CAS NUMBER: 107-22-2
EC NUMBER: 203-474-9
GLYOXAL; Ethanedial; 107-22-2; Oxalaldehyde; oxaldehyde; 1,2-Ethanedione; Glyoxylaldehyde;Diformyl; Biformal; Biformyl; Diformal; Aerotex glyoxal 40; Glyoxal aldehyde; Ethanedial, trimer; Ethanediol, trimer; Glyoxal, 40%; Glyoxal solution; Glyoxal solutions; CCRIS 952; UNII-50NP6JJ975; Ethane-1,2-dione; C2H2O2; HSDB 497; Glyoxal, 29.2%; EINECS 203-474-9; Glyoxal, 40% in water; BRN 1732463; AI3-24108; CHEBI:34779; LEQAOMBKQFMDFZ-UHFFFAOYSA-N; Ethane-1,2-dione; C2H2O2; HSDB 497; Glyoxal, 29.2%; EINECS 203-474-9; Glyoxal, 40% in water; BRN 1732463; AI3-24108; CHEBI:34779; LEQAOMBKQFMDFZ-UHFFFAOYSA-N; MFCD00006957; NCGC00091228-01; DSSTox_CID_5364; DSSTox_RID_77764; DSSTox_GSID_25364; 40094-65-3; Ethanedione; CAS-107-22-2; Glyoxal solution, ~40% in H2O (~8.8 M); bisformyl; oxypolygelatine; Gelifundol; Oxypolygelatin; Ethandial; Glycoxal; Glyfosfin; ethane dial; (oxo)acetaldehyde; ethane-1,2-dial; Protectol GL 40; ODIX; NSC 262684; AC1L1PPU; ACMC-1BV6U; Glyoxal, 40 % Solution; Glyoxal solution, 40.0%; 4-01-00-03625 (Beilstein Handbook Reference); BIDD:ER0284; (CHO)2; AC1Q28J9; Glyoxal, Biformyl, Oxalaldehyde; CHEMBL1606435; DTXSID5025364; CTK0H4953; Glyoxal, 40% w/w aq. soln.; MolPort-001-780-154; 50NP6JJ975; BB_SC-7204; ZINC8437750; Tox21_111105; Tox21_202517; NW-43524; BBL011519; LS-36; NSC262684; STL146635; AKOS000119169; Glyoxal solution, 40 wt. % in H2O; MCULE-3212938778; NSC-262684; RP18241; RTR-001406; TRA0067179; KS-00000V42; GLYOXAL, 76%, POWDER (TRIMER); NCGC00260066-01; AN-22473; KB-52297; OR034237; OR369233; SC-19118; Glyoxal solution, CP, 40 wt. % in H2O; TR-001406; FT-0626792; G0152; X8004; Glioxaldehit; etandial, 1,2-Etandiol; Diformil; Etandione; Glioxal aldehit; C14448; Glyoxal solution, 40 wt. % in water 100ml; 57421-EP2269977A2; 57421-EP2270006A1; 57421-EP2289896A1; 57421-EP2308878A2; 57421-EP2377845A1; Gelatins, reaction products with glyoxal, oxidized; J-001740; S14-1487; F2191-0152; Glyoxal solution, ~40% in H2O, for HPLC derivatization; Glyoxal solution, BioReagent, for molecular biology, ~40% in H2O (~8.8 M); 83513-30-8; 9005-91-8; Ethanedial; Ethanedione; Glyoxal; 40094-65-3; 1162; 262684; MD2700000; 2810; 50NP6JJ975; Oxaldehyde; InChI=1S/C2H2O2/c3-1-2-4/h1-2H; LEQAOMBKQFMDFZ-UHFFFAOYSA-N; C(=O)C=O; OHCCHO; 1,2-Ethanedione; Diformal; ethandial; Ethanedial; Ethanedione; MFCD00006957; Oxalaldehyd; Oxalaldehyde; GXT; ODIX; oxal; Protectol GL 40; trans-glyoxal; UNII:50NP6JJ975; EDO; Gelifundol; gliksol; glioksal; gilioksal; gilioxal; glioxal; glyoksal; glyoxale; glioksale; glyoxal; ODIX; Oxal; (CHO)2; GLYOXA; GLYOXAL; DIFORMYL; Biformal; Biformyl; Diformal; GLYOXALE; CB1280241; InChIKeyLEQAOMBKQFMDFZ-UHFFFAOYSA-N; NIST Chemistry Reference; Ethanedial(107-22-2); Glyoxal; (Ethanedione, 1, 2-) (107-22-2); AEROTEX GLYOXAL 40; BIFORMAL; BIFORMYL; DAICEL GY 60; DIFORMAL; DIFORMYL; ETHANDIAL; ETHANEDIAL; ETHANEDIOL; ETHANEDIONE; 1,2-ETHANEDIONE; GLYFIX CS 50; GLYOXAL; GLYOXAL ALDEHYDE; GLYOXAL, 40% SOLUTION; GLYOXYLALDEHYDE; GOHSEZAL P; OXAL; OXALALDEHYDE; OXALDEHYDE; PERMAFRESH 114; MFCD00006957; Biformyl; Ethanedial; 1,2-Ethanedione; Oxalaldehyde; Ethanedial; Biformal; Biformyl; Diformyl; Ethanedione; Glyoxal aldehyde; Glyoxylaldehyde; Oxal; Oxalaldehyde; 1,2-Ethanedione; (CHO)2; Diformal; Ethane-1,2-dione; Ethandial; Aerotex glyoxal 40; ODIX; Protectol GL 40; LEQAOMBKQFMDFZ-UHFFFAOYSA-N; GLYOXAL; 1,2-ETHANEDIONE; ETHANEDIAL; DIFORMYL; BIFORMYL; OXALDEHYDE; Ethanedial; oxalaldehyde; Glyoxal, 40 % Solution; 83513-30-8; 50NP6JJ975; 1732463; MFCD00006957; 58.03634000; diformal; ethandial; ethane dial; ethane-1,2-dial; ethanedial; ethanedione; 1,2-ethanedione; gelifundol; glyoxal aldehyde; glyoxylaldehyde; oxalaldehyde; oxaldehyde; Glyoxaldehyde; Ethanedial; 1,2-Ethanedione; Diformyl; Ethanedione; Glyoxal aldehyde; 1,2-Ethanedione; Biformyl; Ethanedial; Oxalaldehyde; C2H2O2 / OHCCHO; Molecular mass: 58.0; ICSC # 1162; Glyoxal, 40 wt% solution in water; AC156220000; AC156220010, AC156220025; AC156220050; AC156225000; BP1370-500; Biformal; Diformal; Ethandial; Glyoxylaldehyde; 231-791-2; 203-474-9; 7732-18-5; ZC0110000; 107-22-2;MD2625000; MD2650000; MD2700000; 7-(2-Hydroxyethyl)decahydro-1H,6H-3a,5a,8a,10a-tetraazapyrene; 1435472-42-6
