GLYOXYLIC ACID (OXOACETIC ACID)

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

IUPAC Name: Oxoethanoic acid
CAS Number: 298-12-4
EC Number: 206-058-5
Chemical Formula: C2H2O3

Other names: Glyoxylic acid, 298-12-4, 2-Oxoacetic Acid, Glyoxalic acid, Oxoacetic acid, Oxoethanoic acid, Formylformic acid, Acetic acid, oxo-, Oxalaldehydic acid, alpha-Ketoacetic acid, oxaldehydic acid, Formic acid, formyl-, Acetic acid, 2-oxo-, glyoxalate, Kyselina glyoxylova, NSC 27785, CCRIS 1455, HSDB 5559, 563-96-2, .alpha.-Ketoacetic acid, JQ39C92HH6, CHEBI:16891, glyox, oxoacetate, NSC27785, MFCD00006958, NSC-27785, 2-OxoaceticAcid, alpha-ketoaceticacid, GLV, OCHCOOH, EINECS 206-058-5, BRN 0741891, UNII-JQ39C92HH6, Formylformate, Glyoxalsaeure, Glyoxylsaeure, Oxalaldehydate, Oxoethanoate, glyoxilic acid, a-Ketoacetate, C2H2O3, alpha-Ketoacetate, 2-Oxoacetate, (oxo)acetic acid, a-Ketoacetic acid, Acetic acid, oxo, Formic acid, formyl, OHCCO2H, Glyoxylic acid (8CI), Glyoxylic acid anhydrous, WLN: VHVQ, dioxymethylene formaldehyde, EC 206-058-5, Acetic acid, oxo- (9CI), GLYOXALATE; GLYOXYLATE, 4-03-00-01489 (Beilstein Handbook Reference), CHEMBL1162545, DTXSID5021594, BDBM19472, AMY40947, STR06186, AKOS005367012, CS-W019807, DB04343, HY-79494, FT-0626797, G0366, NS00003540, EN300-20485, C00048, D70821, Q413552, W-105518, F2191-0150, 0ADD8E81-5E77-4171-9241-E74AC05D4C8D

Structure and nomenclature
The structure of Glyoxylic acid (oxoacetic acid) is shown as having an aldehyde functional group.
The aldehyde is only a minor component of the form most prevalent in some situations.
Instead, glyoxalic acid often exists as a hydrate or a cyclic dimer.

For example, in the presence of water, the carbonyl rapidly converts to a geminal diol (described as the "monohydrate").
The equilibrium constant (K) is 300 for the formation of dihydroxyacetic acid at room temperature.
Dihydroxyacetic acid has been characterized by X-ray crystallography.

In aqueous solution, this monohydrate exists in equilibrium with a hemiacylal dimer form.
In isolation, the aldehyde structure has as a major conformer a cyclic hydrogen-bonded structure with the aldehyde carbonyl in close proximity to the carboxyl hydrogen.

Preparations
The conjugate base of Glyoxylic acid (oxoacetic acid) is known as glyoxylate and is the form that the compound exists in solution at neutral pH. Glyoxylate is the byproduct of the amidation process in biosynthesis of several amidated peptides.

For the historical record, Glyoxylic acid (oxoacetic acid) was prepared from oxalic acid electrosynthetically
in organic synthesis, lead dioxide cathodes were applied for preparing Glyoxylic acid (oxoacetic acid) from oxalic acid in a sulfuric acid electrolyte.

Hot nitric acid can oxidize glyoxal to glyoxylic; however this reaction is highly exothermic and prone to thermal runaway.
In addition, oxalic acid is the main side product.
Also, ozonolysis of maleic acid is effective.

Biological role
Glyoxylate is an intermediate of the glyoxylate cycle, which enables organisms, such as bacteria, fungi, and plants to convert fatty acids into carbohydrates.
The glyoxylate cycle is also important for induction of plant defense mechanisms in response to fungi.

The glyoxylate cycle is initiated through the activity of isocitrate lyase, which converts isocitrate into glyoxylate and succinate.
Research is being done to co-opt the pathway for a variety of uses such as the biosynthesis of succinate.

In humans
Glyoxylate is produced via two pathways: through the oxidation of glycolate in peroxisomes or through the catabolism of hydroxyproline in mitochondria.
In the peroxisomes, glyoxylate is converted into glycine by AGT1 or into oxalate by glycolate oxidase.

In the mitochondria, glyoxylate is converted into glycine by AGT2 or into glycolate by glyoxylate reductase.
A small amount of glyoxylate is converted into oxalate by cytoplasmic lactate dehydrogenase.

