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D54702 Sigma-Aldrich

Dichloroacetic acid

ReagentPlus®, ≥99%

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Properties

Related Categories Acids, Acids & Bases, Aerobic Glycolysis (the Warburg Effect), Cancer Metabolism, Cancer Research,
grade   ReagentPlus®
vapor density   4.5 (vs air)
vapor pressure   0.19 mmHg ( 20 °C)
assay   ≥99%
refractive index   n20/D 1.466(lit.)
bp   194 °C(lit.)
mp   9-11 °C(lit.)
density   1.563 g/mL at 25 °C(lit.)
storage temp.   2-8°C
Gene Information   human ... ALDH1A1(216), PDK1(5163)
rat ... Pdk1(116551)

Description

Packaging

100, 4×100, 500 mL in glass bottle

2.5 L in glass bottle

Legal Information

ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Price and Availability


Aerobic Glycolysis in Oncogenesis

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Dichloroacetic acid

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Safety & Documentation

Safety Information

Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
UN 1764 8 / PGII
WGK Germany 
2
RTECS 
AG6125000
Flash Point(F) 
235.4 °F
Flash Point(C) 
113 °C

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Articles

Aerobic Glycolysis and the Warburg Effect

The Warburg effect is the enhanced conversion of glucose to lactate observed in tumor cells, even in the presence of normal levels of oxygen. Otto Heinrich Warburg demonstrated in 1924 that cancer ce...
Keywords: Aerobic, Biofiles, Cancer, Cell proliferation, Clinical, Glycolysis, PAGE, Phosphorylations, Support, Transcription

Determination of Water Content in Dichloroacetic acid Using Karl Fischer Titration

The determination of water in carboxylic acids is usually straightforward provided the substances are soluble. Strong acids must be neutralized. Acetic acid and related compounds have a tendency to u...
Keywords: Esterifications, Titrations

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Molarity Calculator and Normality Calculator for Acids and Bases

The molarity calculator tool provides lab-ready directions describing how to prepare an acid or base solution of specified Molarity (M) or Normality (N) from a concentrated acid or base solution.  To...

Peer-Reviewed Papers

References

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FOXO1-mediated upregulation of pyruvate dehydrogenase kinase-4 (PDK4) decreases glucose oxidation and impairs right ventricular function in pulmonary hypertension: therapeutic benefits of dichloroacetate. Piao L, Sidhu VK, Fang YH, et al. J. Mol. Med. 91(3), 333-46, (2013)

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The contribution of dissolved organic nitrogen and chloramines to nitrogenous disinfection byproduct formation from natural organic matter. Chuang YH, Lin AY, Wang XH, et al. Water Res. 47(3), 1308-16, (2013)

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Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds. R Scott Obach et al Drug Metab. Dispos. 36, 1385-405, (2008)

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Dichloroacetic acid. IARC Monogr. Eval. Carcinog. Risks Hum. 63, 271-90, (1995)

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Dichloroacetate and cancer: new home for an orphan drug? Kankotia S and Stacpoole PW Biochim. Biophys. Acta 1846(2), 617-29, (2014)

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Mitochondrial metabolism - neglected link of cancer transformation and treatment. Pokorný J, Jandová A, Nedbalová M, et al. Prague Med. Rep. 113(2), 81-94, (2012)

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Stimulation of mitochondrial embryo metabolism by dichloroacetic acid in an aged mouse model improves embryo development and viability. McPherson NO, Zander-Fox D, and Lane M Fertil. Steril. 101(5), 1458-66, (2014)

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Calculating virtual log P in the alkane/water system (log P(N)(alk)) and its derived parameters deltalog P(N)(oct-alk) and log D(pH)(alk). Giulia Caron et al J. Med. Chem. 48, 3269-79, (2005)

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Heterogeneity in lung (18)FDG uptake in pulmonary arterial hypertension: potential of dynamic (18)FDG positron emission tomography with kinetic analysis as a bridging biomarker for pulmonary vascular remodeling targeted treatments. Zhao L, Ashek A, Wang L, et al. Circulation 128(11), 1214-24, (2013)

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Metabolic reprogramming is required for antibody production that is suppressed in anergic but exaggerated in chronically BAFF-exposed B cells. Caro-Maldonado A, Wang R, Nichols AG, et al. J. Immunol. 192(8), 3626-36, (2014)

