Glyoxylic acid

74.035

74.04

206-058-5

JQ39C92HH6

27785

3265

DTXSID5021594

Monoclinic crystals from water|Rhombic prisms obtained from water with 1/2 mol of water of crystallization.

2918300090

54.4

-0.3

Supplied as a 50% aqueous solution. Colorless to straw yellow. (USCG, 1999)

1.42 g/cm³ @ Temp: 20 °C

98 °C

111ºC

103.9±19.1 °C

1.403

Very soluble in water; slightly soluble in ethanol, ethyl ether, and benzene

2-8ºC

0.0331mmHg at 25°C

Obnoxious odor

3.3(at 25 °C)

3.3 (at 25 °C)|pKa = 3.30 @ 25 °C

No rapid reaction with air No rapid reaction with water

Acids, Carboxylic

GLYOXYLIC ACID is a carboxylic acid. Preparative hazard, nitric acid and glyoxal to produce glyoxylic 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. 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.

Corrosive

III

8

UN 3265 8/PG 2

1

R41;R43

S26-S36/37/39-S45-S37/39-S24

MD4550000

Xi:Irritant;

FORMS A SYRUP ON SHORT EXPOSURE TO AIR /GLYOXYLIC ACID HEMIHYDRATE/

P280-P305 + P351 + P338 + P310-P333 + P313

H290-H317-H318

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Deliquesces quickly and forms a syrup on short exposure to air.

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. 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. (ERG, 2016)

|Warning|H319: Causes serious eye irritation [Warning Serious eye damage/eye irritation]|P264, P280, P305+P351+P338, and P337+P313

Fire Extinguishing Agents Not to Be Used: Avoid direct contact between water and acid. Fire Extinguishing Agents: Dry chemical, carbon dioxide or water spray. (USCG, 1999)

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Neutralizing Agents for Acids and Caustics: Lime. (USCG, 1999)

Wear full impervious protective clothing and approved respirator. Where splashing is possible wear full face shield or chemical safety goggles. Use approved respirator to protect against vapors. (USCG, 1999)

SRP: The scientific literature supports the wearing of contact lenses in industrial environments, as part of a program to protect the eye against chemical compounds and minerals causing eye irritation. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases contact lenses should not be worn.

A skin, eye, and mucous membrane irritant.

SUCCINIMIDE HAS A HYPOOXALURIC EFFECT IN NORMAL RATS & IN RATS WITH GLYOXYLIC ACID-INDUCED LITHIASIS.|IN PRESENCE OF NADH, HYDROXYPYRUVATE STIMULATED THE OXIDN OF GLYOXYLATE TO OXALATE & DECR THE REDN OF GLYOXYLATE IN VITRO PREPARATIONS FROM NORMAL HUMAN ERYTHROCYTES & LEUKOCYTES, RAT LIVER, & WITH PURIFIED LACTATE DEHYDROGENASE FROM BEEF HEART.|INJECTIONS OF OXALOACETATE TOGETHER WITH LETHAL DOSE OF GLYOXYLATE PROTECTED RAT FROM DEATH, BUT PRODUCED A SEVERE INHIBITION OF BOTH MITOCHONDRIAL AND CYTOPLASMIC ACONITATE HYDRATASE & ISOCITRATE DEHYDROGENASE. OXIDN OF CITRATE EITHER ADDED OR FORMED FROM PYRUVATE & FUMARATE IN MITOCHONDRIA WAS STRONGLY INHIBITED. DATA SUGGEST THAT THE INHIBITION OF ACONITATE HYDRATASE & ISOCITRATE (NADP+) DEHYDROGENASE WAS DUE TO OXALOMALATE FORMED IN VIVO WITH THE SAME MECHANISM OF CONDENSATION OF GLYOXYLATE PLUS OXALOACETATE.|It has been proposed that administration of non-nitrogenous precursors to glycine is necessary to realize the full potential of benzoate metabolism as a pathway for disposal of waste nitrogen during ammonia intoxication. However, when glyoxylate, a keto acid precursor to glycine, was administered with benzoate 1 hr prior to a challenge of ammonia, protection against ammonia toxicity was less successful than with benzoate alone. At the cellular and subcellular levels, glyoxylate and benzoate each inhibited the urea cycle in isolated hepatocytes and pyruvate carboxylase in isolated mitochondria. The action of each drug was associated with depletion of aspartate content in isolated hepatocytes and reduction of pyruvate-dependent incorporation of carbon dioxide into aspartate in assays with isolated mitochondria. Depression of aspartate regeneration by inhibition of pyruvate carboxylase is a likely mechanism for impairment of urea cycle activity by both drugs. In whole animals, inhibition of pyruvate carboxylase may contribute to benzoate toxicity and the adverse influence of glyoxylate on benzoate therapy.

Glyoxylic acid occurs in unripe fruit and in young green leaves(1); it has also been found in very young sugarbeets(1). Glyoxylic acid is found in plants and is a metabolite in mammalian biochemical pathways(2).

