In a study published on Thursday in the journal Science, researchers found evidence that a compound called indole-3-carbinol (i33c) blocks an enzyme that inhibits the activity of Pten.
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When eaten, cruciferous vegetables are a source of indole-3-carbinol, which has been studied, along with other indoles, for the role it may play in lowering the risk of several types of cancer.
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Investigation of mechanisms by which consumption of indole-3-carbinol might influence cancer incidence focuses 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.
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Indole-3-carbinol can shift estrogen metabolism towards less estrogenic metabolites. Systemic lupus erythematosus (SLE, or lupus), an autoimmune disease, is associated with estrogen. In a study using mice bred to develop lupus, indole-3-carbinol was fed to one group while another group was fed a standard mouse diet; the group fed the indole-3-carbinol diet lived longer and had fewer signs of disease. Another study of lupus prone mice with indole-3-carbinol defined the mechanism for the improvement of their disease to be due to sequential blocks in the development of B and T cells of these mice.
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Indole-3-carbinol (C9H9NO) is produced by the breakdown of the glucosinolate glucobrassicin, which can be found at relatively high levels in cruciferous vegetables such as broccoli, cabbage, cauliflower, brussels sprouts, collard greens and kale. It is also available in dietary supplements. 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.
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Cabbage is a source of indole-3-carbinol, a chemical under basic research for its possible properties.
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Indole-3-carbinol causes proliferation arrest and apoptosis in human melanoma cells. Kim YS et al showed that the master regulator of melanoma biology, microphthalmia-associated transcription factor (MITF-M) was downregulated by Indole-3-carinol to induce apoptosis. Kundu A et al demonstrated that the anticancer property of Indole-3-carbinol is driven by specific targeting of oncogenic pathways. In two different studies using xenografted mouse model of melanoma, they observed that subcutaneous injection of Indole-3-carbinol could bring down tumor burden significantly.
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In a second study Kundu et al showed that in melanoma cells where PTEN is downregulated, Indole-3-carbinol directly interacts with NEDD4_1 to prevent PTEN ubiquitination and subsequent proteasomal degradation. This results in stabilization of PTEN and inhibition of proliferation by downstream AKT signaling. Overall scientific evidence shows that in melanoma, Indole-3-carbinol specifically inhibits the two most commonly associated driver mutation signaling pathways to cause proliferation, a fact that can be used to design clinical trial to treat human patients with Indole-3-carbinol in future.
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A variety of compounds are added to stabilize the foams. These additives include pine oil, various alcohols (methyl isobutyl carbinol (MIBC)), polyglycols, xylenol (cresylic acid).
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The underlying molecular mechanism of this anti-tumor effect was found to be by the specific inhibition of activity of oncogenic BRAFV600E in tumors that harbored the mutation. However, in tumors that expressed wild type BRAF, Indole-3-carbinol did not cause any comparable antiproliferative effect. Additionally Indole-3-carbinol did not cause antiproliferation even in normal epidermal melanocytes underscoring the specificity and selectivity of its action. Kundu et al further showed that inhibition of BRAF V600E activity by Indole-3-carbinol resulted in downregulation of MITF-M by downstream signaling which caused a G1 cell cycle arrest leading to the observed antiproliferative effect.
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There is evidence suggesting that indole-3-carbinol may have an effect on human papillomavirus-infected cells in both pediatrics and adult patients. Research is ongoing.
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Mesityl oxide is used as a solvent and in the production of methyl isobutyl ketone by hydrogenation: :250px Complete hydrogenation gives 4-methyl-2-pentanol (methyl isobutyl carbinol).
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The maturation arrests resulted in a fall in autoantibody production, thought to be a crucial component of lupus causation. In addition, I3C supplementation of the disease prone mice led to a normalization of their T cell function. Women with lupus can manifest a metabolic response to indole-3-carbinol and might also benefit from its antiestrogenic effects. Clinical trials are currently underway to determine the efficacy of treating human patients suffering from lupus with indole-3-carbinol.
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Studies on cruciferous vegetables, including cabbage, include whether they may lower the risk against colon cancer. Cabbage is a source of indole-3-carbinol, a chemical under basic research for its possible properties.
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Several dietary phytochemicals have been shown to be effective HDAC inhibitors. These include sulphorphane, indole-3-carbinol, and phenethyl isothiocyanates, found in broccoli, kale, and watercress, and epigallocatecehin-3-gallate, found in green tea.
