HYDROXYACETIC ACID
Hydroxyacetic acid is a type of alpha hydroxy acid (AHA) that is commonly used in skincare products and cosmetic treatments.
Hydroxyacetic acid is a colorless, odorless and hygroscopic crystalline solid, highly soluble in water.
Hydroxyacetic acid is a deliquescent crystals that occur naturally as a component in sugarcane.
CAS Number: 79-14-1
EC Number: 201-180-5
Molecular Formula: C2H4O3
Molecular Weight: 76.05
Synonyms: glycolic acid, 2-Glycolic acid, Glycolic acid, 79-14-1, Glycollic acid, Hydroxyethanoic acid, Acetic acid, hydroxy-, glycolate, Polyglycolide, Caswell No. 470, Kyselina glykolova, alpha-Glycolic acid, Kyselina hydroxyoctova, 2-Hydroxyethanoic acid, HOCH2COOH, EPA Pesticide Chemical Code 000101, HSDB 5227, NSC 166, Kyselina glykolova [Czech], AI3-15362, Kyselina hydroxyoctova [Czech], C2H4O3, Glycocide, GlyPure, BRN 1209322, NSC-166, Acetic acid, 2-hydroxy-, EINECS 201-180-5, UNII-0WT12SX38S, MFCD00004312, GlyPure 70, 0WT12SX38S, CCRIS 9474, DTXSID0025363, CHEBI:17497, Glycolic acid-13C2, .alpha.-Glycolic acid, GLYCOLLATE, DTXCID105363, NSC166, EC 201-180-5, 4-03-00-00571 (Beilstein Handbook Reference), GLYCOLIC-2,2-D2 ACID, GOA, Glycolic acid (MART.), Glycolic acid [MART.], C2H3O3-, glycolicacid, Glycolate Standard: C2H3O3- @ 1000 microg/mL in H2O, Hydroxyethanoate, a-Hydroxyacetate, hydroxy-acetic acid, 2-Hydroxyaceticacid, alpha-Hydroxyacetate, a-Glycolic acid, 2-hydroxy acetic acid, 2-hydroxy-acetic acid, 2-hydroxyl ethanoic acid, HO-CH2-COOH, Glycolic acid solution, bmse000245, WLN: QV1Q, Glycolic acid [MI], Glycolic acid (7CI,8CI), Glycolic acid [INCI], Glycolic acid [VANDF], Glycolic acid, p.a., 98%, Acetic acid, hydroxy- (9CI), CHEMBL252557, Glycolic acid [WHO-DD], Glycolic acid, Crystal, Reagent, Glycolic acid [HSDB], BCP28762, Glycolic acid, >=97.0% (T), STR00936, Tox21_301298, s6272, STL197955, AKOS000118921, Glycolic acid, ReagentPlus(R), 99%, CS-W016683, DB03085, HY-W015967, SB83760, CAS-79-14-1, USEPA/OPP Pesticide Code: 000101, NCGC00160612-01, NCGC00160612-02, NCGC00257533-01, FT-0612572, FT-0669047, G0110, G0196, Glycolic acid 100 microg/mL in Acetonitrile, EN300-19242, Glycolic acid, SAJ special grade, >=98.0%, C00160, C03547, D78078, Glycolic acid, Vetec(TM) reagent grade, 98%, Glycolic acid; HYDROXYETHANOIC ACID, Glycolic acid, BioXtra, >=98.0% (titration), Q409373, J-509661, F2191-0224, Glycolic acid; Hydroxyethanoic acid; Glycollic acid, Z104473274, 287EB351-FF9F-4A67-B4B9-D626406C9B13, Glycolic acid, certified reference material, TraceCERT(R), InChI=1/C2H4O3/c3-1-2(4)5/h3H,1H2,(H,4,5, Glycolic acid, anhydrous, free-flowing, Redi-Dri(TM), ReagentPlus(R), 99%, Glycolic acid, Pharmaceutical Secondary Standard; Certified Reference Material, O7Z
Hydroxyacetic acid is derived from sugar cane and belongs to a family of naturally occurring acids that are known for their exfoliating and skin-renewing properties.
Hydroxyacetic acid is the smallest alpha-hydroxy acid (AHA).
Hydroxyacetic acid is mainly supplemented to various skin-care products to improve the skin’s appearance and texture.
