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Aminoacetic acid, more commonly known as Glycine, is the simplest and smallest non-essential amino acid found in proteins.
Aminoacetic acid's chemical formula is C₂H₅NO₂.
Aminoacetic acid is an organic compound with the formula C2H5NO2, and is the simplest stable amino acid, distinguished by having a single hydrogen atom as its side chain.
CAS: 56-40-6
MF: C2H5NO2
MW: 75.07
EINECS: 200-272-2
Synonyms
USP24 GLYCINE USP24;GLYCINE TECHNICAL;Glycine (Feed Grade);Glycine (Food Grade);Glycine (Pharm Grade);Glycine 99.0+ % for analysis;Glycine BP;Glycine, MB Grade (1.12008)
As one of the 20 proteinogenic amino acids, glycine is a fundamental building block of proteins in all life and is encoded by all codons starting with GG (GGU, GGC, GGA, and GGG).
Because of its minimal side chain, Aminoacetic acid is the only common amino acid that is not chiral, meaning it is superimposable on its mirror image.
In the body, Aminoacetic acid plays several crucial roles.
Aminoacetic acid's small and flexible structure is vital for the formation of certain protein structures, most notably in collagen, where glycine makes up about 35% of the amino acid content and enables the tight coiling of the collagen triple helix.
Aminoacetic acid disrupts the formation of alpha-helices in secondary protein structure, in favor instead of random coils.
Beyond its structural role, Aminoacetic acid functions as an inhibitory neurotransmitter in the central nervous system, particularly in the spinal cord and brainstem, where it helps regulate motor and sensory signals.
Disruption of Aminoacetic acid signaling can lead to severe neurological disorders and motor dysfunction; for example, the tetanus toxin causes spastic paralysis by blocking glycine release.
Aminoacetic acid also serves as a key precursor for the synthesis of other important biomolecules, including the porphyrins that form heme in blood and the purines used to build DNA and RNA.
Aminoacetic acid is a white, sweet-tasting crystalline solid, leading to its name from Greek word glykys or "sweet".
While the body can synthesize Aminoacetic acid, it is also obtained from the diet and produced industrially by chemical synthesis for use as a food additive, a nutritional supplement, and an intermediate in the manufacture of products such as the herbicide glyphosate.
Aminoacetic acid can fit into hydrophobic environments due to its minimal side chain.
Aminoacetic acid is the simplest (and the only achiral) proteinogenic amino acid, with a hydrogen atom as its side chain.
Aminoacetic acid has a role as a nutraceutical, a hepatoprotective agent, an EC 2.1.2.1 (glycine hydroxymethyltransferase) inhibitor, a NMDA receptor agonist, a micronutrient, a fundamental metabolite and a neurotransmitter.
Aminoacetic acid is an alpha-amino acid, a serine family amino acid and a proteinogenic amino acid.
Aminoacetic acid is a conjugate base of a glycinium.
Aminoacetic acid is a conjugate acid of a glycinate.
Aminoacetic acid is a tautomer of a glycine zwitterion.
Structure
In aqueous solutions, Aminoacetic acid exists predominantly as a zwitterion (H3N+CH2COO-), a polar molecule with both a positive and negative charge.
The zwitterion form is stabilized by hydrogen bonding with solvent water molecules.
Analysis of neutron diffraction data for Aminoacetic acid showed that it was in the zwitterionic form in the solid state and confirmed the presence of hydrogen bonds.
Theoretical calculations have been used to show that zwitterions may also be present in the gas phase for some cases different from the simple carboxylic acid-to-amine transfer.
Aminoacetic acid is of the simplest structure in the 20 members of amino acid series, also known as amino acetate.
Aminoacetic acid is a non-essential amino acid for the human body and contains both acidic and basic functional group inside its molecule.
Aminoacetic acid exhibits as a strong electrolyte an aqueous solution, and has a large solubility in strong polar solvents but almost insoluble in non-polar solvents.
Moreover, Aminoacetic acid also has a relative high melting point and boiling point.
The adjustment of the pH of the aqueous solution can make glycine exhibit different molecular forms.
The side chain of glycine contains only a hydrogen atom.
Owing to another hydrogen atom connecting to the α-carbon atom, the Aminoacetic acid is not optical isomer.
Since the side bond of glycine is very small, Aminoacetic acid can occupy space which can’t be occupied by other amino acids, such as those amino acids located within the collagen helix.