In plants
In addition to being an intermediate in the glyoxylate cycle, glyoxylate is also an important intermediate in the photorespiration pathway.
Photorespiration is a result of the side reaction of RuBisCO with O2 instead of CO2.

While at first considered a waste of energy and resources, photorespiration has been shown to be an important method of regenerating carbon and CO2, removing toxic phosphoglycolate, and initiating defense mechanisms.
In photorespiration, glyoxylate is converted from glycolate through the activity of glycolate oxidase in the peroxisome.

Glyoxylic acid (oxoacetic acid) is then converted into glycine through parallel actions by SGAT and GGAT, which is then transported into the mitochondria.
It has also been reported that the pyruvate dehydrogenase complex may play a role in glycolate and glyoxylate metabolism.

Diabetes
Glyoxylate is thought to be a potential early marker for Type II diabetes.
One of the key conditions of diabetes pathology is the production of advanced glycation end-products (AGEs) caused by the hyperglycemia.

AGEs can lead to further complications of diabetes, such as tissue damage and cardiovascular disease.
They are generally formed from reactive aldehydes, such as those present on reducing sugars and alpha-oxoaldehydes.

In a study, glyoxylate levels were found to be significantly increased in patients who were later diagnosed with Type II diabetes.
The elevated levels were found sometimes up to three years before the diagnosis, demonstrating the potential role for glyoxylate to be an early predictive marker.

Nephrolithiasis
Glyoxylate is involved in the development of hyperoxaluria, a key cause of nephrolithiasis (commonly known as kidney stones).
Glyoxylate is both a substrate and inductor of sulfate anion transporter-1 (sat-1), a gene responsible for oxalate transportation, allowing it to increase sat-1 mRNA expression and as a result oxalate efflux from the cell.
The increased oxalate release allows the buildup of calcium oxalate in the urine, and thus the eventual formation of kidney stones.

The disruption of glyoxylate metabolism provides an additional mechanism of hyperoxaluria development. Loss of function mutations in the HOGA1 gene leads to a loss of the 4-hydroxy-2-oxoglutarate aldolase, an enzyme in the hydroxyproline to glyoxylate pathway. The glyoxylate resulting from this pathway is normally stored away to prevent oxidation to oxalate in the cytosol.

The disrupted pathway, however, causes a buildup of 4-hydroxy-2-oxoglutarate which can also be transported to the cytosol and converted into glyoxylate through a different aldolase.
These glyoxylate molecules can be oxidized into oxalate increasing its concentration and causing hyperoxaluria.

Reactions and uses
Glyoxylic acid (oxoacetic acid) is about ten times stronger an acid than acetic acid, with an acid dissociation constant of 4.7 × 10−4 (pKa = 3.32).

With concentrated base, Glyoxylic acid (oxoacetic acid) disproportionates via a Cannizzaro reaction, forming hydroxyacetic acid and oxalic acid.

Glyoxylic acid (oxoacetic acid) gives heterocycles upon condensation with urea and 1,2-diaminobenzene.

Phenol derivatives
In general, Glyoxylic acid (oxoacetic acid) undergoes an electrophilic aromatic substitution reaction with phenols, a versatile step in the synthesis of several other compounds.

The immediate product with phenol itself is 4-hydroxymandelic acid.
This species reacts with ammonia to give hydroxyphenylglycine, a precursor to the drug amoxicillin.
Reduction of the 4-hydroxymandelic acid gives 4-hydroxyphenylacetic acid, a precursor to the drug atenolol.

The sequence of reactions, in which Glyoxylic acid (oxoacetic acid) reacts with guaiacol the phenolic component followed by oxidation and decarboxylation, provides a route to vanillin as a net formylation process.

Hopkins Cole reaction
Glyoxylic acid (oxoacetic acid) is a component of the Hopkins–Cole reaction, used to check for the presence of tryptophan in proteins.

Environmental chemistry
Glyoxylic acid (oxoacetic acid) is one of several ketone- and aldehyde-containing carboxylic acids that together are abundant in secondary organic aerosols.
In the presence of water and sunlight, Glyoxylic acid (oxoacetic acid) can undergo photochemical oxidation. Several different reaction pathways can ensue, leading to various other carboxylic acid and aldehyde products.

Glyoxylic acid (oxoacetic acid) is a 2-oxo monocarboxylic acid that is acetic acid bearing an oxo group at the alpha carbon atom.
It has a role as a human metabolite, an Escherichia coli metabolite, a Saccharomyces cerevisiae metabolite and a mouse metabolite.
Glyoxylic acid (oxoacetic acid) is a 2-oxo monocarboxylic acid and an aldehydic acid.
Glyoxylic acid (oxoacetic acid) is a conjugate acid of a glyoxylate.