Hydroxyacetic acid can also reduce wrinkles, acne scarring, and hyperpigmentation. In textile industry, Hydroxyacetic acid can be used as a dyeing and tanning agent.
Hydroxyacetic acid is composed of colorless deliquescent leaflets that decompose at approximately 78° C (172 OF).
Hydroxyacetic acid is a 2-hydroxy monocarboxylic acid that is acetic acid where the methyl group has been hydroxylated.
Hydroxyacetic acid is an alpha hydroxy acid that has antibacterial, antioxidant, keratolytic, and anti-inflammatory properties.
Hydroxyacetic acid is soluble in water, alcohol and ether.
Hydroxyacetic acid is a colorless, odorless and hygroscopic crystalline solid, highly soluble in water.
Hydroxyacetic acid is used in various skin-care products.
Hydroxyacetic acid is widespread in nature.
A glycolate (sometimes spelled "glycollate") is a salt or ester of Hydroxyacetic acid.
Hydroxyacetic acid is used in dyeing, tanning, electropolishing,and in foodstuffs.
Hydroxyacetic acid is functionally related to acetic acid and is slightly stronger than it.
The salts or esters of Hydroxyacetic acid are called glycolates.
Hydroxyacetic acid is widespread in nature and can be separated from natural sources like sugarcane, sugar beets, pineapple, cantaloupe, and unripe grapes.
Hydroxyacetic acid is produced by oxidizing glycol with dilute nitric acid.
Hydroxyacetic acid is used in various skin-care products.
Hydroxyacetic acid is used in processing and dyeing textiles and Leather.
Hydroxyacetic acid is also used for cleaning, polishing, and soldering metals.
Hydroxyacetic acid is a colorless, odourless, and hygroscopic crystalline solid with the chemical formula C2H4O3.
Hydroxyacetic acid is widespread in nature.
A glycolate is a salt or ester of Hydroxyacetic acid.
Hydroxyacetic acid is a weak acid.
Hydroxyacetic acid is sold commercially as a 70% solution.
Hydroxyacetic acid is widely used in the skincare and cosmetic industry due to Hydroxyacetic acid ability to exfoliate the skin, promote skin cell turnover, and improve the overall texture and appearance of the skin.
Hydroxyacetic acid, also known as 2-hydroxyacetate or glycolate, belongs to the class of organic compounds known as alpha hydroxy acids and derivatives.
These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon.
This could make Hydroxyacetic acid a potential biomarker for the consumption of these foods.
Once applied, Hydroxyacetic acid reacts with the upper layer of the epidermis, weakening the binding properties of the lipids that hold the dead skin cells together.
Hydroxyacetic acid is a potentially toxic compound.
Hydroxyacetic acid, with regard to humans, has been found to be associated with several diseases such as transurethral resection of the prostate and biliary atresia; Hydroxyacetic acid has also been linked to several inborn metabolic disorders including glutaric acidemia type 2, Hydroxyacetic aciduria, and d-2-hydroxyglutaric aciduria.
Glycolic and oxalic acid, along with excess lactic acid, are responsible for the anion gap metabolic acidosis.
Hydroxyacetic acid exists in all living species, ranging from bacteria to humans.
In humans, Hydroxyacetic acid is involved in rosiglitazone metabolism pathway.
Outside of the human body, Hydroxyacetic acid has been detected, but not quantified in, several different foods, such as sourdocks, pineappple sages, celeriacs, cloves, and feijoa.
Hydroxyacetic acid is an extremely weak basic (essentially neutral) compound (based on Hydroxyacetic acid pKa).
Hydroxyacetic acid works by breaking down the bonds between dead skin cells on the surface of the skin, allowing them to be sloughed off more easily.
This indicates that the hydroxyl group is involved in complex formation, possibly with the loss of Hydroxyacetic acid proton.
Hydroxyacetic acid addresses skin issues by exfoliating dead skin cells that accumulate on the surface of the epidermis and contribute to dull, discolored, and uneven looking skin.
Hydroxyacetic acid can make the skin more sensitive in the sunlight, hence always use sunscreen and protective clothing before you step outdoors.
Plants produce Hydroxyacetic acid during photorespiration.
