Methoxyacetic acid

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Methoxyacetic acid
Methoxyessigsaure Strukturformel.svg
Names
IUPAC name
2-Methoxyacetic acid
Other names
2-Methoxyacetic acid
Methyl glycolic acid
Identifiers
ChEBI
ChemSpider
ECHA InfoCard 100.009.904 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 210-894-6
PubChem CID
UNII
Properties
C3H6O3
Molar mass 90.08 g/mol−1
AppearanceClear, colorless, viscous liquid with a pungent odor
Density 1.1768 g/cm−3
Melting point 7–9 °C (45–48 °F; 280–282 K)
Boiling point 202–204 °C (396–399 °F; 475–477 K)
Soluble in water, ethanol, and diethyl ether
Vapor pressure 1.8 mbar (20 °C)
4.8 mbar (50 °C)
Acidity (pKa)3.57
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Methoxyaceticacid is the organic compound with the formula CH3OCH2CO2H. It can be viewed as a derivative of acetic acid in which a hydrogen atom of the methyl group is replaced by a methoxy group. As indicated by the synonym methyl glycolic acid, and as the simplest ether carboxylic acid, methoxyacetic acid can be understood as a methyl ether of glycolic acid.

Contents

Production

In principle the compound can be prepared by reaction of sodium methoxide with monochloroacetic acid. The industrial route involves the oxidation of 2-methoxyethanol with air or oxygen in the presence of platinum catalysts. [1]

In both humans and animals, 2-methoxyacetic acid forms via the rapid oxidation of 2-methoxyethanol [2] by the action of alcohol dehydrogenases.

Properties

Methoxyacetic acid is a colorless, viscous, and corrosive liquid with a pungent odor which, at 7 °C, freezes to a mass similar to glacial acetic acid. Due to the low solvation energy of its methoxy group, methoxyacetic acid, with a pKa value of 3.57, is more acidic than acetic acid (pKa 4.757) and glycolic acid (pKa 3.832). [3]

Ultra-pure methoxyacetic acid (purity of 99.8%, freezing point of 8.4 °C) can be obtained via the multistep crystallization of the raw distillate, which is free of acid contaminations. [4]

Applications

Methoxyacetic acid is a precursor to two commercial fungicides, oxadixyl and mefenoxam.

Former applications

Due to its reprotoxic properties, earlier consumer and industrial applications of methoxyacetic acid as a disinfectant, biocide, or as a cleaner for the decalcification of surfaces are now obsolete. The same is true for substances such as the solvent 2-methoxyethanol or the PVC plasticizer bis(2-methoxyethyl) phthalate, which are metabolized to methoxyacetic acid.

Safety

Due to its considerable reprotoxic potential, methoxyacetic acid has been adopted into the list of SVHC substances (substances of very high concern) [5] and is only registered as an intermediate product for industrial purposes under strictly controlled conditions.

In laboratory tests, methoxyacetic acid inhibits the growth of tumor cells. [6]

Related Research Articles

<span class="mw-page-title-main">Carboxylic acid</span> Organic compound containing a –C(=O)OH group

In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group attached to an R-group. The general formula of a carboxylic acid is often written as R−COOH or R−CO2H, sometimes as R−C(O)OH with R referring to an organyl group, or hydrogen, or other groups. Carboxylic acids occur widely. Important examples include the amino acids and fatty acids. Deprotonation of a carboxylic acid gives a carboxylate anion.

<span class="mw-page-title-main">Carcinogen</span> Substance, radionuclide, or radiation directly involved in causing cancer

A carcinogen is any agent that promotes the development of cancer. Carcinogens can include synthetic chemicals, naturally occurring substances, physical agents such as ionizing and non-ionizing radiation, and biologic agents such as viruses and bacteria. Most carcinogens act by creating mutations in DNA that disrupt a cell's normal processes for regulating growth, leading to uncontrolled cellular proliferation. This occurs when the cell's DNA repair processes fail to identify DNA damage allowing the defect to be passed down to daughter cells. The damage accumulates over time. This is typically a multi-step process during which the regulatory mechanisms within the cell are gradually dismantled allowing for unchecked cellular division.

<span class="mw-page-title-main">Ether</span> Organic compounds made of alkyl/aryl groups bound to oxygen (R–O–R)

In organic chemistry, ethers are a class of compounds that contain an ether group—an oxygen atom bonded to two organyl groups. They have the general formula R−O−R′, where R and R′ represent the organyl groups. Ethers can again be classified into two varieties: if the organyl groups are the same on both sides of the oxygen atom, then it is a simple or symmetrical ether, whereas if they are different, the ethers are called mixed or unsymmetrical ethers. A typical example of the first group is the solvent and anaesthetic diethyl ether, commonly referred to simply as "ether". Ethers are common in organic chemistry and even more prevalent in biochemistry, as they are common linkages in carbohydrates and lignin.

<span class="mw-page-title-main">Ester</span> Compound derived from an acid

In chemistry, an ester is a functional group derived from an acid in which the hydrogen atom (H) of at least one acidic hydroxyl group of that acid is replaced by an organyl group. Analogues derived from oxygen replaced by other chalcogens belong to the ester category as well. According to some authors, organyl derivatives of acidic hydrogen of other acids are esters as well, but not according to the IUPAC.

<span class="mw-page-title-main">Methanol</span> CH3OH; simplest possible alcohol

Methanol is an organic chemical compound and the simplest aliphatic alcohol, with the chemical formula CH3OH. It is a light, volatile, colorless and flammable liquid with a distinctive alcoholic odor similar to that of ethanol, but is more acutely toxic than the latter. Methanol acquired the name wood alcohol because it was once produced chiefly by the destructive distillation of wood. Today, methanol is mainly produced industrially by hydrogenation of carbon monoxide.

Demethylation is the chemical process resulting in the removal of a methyl group (CH3) from a molecule. A common way of demethylation is the replacement of a methyl group by a hydrogen atom, resulting in a net loss of one carbon and two hydrogen atoms.

<span class="mw-page-title-main">Acetate</span> Salt compound formed from acetic acid and a base

An acetate is a salt formed by the combination of acetic acid with a base. "Acetate" also describes the conjugate base or ion typically found in aqueous solution and written with the chemical formula C
2
H
3
O
2
. The neutral molecules formed by the combination of the acetate ion and a positive ion are also commonly called "acetates". The simplest of these is hydrogen acetate with corresponding salts, esters, and the polyatomic anion CH
3
CO
2
, or CH
3
COO
.

<span class="mw-page-title-main">Alkylation</span> Transfer of an alkyl group from one molecule to another

Alkylation is a chemical reaction that entails transfer of an alkyl group. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene. Alkylating agents are reagents for effecting alkylation. Alkyl groups can also be removed in a process known as dealkylation. Alkylating agents are often classified according to their nucleophilic or electrophilic character. In oil refining contexts, alkylation refers to a particular alkylation of isobutane with olefins. For upgrading of petroleum, alkylation produces a premium blending stock for gasoline. In medicine, alkylation of DNA is used in chemotherapy to damage the DNA of cancer cells. Alkylation is accomplished with the class of drugs called alkylating antineoplastic agents.

<span class="mw-page-title-main">Anisole</span> Organic compound (CH₃OC₆H₅) also named methoxybenzene

Anisole, or methoxybenzene, is an organic compound with the formula CH3OC6H5. It is a colorless liquid with a smell reminiscent of anise seed, and in fact many of its derivatives are found in natural and artificial fragrances. The compound is mainly made synthetically and is a precursor to other synthetic compounds. Structurally, it is an ether with a methyl and phenyl group attached. Anisole is a standard reagent of both practical and pedagogical value.

<span class="mw-page-title-main">Indole-3-acetic acid</span> Chemical compound

Indole-3-acetic acid is the most common naturally occurring plant hormone of the auxin class. It is the best known of the auxins, and has been the subject of extensive studies by plant physiologists. IAA is a derivative of indole, containing a carboxymethyl substituent. It is a colorless solid that is soluble in polar organic solvents.

<span class="mw-page-title-main">Glycolic acid</span> Chemical compound

Glycolic acid is a colorless, odorless and hygroscopic crystalline solid, highly soluble in water. It is used in various skin-care products. Glycolic acid is widespread in nature. A glycolate is a salt or ester of glycolic acid.

<span class="mw-page-title-main">Glyoxylic acid</span> Chemical compound

Glyoxylic acid or oxoacetic acid is an organic compound. Together with acetic acid, glycolic acid, and oxalic acid, glyoxylic acid is one of the C2 carboxylic acids. It is a colourless solid that occurs naturally and is useful industrially.

<span class="mw-page-title-main">4-Anisaldehyde</span> Chemical compound

4-Anisaldehyde, or p-Anisaldehyde, is an organic compound with the formula CH3OC6H4CHO. The molecule consists of a benzene ring with a formyl and a methoxy group. It is a colorless liquid with a strong aroma. It provides sweet, floral and strong aniseed odor. Two isomers of 4-anisaldehyde are known, ortho-anisaldehyde and meta-anisaldehyde. They are less commonly encountered.

Glycol ethers are a class of chemical compounds consisting of alkyl ethers that are based on glycols such as ethylene glycol or propylene glycol. They are commonly used as solvents in paints and cleaners. They have good solvent properties while having higher boiling points than the lower-molecular-weight ethers and alcohols.

<span class="mw-page-title-main">2-Methoxyethanol</span> Chemical compound

2-Methoxyethanol, or methyl cellosolve, is an organic compound with formula C
3
H
8
O
2
that is used mainly as a solvent. It is a clear, colorless liquid with an ether-like odor. It is in a class of solvents known as glycol ethers which are notable for their ability to dissolve a variety of different types of chemical compounds and for their miscibility with water and other solvents. It can be formed by the nucleophilic attack of methanol on protonated ethylene oxide followed by proton transfer:

<span class="mw-page-title-main">Lead(IV) acetate</span> Organometallic compound (Pb(C2H3O2)4)

Lead(IV) acetate or lead tetraacetate is an metalorganic compound with chemical formula Pb(C2H3O2)4. It is a colorless solid that is soluble in nonpolar, organic solvents, indicating that it is not a salt. It is degraded by moisture and is typically stored with additional acetic acid. The compound is used in organic synthesis.

In chemistry, carbonylation refers to reactions that introduce carbon monoxide (CO) into organic and inorganic substrates. Carbon monoxide is abundantly available and conveniently reactive, so it is widely used as a reactant in industrial chemistry. The term carbonylation also refers to oxidation of protein side chains.

<span class="mw-page-title-main">Atiprimod</span> Chemical compound

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<span class="mw-page-title-main">Acetic acid</span> Colorless and faint organic acid found in vinegar

Acetic acid, systematically named ethanoic acid, is an acidic, colourless liquid and organic compound with the chemical formula CH3COOH. Vinegar is at least 4% acetic acid by volume, making acetic acid the main component of vinegar apart from water. It has been used, as a component of vinegar, throughout history from at least the third century BC.

<span class="mw-page-title-main">Neodymium(III) acetate</span> Compound of neodymium

Neodymium(III) acetate is an inorganic salt composed of a neodymium atom trication and three acetate groups as anions where neodymium exhibits the +3 oxidation state. It has a chemical formula of Nd(CH3COO)3 although it can be informally referred to as NdAc because Ac is an informal symbol for acetate. It commonly occurs as a light purple powder.

References

  1. Teles, J. Henrique; Hermans, Ive; Franz, Gerhard; Sheldon, Roger A. (2015). "Oxidation". Ullmann's Encyclopedia of Industrial Chemistry. pp. 1–103. doi:10.1002/14356007.a18_261.pub2. ISBN   978-3-527-30385-4.
  2. Mebus, C.A.; Welsch, F. (1989). "The possible role of one-carbon moieties in 2-methoxyethanol and 2-methoxyacetic acid-induced developmental toxicity". Toxicology and Applied Pharmacology. 99 (1): 98–109. doi:10.1016/0041-008X(89)90115-4. PMID   2471293.
  3. King, Edward J. (1960). "The Thermodynamics of Ionization of Amino Acids. V. The Ionization Constants of 3-Methoxy-DL-alanine (O-Methylserine) and Methoxyacetic Acid 1". Journal of the American Chemical Society. 82 (14): 3575–3578. doi:10.1021/ja01499a025. ISSN   0002-7863.
  4. "Espacenet – search results". worldwide.espacenet.com. Retrieved 2023-12-05.
  5. "Substance Information - ECHA". echa.europa.eu. Retrieved 2023-12-05.
  6. Parajuli, Keshab R.; Zhang, Qiuyang; Liu, Sen; Patel, Neil K.; Lu, Hua; Zeng, Shelya X.; Wang, Guangdi; Zhang, Changde; You, Zongbing (2014). "Methoxyacetic acid suppresses prostate cancer cell growth by inducing growth arrest and apoptosis". American Journal of Clinical and Experimental Urology. 2 (4): 300–312. ISSN   2330-1910. PMC   4297326 . PMID   25606576.