GENERAL DESCRIPTION
Yellow crystals melting at15°C. Hence often encountered as a light yellow liquid with a weak sour odor. GLYOXAL is a 2-carbon aldehyde with carbonyl groups on both carbons.GLYOXAL is a yellow crystals melting at15°C. Hence often encountered as a light yellow liquid with a weak sour odor. Vapor has a green color and burns with a violet flame.
Combustible. Incompatible with strong oxidizing agents. Strong reducingagent. May polyermize exothermically. Incompatible with air, water, oxygen,peroxides, amides, amines, hydroxy-containing material s, nitric acid, aldehydes. Corrodes many metals.
Mechanism of Action
Glyoxal attacks the amino groups of proteins, nucleotides, and lipids with its highly reactive carbonyl groups. A sequence of non-enzymatic reactions, called glycation, yields stable advanced glycation end-products (AGEs) with a background extent of 0.1-1% of lysine and arginine residues in proteins and 1 in 1.0 X 10-7 nucleotides in DNA. ... Glyoxal forms stable adducts with guanosine by reaction with the N-1 as well as with the exocyclic nitrogen of guanine. The rate of glyoxal-guanine adduct formation is rapid under physiological conditions. A stable tricyclic glyoxal-DNA adduct is formed by covalent binding to two nitrogens of guanine under physiological conditions in vitro. Besides 8-hydroxy-deoxyguanosine, the glyoxal-deoxyguanosine (dG) adduct is one of the major deoxyguanosine oxidation products, being formed by oxygen radicals, lipid peroxidation systems, various types of oxidative stress, and UV irradiation and after in vivo exposure to beta-hydroxy-substituted N-nitrosamines.
Glyoxal (O=CH-CH=O) is an α-oxoaldehyde, and it is often grouped with two similar α-oxoaldehydes, methylglyoxal, and 3-deoxyglucosone. All three compounds are products of various metabolic and oxidative reactions and are capable of causing cellular damage and apoptosis. They are also involved in the formation of advanced glycation end-products (AGEs) which have been linked to long-term sequela of chronic diseases such as diabetic retinopathy, neuropathy, and nephropathy. Glyoxal is primarily detoxified by the glyoxalase system present in the cells of bacteria, protozoa, fungi, plants, animals, and humans. However, it has been suggested that several other enzymes are capable of detoxifying glyoxal, including aldehyde dehydrogenase (ALDH) which can oxidize glyoxal to glyoxylate.
Glyoxal, 40% solution in water (AGEs). AGE modification alters protein function and inactivates enzymes, resulting in disturbance of cellular metabolism, impaired proteolysis, and inhibition of cell proliferation and protein synthesis. The extent of AGE modification increases with the increasing life span of proteins. Consequently, AGEs are especially associated with long-lived proteins, such as collagens, lens crystallins, and neurofilaments, but also have been identified in shorter-lived proteins, including hemoglobin, plasma proteins, lipoproteins, and intracellular proteins.
Inhibition studies in bacterial mutagenicity tests demonstrated the production of the reactive oxygen species superoxide, hydrogen peroxide, and singlet oxygen from glyoxal. The mutagenic activity of glyoxal is related to singlet oxygen, as well as to the intracellular GSH level. The hydroxyl radical plays a prominent role in glyoxal-induced DNA cleavage.
Isolated rat hepatocytes were incubated with different concentrations of glyoxal. Glyoxal by itself was cytotoxic at 5mM, depleted GSH, formed reactive oxygen species (ROS) and collapsed the mitochondrial membrane potential. Glyoxal also induced lipid peroxidation and formaldehyde formation. Glycolytic substrates, eg fructose, sorbitol and xylitol inhibited glyoxal-induced cytotoxicity and prevented the decrease in mitochondrial membrane potential suggesting that mitochondrial toxicity contributed to the cytotoxic mechanism. Glyoxal cytotoxicity was prevented by the glyoxal traps d-penicillamine or aminoguanidine or ROS scavengers were also cytoprotective even when added some time after glyoxal suggesting that oxidative stress contributed to the glyoxal cytotoxic mechanism.