Hydroxyacetic acid is recycled by conversion to glycine within the peroxisomes and to tartronic acid semialdehyde within the chloroplasts.
Common side effects of Hydroxyacetic acid include dry skin, erythema (skin redness), burning sensation, itching, skin irritation, and skin rash.
Hydroxyacetic acid is the smallest alpha-hydroxy acid (AHA).
This colourless, odourless, and hygroscopic crystalline solid is highly soluble in water.
Due to its excellent capability to penetrate skin, Hydroxyacetic acid is often used in skin care products, most often as a chemical peel.
Hydroxyacetic acid may reduce wrinkles, acne scarring, and hyperpigmentation and improve many other skin conditions, including actinic keratosis, hyperkeratosis, and seborrheic keratosis.
Acute doses of Hydroxyacetic acid on skin or eyes leads to local effects that are typical of a strong acid (e.g. dermal and eye irritation).
Glycolate is a nephrotoxin if consumed orally.
A nephrotoxin is a compound that causes damage to the kidney and kidney tissues.
Hydroxyacetic acid's renal toxicity is due to its metabolism to oxalic acid.
Glycolic and oxalic acid, along with excess lactic acid, are responsible for the anion gap metabolic acidosis.
Oxalic acid readily precipitates with calcium to form insoluble calcium oxalate crystals.
Once applied, Hydroxyacetic acid reacts with the upper layer of the epidermis, weakening the binding properties of the lipids that hold the dead skin cells together.
This allows the outer skin to dissolve, revealing the underlying skin.
Hydroxyacetic acid is thought that this is due to the reduction of calcium ion concentrations in the epidermis and the removal of calcium ions from cell adhesions, leading to desquamation.
Renal tissue injury is caused by widespread deposition of oxalate crystals and the toxic effects of Hydroxyacetic acid.
Hydroxyacetic acid does exhibit some inhalation toxicity and can cause respiratory, thymus, and liver damage if present in very high levels over long periods of time.
Hydroxyacetic acid is used in the textile industry as a dyeing and tanning agent in food processing as a flavoring agent and as a preservative, and in the pharmaceutical industry as a skin care agent.
Hydroxyacetic acid is also used in adhesives and plastics.
Hydroxyacetic acid is often included in emulsion polymers, solvents and additives for ink and paint in order to improve flow properties and impart gloss.
Hydroxyacetic acid is used in surface treatment products that increase the coefficient of friction on tile flooring.
Hydroxyacetic acid is a known inhibitor of tyrosinase.
This can suppress melanin formation and lead to a lightening of skin colour.
This process can help with various skin concerns, including acne, fine lines and wrinkles, hyperpigmentation, and uneven skin tone.
Hydroxyacetic acid is the active ingredient in the household cleaning liquid.
Physician-strength peels can have a pH as low as 0.6 (strong enough to completely keratolyze the epidermis), while acidities for home peels can be as low as 2.5.
The process converts glycolate into glycerate without using the conventional BASS6 and PLGG1 route.
Hydroxyacetic acid works by speeding up cell turnover Hydroxyacetic acid helps dissolve the bonds that hold skin cells together, allowing dead skin cells to slough off more rapidly than they would on their own.
Hydroxyacetic acid also stimulates your skin to create more collagen.
Collagen is the protein that gives skin its firmness, plumpness, and elasticity.
Hydroxyacetic acid is an incredibly popular treatment because of the many benefits Hydroxyacetic acid has for the skin.
Hydroxyacetic acid has effective skin-renewing properties, so Hydroxyacetic acid is often used in anti-aging products.
Hydroxyacetic acid can help smooth fine wrinkles and improve the skin's tone and texture.
Hydroxyacetic acid is a water-soluble alpha hydroxy acid (AHA) that is derived from sugar cane.
Hydroxyacetic acid is one of the most well-known and widely used alphahydroxy acids in the skincare industry.
Hydroxyacetic acid plumps the skin and helps boost hydration levels.
Hydroxyacetic acid provides far greater solubility than silicafluorides or hydrofluosilicic acid.
Electrochemical Energy Systems permits higher concentrations of acid in solution than citric acid for greater neutralizing efficiency while avoiding salting or rust discoloration problems.
Hydroxyacetic acid reaches a final pH of 5-6 more quickly than silicafluorides, especially at lower wash temperatures.