At room temperature, Aminoacetic acid exhibits as white crystal or light yellow crystalline powder and has a unique sweet taste which can ease the taste of acid and alkaline taste, masking the bitter taste of saccharin in food and enhance the sweetness.
However, if an excessive amount of Aminoacetic acid is absorbed by body, they not only can’t be totally absorbed by the body, but will also break the balance of the body's absorption of amino acids as well as affect the absorption of other kinds of amino acids, leading to nutrient imbalances and negatively affected health.
The milk drink with glycine being the major raw material can easily does harm to the normal growth and development of young people and children.
Aminoacetic acid has a density of 1.1607, melting point of 232~236 °C (decomposition).
Aminoacetic acid is soluble in water but insoluble in alcohol and ether.
Aminoacetic acid is capable of acting together with hydrochloric acid to form hydrochloride salt.
Aminoacetic acid is presented in the muscles of animals.
Aminoacetic acid can be produced from the reaction between monochloro acetate and ammonium hydroxide as well as from the hydrolysis of gelation with further refining.
Aminoacetic acid is an organic compound with the formula NH2CH2COOH.
Having a hydrogen substituent as its side-chain, Aminoacetic acid is the smallest of the 20 amino acids commonly found in proteins.
Aminoacetic acid's codons are GGU, GGC, GGA, GGG of the genetic code.
Aminoacetic acid is a colourless, sweet-tasting crystalline solid.
Aminoacetic acid is unique among the proteinogenic amino acids in that it is not chiral.
Aminoacetic acid can fit into hydrophilic or hydrophobic environments, due to its minimal side chain of only one hydrogen atom.
Aminoacetic acid is also the genus name of the Soybean plant (species name = Glycine max).
Aminoacetic acid Chemical Properties
Melting point: 240 °C (dec.) (lit.)
Boiling point: 233°C
density: 1.595
bulk density: 920kg/m3
vapor pressure: 0.0000171 Pa (25 °C)
FEMA: 3287 | GLYCINE
refractive index: 1.4264 (estimate)
Fp: 176.67°C
storage temp.: 2-8°C
solubility H2O: 100 mg/mL
form: powder
pka: 2.35(at 25℃)
color: <5 (200 mg/mL)(APHA)
PH: 4(0.2 molar aqueous solution)
Odor: Odorless
PH Range: 4
Odor Type: odorless
biological source: synthetic
Water Solubility: 25 g/100 mL (25 ºC)
λmax λ: 260 nm Amax: 0.05
λ: 280 nm Amax: 0.05
JECFA Number: 1421
Merck: 14,4491
BRN: 635782
Henry's Law Constant: 1.2×1011 mol/(m3Pa) at 25℃, Brimblecombe et al. (1992)
Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
Cosmetics Ingredients Functions: ANTISTATIC
BUFFERING
SKIN CONDITIONING
HAIR CONDITIONING
Cosmetic Ingredient Review (CIR): Glycine (56-40-6)
InChI: 1S/C2H5NO2/c3-1-2(4)5/h1,3H2,(H,4,5)
InChIKey: DHMQDGOQFOQNFH-UHFFFAOYSA-N
LogP: -3.21
CAS DataBase Reference: 56-40-6(CAS DataBase Reference)
NIST Chemistry Reference: Aminoacetic acid(56-40-6)
EPA Substance Registry System: Aminoacetic acid (56-40-6)
Absorption: ≤0.15 at 280 at 1M
CAS Number Unlabeled: 73-32-5
A white, odorless, crystalline powder having a sweetish taste.
Aminoacetic acid's solution is acid to litmus.
One g dissolves in about 4 mL of water.
Aminoacetic acid is very slightly soluble in alcohol and in ether.
Aminoacetic acid may be prepared from chloroacetic acid and ammonia; from protein sources, such as gelatin and silk fibroin; from ammonium bicarbonate and sodium cyanide; by catalytic cleavage of serine; from hydrobromic acid and methyleneaminoacetonitrile.
Uses
Used for the pharmaceutical industry, organic synthesis and biochemical analysis.
Used as a buffer for the preparation of tissue culture media and the testing of copper, gold and silver.
In medicine, Aminoacetic acid is used for the treatment of myasthenia gravis and progressive muscular atrophy, hyperacidity, chronic enteritis, and children hyperprolinemia diseases.