The cytosolic GSH-dependent glyoxalase system is the major pathway for the detoxification of glyoxal ... Glyoxal reacts non-enzymatically with GSH with formation of a hemithioacetal, which is subsequently converted to S-glycolylglutathione by glyoxalase I. Glyoxalase II catalyses the hydrolysis of S-glycolylglutathione to glycolate, re-forming the GSH from the first reaction. The activity of glyoxalase I in situ is approximately proportional to the cytosolic concentration of GSH. When GSH is severely depleted (eg, under conditions of oxidative stress), however, 2-oxoaldehyde dehydrogenase and aldose reductase may also metabolize glyoxal. Imbalances in intracellular redox systems may impair these detoxification mechanisms, resulting in higher levels of glyoxal. A further GSH-independent route of detoxification via glyoxalase III exists.
Use and Manufacturing
Fillers
Intermediates
Odor agents
Processing aids, not otherwise listed
Solids separation agents
Water Treatment Products
Its versatile properties the intermediate glyoxal is the product of choice for various applications. In textile manufacturing, for example, this efficient crosslinker decreases water uptake in crosslinking cellulose. In oil recovery, glyoxal crosslinks polymers, thus increasing the viscosity of fracturing fluids.
Glyoxal is also used in the paper, leather and epoxy industries. Beside known applications, glyoxal shows potential for new applications which are still in the early stages of development.
Glyoxal is an organic compound with the chemical formula OCHCHO.
It is the smallest dialdehyde (a compound with two aldehyde groups). It is a crystalline solid, white at low temperatures and yellow near the melting point (15 °C).
The liquid is yellow, and the vapor is green.
Pure glyoxal is not commonly encountered because it forms hydrates, which oligomerize. For many purposes, these hydrated oligomers behave equivalently to glyoxal.
It is produced industrially as a precursor to many products.
Glyoxal 40%
Formula : C2H2O2
Physical form
Anhydrous glyoxal is a liquid at ambient temperature; it crystallizes at 15 °C in the form of yellow prismatic crystals.
Molecular weight : 58.04
Solubility: Very soluble in water (600 g/l), miscible in water in all ratios (40% aqueous solution), soluble in ethanol and ethyl ether
Organoleptic properties : Colourless, deliquescent powder (pure substance) colourless liquid (40% solution)
Melting point : 15 C (pure substance), -10vC (40% solution)
Boiling point : 50.4 C (pure substance), 105 C (40% solution)
Vapour pressure : 293.3 hPa at 20 C (pure substance), < 10-4 kPa (40% solution)
Density : 1.14 g/cm3 at 20oC (pure substance), 1.27 g/cm3 (40% solution)
pH : 2.1 – 2.7 (20 C, 40% solution)
Stability : 40% aqueous solution of glyoxal is stable at room temperature at least for 6 months, when stored in dark
Purity, composition, and substance codes
Anhydrous Glyoxal can only be produced in the laboratory and does not exist in a stable form.
Glyoxal is commonly supplied in the form of aqueous solution at 40% (w/w) (expressed in CHOCHO).
Less concentrated forms have been formerly commercialized (essentially at 30% w/w). Very small quantities of an 80% powder are produced (less than 0.1 % of the marketed quantities).
The hydrated monomer (ethane bis-gemdiol) is the main form of glyoxal in aqueous solution.
However this gemdiol tends to polymerize to acetals and semiacetals. The polymerisation depends on both the pH and the concentration of the solution.
The main oligomeric forms are the dioxolane dimer and the bis(dioxolane) trimer.
The equilibrium between monomer and dimer and trimer depends largely on the glyoxal concentration in the aqueous solution:
- in a 5% solution, 39% of glyoxal is present in the monomer form;
- in a 40% solution, the monomer (I) content amounts to as little as 11% of glyoxal, the dimer (II) and trimer (III) forms being dominant.
The nature of the impurities depends on the synthesis route used. If the process used is the oxidation of acetaldehyde with nitric acid diluted in an aqueous medium, the main impurities are the following:
• <200 ppm formaldehyde
• formic acid, acetic acid, glyoxalin acid and glycolic acid - in total approximately 1500 ppm
If the process used is the oxidation of 1,2-ethanediol with oxygen in the presence of water, glyoxal is mainly contaminated with:
• 5000 ppm hydroxyacetaldehyde
• 1500 ppm 1,2-ethanediol
• approximately 1000-2000 ppm organic acids
Former production processes yielded glyoxal with acid contents of up to 2.1% total acids and 1000 ppm of formaldehyde.
Function and uses
Glyoxal is marketed mainly as a 40% aqueous solution. Glyoxal is used as starting point for the production of a number of other compounds.
The dual functionality and the ability of glyoxal to form heterocyclic compounds are used in the production of resins and for cross-linking functionalized macromolecules such as cellulose, polyacrylamides, polyvinyl alcohol, keratin
and other polycondensates. With cellulose, unstable hemiacetals are obtained in the cold, which irreversibly form acetals when heated in the presence of acid catalysts.