Formulation
Glyoxylic acid (oxoacetic acid) is used in the following products: pH regulators and water treatment products, leather treatment products and polymers.
Glyoxylic acid (oxoacetic acid) has an industrial use resulting in manufacture of another substance (use of intermediates).
Release to the environment of this substance can occur from industrial use: formulation of mixtures.

Uses at industrial sites
Glyoxylic acid (oxoacetic acid) is used in the following products: pH regulators and water treatment products, leather treatment products and polymers.
Glyoxylic acid (oxoacetic acid) has an industrial use resulting in manufacture of another substance (use of intermediates).

Glyoxylic acid (oxoacetic acid) is used for the manufacture of: chemicals, textile, leather or fur, metals and fabricated metal products.
Release to the environment of this substance can occur from industrial use: in the production of articles, as an intermediate step in further manufacturing of another substance (use of intermediates), in processing aids at industrial sites and as processing aid.

Density: 1.384 g/mL
Melting point: 80 °C (176 °F; 353 K)
Boiling point: 111 °C
Molecular Weight: 74.04 g/mol

XLogP3-AA: -0.3
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 3
Rotatable Bond Count: 1

Exact Mass: 74.000393922 g/mol
Monoisotopic Mass: 74.000393922 g/mol
Topological Polar Surface Area: 54.4Å²
Heavy Atom Count: 5

Complexity: 55.9
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0

Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Glyoxylic acid (oxoacetic acid) is an organic compound used as a chemical intermediate across the industries.
Personal care & cosmetics ingredients, aromas, pharmaceutical, and agrochemicals, are the major applications of Glyoxylic acid (oxoacetic acid).
Glyoxylic acid (oxoacetic acid) can be applied successfully in the agro, pharma and fine chemical industries.

Glyoxylic acid (oxoacetic acid) is the material for water purificants, pesticides.
Glyoxylic acid (oxoacetic acid) is used as an intermediate of varnish material and dyes.
It can be used in the preservation of food, as a crosslinking agent of polymerization and as a plating additive.

Glyoxylic acid (oxoacetic acid), also known as a-ketoacetate or glyoxalate, belongs to the class of organic compounds known as carboxylic acids.
Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH.
Glyoxylic acid (oxoacetic acid) is an extremely weak basic (essentially neutral) compound (based on its pKa).
Glyoxylic acid (oxoacetic acid) exists in all living species, ranging from bacteria to humans.
Glyoxylic acid (oxoacetic acid) is a potentially toxic compound.

Glyoxylic acid (oxoacetic acid) is an organic compound. Glyoxylic acid (oxoacetic acid) is a colourless solid that occurs naturally and is useful industrially.

Application
Used as raw material for producing methyl vanillin and ethyl vanillin in spice industry.
Used in the pharmaceutical industry as a synthetic intermediate of the antihypertensive drug atenolol, d-p-hydroxybenzoidine, broad-spectrum antibiotic ampicillin (oral), acetophenone, amino acid and other compounds.

Used as intermediates for varnishes, dyes, plastics and agricultural chemicals.
It is also used in the production of allantoin, an intermediate of anti-ulcer drugs, pharmaceutical products and household

Glyoxylic acid (oxoacetic acid) is a colourless solid that occurs naturally and is useful industrially.
Aqueous solution of Glyoxylic acid (oxoacetic acid) is transparent colorless or light yellow liquid.
Soluble in water and ethanol, slightly soluble in organic solvents like ether or benzene, insoluble in esters aromatic solvents.
This solution is not stable but will not decay in the air.

Glyoxylic acid (oxoacetic acid) is a strong organic acid and a highly reactive chemical intermediate having two functional groups: the aldehyde group and the carboxylic acid group.
Because of its bi-functionality is a versatile reagent in organic and fine chemicals syntheses.

Glyoxylic acid (oxoacetic acid) is transparent organic solid compound. It occurs naturally or produced synthetically using glyoxal as a primary raw materials.
Glyoxylic acid (oxoacetic acid) or its downstream products are used in variety of end-use industries.
The prominent downstream products of Glyoxylic acid (oxoacetic acid) include vanillin, p-hydroxyphenylglycine, 2- hydroxyl- phosphine acetic acid, among others.

Uses at industries of the global Glyoxylic acid (oxoacetic acid) market comprises personal care and cosmetics ingredient, agrochemicals, pharmaceuticals, aromas, polymers, and others.
The global market is driven by increasing demand in these end use industries.
Among all such end use industries, personal care and food and beverage industries are prominently driving the demand of global market.