High solubility means a lower possibility of damaged fabric—even if it’s ironed while wet.
Hydroxyacetic acid fulfills many roles across a wide range of industries, thanks to Hydroxyacetic acid low odor and toxicity, biodegradability, phosphate-free composition, and ability to chelate metal salts.
A glycolate or glycollate is a salt or ester of Hydroxyacetic acid.
(C6H5C(=O)OCH2COOH), which they called "benzoHydroxyacetic acid" (Benzoglykolsäure; also benzoyl Hydroxyacetic acid).
They boiled the ester for days with dilute sulfuric acid, thereby obtaining benzoic acid and Hydroxyacetic acid.
Hydroxyacetic acid liquid doesn’t cake in storage and measures easily out of automatic dispensing equipment.
Once applied, Hydroxyacetic acid reacts with the upper layer of the epidermis, weakening the binding properties of the lipids that hold the dead skin cells together.
This allows the stratum corneum to be exfoliated, exposing live skin cells.
Hydroxyacetic acid is a useful intermediate for organic synthesis, in a range of reactions including: oxidation-reduction, esterification and long chain polymerization.
Other alpha-hydroxy acids include lactic acid, malic acid, tartaric acid, and citric acid.
Hydroxyacetic acid has the smallest sized molecules of all the alpha-hydroxy acids Because of these super tiny molecules, Hydroxyacetic acid can easily penetrate the skin.
This allows Hydroxyacetic acid to exfoliate the skin more effectively than other AHAs.
Hydroxyacetic acid is used as a monomer in the preparation of polyHydroxyacetic acid and other biocompatible copolymers (e.g. PLGA).
Commercially, important derivatives include the methyl and ethyl esters which are readily distillable (boiling points 147–149 °C and 158–159 °C, respectively), unlike the parent acid.
The butyl ester (b.p. 178–186 °C) is a component of some varnishes, being desirable because Hydroxyacetic acid is nonvolatile and has good dissolving properties.
Many plants make Hydroxyacetic acid during photorespiration.
Hydroxyacetic acids role consumes significant amounts of energy.
Hydroxyacetic acid penetrates the skin effectively due to its small molecular size, helping to remove dead skin cells and debris from the surface.
This can lead to a smoother, brighter complexion.
The use of Hydroxyacetic acid in skincare products is associated with several benefits, including reducing the appearance of fine lines and wrinkles, improving skin texture, minimizing the appearance of pores, and fading hyperpigmentation and acne scars.
The concentration of Hydroxyacetic acid in these products can vary, with higher concentrations generally being available in professional treatments.
While Hydroxyacetic acid can benefit many skin types, Hydroxyacetic acid may not be suitable for everyone, especially those with very sensitive or reactive skin.
In 2017 researchers announced a process that employs a novel protein to reduce energy consumption/loss and prevent plants from releasing harmful ammonia.
Sun protection helps prevent sunburn and further skin damage.
Hydroxyacetic acid can be found in a range of skincare products, including cleansers, toners, serums, and creams.
Hydroxyacetic acid can be isolated from natural sources, such as sugarcane, sugar beets, pineapple, cantaloupe and unripe grapes.
Hydroxyacetic acid can be used as part of an acne treatment regimen.
Hydroxyacetic acid helps to unclog pores, reduce the formation of comedones (blackheads and whiteheads), and promote the shedding of dead skin cells that can contribute to acne.
Dermatologists often use Hydroxyacetic acid in chemical peels, which are cosmetic procedures designed to improve the skin's appearance.
Hydroxyacetic acid is a simple organic compound with a hydroxyl group (-OH) and a carboxylic acid group (-COOH) on adjacent carbon atoms in its chemical structure.
Hydroxyacetic acid is known for its exfoliating properties.
Hydroxyacetic acid is an Alpha Hydroxy Acid (AHA).
The word acid might scare, but Hydroxyacetic acid usually comes in lower concentrations for at-home use.
Hydroxyacetic acid works as an exfoliant to turn over dead skin cells and reveal new skin cells.
Hydroxyacetic acid’s also one of the smallest AHAs, meaning that Hydroxyacetic acid can penetrate deeply to give the best results.
Applications of Hydroxyacetic Acid:
Hydroxyacetic acid is used in the textile industry as a dyeing and tanning agent.