In Annex I of the Cosmetic Directive several cosmetic products using hydroxyl-ethyl cellulose R-types are listed (e.g., creams, emulsions, lotions, gels and oils for skin, face masks, tinted bases, different powders (make-up, after bath, hygienic), hair-care products (tints, bleaches, cleansing and conditioning products), shaving products, sunbathing, tanning etc.).
The maximum glyoxal level is 100 ppm in the cosmetic product. In finished cosmetic products, glyoxal is present only as residual from polymerising reactions.
Odor: characteristic
Use: Glyoxal shows a wide range of activities, e.g. as a versatile crosslinker, as an intermediate for organic syntheses, as a biocide, and as a scavenger for a diverse range of nucleophiles.
Glyoxal is an organic compound with a complex structure. In its liquid state it is yellow in color and when it evaporates it turns to a green colored gas. The compound is often a preferred choice for use in many different types of manufacturing.
The substance is available for purchase to those who use it in the manufacturing of their products.
Chemical Properties
The chemical formula for Glyoxal is OCHCHO or C2H2O2. It’s the smallest dialdehyde which is a more complex structure.
The compound is commonly prepared using the Laporte process or through the liquid-phase oxidation of acetaldehyde with nitric acid.
It was first produced commercially in France in 1960.
Since then, there have been many uses found for this compound. It is used in a great many instances as a solubilizer, an agent that increases the solubility of a substance.
For this reason it is used commonly as an additive to many commercial formulas where increased solubility is desired.
It is also known as ethanedial or ethane 1,2-dione. Another common name is Glyoxyladehyde. It is provided as SDS Glyoxal40; it has 40% strength. It is a colorless, transparent liquid with a content of 40% plus or minus .5%.
Uses
Glyoxal is used to crosslink starch-based formulas in textile finishes and in coated paper. It’s also used in textile production, leather tanning, cosmetics, epoxy, oil and gas industries and disinfection. Glyoxylic acid has industrial uses including the curing of wood and wood hardening. It is also used as a fixative in a method of preserving cells for examination under a microscope. Various concentrations are used in different types of uses.
There are many specific uses in the manufacturing of various products. For example, it is used in disinfectants that are used both in the health industry and for veterinary hygiene. When used in cosmetics it improves the viscosity of the products. In leather production, it helps preserve the leather quality. It is often used in epoxy to give it more stability and better performance.
It is also accredited for use in the manufacture of food packaging. It is important to note that it is readily biodegradable when used according to OECD guidelines.
ODIX;Oxal;(CHO)2;GLYOXA;GLYOXAL;DIFORMYL;GLYOXALE;Biformal;Biformyl;Diformal
Chemical Properties: colourless or light yellow liquid
Uses : Permanent-press fabrics; dimensional stabilization of rayon and other fibers. Insolubilizing agent for compounds containing polyhydroxyl groups (polyvinyl alcohol, starch, and cellulosic materials); insolubilizing of proteins (casein, gelatin, and animal glue); embalming fluids; leather tanning; paper coatings with hydroxyethylcellulose; reducing agent in dyeing textiles.
Uses: Glyoxal is used in the production of textiles and glues and in organic synthesis.
Definition: ChEBI: The dialdehyde that is the smallest possible and which consists of ethane having oxo groups on both carbons.
General Description : Yellow crystals melting at15°C. Hence often encountered as a light yellow liquid with a weak sour odor. Vapor has a green color and burns with a violet flame.
Air & Water Reactions: Mixtures with air may explode. Polymerizes quickly on standing, or on contact with a trace of water (possibly a violent reaction), or when dissolved in solvents containing water, [Merck, 502(1968)]. Soluble in water. An aqueous solution contains mono molecular Glyoxal. [Hawley]
Reactivity Profile: Glyoxal reacts vigorously with strong oxidizing agents such as nitric acid. Polymerizes rapidly even at low temperature if anhydrous [Noller]. Aqueous solutions are more stable but also polymerize on standing. Reacts with itself in the presence of base to give glyconates. Undergoes addition and condensation reactions that may be exothermic with amines, amides, aldehydes, and hydroxide-containing materials. Mixing in equal molar portions with any of the following substances in a closed container caused the temperature and pressure to increase: chlorosulfonic acid, oleum, ethyleneimine, nitric acid, sodium hydroxide [NFPA 1991].
Hazard: Mixture of vapor and air may explode. Questionable carcinogen.
Health Hazard: Glyoxal is a skin and eye irritant; the effectmay be mild to severe. Its vapors are irritatingto the skin and respiratory tract. Anamount of 1.8 mg caused severe irritation inrabbits’ eyes. Glyoxal exhibited low toxicityin test subjects. Ingestion may cause somnolenceand gastrointestinal pain.
LD50 value, oral (guinea pigs): 760 mg/kg.
Health Hazard: Inhalation causes some irritation of nose and,40% solution throat. Contact with liquid,40% solution irritates eyes and causes mild irritation of skin; stains skin yellow. (No information available on symptoms of ingestion.)
Fire Hazard: Behavior in Fire: Heat may cause polymerization to a combustible, viscous material.
Safety Profile: Low toxicity by SYN: AEROTEX GLYOXAL 40 ingestion and skin contact. A skin irritant. A powerful reducing agent. May explode on contact with air. Polymerizes violently on contact with water. During storage it may spontaneously polymerize and ignite. Reacts violently with chlorosulfonic acid, ethylene imine, HNO3, oleum, NaOH, can cause violent reactions. Can explode during manufacture. When heated to decomposition it emits acrid smoke and irritating fumes. See also ALDEHYDES.