Used for the treatment of myasthenia gravis and progressive muscular atrophy; treatment of excess stomach acid ester disease, chronic enteritis (often in combination antacid); using in combination with aspirin can reduce the irritation of the stomach; treatment of children hyperprolinemia; as the nitrogen source for generating non-essential amino acid and can be added to a mixed amino acid injection.
Aminoacetic acid is primarily used as a nutritional additive in chicken feed.
Used as a kind of nutritional supplement which is mainly used for flavoring.
Flavoring agent: Used for alcoholic beverage in combination with alanine; the addition amount: grape wine: 0.4%, whiskey: 0.2%, champagne: 1.0%.
Others such as powder soup: 2%; lees marinated foods: 1%.
Because Aminoacetic acid is tasted like shrimp and cuttlefish, and thus can be used in sauces.
Aminoacetic acid has some certain inhibitory effects on the Bacillus subtilis and E. coli and thus can be used as the preservatives of surimi products and peanut butter with the added amount being 1% to 2%.
Buffering effect: Because Aminoacetic acid is amphiprotic ions containing both amino and carboxyl groups, Aminoacetic acid has a strong buffering property on the taste feeling of salt and vinegar.
The added amount is: salted products: 0.3% to 0.7%, acid stain product: 0.05% to 0.5%.
Antioxidant effect (with its metal chelation): being added to butter, cheese, and margarine extend the storage duration by 3 to 4 times.
To make the lard oil in baked food be stable, we can add 2.5% glucose and 0.5% Aminoacetic acid.
Adding 0.1% to 0.5% glycine to the wheat flour for making convenient noodles can play a role of flavoring.
In pharmacy, Aminoacetic acid is used as antacids (hyperacidity), therapeutic agent for muscle nutritional disorder as well as antidotes.
Moreover, Aminoacetic acid can also be used as the raw material for synthesizing amino acids like threonine.
Aminoacetic acid can be used as a spice according to the provisions of GB 2760-96.
Aminoacetic acid is also known as aminoacetic acid.
In the field of pesticide production, Aminoacetic acid is used for synthesizing the glycine ethyl ester hydrochloride which is the intermediate for the synthesis of pyrethroid insecticides.
Moreover, Aminoacetic acid can also be used for synthesizing fungicides iprodione and solid glyphosate herbicide; in addition Aminoacetic acid is also used in various kinds of other industries such as fertilizer, medicine, food additives, and spices.
Used as a solvent to remove carbon dioxide in the fertilizer industry.
In the pharmaceutical industry, Aminoacetic acid can be used as amino acid preparations, the buffer of chlortetracycline buffer and as the raw material for synthesizing the anti-Parkinson's disease drugs L-dopa.
Moreover, Aminoacetic acid is also the intermediate for producing ethyl imidazole.
Aminoacetic acid is also an adjunct therapy medicine for treating neural hyperacidity and effectively suppressing excess amount of gastric ulcer acid.
In the food industry, Aminoacetic acid is used for the synthesis of alcohol, brewing products, meat processing and cold drinks formula.
As a food additive, Aminoacetic acid can be used alone as a condiment and also used in combination with sodium glutamate, DL-alanine acid, and citric acid.
In other industries, Aminoacetic acid can be used as a pH adjusting agent, being added to the plating solution, or used as the raw material for making other amino acids.
Aminoacetic acid can further be used as biochemical reagents and solvent in organic synthesis and biochemistry.
Used as the intermediates of pharmaceutical and pesticide, decarbonation solvents of fertilizers, plating fluid, etc.
Used as a solvent for removing carbon dioxide in the fertilizer industry.
In pharmaceutical industry, Aminoacetic acid is used as the buffer of chlortetracycline, amino antacids, and used for the preparation of L-dopa.
In food industry, Aminoacetic acid can be used as flavoring agents, agent for removing saccharine bitter taste, for brewing, meat processing, and preparation of soft drinks.
In addition, Aminoacetic acid can also be used as a pH adjusting agent and used in the preparation of the plating solution.
Used as biochemical reagents for the pharmaceutical, food and feed additives; Aminoacetic acid can also be used as a non-toxic decarbonization agent in the field of fertilizer industry.
In the US, Aminoacetic acid is typically sold in two grades: United States Pharmacopeia (“USP”), and technical grade.
Most Aminoacetic acid is manufactured as USP grade material for diverse uses.
USP grade sales account for approximately 80 to 85 percent of the U.S. market for glycine.