Allantoin, a Glyoxylic acid (oxoacetic acid) derivative, is used hair care and skin care products owing to its moisturizing and emulsifying properties.
Increasing demand of hair care products such as straightening products, shampoos, conditioners, lotions, and hair creams is expected to drive the demand in personal care industry.
On similar lines, increasing application of vanillin in aromas and flavors in food and beverage industry is another driving factor for the global market

Glyoxylic acid (oxoacetic acid) as an alternative reducing agent for electroless copper plating was investigated.
Plating rates and bath stability were superior to that of the formaldehyde bath under standard conditions.

Glyoxylate ions in the plating bath have no vapor pressure and showed good reducing power in the electroless copper plating.
Therefore, Glyoxylic acid (oxoacetic acid) can replace formaldehyde, and eliminate health and environmental problems resulting from generation of the fumes (research overview).

The Glyoxylic acid (oxoacetic acid) condensation reaction is commonly used for visual detection of biogenic amines in histological sections.
This is the sucrose-phosphate-Glyoxylic acid (oxoacetic acid) (SPG) histofluorescence method for the visualization of monoamines in tissues where the fluorescence is analyzed by fluorescence microscopy.

The glyoxilic acid derivatives were discoverd as a new class of Oomycete fungicides.
The Glyoxalic derivatives exhibit specific activity against oomycetes, including dwony mildew on grapes (Plasmopara viticola) and late blight on potatoes an tomatoes (Phytophthora infestans).

They are active against Oomycetes in soil such as Phytophthora in tabacoo and citrus.
They exhibit protective, curative, eradicative and antisporulant activity.
This class of compounds can be synthesized wih a simple synthetic approach where in the second step the glycolic acid ester is needed.

There is formaldehyde-free aminoresin wood adhesives based on dimethoxyethanal (DME).
It's precursors prepared by the addition of DME to melamine or urea gave resins for boards that were able to harden.

Melamine and urea reacts with one and two (melamine up to three) molecules of DME to form M-DME and U-DME (called DU), and the subsequent cross-linking reaction to form bridges occurs when the reaction is catalyzed during resin preparation by the addition of Glyoxylic acid (oxoacetic acid).

That has allowed the formation of different oligomers formed by both aldol condensation and condensation of melamine and Glyoxylic acid (oxoacetic acid) with two molecules of melamine to form dimers.

Hair styling ingredient with semi-permanent hair straightening & hair conditioning effect.
The carboxylic and aldehyde groups of Glyoxylic acid (oxoacetic acid) react with the amine groups present in hair keratin resulting in the formation of stable bonds.

In particular, Glyoxylic acid (oxoacetic acid) produces semi-permanent hair straightening without breaking the cystine disulfide bridge.
It provides long lasting relaxing effect of hair fibres, without causing damage to the hair and scalp irritations typical of alkaline chemical and other straightening agents.

Glyoxylic acid (oxoacetic acid) 50H is high purity cosmetic grade with only trace content of the CMR impurity glyoxal and without formaldehyde.
This allows formulators to use levels up to 25% in hair straightening cosmetics without exceeding the maximum permitted level of 100 ppm glyoxal established by EU & other cosmetic regulations.

Glyoxylic acid (oxoacetic acid) 50H finds use in hair straightening formulations to smooth wavy & tightly curly hair. When applied with flat iron it softens natural curls providing shiny silk appearance and improving hair maneageability.

Glyoxylic acid (oxoacetic acid) is a highly reactive chemical intermediate having two functional groups: the aldehyde group and the carboxylic acid group.
Strong organic acid (Ka=4.7x10-4), miscible in water & alcohol, insoluble in organic solvents.
It is supplied as a 50% water solution.

Glyoxylic acid (oxoacetic acid) is an important C2 building block for many organic molecules of industrial importance, used in the production of agrochemicals, aromas, cosmetic ingredients, pharmaceutical intermediates and polymers.

Glyoxylic acid (oxoacetic acid) finds application in personal care as neutralizing agent, it is widely used in hair straightening products in particular (shampoos, conditioners, lotions, creams) at levels of 0.5-10%.

Glyoxylic acid (oxoacetic acid) is acetic acid bearing an oxo group at the alpha carbon atom. It has a role as a human metabolite, an Escherichia coli metabolite, a Saccharomyces cerevisiae metabolite and a mouse metabolite.
It is a 2-oxo monocarboxylic acid and an aldehydic acid.
It is a conjugate acid of a glyoxylate.

Although the structure of Glyoxylic acid (oxoacetic acid) is described as having an aldehyde functional group, the aldehyde is only a minor component of the form most prevalent in some situations

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

Hair styling ingredient with semi-permanent hair straightening & hair conditioning effect. The carboxylic and aldehyde groups of Glyoxylic acid (oxoacetic acid) react with the amine groups present in hair keratin resulting in the formation of stable bonds.