Waste Disposal: Glyoxal is mixed with a combustible solventand burned in a chemical incineratorequipped with an afterburner and scrubber.
Synonyms:
diformal
ethandial
ethane dial
ethane-1,2-dial
ethanedial
ethanedione
1,2- ethanedione
gelifundol
glyoxal aldehyde
glyoxylaldehyde
oxalaldehyde
oxaldehyde
Preferred IUPAC name
Ethanedial
Other names
Glyoxal
Oxaldehyde
oxaldehyde
Oxalaldehyde
CAS Number
107-22-2 check
Properties
Chemical formula: C2H2O2
Molar mass: 58.036 g·mol−1
Density: 1.27 g/cm3
Melting point: 15 °C
Boiling point: 51 °C
Heat capacity (C): 1.044 J/(K·g)
Flash point: −4 °C
Autoignition temperature: 285 °C
Related aldehydes acetaldehyde
glycolaldehyde
propanedial
methylglyoxal
Related compounds glyoxylic acid
glycolic acid
oxalic acid
pyruvic acid
diacetyl
acetylacetone
Ethanedial
107-22-2
Oxalaldehyde
oxaldehyde
Molecular Weight: 58.04 g/mol
Name: oxaldehyde
CAS Number:107-22-2
Other: 83513-30-8
Molecular Weight:58.03634000
Formula:C2 H2 O
Cosmetic Uses: antimicrobial agents
Primary name and/or INCI name: Glyoxal (INCI name)
Chemical names: Ethandial (IUPAC), Biformal, Biformyl, Diformyl, 1,2-Ethandial, Ethanedione, Glyoxalaldehyde, Glyoxal aldehyde, Oxal, Oxalaldehyde, Oxaldehyde, Odix
Trade names and abbreviations: Aerotex Glyoxal 40, Daicel GY 60, Glyfix CS 50, Glyoxal 40, Glyoxal P, Gohsezal P, Odix, Parez 802, Permafresh 144, Protectol GL
CAS : 107-22-2
EINECS : 203-474-9
Glyoxal can undertake rotational isomerization between the planar cis and trans conformations,with trans-glyoxal being the more stable isomer
Suppliers:
Glyoxal 40%
Odor: characteristic
Use: Glyoxal shows a wide range of activities, e.g. as a versatile crosslinker, as an intermediate for organic syntheses, as a biocide, and as a scavenger for a diverse range of nucleophiles.
Odor: characteristic
Use: Glyoxal links a wide range of polymers, e.g. starch, cellulose, proteinaceous material, polyacrylamide, polyvinyl alcohols.
Ethanedial, Oxalaldehyde
Odor: characteristic
Use: Is used as a solubilizer and cross-linking agent in polymer chemistry for: proteins (leather tanning process), collagen, cellulose derivatives (textiles), hydrocolloids, and starch (paper coatings).
Safety Information:
Xn - Harmful.
R 20 - Harmful by inhalation.
R 36/38 - Irritating to skin and eyes.
R 43 - May cause sensitisation by skin contact.
R 68 - Possible risk of irreversible effects.
S 02 - Keep out of the reach of children.
S 20/21 - When using do not eat, drink or smoke.
S 23 - Do not breath fumes.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36/37 - Wear suitable protective clothing and gloves.
Formulations/Preparations:
•commercially available in anhydrous form as crystalline dihydrate, or as a 40% aqueous solution which may contain polymerization inhibitors.
dihydrate grades: 40% solution; pure, solid; vp.
•glyoxal is a dialdehyde supplied commercially as 30% aqueous solution, consisting of mixture of monomeric & polymeric hydrates along with small amounts of impurities which render the solution acid.
•glyoxal can undertake rotational isomerization between the planar cis and trans conformations, with trans-glyoxal being the more stable isomer.
•...it is generally employed as an aqueous solutionin which hydrated oligomers are present due to nucleophilic addition. ...some of the most important hydrated derivatives of glyoxal formed by nucleophilic addition in aqueous solutioninclude the monomer ethane-1,1,2,2-tetraol (i), the dimer 2-dihydroxymethyl-(1,3)dioxolane-4,5-transdiol (ii), and the trimer bis(dioxolane) (i.e., 2,2'-bi-1,3-dioxolanyl-4,4',5,5'-tetraol) (iii) - both cis and trans configurations. however, the proportion of the different structures varies with concentration and ph.
Glyoxal is the dialdehyde that is the smallest possible and which consists of ethane having oxo groups on both carbons. It has a role as a pesticide, an agrochemical and an allergen.
Glyoxal appears as yellow crystals melting at15°C. Hence often encountered as a light yellow liquid with a weak sour odor. Vapor has a green color and burns with a violet flame.
Production
Glyoxal was first prepared and named by the German-British chemist Heinrich Debus (1824–1915) by reacting ethanol with nitric acid.
Commercial glyoxal is prepared either by the gas-phase oxidation of ethylene glycol in the presence of a silver or copper catalyst (the Laporte process) or by the liquid-phase oxidation of acetaldehyde with nitric acid.
The first commercial glyoxal source was in Lamotte, France, started in 1960.
The single largest commercial source is BASF in Ludwigshafen, Germany, at around 60,000 tons per year.
Other production sites exist also in the US and China.