Glyoxylic acid's use as a cleaning agent for a variety of industrial applications, as a speciality chemical and biodegradable copolymer feedstock(1) and as an ingredient in cosmetics(2) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that glyoxylic acid is expected to have very high mobility in soil(SRC). The pKa of glyoxylic acid is 3.3(3), which indicates that this compound will exist primarily as an anion in moist soil surfaces and anions are expected to have very high mobility in soils(SRC). Volatilization of glyoxylic acid from moist soil surfaces is not expected to be an important fate process(SRC) since the anion will not volatilize and the neutral species has an estimated Henry's Law constant of 3X10-9 atm-cu m/mole at 25 °C(SRC), using a fragment constant estimation method(4). Glyoxylic acid may volatilize from dry soil surfaces(SRC) based upon its vapor pressure of 1 mm Hg at 25 °C(5). By analogy to other aliphatic acids(6-8), biodegradation is expected to be an important degradation process for glyoxylic acid in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that glyoxylic acid is not expected to adsorb to suspended solids and sediment(SRC). The pKa of glyoxylic acid is 3.3(3), which indicates that this compound will exist primarily as an anion in water(SRC). Volatilization of glyoxylic acid from water surfaces is not expected to be an important fate process(SRC) since the anion will not volatilize and the neutral species has an estimated Henry's Law constant of 3X10-9 atm-cu m/mole at 25 °C(SRC), using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from an estimated log Kow of -1.4(SRC) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Direct photolysis in sunlit surface waters may also be an important fate pathway since glyoxylic acid undergoes rapid direct photolysis in ambient air(7). By analogy to other aliphatic acids(8-10), biodegradation is expected to be an important degradation process for glyoxylic acid in water(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), glyoxylic acid, which has an estimated vapor pressure of 1 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase glyoxylic acid is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 29 hours(SRC), calculated from its rate constant of 1.3X10-11 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3). Glyoxylic acid also occurs in the dissolved-phase in rainwater, clouds, fog and mist(4,5). Vapor-phase glyoxylic acid undergoes rapid direct photolysis in the ambient atmosphere and has a daytime persistence that is not expected to exceed a few hours(4).

The rate constant for the vapor-phase reaction of glyoxylic acid with photochemically-produced hydroxyl radicals has been estimated as 1.3X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 29 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Glyoxylic acid has an absorption maxima of 351 nm in 60% acetonitrile/water solution(2) which indicates a potential for direct photolysis in the environment(SRC). Glyoxylic acid undergoes rapid direct photolysis in the vapor-phase(3); the atmospheric daytime persistence of glyoxylic acid is not expected to exceed a few hours(3). A pKa of 3.3(4), indicates that glyoxylic acid will primarily exist in the ionized form in the environment.

An estimated BCF of 3 was calculated for glyoxylic acid(SRC), using an estimated log Kow of -1.4(SRC) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc for glyoxylic acid can be estimated to be 1(SRC). According to a classification scheme(2), this estimated Koc value suggests that glyoxylic acid is expected to have very high mobility in soil. The pKa of glyoxylic acid is 3.3(3), which indicates that this compound will exist primarily as an anion in moist soil surfaces and anions are expected to have very high mobility in soils(SRC).

The Henry's Law constant for glyoxylic acid is estimated as 3X10-9 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that glyoxylic acid is not expected to volatilize from moist soil or water surfaces(2). The pKa of glyoxylic acid is 3.3(3), indicating that this compound will exist primarily in the ionized form in water and moist soils and the anionic form of glyoxylic acid will not volatilize(SRC). Glyoxylic acid may volatilize from dry soil surfaces(SRC) based upon its vapor pressure of 1 mm Hg at 25 °C(SRC), determined from a fragment constant estimation method(4).

RAIN/SNOW: The following glyoxylic acid concentrations (in micromoles/liter) were detected in atmospheric water samples collected in Los Angeles, CA between June and Sept 1983(1) rainwater: 3.2-6.5; mist: 7.0-27.2; fog: 8.7-39.2(1); the source of the glyoxylic acid is not clear, but may result from the photooxidation of alpha-dicarbonyls which are photooxidation products of uncombusted aromatic hydrocarbons(1). Glyoxylic acid was detected in snow/sleet samples taken in 1992 in Tokyo ranging in concentration from 3.86 to 5.27 ug/l(2). Glyoxylic acid was detected in rain samples taken in 1992 in Tokyo ranging in concentration from 0.2 to 62.2 ug/l(2). Similarly, glyoxylic acid was detected in aerosol samples collected in 1992 from Tokyo ranging in concentration from 120 to 238 ng/cu m(2).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 4,281 workers (2,045 of these are female) are potentially exposed to glyoxylic acid in the US(1). Occupational exposure to glyoxylic acid may occur through inhalation and dermal contact with this compound at workplaces where glyoxylic acid is produced or used(SRC). Since glyoxylic acid is used in cosmetic preparation, the general population may be exposed to this compound through the use of these products(SRC).