Glyoxylic acid (oxoacetic acid) 50H finds use in hair straightening formulations to smooth wavy & tightly curly hair.
When applied with flat iron it softens natural curls providing shiny silk appearance and improving hair maneageability.

Reactivity Profile
Glyoxylic acid (oxoacetic acid) is a carboxylic acid. Preparative hazard, nitric acid and glyoxal to produce Glyoxylic acid (oxoacetic acid) has had explosive consequences.
Carboxylic acids donate hydrogen ions if a base is present to accept them.
They react in this way with all bases, both organic (for example, the amines) and inorganic.
Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat.

Neutralization between an acid and a base produces water plus a salt.
Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water.
Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions.
The pH of solutions of carboxylic acids is therefore less than 7.0.

Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt.
Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt.
Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry.

Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in Glyoxylic acid (oxoacetic acid) to corrode or dissolve iron, steel, and aluminum parts and containers.
Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide.
The reaction is slower for dry, solid carboxylic acids.
Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide.

Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides.
Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat.
Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat.

Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents.
These reactions generate heat.
A wide variety of products is possible.
Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions.

Glyoxylic acid (oxoacetic acid) is a nonvolatile chemical that showed good reducing power in electroless copper plating, and can therefore replace formaldehyde, alleviating the environmental problems associated with the latter.

Glyoxylic acid (oxoacetic acid) is an organic compound that is both an aldehyde and a carboxylic acid.
Glyoxylic acid (oxoacetic acid) is a liquid with a melting point of -93°C and a boiling point of 111°C.
It is an intermediate of the glyoxylate cycle, which enables certain organisms to convert fatty acids into carbohydrates.
The conjugate base of Glyoxylic acid (oxoacetic acid) is known as glyoxylate (PMID: 16396466 ).

In humans, glyoxylate is produced via two pathways:
(1) through the oxidation of glycolate in peroxisomes and
(2) through the catabolism of hydroxyproline in mitochondria.
In the peroxisomes, glyoxylate is converted into glycine by glyoxylate aminotransferase (AGT1) or into oxalate by glycolate oxidase.

In the mitochondria, glyoxylate is converted into glycine by mitochondrial glyoxylate aminotransferase AGT2 or into glycolate by glycolate reductase.
A small amount of glyoxylate is converted into oxalate by cytoplasmic lactate dehydrogenase.
Glyoxylic acid (oxoacetic acid) is found to be associated with primary hyperoxaluria I, which is an inborn error of metabolism.

Under certain circumstances, glyoxylate can be a nephrotoxin and a metabotoxin.
A nephrotoxin is a compound that causes damage to the kidney and kidney tissues.
A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. High levels of glyoxylate are involved in the development of hyperoxaluria, a key cause of nephrolithiasis (commonly known as kidney stones).

Glyoxylate is both a substrate and inductor of sulfate anion transporter-1 (SAT-1), a gene responsible for oxalate transportation, allowing it to increase SAT-1 mRNA expression, and as a result oxalate efflux from the cell.
The increased oxalate release allows the buildup of calcium oxalate in the urine, and thus the eventual formation of kidney stones.
As an aldehyde, glyoxylate is also highly reactive and will modify proteins to form advanced glycation products (AGEs).

Glyoxylic acid (oxoacetic acid) is an important organic acid in the chemical, cosmetic, pharmaceutical, and food industries.
It is found in plants and involved in the metabolic cycle of animals.
Glyoxylic acid (oxoacetic acid) is produced in several ways: by nitric acid oxidation of glyoxal, by catalytic oxidation of ethylene or acetaldehyde, and by electrochemical reduction of oxalic acid.

The determination of Glyoxylic acid (oxoacetic acid) in its electrochemical synthesis reaction mixture is a difficult process because this mixture contains carboxylic acids with convergent acidic dissociation constants and other compounds carrying organic groups that can undergo oxidation or reduction such as ethylene glycol, glyoxal, and glycolic acid.
Thus, it is expected that Glyoxylic acid (oxoacetic acid) will be very difficult to determine quantitatively using traditional analytical methods such as acid-base or redox titrations, separation, or precipitation

Glyoxylic acid (oxoacetic acid) is a reagent for sulfinylmaleate synthesis.
Glyoxylic acid (oxoacetic acid) is one of the chemicals used in the Hopkins Cole reaction.
Glyoxylic acid (oxoacetic acid) is involved to check the presence of tryptophan in proteins.
Glyoxylic acid (oxoacetic acid) is condensed with urea and 1,2-diaminobenzene to form heterocycles.