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Inactivation of the HIF-1α/PDK3 signaling axis drives melanoma toward mitochondrial oxidative metabolism and potentiates the therapeutic activity of pro-oxidants. Kluza J, Corazao-Rozas P, Touil Y, et al. Cancer Res. 72(19), 5035-47, (2012)

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Combination of sulindac and dichloroacetate kills cancer cells via oxidative damage. Ayyanathan K, Kesaraju S, Dawson-Scully K, et al. PLoS ONE 7(7), e39949, (2012)

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PDK1 inhibition is a novel therapeutic target in multiple myeloma. Fujiwara S, Kawano Y, Yuki H, et al. Br. J. Cancer 108(1), 170-8, (2013)

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Metabolic response of glioma to dichloroacetate measured in vivo by hyperpolarized (13)C magnetic resonance spectroscopic imaging. Park JM, Recht LD, Josan S, et al. Neuro. Oncol. 15(4), 433-41, (2013)

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Investigation of H-bonding and halogen-bonding effects in dichloroacetic acid: DFT calculations of NQR parameters and QTAIM analysis. Esrafili MD J. Mol. Model. 18(12), 5005-16, (2012)

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In vivo mouse cardiac hyperpolarized magnetic resonance spectroscopy. Dodd MS, Ball V, Bray R, et al. J. Cardiovasc. Magn. Reson. 15, 19, (2013)

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Dichloroacetate improves immune dysfunction caused by tumor-secreted lactic acid and increases antitumor immunoreactivity. Ohashi T, Akazawa T, Aoki M, et al. Int. J. Cancer 133(5), 1107-18, (2013)

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Novel molecular mechanisms of antitumor action of dichloroacetate against T cell lymphoma: Implication of altered glucose metabolism, pH homeostasis and cell survival regulation. Kumar A, Kant S, and Singh SM Chem. Biol. Interact. 199(1), 29-37, (2012)

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Sensitization of metformin-cytotoxicity by dichloroacetate via reprogramming glucose metabolism in cancer cells. Choi YW and Lim IK Cancer Lett. 346(2), 300-8, (2014)

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Haloacetic acid removal by sequential zero-valent iron reduction and biologically active carbon degradation. Tang S, Wang XM, Yang HW, et al. Chemosphere 90(4), 1563-7, (2013)

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Comparison of spheroids formed by rat glioma stem cells and neural stem cells reveals differences in glucose metabolism and promising therapeutic applications. Morfouace M, Lalier L, Bahut M, et al. J. Biol. Chem. 287(40), 33664-74, (2012)

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A dual-targeting hybrid platinum(IV) prodrug for enhancing efficacy. Xiao H, Yan L, Zhang Y, et al. Chem. Commun. (Camb.) 48(87), 10730-2, (2012)

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Treatment for mitochondrial disorders. Pfeffer G, Majamaa K, Turnbull DM, et al. Cochrane Database Syst. Rev. 4, CD004426, (2012)

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Modulation of astrocytic mitochondrial function by dichloroacetate improves survival and motor performance in inherited amyotrophic lateral sclerosis. Miquel E, Cassina A, Martínez-Palma L, et al. PLoS ONE 7(4), e34776, (2012)

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Use of hyperpolarized [1-13C]pyruvate and [2-13C]pyruvate to probe the effects of the anticancer agent dichloroacetate on mitochondrial metabolism in vivo in the normal rat. Hu S, Yoshihara HA, Bok R, et al. Magn. Reson. Imaging 30(10), 1367-72, (2012)

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Antitumor and chemosensitizing action of dichloroacetate implicates modulation of tumor microenvironment: a role of reorganized glucose metabolism, cell survival regulation and macrophage differentiation. Kumar A, Kant S, and Singh SM Toxicol. Appl. Pharmacol. 273(1), 196-208, (2013)

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Lipoic acid inhibits cell proliferation of tumor cells in vitro and in vivo. Feuerecker B, Pirsig S, Seidl C, et al. Cancer Biol. Ther. 13(14), 1425-35, (2012)

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DCA increases the antitumor effects of capecitabine in a mouse B16 melanoma allograft and a human non-small cell lung cancer A549 xenograft. Zheng MF, Shen SY, and Huang WD Cancer Chemother. Pharmacol. 72(5), 1031-41, (2013)