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3-Hexanol (IUPAC name: hexan-3-ol; also called ethyl propyl carbinol) is an organic chemical compound. It occurs naturally in the flavor and aroma of plants such as pineapple and is used as a food additive to add flavor.
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Acetoin, also known as 3-hydroxybutanone or acetyl methyl carbinol, is an organic compound with the formula CH3CH(OH)C(O)CH3. It is a colorless liquid with a pleasant, buttery odor. It is chiral. The form produced by bacteria is (R)-acetoin.
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Isoamyl alcohol is a colorless liquid with the formula , specifically (H3C–)2CH–CH2–CH2–OH. It is one of several isomers of amyl alcohol (pentanol). It is also known as isopentyl alcohol, isopentanol, or (in the IUPAC recommended nomenclature) 3-methyl-butan-1-ol. An obsolete name for it was isobutyl carbinol.
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4-Methyl-2-pentanol (IUPAC name: 4-methylpentan-2-ol) or methyl isobutyl carbinol (MIBC) is an organic chemical compound used primarily as a frother in mineral flotation. It is also used as a solvent, in organic synthesis, and in the manufacture of brake fluid and as a precursor to some plasticizers.
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A significant deactivating metabolic transformation of natural prostaglandins is enzymatic oxidation of the C-15 hydroxyl to the corresponding ketone. This is prevented, with retention of activity, by methylation to give the C-15 tertiary carbinol series. Carboprost synthesis: G. L. Bundy et al., ; G. L. Bundy, (1971, 1973 both to Upjohn).
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Some spiro compounds can be synthesized using the Pinacol-pinacolone rearrangement; for example, spiro[5.4]decane (final compound in following two line scheme) can be synthesized from symmetric 1,2-diols of the sort shown below [e.g., this route's starting material, (1,1′-bicyclopentyl)-1,1′-diol]. Initially, one of the carbinol moieties is protonated, allowing water to leave, and yielding the corresponding carbocation (second structure, first row); this intermediate then undergoes a bond migration, resulting in ring expansion of the adjacent ring, with deprotionation unmasking the ketone functional group to complete the first line of the mechanism. This first product, a spirobicyclic ketone, is a spiro compound in its own right, and yields the further spiro carbinol and the alicyclic spiro hydrocarbon after two further reduction reactions.
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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 benefits.
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Letrozole distributes rapidly around the body and is thoroughly distributed to tissues. Around 60% of the drug is bound to plasma proteins, especially albumin (55%). The elimination of letrozole is very slow and the elimination half-life is approximately 2 days. The main route of elimination of the drug is metabolism in the liver to the pharmacologically inactive metabolite carbinol.
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3,3′-Diindolylmethane (DIM) is a compound derived from the digestion of indole-3-carbinol, found in cruciferous vegetables such as broccoli, Brussels sprouts, cabbage and kale. The reputation of Brassica vegetables as healthy foods rests in part on the activities of diindolylmethane. Limited data from clinical studies indicate that DIM may have some benefits for patients suffering from types of prostate cancer, however more studies are required.
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Overuse of indole-3-carbinol supplements in the hope of preventing cancer may be unwise, as the 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). It promotes liver cancer in trout when it is combined with aflatoxin B1 and demotes metastasis.
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Ethchlorvynol is a member of the class of sedative-hypnotic carbinols, which includes methylparafynol and tert-amyl alcohol. It is not a benzodiazepine, carbamate, or barbituric acid derivative, and its molecular structure is considerably simpler. The systematic name of ethchlorvynol is usually given as ethyl 2-chlorovinyl ethynyl carbinol or 1-chloro-3-ethylpent-1-en-4-yn-3-ol. Its empirical formula is C7H9ClO.
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Ptaquiloside has unstable chemical structure and readily undergoes glucose liberation. The resulting ptaquilodienone is the active form of ptaquiloside and accounts for the observed biological effects. The cyclopropyl group in the dienone is highly reactive as an electrophile, not only because it is conjugated with the keto group, but because it also constitutes a cyclopropyl carbinol system, from which the facile formation of the stable non-classical cation is well-known.