Glyoxylic acid (oxoacetic acid) also undergoes Friedel-Crafts and cyclocondensation reactions to form bis(pentamethylphenyl) acetic acid and a beta-carboline respectively.
Glyoxylic acid (oxoacetic acid) is employed in the synthesis of a sulfinylmaleate, which serves as an efficient dienophile for enantioselective Diels-Alder cycloadditions.

Glyoxylic acid (oxoacetic acid) as a hair straightener
Glyoxylic acid (oxoacetic acid) is for various applications such as straightening, undulating, smoothing, loosening curls, doing the so-called Afro perm, defining, relaxing, and the very famous progressive brush treatment, among others, depending on the desired result for each type of hair.

Demand for Glyoxylic acid (oxoacetic acid) is expected to increase, due to its application as a substitute for lignin in the manufacture of vanillin.
Dr Nigel Freestone reviews some of the most eco-friendly production routes.

Glyoxylic acid (oxoacetic acid) is currently manufactured either by the nitric acid oxidation of glyoxal or via a three-step reaction which involves ozonolysis of dimethyl maleate, hydrogenation of the resulting hydroperoxide intermediate, and hydrolysis of the resulting methylglyoxylate.

The major use of Glyoxylic acid (oxoacetic acid) is in the manufacture of vanillin, and the demand for vanillin produced from Glyoxylic acid (oxoacetic acid) is expected to increase as the availability of vanillin from lignin (a byproduct of paper production) decreases due to environmental concerns.
Vanillin in turn is used as a flavour and fragrance ingredient, as well as in the manufacture of pharmaceuticals and agrochemicals.

DiCosimo and co-workers have developed an alternative biocatalytic process for the production of Glyoxylic acid (oxoacetic acid).
The enzymes, glycolate oxidase and catalase in the presence of ethylenediamine (0.78M; pH8.9) oxidise aqueous solutions of glycolic acid (0.75M; 5.7% w/v) to Glyoxylic acid (oxoacetic acid) with greater than 99% selectivity at greater than 99% conversion at 150 C.

The almost quantitative conversion of glycolate to glyoxylate is primarily due to the use of the catalase in combination with ethylenediamine, where catalase destroys the byproduct hydrogen peroxide and ethylenediamine protects both the glyoxylate from further oxidation by hydrogen peroxide and limits product inhibition of glycolate oxidase.

The final product, a 50 wt% solution of Glyoxylic acid (oxoacetic acid) in water, is chemically equivalent to existing commercially available material. Additionally, this biocatalytic process produces a yield of Glyoxylic acid (oxoacetic acid) and fewer undesirable waste streams (NaCl being the only byproduct generated in the final ion-exchange separation of the desired product) than current methods of production.

GLYOXYLIC ACID is a carboxylic acid. Preparative hazard, nitric acid and glyoxal to produce Glyoxylic acid (oxoacetic acid) has had explosive consequences.
Carboxylic acids donate hydrogen ions if a base is present to accept them.
They react in this way with all bases, both organic (for example, the amines) and inorganic.
Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat.

Neutralization between an acid and a base produces water plus a salt. Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water.
Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions.
The pH of solutions of carboxylic acids is therefore less than 7.0.
Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt.

Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt.
Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry.

Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in it to corrode or dissolve iron, steel, and aluminum parts and containers.
Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide.

The reaction is slower for dry, solid carboxylic acids.
Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide.
Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides.

Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat.
Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat.

Glyoxylic acid (oxoacetic acid) is an organic compound used as a chemical intermediate in various industries.
Glyoxylic acid (oxoacetic acid) is one of the prominent C2-carboxylic acid compound after acetic acid, and oxalic acid.

Glyoxylic acid (oxoacetic acid) is produced from catalytic oxidation of glyoxal.
Glyoxylic acid (oxoacetic acid) is used in to produce various downstream products which are used in range of end use industries.
The prominent derivatives of Glyoxylic acid (oxoacetic acid) are allantoin, vanillin, P-hydroxyphenylglycine, DL-p-hydroxy phenylhydantoin, 2-hydroxyl-phosphine acetic acid and others.
Among all these derivatives, allantoin and vanillin are the most prominently used in several end use industries.

Allantoin is used as a keratolitic ingredient in skin care products and is estimated to account highest market share in the global market by 2017 end.
Allantoin segment is followed by vanillin market segment owing to its high use in food & beverage industry in aroma application.

Furthermore, prominent Glyoxylic acid (oxoacetic acid) applications are personal care & cosmetics, aromas, pharmaceutical, agrochemicals and others.
Personal care & cosmetics and pharmaceutical are estimated to be the leading Glyoxylic acid (oxoacetic acid) application accounting for more than 30% of the overall Glyoxylic acid (oxoacetic acid) consumption in 2017.
Agrochemicals is relatively smaller market segment accounting for niche share in the overall market.
The segment is witnessing slower growth owing to presence of suitable alternatives in the market.