Commercial bulk glyoxal is made and reported as a 40%-strength solution in water.
Laboratory methods
Glyoxal may be synthesized in the laboratory by oxidation of acetaldehyde with selenious acid.
Anhydrous glyoxal is prepared by heating solid glyoxal hydrate(s) with phosphorus pentoxide and condensing the vapors in a cold trap.
Advanced glycation end-products (AGEs) are proteins or lipids that become glycated as the result of a high-sugar diet.
They are a bio-marker implicated in aging and the development, or worsening, of many degenerative diseases, such as diabetes, atherosclerosis, chronic kidney disease, and Alzheimer's disease.
Applications
Coated paper and textile finishes use large amounts of glyoxal as a crosslinker for starch-based formulations. It condenses with urea to afford 4,5-dihydroxy-2-imidazolidinone, which further reacts with formaldehyde to give the bis(hydroxymethyl) derivative dimethylol ethylene urea, which is used for wrinkle-resistant chemical treatments of clothing, i.e. permanent press.
Glyoxal is used as a solubilizer and cross-linking agent in polymer chemistry.
Glyoxal is a valuable building block in organic synthesis, especially in the synthesis of heterocycles such as imidazoles.
A convenient form of the reagent for use in the laboratory is its bis(hemiacetal) with ethylene glycol, 1,4-dioxane-2,3-diol. This compound is commercially available.
Glyoxal solutions can also be used as a fixative for histology, that is, a method of preserving cells for examining them under a microscope.
Glyoxal and its derivatives are also used in the chemical probing of RNA structure, as they react with free guanines in RNAs.
Glyoxal is supplied typically as a 40% aqueous solution.
Like other small aldehydes, glyoxal forms hydrates. Furthermore, the hydrates condense to give a series of oligomers, some of which remain of uncertain structure.
For most applications, the exact nature of the species in solution is inconsequential.
At least one hydrate of glyoxal is sold commercially, glyoxal trimer dihydrate: [(CHO)2]3(H2O)2 (CAS 4405-13-4).
Other glyoxal equivalents are available, such as the ethylene glycol hemiacetal 1,4-dioxane-trans-2,3-diol (CAS 4845-50-5, m.p. 91–95 °C),
It is estimated that, at concentrations less than 1 M, glyoxal exists predominantly as the monomer or hydrates thereof, i.e., OCHCHO, OCHCH(OH)2, or (HO)2CHCH(OH)2.
At concentrations above 1 M, dimers predominate. These dimers are probably dioxolanes, with the formula [(HO)CH]2O2CHCHO.
Dimer and trimers precipitate as solids from cold solutions.
Other occurrences
Glyoxal has been observed as a trace gas in the atmosphere, e.g. as an oxidation product of hydrocarbons.
Tropospheric concentrations of 0–200 ppt by volume have been reported, in polluted regions up to 1 ppb by volume.
Safety
The LD50 (oral, rats) is 3300 mg/kg, which is very high.
GLYOXAL
Ethanedial
107-22-2
Oxalaldehyde
oxaldehyde
1,2-Ethanedione
Glyoxylaldehyde
Biformal
Biformyl
Diformal
Diformyl
Ethanedial, trimer
Aerotex glyoxal 40
Glyoxal aldehyde
Ethanediol, trimer
Glyoxal, 40%
Glyoxal solutions
C2H2O2
Glyoxal, 29.2%
EINECS 203-474-9
Glyoxal, 40% in water
Ethanedione
CAS-107-22-2
Glyoxal, pure, 40 wt.% solution in water
Glyoxal solution, ~40% in H2O (~8.8 M)
hydroxyketene
oxypolygelatine
Gelifundol
Oxypolygelatin
Ethandial
Glycoxal
ethane dial
Glyoxal solution
(oxo)acetaldehyde
2-hydroxyethenone
2-oxoacetaldehyde
ethane-1,2-dial
Protectol GL 40
glyoxal (ethanedial)
ODIX
oxalic acid dihydride
hydroxymethylene ketone
Glyoxal, 40 % Solution
EC 203-474-9
Glyoxal solution, 40.0%
4-01-00-03625 (Beilstein Handbook Reference)
(CHO)2
Glyoxal, Biformyl, Oxalaldehyde
Glyoxal, 40% solution in water
Glyoxal, 40% w/w aq. soln.