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Procyclidine synthesis: Procyclidine, 1-cyclohexyl-1-phenyl-3-pyrrolidinopropan-1-ol, is synthesized in exactly the same manner as was seen for trihexyphenidyl, except this time the linear synthesis begins with the preparation of 3-(1-pyrrolidino)propiophenone. Procyclidine synthesis 2 In an interesting variation, the ketone is first reacted with phenylmagnesium bromide. Catalytic hydrogenation of the carbinol thus obtained can be stopped after the reduction of only one aromatic ring.
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The synthesis starts with a standard scheme for preparing indoxyls. Thus, acylation of diphenylamine with oxalyl chloride leads to the amide. The acid chloride then cyclizes into the ring on heating to afford (3). Reaction of that product with 4-picoline under phase-transfer conditions catalyzed by a quaternary salt affords the carbinol (4) from addition of the transient anion on the methyl group of the picoline to the more electrophilic carbonyl group.
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The second principal side reaction is the reduction of the ketone or aldehyde to the corresponding alcohol. After initial hydrolysis of the hydrazone, the free carbonyl derivative is reduced by alkoxide to the carbinol. In 1924, Eisenlohr reported that substantial amounts of hydroxydecalin were observed during the attempted Wolff–Kishner reduction of trans-β-decalone. In general, alcohol formation may be repressed by exclusion of water or by addition of excess hydrazine.
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This forms the corresponding trichloromethyl carbinol or -alkoxide, in a similar way to the Grignard reaction. This trihalogenated product is subject to addition via a base-induced intramolecular etherification gem-dichloro epoxy. The amine can attack the oxirane due to formation of tertiary carbocation in a nucleophilic substitution SN1 concerted elimination of one atom of chlorine. The nucleophilic intermediate is highly reactive and regioselective at the α-carbon, resulting in the formation of a α-substituted carboxylic acid chloride.
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He did research on nitric acid, discovering a new acidity function for nitration reactions. He hesitated to discuss his work on the triphenyl carbinol series with physical chemists because of the secrecy requirements of the project. Other researchers such as Christopher Ingold were first to publish in the area. Westheimer was also influenced by the development of statistical mechanics by physicists Joseph Edward Mayer and Maria Goeppert-Mayer, who moved to the University of Chicago in 1945.
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The Meyer–Schuster rearrangement has been used in a variety of applications, from the conversion of ω-alkynyl-ω-carbinol lactams into enamides using catalytic PTSAChihab- Eddine, A.; Daich, A.; Jilale, A.; Decroix, B. J. Heterocycl. Chem. 2000, 37, 1543–1548.() to the synthesis of α,β-unsaturated thioesters from γ-sulfur substituted propargyl alcoholsYoshimatsu, M.; Naito, M.; Kawahigashi, M.; Shimizu, H.; Kataoka, T. J. Org. Chem. 1995, 60, 4798–4802.() to the rearrangement of 3-alkynyl-3-hydroxyl-1H-isoindoles in mildly acidic conditions to give the α,β-unsaturated carbonyl compounds.
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A hemiaminal is the first step in the reaction of an aldehyde or ketone with an amine. Being one of the most reactive carbonyls, formaldehyde is well known to give carbinolamines. Illustrative is the reaction of the weakly basic secondary amine carbazole with formaldehyde.Carbazol-9-yl-methanol Milata Viktora, Kada Rudolfa, Lokaj J¨¢nb Molbank 2004, M354 open access publication reaction of carbazole with formaldehyde to Carbazol-9-yl-methanol As is typical with a secondary amine derivative, this carbinol converts readily to the methylene-linked bis(carbazole).
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Other chemicals may reduce mutagenesis or prevent cancer via other mechanisms, although for some the precise mechanism for their protective property may not be certain. Selenium, which is present as a micronutrient in vegetables, is a component of important antioxidant enzymes such as gluthathione peroxidase. Many phytonutrients may counter the effect of mutagens; for example, sulforaphane in vegetables such as broccoli has been shown to be protective against prostate cancer. Others that may be effective against cancer include indole-3-carbinol from cruciferous vegetables and resveratrol from red wine.
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Rxn of p-fluorobenzyl chloride (1) with the anion of diethylmethyl malonate (2) gives intermediate diester (3), saponification of which and subsequent decarboxylation leads to 4. {Alternatively it can be formed by Perkin reaction between p-fluorobenzaldehyde and propionic anhydride in the presence of NaOAc, followed by catalytic hydrogenation of the olefinic bond using a palladium on carbon catalyst.} Polyphosphoric acid (PPA) cyclization leads to 5-fluoro-2-methyl-3-indanone (4). A Reformatsky reaction with zinc amalgam and bromoacetic ester leads to carbinol (5), which is then dehydrated with tosic acid to indene 6.