The global Glyoxylic acid (oxoacetic acid) market is segmented on the basis of derivatives, application and region.
On the basis of derivatives, global Glyoxylic acid (oxoacetic acid) market is segmented into allantoin, vanillin, P-hydroxyphenylglycine, DL-p-hydroxy phenylhydantoin, and 2-hydroxyl-phosphine acetic acid among others.
Based on application, the global Glyoxylic acid (oxoacetic acid) is segmented into— Personal Care & Cosmetic Ingredient, Pharmaceuticals, Aroma, and Agrochemicals among others.

The global Glyoxylic acid (oxoacetic acid) market is majorly segmented on the basis of derivatives, application and region.
Based on derivatives of Glyoxylic acid (oxoacetic acid) the market is segmented into p-hydroxyphenylglycine, DL-pâ€”hydroxy phenylhydantoin, vanillin, 2- hydroxyl- phosphine acetic acid, and others (diphenylacetic acid etc.).
Based on application the market segmented into personal care and cosmetics ingredient, agrochemicals, pharmaceuticals, aromas, and others.

The global Glyoxylic acid (oxoacetic acid) market Growth is anticipated to rise at a considerable rate during the forecast period, between 2021 and 2023.
In 2021, the market was growing at a steady rate and with the rising adoption of strategies by key players, the market is expected to rise over the projected horizon.
Glyoxylic acid (oxoacetic acid) Market provides sizing and growth opportunities for the period 2021-2023.
Provides comprehensive insights on the latest industry trends, forecast, and growth drivers in the market.

Report Includes a detailed analysis of growth drivers, challenges, and investment opportunities.
Delivers a complete overview of segments and the regional outlook of the market.
Glyoxylic acid (oxoacetic acid) Market Offers an exhaustive summary of the vendor landscape, competitive analysis, and key strategies to gain competitive advantage.

Glyoxylic acid (oxoacetic acid) Market Trend for Development and marketing channels are analysed.
Finally, the feasibility of new investment projects is assessed and overall research conclusions offered.
Glyoxylic acid (oxoacetic acid) Market Forecast by regions, type and application, with sales and revenue, from 2021 to 2023.

Glyoxylic acid (oxoacetic acid) is transparent organic solid compound.
It occurs naturally or produced synthetically using glyoxal as a primary raw materials.
Glyoxylic acid (oxoacetic acid) or its downstream products are used in variety of end-use industries.
The prominent downstream products of Glyoxylic acid (oxoacetic acid) include vanillin, p-hydroxyphenylglycine, 2- hydroxyl- phosphine acetic acid, among others.

Uses industries of the global Glyoxylic acid (oxoacetic acid) market comprises personal care and cosmetics ingredient, agrochemicals, pharmaceuticals, aromas, polymers, and others.
The global market is driven by increasing demand in these end use industries.
Among all such end use industries, personal care and food and beverage industries are prominently driving the demand of global market.

On similar lines, increasing application of vanillin in aromas and flavors in food and beverage industry is another driving factor for the global market.
Consequently, the global market is estimated to exhibit CAGR of 5.27% in order to reach USD 849.1 Mn by 2023 end.

Among all the derivatives, allantoin and vanillin segments accounted more than half of the overall Glyoxylic acid (oxoacetic acid) consumption.
This is attributed to their prominent use in personal care and food and beverage industries, respectively.
In 2016, allantoin segment accounted for approximate value share of 28.9% in the overall market.

Formaldehyde replacement with Glyoxylic acid (oxoacetic acid) in semipermanent hair straightening: a new and multidisciplinary investigation
Formaldehyde is an effective and popular semipermanent hair straightener, but the severe consequences for human health due to its toxicity have prompted the search for safer alternatives.

Different carbonyl compounds, including Glyoxylic acid (oxoacetic acid), have recently been proposed as promising candidates.
Despite the interest in this topic, there is a lack of information about the interactions between hair keratin and straightener agents.
This study addresses this issue to gain new insights useful in the development of new products for safe, semipermanent hair deformation.

Glyoxylic acid (oxoacetic acid) can be used to synthesize cosmetics and spices, such as allantoin and vanillic aldehyde; in the pharmaceuticals industry, Glyoxylic acid (oxoacetic acid) is applied in the production of antihypertension, antiulcer, and tumor inhibition medicines; and in agriculture, Glyoxylic acid (oxoacetic acid) is mainly used for the synthesis of insecticides, herbicides, fungicides, and plant growth regulators.