Organic synthesis:
Hydroxyacetic acid is a useful intermediate for organic synthesis, in a range of reactions including: oxidation-reduction, esterification and long chain polymerization.
Hydroxyacetic acid is used as a monomer in the preparation of polyHydroxyacetic acid and other biocompatible copolymers.
Commercially, important derivatives include the methyl and ethyl esters which are readily distillable (boiling points 147–149 °C and 158–159 °C, respectively), unlike the parent acid.
The butyl ester is a component of some varnishes, being desirable because Hydroxyacetic acid is nonvolatile and has good dissolving properties.
Occurrence:
Plants produce Hydroxyacetic acid during photorespiration.
Hydroxyacetic acid is recycled by conversion to glycine within the peroxisomes and to tartronic acid semialdehyde within the chloroplasts.
Because photorespiration is a wasteful side reaction in regard to photosynthesis, much effort has been devoted to suppressing its formation.
One process converts glycolate into glycerate without using the conventional BASS6 and PLGG1 route; see glycerate pathway.
Uses of Hydroxyacetic Acid:
Hydroxyacetic acid acts by dissolving the internal cellular cement responsible for abnormal keratinization, facilitating the sloughing of dead skin cells.
Hydroxyacetic acid is also the AHA that scientists and formulators believe has greater penetration potential largely due to its smaller molecular weight.
Hydroxyacetic acid is mildly irritating to the skin and mucous membranes if the formulation contains a high Hydroxyacetic acid concentration and/ or a low pH.
Hydroxyacetic acid proves beneficial for acne-prone skin as Hydroxyacetic acid helps keep pores clear of excess keratinocytes.
Hydroxyacetic acid is naturally found in sugarcane but synthetic versions are most often used in cosmetic formulations.
Hydroxyacetic acid is used as a monomer in the preparation of polyHydroxyacetic acid and other biocompatible copolymers (e.g. PLGA).
Hydroxyacetic acid also improves skin hydration by enhancing moisture uptake as well as increasing the skin’s ability to bind water.
Hydroxyacetic acid is also used for diminishing the signs of age spots, as well as actinic keratosis.
However, Hydroxyacetic acid is most popularly employed in anti-aging cosmetics because of its hydrating, moisturizing, and skin-normalizing abilities, leading to a reduction in the appearance of fine lines and wrinkles.
Commercially, important derivatives include the methyl and ethyl esters which are readily distillable (boiling points 147–149 °C and 158–159 °C, respectively), unlike the parent acid.
Hydroxyacetic acid can be used with hydrochloric or sulfamic acids to prevent iron precipitation in cleaning operations or water flooding.
Regardless of the G skin type, Hydroxyacetic acid use is associated with softer, smoother, healthier, and younger looking skin.
This occurs in the cellular cement through an activation of Hydroxyacetic acid and the skin’s own hyaluronic acid content.
Hydroxyacetic acid also effectively eliminates harmful deposits while minimizing corrosion damage to steel or copper systems.
Hydroxyacetic acid reacts more slowly and thus penetrates more deeply into formations before fully reacting.
That characteristic leads to enhanced worm holing, because Hydroxyacetic acid dissolves the equivalent amount of calcium carbonate (CaCO₃) as hydrochloric acid without the resulting corrosion.
One of the primary uses of Hydroxyacetic acid in skincare is as an exfoliant.
Hydroxyacetic acid helps remove dead skin cells from the surface of the skin, resulting in a smoother and more radiant complexion.
Hydroxyacetic acid is used to treat acne by unclogging pores, reducing the formation of comedones (blackheads and whiteheads), and promoting the shedding of dead skin cells that can contribute to acne.
In addition to over-the-counter products, dermatologists and skincare professionals often use Hydroxyacetic acid in more concentrated forms for in-office treatments like chemical peels and microdermabrasion.
These treatments can provide more immediate and dramatic results but require professional oversight.
Hyaluronic acid is known to retain an impressive amount of moisture and this capacity is enhanced by Hydroxyacetic acid.
As a result, the skin’s own ability to raise its moisture content is increased.
Hydroxyacetic acid is the simplest alpha hydroxyacid (AHA).
Hydroxyacetic acid is used in the textile industry as a dyeing and tanning agent.
