Dichloroacetic acid Chemical Properties
- Melting point:
- 9-11 °C(lit.)
- Boiling point:
- 194 °C(lit.)
- 1.563 g/mL at 25 °C(lit.)
- vapor density
- 4.5 (vs air)
- vapor pressure
- 0.19 mm Hg ( 20 °C)
- refractive index
- Flash point:
- >230 °F
- storage temp.
- 1.48(at 25℃)
- APHA: <50
- 1.2 (129g/l, H2O, 20℃)
- Water Solubility
- Stable. Incompatible with strong oxidizing agents, strong bases, strong reducing agents. Reacts with water. Protect from moisture. Hygroscopic.
- CAS DataBase Reference
- 79-43-6(CAS DataBase Reference)
- NIST Chemistry Reference
- Acetic acid, dichloro-(79-43-6)
- EPA Substance Registry System
- Dichloroacetic acid (79-43-6)
- Hazard Codes
- Risk Statements
- Safety Statements
- UN 1764 8/PG 2
- WGK Germany
- HS Code
- 2915 40 00
- Hazardous Substances Data
- 79-43-6(Hazardous Substances Data)
- LD50 orally in rats: 2.82 g/kg (Smyth)
Dichloroacetic acid Usage And Synthesis
Dichloroacetic acid (DCA) is an analogous form of acetic acid where 2 out 3 of the hydrogen atoms from the methyl group are substituted by chlorine atoms. Dichloroacetic acid salts and esters have been used as active ingredients in medical drugs based on their ability to suppress the enzyme pyruvate dehydrogenase kinase. It is also administered to stem the secretion of lactic acid as a method of treatment for lactic acidosis. Dichloroacetic acid is clinically fundamental in children for the treatment of lactic acidosis. It slows down the growth of brain cancer cells hence DCA has been used as an effective self-treatment medication. DCA is generally safe for this indication, but its overall effectiveness is not established.
Dichloroacetic acid can be administered intravenously or orally, but it is most effective when administered intravenously. The side effects associated with DCA are significantly minimal when the drug is administered intravenously, which makes it the optimum method of delivery.
Physical and Chemical Properties
DCA has a molecular weight of 128.936 g/mol, a monoisotopic mass of 127.943 g/mol and an exact mass of 127.943 g/mol. DCA is a colorless crystalline solid that melts at 490 F. Dichloroacetic acid is miscible in acetone, diethyl ether, and ethanol; partially dissolves in carbon tetrachloride; soluble in water (1000000 mg/l at 200 C. When heated, the crystalline solid decomposes to produce hydrogen chloride and nitrogen oxide, which are both toxic vapors.
Mechanism of Action
DCA is an established cancer agent as it does not necessarily kill the cancerous cells, but instead, it modifies the metabolic properties of the cancer cells. This differs from the basic mechanism of a majority of chemo agents hence implying that they can result in notable toxicity. Cancer cells secrete copious amounts of glucose which results in immense energy in a dysfunctional manner. Cancer cells also hold the potential to increase the frequency of transcription of insulin receptors whose function is to convey glucose molecules into the cancer cell. Through glycolysis, glucose is converted into energy in the presence or absence of oxygen. Tumor cells illustrate about 200 times the rate of glycolysis as compared to healthy cells and the subsequent energy is used as a key factor in influencing the rapid growth of cancer. Healthy cells do not primarily depend on glycolysis for energy production as it is an ineffective method hence their intracellular activity revolves around the integration of oxygen as a key ingredient for the production of energy in the mitochondria. The mitochondria induce apoptosis where the functionality of mitochondria is reduced, and they can undergo mitosis. Not all tumor cells function this way, but those that take on this mechanism become the dominant cells in charge of growth, metastasis, and reoccurrence of the disease. Dichloroacetic acid aims at these dominant cells to influence total cure or stabilization of disease.
Based on its mechanism of action, Dichloroacetic acid can be relevant to breast cancer, colorectal and colon cancer, lung cancer, neuroblastoma, ovarian cancer, glioblastoma, acute myeloid leukemia, prostate cancer, non-Hodgkin’s Follicular Lymphoma and oral squamous cell carcinoma amongst other types of cancer.
DCA treatment can result in peripheral neuropathy, reduced memory/confusion, and fatigue when administered orally. All the side effects associated with DCA are reversible and short-lived. There are no significant observations of hypersensitivity to DCA.
Concentrated DCA can irritate when it comes to contact with the eyes or skin when inhaled or ingested. Prolonged use of the drug can result in organ damage, bronchial infection or respiratory tract irritation especially when a spray mist is in use.
Dichloroacetic acid, CHCI2COOH, also known as dichlorethanoic acid, is a colorless,strong liquid acid. It is soluble in water and alcohol. Dichloroacetic acid is prepared by the chlorination of acetic acid.It is used in organic synthesis.
DCA is a corrosive, combustible, colorless liquid with a pungent odor.
ChEBI: An organochlorine compound comprising acetic acid carrying two chloro substituents at the 2-position. It occurs in nature in seaweed, Asparagopsis taxiformis.
A colorless crystalline solid melting at 49°F. Corrosive to metals and tissue.
Air & Water Reactions
Soluble in water.
Dichloroacetic acid is probably hygroscopic. Dichloroacetic acid reacts with water or steam. Dichloroacetic acid is incompatible with strong oxidizing agents, strong bases and strong reducing agents.
TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.
Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.
Moderately toxic by skin contact and ingestion. It is corrosive to the skin, eyes, and mucous membranes. Questionable carcinogen with experimental tumorigenic data. Will react with water or steam to produce toxic and corrosive fumes. When heated to decomposition it emits toxic fumes of Cl-. See also CHLORIDES.
This haloacetic acid can be a byproduct of drinking water disinfection and may increase the risk of cancer. This chemical is used as starting material for the production of glyoxylic; dialkyloxy acids; and sulfonamides. It is also used as a fungicide, a medication; and a chemical intermediate in pharmaceuticals
UN1764 Dichloricacetic acid, Hazard class: 8; Labels: 8-Corrosive material.
Crystallise this strong acid from *benzene or pet ether. Dry it with MgSO4 and fractionally distil it. [Bernasconi et al. J Am Chem Soc 107 3612 1985, Beilstein 2 IV 498.]
DCA is a medium strong acid; incompatible with nonoxidizing mineral acids; organic acids; bases, acrylates, aldehydes, alcohols, alkylene oxides; ammonia, aliphatic amines; alkanolamines, aromatic amines; amides, furfuryl alcohol (explosion hazard), glycols, isocyanates, ketones. Attacks metals generating flammable hydrogen gas. Attacks some plastics, rubber, and coatings
- DICHLOROACETIC ACID ETHYL ESTER,DICHLOROACETIC ACID ETHYL ESTER
- Dichloroacetic acid
- Thionyl chloride
- Diisopropylammonium dichloroacetate
- Sodium dichloroisocyanurate
- phosphoric acid
- Ascoric Acid
- Ethyl 2-(Chlorosulfonyl)acetate
- 2,4-Dichlorophenoxyacetic acid
- Folic acid
- Dichloroacetic acid methyl,DICHLOROACETIC ACID METHYL ESTER,Dichloroacetic acid methyl,DICHLOROACETIC ACID METHYL ESTER
- Citric acid
- DICHLOROACETIC ACID SODIUM SALT,SODIUM DICHLOROACETIC ACID,DICHLOROACETIC ACID SODIUM SALT,SODIUM DICHLOROACETIC ACID
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