Glyoxal solution, 40 wt. % in H2O
1,2-Ethanedione
Other
Aerotex glyoxal 40
Biformal
Biformyl
Diformal
Diformyl
ethandial
ethandial … %
Ethanedial
Glyoxal
glyoxal
Glyoxal, 29.2%
Glyoxal, 40%
glyoxal; ethandial
Glyoxylaldehyde
Oxal
Oxalaldehyde
Translated names
...% glioksalis (lt)
Etaandiaal … % (et)
etan-1,2-dion ... % (no)
etandial ... % (no)
etandial … % (ro)
etandial … % (sl)
etandial...% (hr)
etandiale...% (it)
etanodial ...% (pl)
etanodial...% (pt)
ethandial ... % (cs)
Ethandial … % (de)
etándiál (sk)
etándiál ...% (hu)
etándiál...% (sk)
Glioksal (hr)
Glioksal (pl)
Glioksal (sl)
glioksal ...% (pl)
glioksal...% (hr)
glioksal...% (sl)
Glioksalis (lt)
Glioksāls (lv)
Gliossal (mt)
Gliossale (it)
gliossale...% (it)
Glioxal (es)
Glioxal (pt)
Glioxal (ro)
glioxal … % (ro)
glioxal...% (es)
glioxal...% (pt)
Glioxál (hu)
glioxál …% (hu)
Glyoksaali (fi)
glyoksaali...% (fi)
glyoksal ... % (no)
glyoxal (cs)
glyoxal (da)
Glyoxal (de)
Glyoxal (fr)
Glyoxal (nl)
Glyoxal (no)
Glyoxal (sv)
glyoxal ... % (cs)
glyoxal à …%; éthanedial à…% (fr)
glyoxal...% (da)
Glyoxal...% (de)
glyoxal...% (nl)
glyoxal...% (sv)
glyoxál...% (sk)
Glükoksaal … % (et)
Glüoksaal (et)
éthanedial...% (fr)
Γλυοξάλη (el)
γλυοξάλη ...% (el)
Глиоксал (bg)
глиоксал...% (bg)
етандиал...% (bg)
…% etandialis (lt)
…% etāndiāls (lv)
…% glioksāls (lv)
CAS names: Ethanedial
IUPAC names: 1,2 ethandial
ethandial
ethandial 40%
ethandial … %
Ethanedial
ethanedial
GLYOXAL
Glyoxal
glyoxal
Glyoxal
oxalaldehyde
oxalaldehyde
oxaldehyde
Trade names
1,2-Ethanedial (chemical name)
1,2-Ethanedione
Biformal
Biformyl
Daicel GY 60
Diformyl
Ethanedial (9CI)
Ethanedione
Glyfix CS 50
Glyoxal (8CI)
Glyoxal (common name)
Glyoxal 40 liq
Glyoxal aldehyde
Glyoxylaldehyde
Gohsezal P
Oxal
Oxalaldehyde
Permafresh 114
Protectol GL
Protectol GL 40
Index Number
83513-30-8
Other
CAS number
83513-30-8
Other
Deleted CAS number
1,2-Ethanedione
107-22-2 [RN]
1732463 [Beilstein]
203-474-9 [EINECS]
50NP6JJ975
Diformal
ethandial
Ethanedial [ACD/Index Name]
Ethanedione
Glyfosfin
Glyoxal [Wiki]
MFCD00006957 [MDL number]
Oxalaldehyd [German] [ACD/IUPAC Name]
Oxalaldehyde [ACD/IUPAC Name]
Oxalaldéhyde [French] [ACD/IUPAC Name]
(CHO)2 [Formula]
203-474-9MFCD00006957
40% aqueous solution
4-01-00-03625 (Beilstein Handbook Reference) [Beilstein]
Acetal
Biformal
Biformyl
DIFORMYL
EDO
ethane-1,2-dial
ethane-1,2-dione
Gelifundol
Glyoxal (40per cent w/w in H2O)
glyoxal aldehyde
Glyoxal, 40% in water
Glyoxal, 40% solution in water
Glyoxylaldehyde
GXT
ODIX
oxal
Oxaldehyde
oxaldehyde（库存处理）
Protectol GL 40 [Trade name]
STR01281
trans-glyoxal
UNII:50NP6JJ975
乙二醛 [Chinese]
GENEL TANIM
15 ° C`de eriyen sarı kristallerdir. Bu nedenle sıklıkla zayıf bir ekşi kokuya sahip açık sarı bir sıvı olarak karşılaşılır. Glyoxal, Buharın yeşil bir rengi vardır ve mor bir alevle yanar. Glyoxal, Yanıcıdır. Güçlü oksitleyici ajanlarla uyuşmaz. Glyoxal, Güçlü indirgeyicidir. Egzotermik olarak polimerize olabilir. Hava, su, oksijen, peroksitler, amidler, aminler, hidroksi içeren maddeler, nitrik asit, aldehitlerle uyuşmaz. Glyoxal, Birçok metali korozif hale getirir.
HAREKET MEKANİZMASI
Glyoxal, proteinleri, nükleotidleri ve lipidlerin amino gruplarına yüksek oranda reaktif karbonil gruplarıyla saldırır. Glikasyon denilen enzimatik olmayan reaksiyonlardan oluşan bir dizi, DNA`da linyin ve arginin artıklarını ve DNA`da 1.0 x 10-7 nükleotidde 1`lik bir arka plan kapsamı ile kararlı ilerlemiş glikasyon son ürünler (AGE`ler) üretir. ... Glyoksal, Guanin`in ekzosiklik azotunun yanı sıra N-1 ile reaksiyona girerek guanozin ile kararlı adüktler oluşturur. Glioksal-guanin adükt oluşumu fizyolojik koşullar altında hızlıdır. Stabil bir trisiklik glioksal-DNA adüktü, in vitro fizyolojik koşullar altında iki guanin azotuna kovalent bağlanma yoluyla oluşur. 8-hidroksi-deoksiguanozin yanı sıra, glioksal-deoksiguanozin (dG) adükt, oksijen radikalleri, lipit peroksidasyon sistemleri, çeşitli oksidatif stres tipleri ve UV ışınlaması ile ve in vivo beta maruziyetinden sonra oluşmakta olan önemli deoksiguanozin oksidasyon ürünlerinden biridir -hidroksi-ikameli N-nitrosaminler.