In the processing of textiles, leather, and metals; in pH control, and wherever a cheap organic acid is needed, e.g. in the manufacture of adhesives, in copper brightening, decontamination cleaning, dyeing, electroplating, in pickling, cleaning and chemical milling of metals.
Hydroxyacetic acid is used as an intermediate in organic synthesis and several reactions, such as oxidation-reduction, esterification, and long chain polymerization.
Hydroxyacetic acid is used as a monomer in the preparation of Poly(lactic-co-Hydroxyacetic acid) (PLGA).
Hydroxyacetic acid reacts with lactic acid to form PLGA using ring-opening co-polymerization.,
Hydroxyacetic acid is commonly used in anti-aging products to stimulate collagen production, which can improve skin elasticity and reduce the appearance of fine lines and wrinkles.
Hydroxyacetic acid can help fade dark spots, sunspots, and post-inflammatory hyperpigmentation by promoting even skin tone.
Hydroxyacetic acid can improve skin texture, making it feel smoother and look more youthful.
Hydroxyacetic acid can minimize the appearance of enlarged pores.
Hydroxyacetic acid is used in chemical peels, both at home and in dermatologist's offices or skincare clinics.
Chemical peels with Hydroxyacetic acid can be tailored to address various skin concerns, including wrinkles, uneven skin tone, and acne scars.
PolyHydroxyacetic acid (PGA) is prepared from the monomer Hydroxyacetic acid using polycondensation or ring-opening polymerization.
Hydroxyacetic acid is widely used in skin care products as an exfoliant and keratolytic.
Hydroxyacetic acid is used in the textile industry as a dyeing and tanning agent.
These peels involve the application of a higher concentration of Hydroxyacetic acid to the skin, followed by exfoliation and skin rejuvenation.
While Hydroxyacetic acid is commonly associated with facial skincare, Hydroxyacetic acid can also be used on other parts of the body to address issues like keratosis pilaris, rough skin on elbows and knees, and body acne.
Hydroxyacetic acid may be used to adjust the pH level of Hydroxyacetic acid.
This can help optimize the effectiveness of other active ingredients.
Hydroxyacetic acid can also act as a humectant, meaning Hydroxyacetic acid can attract and retain moisture in the skin, which is beneficial for individuals with dry or dehydrated skin.
However, it's essential to use moisturizers alongside Hydroxyacetic acid products to prevent excessive dryness.
In industrial and household applications, Hydroxyacetic acid is sometimes used to remove stains and scale deposits, such as those caused by hard water, rust, or mineral buildup.
When using Hydroxyacetic acid-containing products in your skincare routine, be cautious about mixing them with other active ingredients, especially strong acids like salicylic acid or vitamin C.
Combining certain active ingredients can lead to skin irritation or reduce effectiveness, so it's advisable to consult with a skincare professional for guidance.
In medicine, Hydroxyacetic acid has been used in wound care products to help promote the healing of minor cuts, abrasions, and surgical incisions.
Hydroxyacetic acid can be used to manage keratosis pilaris, a common skin condition characterized by small, rough bumps on the skin, often found on the arms and thighs.
Some over-the-counter products containing Hydroxyacetic acid are used to soften and help remove calluses and corns on the feet.
In some hair care products, Hydroxyacetic acid may be included to help exfoliate the scalp, remove product buildup, and improve hair texture.
Hydroxyacetic acid can help repair sun-damaged skin by promoting the shedding of damaged skin cells and stimulating the production of healthier, more youthful-looking skin.
Hydroxyacetic acid is often used in products designed for sun-damaged or aging skin.
Hydroxyacetic acid can be used to prevent and treat ingrown hairs, particularly in areas prone to razor bumps and irritation, such as the beard area in men.
Hydroxyacetic acid is sometimes combined with other skincare ingredients like salicylic acid, hyaluronic acid, and retinol to create more comprehensive skincare products that address multiple concerns, such as acne, aging, and hydration.
Hydroxyacetic acid is used in the processing of textiles, leather, and metals.
Hydroxyacetic acid is used as an intermediate in organic synthesis and several reactions, such as oxidation-reduction, esterification, and long chain polymerization.