RATS METABOLIZED DICHLORACETATE TO GLYOXYLATE & OXALATE.|METABOLIC STUDIES USING VARIOUS SUBSTATES INDICATED THAT AT LOW LEVELS OF EXPOSURE, ADVERSE EFFECTS OF ETHYLENE GLYCOL ON MITOCHONDRIA WERE ATTRIBUTABLE TO FORMATION OF GLYOXYLATE & INTERACTION OF THIS METABOLITE WITH CITRIC ACID CYCLE INTERMEDIATES.|UNDER SOME PATHOLOGICAL CONDITIONS MALFUNCTIONING XANTHINE OXIDASE MAY PROMOTE DIRECT OXIDATION OF GLYOXYLIC ACID TO OXALIC ACID.|URINARY EXCRETING OF (14)C ACCOUNTED FOR 34-69% OF (14)C-LABELED GLYOXYLIC ACID WITHIN 96 HR OF ORAL ADMIN OF 500 MG/KG TO RHESUS MONKEYS. FROM THE GLYOXYLATE DOSE, 24-59% WAS EXCRETED UNCHANGED, & 0.1%, 3% & 2% WAS EXCRETED AS HIPPURATE, OXALATE, & GLYCOLLATE, RESPECTIVELY. WHEN DOSE OF GLYOXYLATE WAS DECR TO 60 MG/KG, ONLY 20% OF THE (14)C APPEARED IN URINE WITHIN 96 HR, & ONLY 1-1.5% WAS EXCRETED UNCHANGED, & PREDOMINANT LABELED URINARY ACID WAS OXALIC ACID.|For more Metabolism/Metabolites (Complete) data for GLYOXYLIC ACID (10 total), please visit the HSDB record page.

GLYOXYLATE INHIBITED OXYGEN UPTAKE BY MOUSE BRAIN HOMOGENATES, RAT MYOCARDIAL HOMOGENATES, & RAT MYOCARDIAL SARCOSOMES. GLYOXYLATE MAY THUS ACT AT THE LEVEL OF REACTIONS LEADING TO ATP SYNTH OR AT LEVEL OF ATP HYDROLYSIS.

Contact will cause severe eye and skin burns. Vapor exposure may cause eye and skin irritation. (USCG, 1999)

Get medical attention. INHALATION: Remove to fresh air. If breathing is difficult, give oxygen. EYES: Flush with water for at least 15 min., lifting lids occasionally. SKIN: Remove contaminated clothing and shoes. Flush with water. INGESTION: Dilute with milk, lime water, or aluminum hydroxide. (USCG, 1999)

Piridoxilate is given in cases of angina pectoris or arteritis. It is an intramolecular association of glyoxylic hemiacetal salts of pyridoxine. Glyoxylate has a membranous protective action; pyridoxine is used for the theoretical purpose of preventing oxidation of glyoxylic acid to oxalic acid. Twelve patients were observed with an active calcium oxalate lithiasis who had been taking piridoxilate for many years. Hyperoxaluria was present in all patients and decreased significantly when the drug was interrupted. Significant hyperoxaluria was also observed in volunteers after ingestion of piridoxilate (600 mg per day) or iv (200 mg). ...

glyoxalic acid

SUPPLIED AS A 50% SOLN ... .

All other basic inorganic chemical manufacturing|Acetic acid, 2-oxo-: ACTIVE|PATIENTS SUFFERING FROM PRIMARY HYPEROXALURIA SHOW ELEVATED PLASMA CONCN OF OXALIC ACID & GLYOXYLIC ACID. IN VITRO ADSORPTION OF THESE CMPD INTO VARIOUS SUBSTANCES WAS INVESTIGATED. HYDROUS ZIRCONIUM OXIDE WAS MOST EFFECTIVE SORBENT STUDIED FOR REMOVAL OF OXALIC ACID & GLYOXYLIC ACID. IN BATCH EXPT, ZIRCONIUM OXIDE WAS CAPABLE OF BINDING 5.5 UMOL OXALIC ACID & 8 UMOL OF GLYOXYLIC ACID/G SORBENT USING 0.5 G SORBENT/L & IONIC COMPOSITION RESEMBLING THAT OF PLASMA. RECIRCULATION OF 2 L OF THE SAME SOLN THROUGH 12 G OF MIXT OF HYDROUS ZIRCONIUM OXIDE & ALUMINA FOR 6 HR AT FLOW RATE OF 12 ML/MIN, RESULTED IN FINAL CONCN OF 70 UMOL/L OF OXALIC ACID & 50 UMOL/L OF GLYOXYLIC ACID.

GLYOXALIC ACID WAS DETERMINED IN SEAWATER BY REVERSED PHASE LIQUID CHROMATOGRAPHIC SEPARATION OF FLUORESCENT QUINOXILINAL DERIVATIVES.|PHOTOMETRIC METHOD BASED ON COLOR REACTION OF ANALYZED SUBSTANCE WITH INDOLE OR ITS DERIV IN SULFURIC ACID. COLOR INTENSITY & POSITION OF THE ABSORPTION MAX DEPEND ON TYPE OF INDOLE REAGENT USED. MAX SENSITIVITY OF METHOD IS 5 UG OF SUBSTANCE IN 5 ML OF TEST SOLN.

Cosmetics -> Buffering