Glyoxal, gelişmiş glikasyon son ürünler (AGE`ler) oluşumunda önemli bir ara ürün olarak düşünülür. AGE modifikasyonu protein fonksiyonunu değiştirir ve enzimleri inaktive eder, bu da hücresel metabolizma bozukluğuna, bozulmuş proteolize ve hücre proliferasyonunun ve protein sentezinin inhibisyonuna neden olur. AGE modifikasyonunun derecesi, proteinlerin ömrünün uzamasına bağlı olarak artmaktadır. Sonuç olarak, AGE`ler özellikle kollajen, mercek kristalinleri ve nörofilamentler gibi uzun ömürlü proteinlerle ilişkilidir ancak aynı zamanda hemoglobin, plazma proteinleri, lipoproteinler ve hücre içi proteinler de dahil olmak üzere daha kısa süren proteinlerde tanımlanmıştır.
Bakteriyel mutajenite testlerinde yapılan inhibisyon çalışmaları, glioksaldan süperoksit, hidrojen peroksit ve singlet oksijen üretildiğini göstermiştir. Glioksalın mutajenik aktivitesi, singlet oksijene ve hücre içi GSH seviyesine ilişkindir. Hidroksil radikali glioksal kaynaklı DNA bölünmesinde belirgin bir rol oynamaktadır.
İzole edilmiş sıçan hepatositleri farklı glıkoksal konsantrasyonları ile inkübe edildi. Glyoxal tek başına 5 mM`de sitotoksik, tükenmiş GSH, reaktif oksijen türleri (ROS) oluşturdu ve mitokondriyal membran potansiyelini çökertti. Glyoksal aynı zamanda lipit peroksidasyonu ve formaldehit oluşumuna neden olmuştur. Glikolitik substratlar, örneğin fruktoz, sorbitol ve ksilitol glioksal kaynaklı sitotoksisiteyi inhibe etti ve mitokondriyal membran potansiyelindeki azalmayı önledi, mitokondriyal toksisitenin sitotoksik mekanizmaya katkıda bulunduğunu düşündürdü. Glioksal sitotoksisite, glioksal tuzaklar d-penisilamin veya aminoguanidin ile engellendi veya ROS atıcılar, glioksal sonrası bir süre ilave edildiklerinde bile sitoprotektifti; oksidatif stresin glioksal sitotoksik mekanizmaya katkıda bulunduğunu düşündürdü.
Sitozolik GSH`ye bağlı glioksalaz sistemi, glioksalın detoksifikasyonunun başlıca yoludur. Glikoksal, gliokzalaz I ile daha sonra S-glikolglutatiyona dönüştürülen bir hemitiyoasetal oluşumu ile enzimatik olmayan şekilde GSH ile tepkimeye girer. Glikozalaz II, hidrolizini katalize eder S-glikolglutatyonun glikolata dönüştürülmesi, ilk reaksiyondan GSH`nin yeniden oluşturulması. Gloksalaz I in in situ aktivitesi, GSH`nin sitozolik konsantrasyonu ile yaklaşık olarak orantılıdır. GSH şiddetle tükendiğinde (örneğin, oksidatif stres koşulları altında), 2-oksoaldehid dehidrojenaz ve aldoz redüktaz da glioksal metabolize edebilir. Hücre içi redoks sistemindeki dengesizlikler bu detoksifikasyon mekanizmalarını bozabilir ve bu da glioksal düzeyinin yükselmesine neden olabilir. Glyokzalaz III yoluyla GSH`den bağımsız bir başka detoksifikasyon yolu mevcuttur.
KULLANIM VE İMALAT
Dolgu
Ara ürünler
Koku maddeleri
İşleme yardımcıları
Katı ayırma maddeleri
Su Arıtma Ürünleri
Çok yönlü özellikleri ara glioksal, çeşitli uygulamalar için tercih edilen üründür. Örneğin, tekstil imalatında, bu verimli çapraz bağlayıcı, çapraz bağlayıcı selülozdaki su alımı miktarını düşürür. Yağ geri kazanımında, glioksal, polimerleri çapraz bağlar ve böylece kırık akışkanların viskozitesini arttırır.
Glyoxal kağıt, deri ve epoksi endüstrilerinde de kullanılır. Bilinen uygulamaların yanında, glioksal, gelişimin erken evrelerinde olan yeni uygulamalar için potansiyel göstermektedir. İlaçların, yapıştırıcılar ve kaplayıcıların, tekstil reçinelerinin ve tekstil reaktan ürünlerin üretiminde, kağıt reçinelerinin üretiminde ve of set-özel kaplama banyolarında kullanılır. Çapraz bağlayıcıların üretiminde ara madde olarak kullanılır. Örneğin; kopolimerlerin üretimi, boya ara maddeleri, ilaçlar, mahsül (ürün) koruma ajanları, böcek ilaçları, kağıt, tekstil ve deri yardımcıları, korozyon önleyiciler ve fotoğraf kimyasalları için kullanılır. Organik sentezlerde (tıbbi ürünler, boya maddeleri vs...), ev ve hastane dezenfeksiyonu biositlerinde, çeşitli muhteliflerin kullanımı, çeşitli doldurucuların yığınlanması ve mineral doldurucu muamelesinde, selüloz eterlerinin yumrulaşma karşıtı işlenmesinde ve hava koku giderici ajanlarda kullanılır. Ayrıca hidrokolloidlerin üretimi, epoksi ve fenolik reçinelerin üretiminde ve tütün katkısı olarak da kullanılmaktadır.