Hydroxyacetic acid (Hydroxyacetic acid) reduces corenocyte cohesion and corneum layer thickening where an excess buildup of dead skin cells can be associated with many common skin problems, such as acne, dry and severely dry skin, and wrinkles.
Hydroxyacetic acid can also be used as a flavoring agent in food processing, and as a skin care agent in the pharmaceutical industry.
Hydroxyacetic acid can also be added into emulsion polymers, solvents and ink additives to improve flow properties and impart gloss.
Moreover, Hydroxyacetic acid is a useful intermediate for organic synthesis including oxidative-reduction, esterification and long chain polymerization.
Preparation of Hydroxyacetic Acid:
Hydroxyacetic acid can be synthesized in various ways.
The predominant approaches use a catalyzed reaction of formaldehyde with synthesis gas (carbonylation of formaldehyde), for Hydroxyacetic acid low cost.
Hydroxyacetic acid is also prepared by the reaction of chloroacetic acid with sodium hydroxide followed by re-acidification.
Other methods, not noticeably in use, include hydrogenation of oxalic acid, and hydrolysis of the cyanohydrin derived from formaldehyde.
Some of today's Hydroxyacetic acids are formic acid-free.
Hydroxyacetic acid can be isolated from natural sources, such as sugarcane, sugar beets, pineapple, cantaloupe and unripe grapes.
Hydroxyacetic acid can also be prepared using an enzymatic biochemical process that may require less energy.
Typical Properties of Hydroxyacetic Acid:
Hydroxyacetic acid is slightly stronger than acetic acid due to the electron-withdrawing power of the terminal hydroxyl group.
The carboxylate group can coordinate to metal ions, forming coordination complexes.
Of particular note are the complexes with Pb2+ and Cu2+ which are significantly stronger than complexes with other carboxylic acids.
This indicates that the hydroxyl group is involved in complex formation, possibly with the loss of Hydroxyacetic acid proton.
History of Hydroxyacetic Acid:
The name "Hydroxyacetic acid" was coined in 1848 by French chemist Auguste Laurent (1807–1853).
He proposed that the amino acid glycine—which was then called glycocolle—might be the amine of a hypothetical acid, which he called "Hydroxyacetic acid" (acide glycolique).
Hydroxyacetic acid was first prepared in 1851 by German chemist Adolph Strecker (1822–1871) and Russian chemist Nikolai Nikolaevich Sokolov (1826–1877).
They produced Hydroxyacetic acid by treating hippuric acid with nitric acid and nitrogen dioxide to form an ester of benzoic acid and Hydroxyacetic acid (C6H5C(=O)OCH2COOH), which they called "benzoHydroxyacetic acid" (Benzoglykolsäure; also benzoyl Hydroxyacetic acid).
They boiled the ester for days with dilute sulfuric acid, thereby obtaining benzoic acid and Hydroxyacetic acid (Glykolsäure).
Safety Profile of Hydroxyacetic Acid:
Hydroxyacetic acid can cause skin irritation, especially for individuals with sensitive skin.
This may manifest as redness, burning, itching, or stinging.
Hydroxyacetic acid's essential to perform a patch test before using Hydroxyacetic acid products.
Hydroxyacetic acid can make the skin more sensitive to ultraviolet (UV) radiation from the sun.
This increased sensitivity can lead to a higher risk of sunburn and skin damage.
Hydroxyacetic acid is crucial to use sunscreen and protective clothing when using Hydroxyacetic acid products and avoid excessive sun exposure.
As an exfoliant, Hydroxyacetic acid can cause dryness and peeling, especially when used in high concentrations or too frequently.
This can be managed by using moisturizers and reducing the frequency of Hydroxyacetic acid application.
While rare, some individuals may be allergic or hypersensitive to Hydroxyacetic acid, leading to more severe skin reactions.
In cases where high concentrations of Hydroxyacetic acid are used without proper supervision or inappropriately, chemical burns can occur.
This is more common in professional treatments like chemical peels and should only be administered by trained professionals.
First aid measures of Hydroxyacetic Acid:
General advice:
First aiders need to protect themselves.
Show Hydroxyacetic acid safety data sheet to the doctor in attendance.
If inhaled:
After inhalation:
Immediately call in physician.
If breathing stops:
Immediately apply artificial respiration, if necessary also oxygen.
In case of skin contact:
Take off immediately all contaminated clothing.
