Glyoxylic acid Property

Melting point:

-93°C

Boiling point:

111°C

Density 

1.33 g/mL at 20 °C

vapor pressure 

14hPa at 19.85℃

refractive index 

n20/D 1.414

Flash point:

111°C

storage temp. 

Store below +30°C.

solubility 

Miscible with ethanol. Slightly miscible with ether and benzene. Immiscible with esters.

pka

3.18(at 25℃)

form 

clear liquid

color 

Colorless to Light orange to Yellow

Water Solubility 

miscible

Merck 

14,4511

BRN 

741891

InChIKey

HHLFWLYXYJOTON-UHFFFAOYSA-N

LogP

-0.930 (est)

CAS DataBase Reference

298-12-4(CAS DataBase Reference)

NIST Chemistry Reference

Acetic acid, oxo-(298-12-4)

EPA Substance Registry System

Acetic acid, 2-oxo- (298-12-4)

Safety

Hazard Codes 

C,Xi

Risk Statements 

34-43-41

Safety Statements 

26-36/37/39-45-37/39-24

RIDADR 

UN 3265 8/PG 2

WGK Germany 

1

RTECS 

MD4550000

TSCA 

Yes

HazardClass 

8

PackingGroup 

III

HS Code 

29183000

Hazardous Substances Data

298-12-4(Hazardous Substances Data)

Toxicity

rat,LDLo,intramuscular,250mg/kg (250mg/kg),Bolletino della Societe Italiana di Biologia Sperimentale. Vol. 36, Pg. 1937, 1960.

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H290May be corrosive to metals

H317May cause an allergic skin reaction

H318Causes serious eye damage

Precautionary statements

P234Keep only in original container.

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P272Contaminated work clothing should not be allowed out of the workplace.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Glyoxylic acid Chemical Properties,Usage,Production

Structure

Glyoxylic 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.

Chemical Properties

Colorless clear liquid.

Uses

Glyoxalic acid can be used in the synthesis of a variety of reactions.
Glyoxylic acid is used in Hopkins Cole reaction, which is used in the detection of tryptophan in proteins.
It reacts with phenol to get 4-hydroxymandelic acid, which on further reaction with ammonia gives hydroxyphenylglycine, as a precursor to the drug amoxicillin.
It is also used as a starting material for the preparation of 4-hydroxyphenylacetic acid, which is used to get atenolol.

Definition

ChEBI: A 2-oxo monocarboxylic acid that is acetic acid bearing an oxo group at the alpha carbon atom.

General Description

Supplied as a 50% aqueous solution.

Health Hazard

Contact will cause severe eye and skin burns. Vapor exposure may cause eye and skin irritation.

Flammability and Explosibility

Non flammable

Biological Activity

nsc 27785 is an organic compound that is both an aldehyde and a carboxylic acid.

Synthesis

Add to 3500ml reactor equipped with reflux condenser, stirrer and thermometer300ml (3.55mol) of 50% glyoxal solution, stir and cool, control the temperature to 7±2,Slowly drip 300ml (3.55mol) of 35% hydrogen peroxide solution at the same time within 3 hours,280ml (0.355mol) of 17% ferrous sulfate solution and 120ml (0.75mol) of 15% aqueous ammonia solution, keep at 8±2, react for 3 hours, and let stand overnight, The reaction liquid was filtered to remove the solid by-products, and 350ml of water-carrying toluene was added to the reaction mother liquid.Heat to reflux, remove water, and distill toluene with water-carrying agent to obtain oxidation product.Add 120ml of concentrated sulfuric acid and 700ml of absolute ethanol to the oxidation products.Esterification reaction at 140°C for 3 hours, then distillation under reduced pressure, at 0.02Mpa,The esterification product was collected at 185°C.Add 120ml of 18% sulfuric acid to the esterified product and heat under stirring.The hydrolysis reaction is carried out at 95-98 for 2 hours; the hydrolysis liquid is cooled to room temperature,The precipitated white solid product was filtered, washed 4 times with 120ml of toluene each time, and dried.Obtain 180 g of the target product glyoxylic acid with a purity of 99.5% (HPLC) and a yield of 88%.Melting point is 98.1-98.6.

Source

Glyoxylic acid occurs in unripe fruit and in young green leaves. It has also been found in very young sugarbeets. Glyoxylic acid is found in plants and is a metabolite in mammalian biochemical pathways.

Environmental Fate

Glyoxylic acid's production and use as a cleaning agent for a variety of industrial applications, as a specialty chemical and biodegradable copolymer feedstock, and as an ingredient in cosmetics may result in its release to the environment through various waste streams. The pKa of glyoxylic acid is 3.3, indicating this compound will exist primarily as an anion in moist soil surfaces and anions are expected to have very high mobility in soils. If released to soil or water, glyoxylic acid is expected to biodegrade. Degradation may also occur in sunlit water through direct photolysis.