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Pharmacological activation of the pyruvate dehydrogenase complex reduces statin-mediated upregulation of FOXO gene targets and protects against statin myopathy in rodents. Mallinson JE, Constantin-Teodosiu D, Glaves PD, et al. J. Physiol. 590(Pt 24), 6389-402, (2012)

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Influence of dichloroacetate (DCA) on lactate production and oxygen consumption in neuroblastoma cells: is DCA a suitable drug for neuroblastoma therapy? Niewisch MR, Kuçi Z, Wolburg H, et al. Cell Physiol. Biochem. 29(3-4), 373-80, (2012)

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Tumor cell differentiation by label-free fluorescence microscopy. Weber P, Wagner M, Kioschis P, et al. J. Biomed. Opt. 17(10), 101508, (2012)

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A review of analytical methods for the determination of trichloroethylene and its major metabolites chloral hydrate, trichloroacetic acid and dichloroacetic acid. Delinsky AD, Bruckner JV, and Bartlett MG Biomed. Chromatogr. 19(8), 617-39, (2005)

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Halogenated derivatives QSAR model using spectral moments to predict haloacetic acids (HAA) mutagenicity. Alfonso Pérez-Garrido et al Bioorg. Med. Chem. 16, 5720-32, (2008)

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Co-treatment of dichloroacetate, omeprazole and tamoxifen exhibited synergistically antiproliferative effect on malignant tumors: in vivo experiments and a case report. Ishiguro T, Ishiguro R, Ishiguro M, et al. Hepatogastroenterology. 59(116), 994-6, (2012)

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Predictive model for disinfection by-product in Alexandria drinking water, northern west of Egypt. Abdullah AM and Hussona Sel-D Environ. Sci. Pollut. Res. Int. 20(10), 7152-66, (2013)

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Chloride and other anions inhibit dichloroacetate-induced inactivation of human liver GSTZ1 in a haplotype-dependent manner. Zhong G, Li W, Gu Y, et al. Chem. Biol. Interact. 215, 33-9, (2014)

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Comparative analysis of the relationship between trichloroethylene metabolism and tissue-specific toxicity among inbred mouse strains: kidney effects. Yoo HS, Bradford BU, Kosyk O, et al. J. Toxicol. Environ. Health A 78(1), 32-49, (2015)

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Comparative analysis of the relationship between trichloroethylene metabolism and tissue-specific toxicity among inbred mouse strains: liver effects. Yoo HS, Bradford BU, Kosyk O, et al. J. Toxicol. Environ. Health A 78(1), 15-31, (2015)

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Prediction of death in the SMNΔ7 mouse model of spinal muscular atrophy: insight into disease stage and progression. El-Khodor BF, Cirillo K, Beltran JA, et al. J. Neurosci. Methods 209(2), 259-68, (2012)

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Synergistic effect of the combination of immobilized TiO2, UVA and ozone on the decomposition of dichloroacetic acid. Mehrjouei M, Müller S, and Möller D J. Environ. Sci. Health. A. Tox. Hazard. Subst. Environ. Eng. 47(8), 1073-81, (2012)

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Adsorption equilibrium, kinetics and thermodynamics of dichloroacetic acid from aqueous solution using mesoporous carbon. Ding Y, Zhu J, Cao Y, et al. Environ. Technol. 35(13-16), 1962-70, (2014)

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A patient with scirrhous stomach cancer treated with combination of hyperthermotherapy and 5-aminolevulinic acid (ALA). Saito M, Yano K, Kamigaki T, et al. Anticancer Res. 33(7), 2957-63, (2013)

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Dichloroacetate induces different rates of cell death in cancer and noncancer cell lines in vitro. Washington JT and Quintyne NJ Tumori 98(1), 142-51, (2012)

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Finding a job for dichloroacetate. Luft FC J. Mol. Med. 91(3), 329-31, (2013)

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Merck 14,3050

Beil. 2,IV,498

Fieser 16,115

Aldrich MSDS 1, 601:A / Corp MSDS 1 (1), 1109:A / FT-IR 1 (1), 508:B / FT-IR 2 (1), 790:D / FT-NMR 1 (1), 792:A / IR-Spectra (3), 298:C / IR-Spectra (2), 268:H / NMR-Reference 2 (1), 444:B / RegBook 1 (1), 555:H / Sax 6, 928 / Sigma FT-IR 1 (1), 1380:C / Structure Index 1, 79:C:1 / Vapor Phase 3, 591:C

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