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In the yellow form, all three nitrogen atoms carry a positive charge, of which two are protonated, while the green colour corresponds to a form of the dye with two of the nitrogen atoms positively charged. At neutral pH, both extra protons are lost to the solution, leaving only one of the nitrogen atoms positive charged. The pKa for the loss of the two protons are approximately 1.15 and 1.8. In alkaline solutions, nucleophilic hydroxyl ions attack the electrophilic central carbon to produce the colourless triphenylmethanol or carbinol form of the dye.
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Treatment of that intermediate with Raney nickel reduces the cyano group to the corresponding primary amine; this product then undergoes an internal ester-amine interchange to yield the cyclized lactam (5). LAH serves to reduce the lactam to an amine; the ester on the other ring is reduced to a carbinol in the process, affording the aminoalcohol (7). The basic function is next alkylated with 2-chloropyrimidine (7). Rxn of the alcoholin (8) with MsCl leads to the mesylate; that group is next displaced by sodium azide (9); the azide group is next reduced to the primary amine.
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Typical reagents include potassium ethylxanthate and sodium ethylxanthate, but dithiophosphates and dithiocarbamates are also used. The treated ore is introduced to a water-filled aeration tank containing surfactant such as methylisobutyl carbinol (MIBC). Air is constantly forced through the slurry and the air bubbles attach to the hydrophobic copper sulfide particles, which are conducted to the surface, where they form a froth and are skimmed off. These skimmings are generally subjected to a cleaner-scavenger cell to remove excess silicates and to remove other sulfide minerals that can deleteriously impact the concentrate quality (typically, galena), and the final concentrate sent for smelting.
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1,3,8-Trihydroxyanthraquinone is an organic compound. It is one of many trihydroxyanthraquinone isomers, formally derived from anthraquinone by replacement of three hydrogen atoms by hydroxyl (OH) groups. The compound occurs in some microorganisms and in alcoholic extracts of the wood of the South American plant Senna reticulata (mangerioba grande or maria mole in Portuguese), used in the local folk medicine for liver problems and rheumatism. The extract also contained, among other products chrysophanol (1,8-dihydroxy-3-methylanthraquinone), physcion (1,8-dihydroxy-3-methyl-6-methoxyanthraquinone), aloe-emodin (3-carbinol-1,8-dihydroxyanthraquinone), lunatin (3-methoxy-1,6,8-trihydroxyanthraquinone), emodin (6-methyl-1,3,8-trihydroxyanthraquinone), and chrysophanol-10,10'-bianthrone.
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Upon heating α-picolinic acid will spontaneously decarboxylate forming the so-called 'Hammick Intermediate' (2), which can be viewed as an aromatic ylide. In the presence of a strong electrophile, such as an aldehyde or ketone, this species will undergo nucleophilic attack faster than proton transfer. After nucleophilic attack intramolecular proton transfer yields the desired carbinol (4). The mechanism of the Hammick reaction The scope of the reaction is effectively limited to decarboxylating acids where the carboxyl group is α to the nitrogen, (reactivity has been reported when the acids are located elsewhere on the molecule but with low yields) thus suitable substrates are limited to the derivatives of α-picolinic acid including the α-carboxylic acids of quinoline and isoquinoline.
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Clinical data for the effects of DIM are limited, but because of potential anticancer properties, the National Cancer Institute of the United States has begun clinical trials of DIM as a therapeutic for numerous forms of cancer. Much of the scientific interest is due to its action as a histone deacetylase inhibitor in vitro, specifically against HDAC1, HDAC2, and HDAC3. DIM is a metabolite of the Indole-3-carbinol (I3C), also known as Indolylmethanol, which has been shown to have some cancer-preventative effects and some anti-cancer properties. A study conducted in 2013 to research the use of DIM as a treatment to prevent or reduce the effects of acute radiation syndrome due to whole body exposure found that the compound may be useful in preventing or mitigating tissue damage due to partial body radiation exposure which occurs routinely during radiotherapy-based cancer treatment.
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