Pharmaceutical grade Aminoacetic acid is produced for some pharmaceutical applications, such as intravenous injections, where the customer’s purity requirements often exceed the minimum required under the USP grade designation.
Pharmaceutical grade Aminoacetic acid is often produced to proprietary specifications and is typically sold at a premium over USP grade glycine.
Technical grade Aminoacetic acid, which may or may not meet USP grade standards, is sold for use in industrial applications; e.g., as an agent in metal complexing and finishing.
Technical grade Aminoacetic acid is typically sold at a discount to USP grade glycine.
Animal and human foods
Other markets for USP grade Aminoacetic acid include its use an additive in pet food and animal feed. For humans, Aminoacetic acid is sold as a sweetener/taste enhancer.
Certain food supplements and protein drinks contain glycine.
Certain drug formulations include glycine to improve gastric absorption of the drug.
Cosmetics and miscellaneous applications
Aminoacetic acid serves as a buffering agent in antacids, analgesics, antiperspirants, cosmetics, and toiletries.
Many miscellaneous products use Aminoacetic acid or its derivatives, such as the production of rubber sponge products, fertilizers, metal complexants.
Aminoacetic acid is an intermediate in the synthesis of a variety of chemical products.
Aminoacetic acid is used in the manufacture of the herbicide glyphosate.
Glyphosate is a non-selective systemic herbicide used to kill weeds, especially perennials and broadcast or used in the cutstump treatment as a forestry herbicide.
Non-essential amino acid for human development.
An inhibitory neurotransmitter in spinal cord, allosteric regulator of NMDA receptors.
Aminoacetic acid is a non-essential amino acid for human development.
Aminoacetic acid is an inhibitory neurotransmitter in spinal cord, allosteric regulator of NMDA receptors.
Aminoacetic acid is an amino acid used as a texturizer in cosmetic formulations.
Aminoacetic acid makes up approximately 30 percent of the collagen molecule.
Aminoacetic acid is a nonessential amino acid that functions as a nutrient and dietary supplement.
Aminoacetic acid has a solubility of 1 g in 4 ml of water and is abundant in collagen.
Aminoacetic acid is used to mask the bitter aftertaste of sac- charin, for example, in artificially sweetened soft drinks.
Aminoacetic acid retards rancidity in fat.
Production
Although Aminoacetic acid can be isolated from hydrolyzed proteins, this route is not used for industrial production, as Aminoacetic acid can be manufactured more conveniently by chemical synthesis.
The two main processes are amination of chloroacetic acid with ammonia, giving Aminoacetic acid and hydrochloric acid, and the Strecker amino acid synthesis, which is the main synthetic method in the United States and Japan.
About 15 thousand tonnes are produced annually in this way.
Aminoacetic acid is also co-generated as an impurity in the synthesis of EDTA, arising from reactions of the ammonia co-product.
In the late 1980s, Japan's Mitsubishi Corporation added the screened aerobic Agrobacterium, Brevibacterium, Corynebacterium genus to the medium containing carbon, nitrogen and inorganic nutrient solution for cultivation, and then applied this class of bacteria for converting ethanolamine to Aminoacetic acid in 25~45 °C and pH value from 4 to 9 and further applied concentration, neutralization ion exchange treatment to get the Aminoacetic acid product.
After entering the 1990s, there had been new progress on the production technology of glycine in foreign countries.
The Nitto Chemical Industry Co (Japan) add cultured pseudomonas genus, casein bacteria genus, and alcaligenes genus and other species in 0.5% (mass fraction, dry weight) to the Aminoacetic acid amine-containing matrix for reaction of 45 h under 30 °C and pH value of 7.9 to 8.1 with almost all glycine amine being hydrolyzed into glycine with the conversion rate of 99%.
Although biological methods are still in the research stage, however, owing to its high selectivity, non-pollution property, Aminoacetic acid will be a synthetic route with highly development potential.
Production Methods
Aminoacetic acid was discovered in 1820, by Henri Braconnot who boiled gelatin with sulfuric acid.
Aminoacetic acid is manufactured industrially by treating chloroacetic acid with ammonia :
ClCH2COOH + 2 NH3→H2NCH2COOH + NH4Cl
About 15 million kg are produced annually in this way.
In the USA (by GEO Specialty Chemicals, Inc.) and in Japan (by Shoadenko), Aminoacetic acid is produced via the Strecker amino acid synthesis.
