3-carbinol on the induction of the mixed-function oxidases of rat tissue.
PubMed:Dietary constituents altering the responses to chemical carcinogens.
PubMed:Effects of dietary constituents on the metabolism of chemical carcinogens.
 
Notes:
occurs in edible cruciferous vegetables. Produced from glucosinolates in Brassica sp. on crushing or cooking. Potential nutriceutical 16082211).; Indole-3-carbinol is produced by members of the family Cruciferae and particularly members of the genus Brassica, for example, cabbage, radishes, cauliflower, broccoli, Brussels sprouts, and daikon). Indole-3-carbinol is metabolized to a number of products, including the dimeric 3,3'-diindolylmethane. Both 3,3'-diindolylmethane and Indole-3-carbinol are thought to have biological effects. Indole-3-carbinol is a natural chemopreventive compound. It has multiple anticarcinogenic and antitumorigenic properties by suppressing the proliferation of certain cancer cells, including breast cancer, prostate cancer, endometrial cancer, colon cancer, and leukemic cells (PMID: 16634522
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