Glyoxylic acid (oxoacetic acid) or glyoxylate for its conjugate base is a C2 carboxylic acid.
Glyoxylic acid (oxoacetic acid) is an intermediate of the glyoxylate cycle, which enables organisms, such as bacteria, fungi and plants to convert fatty acids into carbohydrates.
Glyoxylate is the byproduct of the amidation process in biosynthesis of several amidated peptides.

It is a colourless solid that occurs naturally and is useful industrially.
It is used as a cleaning agent for a variety of industrial applications, as a specialty chemical and biodegradable copolymer feedstock and as an ingredient in cosmetics.
It is a useful compound for agricultural and pharmaceutical chemicals.

Indeed, Glyoxylic acid (oxoacetic acid) can be used in pharmaceutical industry since its condensation with phenols gives 4-hydroxymandelic acid which reacts with ammonia to give hydroxyphenylglycine, a precursor to the drug amoxicillin or which can be reduced to give 4-hydroxyphenylacetic acid, a precursor to the drug atenolol.

Moreover acid-catalysed reaction of Glyoxylic acid (oxoacetic acid) with urea leads to the production of allantoin used in cosmetics, ointments and in the treatment of some cancers (Cativiela et al., 2003).
Finally, condensation with guaiacol in place of phenol provides a route to vanillin, used as a flavoring agent in foods, beverages, and pharmaceuticals.

Although Glyoxylic acid (oxoacetic acid) occurs naturally as a trace component in unripe fruit and young green leaves, it is mainly synthetically produced. Other technologies to produce Glyoxylic acid (oxoacetic acid) are described in the literature or in patent applications.
For instance, Glyoxylic acid (oxoacetic acid) may be chemically produced by heating dibromoacetic acid with some water or by electrolytic reduction of oxalic acid or by nitric oxidation of glyoxal.

Some patent applications describe processes of production of Glyoxylic acid (oxoacetic acid) by bioconversion, such as patent applications WO 1993/14214, U.S. Pat. No. 5,439,813, and WO 1994/28155 disclosing the bioconversion from glycolic acid using glycolate oxidase produced by a microorganism, as well as Isobe & Nishise (1999).
Patent application US 2007/0026510 discloses the bioconversion from glyoxal using an aldehyde oxidase.

The industrial interest of glycolic acid and Glyoxylic acid (oxoacetic acid) coupled with environmental concerns due to chemical by-products formed during chemical productions render microbial production of such carboxylic acids an attractive prospect.

The inventors have identified new methods for the production of glycolic acid and/or Glyoxylic acid (oxoacetic acid) from carbohydrates as sole carbon source involving at least one fermentative step and a modified microorganism in which activity of phosphoketolase is enhanced.

Glyoxylic acid (oxoacetic acid) is a 2-oxo monocarboxylic acid that is acetic acid bearing an oxo group at the alpha carbon atom.
It has a role as a human metabolite, an Escherichia coli metabolite, a Saccharomyces cerevisiae metabolite and a mouse metabolite.
It is a 2-oxo monocarboxylic acid and an aldehydic acid. It is a conjugate acid of a glyoxylate.

Hair styling ingredient with semi-permanent hair straightening & hair conditioning effect. The carboxylic and aldehyde groups of Glyoxylic acid (oxoacetic acid) react with the amine groups present in hair keratin resulting in the formation of stable bonds.

In particular, Glyoxylic acid (oxoacetic acid) produces semi-permanent hair straightening without breaking the cystine disulfide bridge. It provides long lasting relaxing effect of hair fibres, without causing damage to the hair and scalp irritations typical of alkaline chemical and other straightening agents.

Glyoxylic acid (oxoacetic acid) 50H is high purity cosmetic grade with only trace content of the CMR impurity glyoxal and without formaldehyde. This allows formulators to use levels up to 25% in hair straightening cosmetics without exceeding the maximum permitted level of 100 ppm glyoxal established by EU & other cosmetic regulations.

Reactivity Profile
GLYOXYLIC ACID is a carboxylic acid. Preparative hazard, nitric acid and glyoxal to produce Glyoxylic acid (oxoacetic acid) has had explosive consequences.
Carboxylic acids donate hydrogen ions if a base is present to accept them.
They react in this way with all bases, both organic (for example, the amines) and inorganic.
Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat.

Neutralization between an acid and a base produces water plus a salt.
Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water.
Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. The pH of solutions of carboxylic acids is therefore less than 7.0.

Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in Glyoxylic acid (oxoacetic acid) to corrode or dissolve iron, steel, and aluminum parts and containers.
Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide.
The reaction is slower for dry, solid carboxylic acids. Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide.

Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat.
Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat.
A wide variety of products is possible.
Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions.