Methyl pyruvate

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Methyl pyruvate
Brenztraubensauremethylester.svg
Names
Preferred IUPAC name
Methyl 2-oxopropanoate
Identifiers
3D model (JSmol)
1361953
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.009.081 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 209-987-4
PubChem CID
UNII
  • InChI=1S/C4H6O3/c1-3(5)4(6)7-2/h1-2H3
    Key: CWKLZLBVOJRSOM-UHFFFAOYSA-N
  • CC(=O)C(=O)OC
Properties
C4H6O3
Molar mass 102.089 g·mol−1
AppearanceColorless liquid
Melting point −22 °C (−8 °F; 251 K)
Boiling point 135 °C (275 °F; 408 K)
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-acid.svg GHS-pictogram-exclam.svg
Danger
H226, H317, H318, H335
P210, P233, P240, P241, P242, P243, P261, P271, P272, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P333+P313, P363, P370+P378, P403+P233, P403+P235, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Methyl pyruvate is the organic compound with the formula CH3C(O)CO2CH3. This colorless liquid is the methyl ester of pyruvic acid. It has attracted interest as a prochiral precursor to alanine and lactic acid. [1] It is prepared by esterification of pyruvic acid. [2]

Related Research Articles

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

In chemistry, an ester is a compound 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">Alanine</span> Α-amino acid that is used in the biosynthesis of proteins

Alanine (symbol Ala or A), or α-alanine, is an α-amino acid that is used in the biosynthesis of proteins. It contains an amine group and a carboxylic acid group, both attached to the central carbon atom which also carries a methyl group side chain. Consequently, its IUPAC systematic name is 2-aminopropanoic acid, and it is classified as a nonpolar, aliphatic α-amino acid. Under biological conditions, it exists in its zwitterionic form with its amine group protonated (as −NH3+) and its carboxyl group deprotonated (as −CO2). It is non-essential to humans as it can be synthesised metabolically and does not need to be present in the diet. It is encoded by all codons starting with GC (GCU, GCC, GCA, and GCG).

Valine (symbol Val or V) is an α-amino acid that is used in the biosynthesis of proteins. It contains an α-amino group (which is in the protonated −NH3+ form under biological conditions), an α-carboxylic acid group (which is in the deprotonated −COO form under biological conditions), and a side chain isopropyl group, making it a non-polar aliphatic amino acid. It is essential in humans, meaning the body cannot synthesize it: it must be obtained from the diet. Human dietary sources are foods that contain protein, such as meats, dairy products, soy products, beans and legumes. It is encoded by all codons starting with GU (GUU, GUC, GUA, and GUG).

<span class="mw-page-title-main">Acetyl group</span> Chemical group, –C(=O)CH₃

In organic chemistry, acetyl is a functional group with the chemical formula −COCH3 and the structure −C(=O)−CH3. It is sometimes represented by the symbol Ac. In IUPAC nomenclature, acetyl is called ethanoyl, although this term is barely heard.

Pyruvic acid (IUPAC name: 2-oxopropanoic acid, also called acetoic acid) (CH3COCOOH) is the simplest of the alpha-keto acids, with a carboxylic acid and a ketone functional group. Pyruvate, the conjugate base, CH3COCOO, is an intermediate in several metabolic pathways throughout the cell.

<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
.

Mesitylene or 1,3,5-trimethylbenzene is a derivative of benzene with three methyl substituents positioned symmetrically around the ring. The other two isomeric trimethylbenzenes are 1,2,4-trimethylbenzene (pseudocumene) and 1,2,3-trimethylbenzene (hemimellitene). All three compounds have the formula C6H3(CH3)3, which is commonly abbreviated C6H3Me3. Mesitylene is a colorless liquid with sweet aromatic odor. It is a component of coal tar, which is its traditional source. It is a precursor to diverse fine chemicals. The mesityl group (Mes) is a substituent with the formula C6H2Me3 and is found in various other compounds.

The iron–sulfur world hypothesis is a set of proposals for the origin of life and the early evolution of life advanced in a series of articles between 1988 and 1992 by Günter Wächtershäuser, a Munich patent lawyer with a degree in chemistry, who had been encouraged and supported by philosopher Karl R. Popper to publish his ideas. The hypothesis proposes that early life may have formed on the surface of iron sulfide minerals, hence the name. It was developed by retrodiction from extant biochemistry in conjunction with chemical experiments.

<span class="mw-page-title-main">Dicarbonyl</span> Molecule containing two adjacent C=O groups

In organic chemistry, a dicarbonyl is a molecule containing two carbonyl groups. Although this term could refer to any organic compound containing two carbonyl groups, it is used more specifically to describe molecules in which both carbonyls are in close enough proximity that their reactivity is changed, such as 1,2-, 1,3-, and 1,4-dicarbonyls. Their properties often differ from those of monocarbonyls, and so they are usually considered functional groups of their own. These compounds can have symmetrical or unsymmetrical substituents on each carbonyl, and may also be functionally symmetrical or unsymmetrical.

Acetamide (systematic name: ethanamide) is an organic compound with the formula CH3CONH2. It is derived from acetic acid. It finds some use as a plasticizer and as an industrial solvent. The related compound N,N-dimethylacetamide (DMA) is more widely used, but it is not prepared from acetamide. Acetamide can be considered an intermediate between acetone, which has two methyl (CH3) groups either side of the carbonyl (CO), and urea which has two amide (NH2) groups in those locations. Acetamide is also a naturally occurring mineral with the IMA symbol: Ace.

Amination is the process by which an amine group is introduced into an organic molecule. This type of reaction is important because organonitrogen compounds are pervasive.

<span class="mw-page-title-main">Oxaloacetic acid</span> Organic compound

Oxaloacetic acid (also known as oxalacetic acid or OAA) is a crystalline organic compound with the chemical formula HO2CC(O)CH2CO2H. Oxaloacetic acid, in the form of its conjugate base oxaloacetate, is a metabolic intermediate in many processes that occur in animals. It takes part in gluconeogenesis, the urea cycle, the glyoxylate cycle, amino acid synthesis, fatty acid synthesis and the citric acid cycle.

<span class="mw-page-title-main">Amidine</span> Organic compounds

Amidines are organic compounds with the functional group RC(NR)NR2, where the R groups can be the same or different. They are the imine derivatives of amides (RC(O)NR2). The simplest amidine is formamidine, HC(=NH)NH2.

Reductive amination is a form of amination that involves the conversion of a carbonyl group to an amine via an intermediate imine. The carbonyl group is most commonly a ketone or an aldehyde. It is considered the most important way to make amines, and a majority of amines made in the pharmaceutical industry are made this way.

<span class="mw-page-title-main">Methyl red</span> Chemical indicator that turns red in acidic solutions

Methyl red (2-(N,N-dimethyl-4-aminophenyl) azobenzenecarboxylic acid), also called C.I. Acid Red 2, is an indicator dye that turns red in acidic solutions. It is an azo dye, and is a dark red crystalline powder. Methyl red is a pH indicator; it is red in pH under 4.4, yellow in pH over 6.2, and orange in between, with a pKa of 5.1. Murexide and methyl red are investigated as promising enhancers of sonochemical destruction of chlorinated hydrocarbon pollutants. Methyl red is classed by the IARC in group 3 - unclassified as to carcinogenic potential in humans.

<span class="mw-page-title-main">Palladium(II) acetate</span> Chemical compound

Palladium(II) acetate is a chemical compound of palladium described by the formula [Pd(O2CCH3)2]n, abbreviated [Pd(OAc)2]n. It is more reactive than the analogous platinum compound. Depending on the value of n, the compound is soluble in many organic solvents and is commonly used as a catalyst for organic reactions.

<span class="mw-page-title-main">Pyruvate decarboxylase</span> Class of enzymes

Pyruvate decarboxylase is an enzyme that catalyses the decarboxylation of pyruvic acid to acetaldehyde. It is also called 2-oxo-acid carboxylase, alpha-ketoacid carboxylase, and pyruvic decarboxylase. In anaerobic conditions, this enzyme is participates in the fermentation process that occurs in yeast, especially of the genus Saccharomyces, to produce ethanol by fermentation. It is also present in some species of fish where it permits the fish to perform ethanol fermentation when oxygen is scarce. Pyruvate decarboxylase starts this process by converting pyruvate into acetaldehyde and carbon dioxide. Pyruvate decarboxylase depends on cofactors thiamine pyrophosphate (TPP) and magnesium. This enzyme should not be mistaken for the unrelated enzyme pyruvate dehydrogenase, an oxidoreductase, that catalyzes the oxidative decarboxylation of pyruvate to acetyl-CoA.

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

Sodium triacetoxyborohydride, also known as sodium triacetoxyhydroborate, commonly abbreviated STAB, is a chemical compound with the formula Na[(CH3COO)3BH]. Like other borohydrides, it is used as a reducing agent in organic synthesis. This colourless salt is prepared by protonolysis of sodium borohydride with acetic acid:

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

Bromopyruvic acid is the organic compound with the formula BrCH2COCO2H. This colorless solid is the brominated derivative of pyruvic acid. It bears structural similarity to lactic acid and pyruvic acid. It has been investigated as a metabolic poison and an anticancer agent. Like other α-bromoketones, it is a strong alkylating agent.

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

Phenylglycine is the organic compound with the formula C6H5CH(NH2)CO2H. It is a non-proteinogenic alpha amino acid related to alanine, but with a phenyl group in place of the methyl group. It is a white solid. The compound exhibits some biological activity.

References

  1. Abdel-Magid, Ahmed F.; Carson, Kenneth G.; Harris, Bruce D.; Maryanoff, Cynthia A.; Shah, Rekha D. (1996). "Reductive Amination of Aldehydes and Ketones with Sodium Triacetoxyborohydride. Studies on Direct and Indirect Reductive Amination Procedures". Journal of Organic Chemistry. 61 (11): 3849–3862. doi:10.1021/JO960057X. PMID   11667239.
  2. A. Weissberger; C. J. Kibler (1944). "Methyl Pyruvate". Org. Synth. 24: 72. doi:10.15227/orgsyn.024.0072.