Rinse skin with water/ shower.
Call a physician immediately.
In case of eye contact:
After eye contact:
Rinse out with plenty of water.
Immediately call in ophthalmologist.
Remove contact lenses.
If swallowed:
After swallowing:
Make victim drink water (two glasses at most), avoid vomiting (risk of perforation).
Call a physician immediately. Do not attempt to neutralise.
Indication of any immediate medical attention and special treatment needed:
No data available
Firefighting measures of Hydroxyacetic Acid:
Suitable extinguishing media:
Water Foam Carbon dioxide (CO2) Dry powder
Unsuitable extinguishing media:
For this substance/mixture no limitations of extinguishing agents are given.
Special hazards arising from the substance or mixture:
Carbon oxides
Combustible.
Vapors are heavier than air and may spread along floors.
Forms explosive mixtures with air on intense heating.
Development of hazardous combustion gases or vapours possible in the event of fire.
Advice for firefighters:
Stay in danger area only with self-contained breathing apparatus.
Prevent skin contact by keeping a safe distance or by wearing suitable protective clothing.
Further information:
Prevent fire extinguishing water from contaminating surface water or the ground water system.
Accidental release measures of Hydroxyacetic Acid:
Personal precautions, protective equipment and emergency procedures:
Advice for non-emergency personnel:
Avoid inhalation of dusts.
Avoid substance contact.
Ensure adequate ventilation.
Evacuate the danger area, observe emergency procedures, consult an expert.
Environmental precautions:
Do not let product enter drains.
Methods and materials for containment and cleaning up:
Cover drains.
Collect, bind, and pump off spills.
Observe possible material restrictions.
Take up dry.
Dispose of properly.
Clean up affected area.
Avoid generation of dusts.
Handling and storage of Hydroxyacetic Acid:
Precautions for safe handling:
Advice on safe handling:
Work under hood.
Do not inhale substance/mixture.
Hygiene measures:
Immediately change contaminated clothing.
Apply preventive skin protection.
Wash hands and face after working with substance.
Conditions for safe storage, including any incompatibilities:
Storage conditions:
Tightly closed.
Dry.
Storage class:
Storage class (TRGS 510): 8A: Combustible, corrosive hazardous materials
Stability and reactivity:
Reactivity of Hydroxyacetic Acid:
Forms explosive mixtures with air on intense heating.
A range from approx. 15 Kelvin below the flash point is to be rated as critical.
The following applies in general to flammable organic substances and mixtures:
In correspondingly fine distribution, when whirled up a dust explosion potential may generally be assumed.
Chemical stability:
Hydroxyacetic acid is chemically stable under standard ambient conditions (room temperature).
Possibility of hazardous reactions:
Violent reactions possible with:
Oxidizing agents
Reducing agents
Conditions to avoid:
Strong heating.
Incompatible materials:
Gives off hydrogen by reaction with metals.
Identifiers of Hydroxyacetic Acid:
CAS Number: 79-14-1
ChEBI: CHEBI:17497
ChEMBL: ChEMBL252557
ChemSpider: 737
DrugBank: DB03085
ECHA InfoCard: 100.001.073
EC Number: 201-180-5
KEGG: C00160
PubChem CID: 757
RTECS number: MC5250000
UNII: 0WT12SX38S
CompTox Dashboard (EPA): DTXSID0025363
InChI: InChI=1S/C2H4O3/c3-1-2(4)5/h3H,1H2,(H,4,5)
Key: AEMRFAOFKBGASW-UHFFFAOYSA-N check
InChI=1/C2H4O3/c3-1-2(4)5/h3H,1H2,(H,4,5)
Key: AEMRFAOFKBGASW-UHFFFAOYAR
SMILES: OC(=O)CO
Linear Formula: HOCH2COOH
CAS Number: 79-14-1
Molecular Weight: 76.05
Beilstein: 1209322
EC Number: 201-180-5
MDL number: MFCD00004312
eCl@ss: 39021303
PubChem Substance ID: 24847624
NACRES: NA.21
Properties of Hydroxyacetic Acid:
Chemical formula: C2H4O3
Molar mass: 76.05 g/mol
Appearance: White powder or colorless crystals
Density: 1.49 g/cm3
Melting point: 75 °C (167 °F; 348 K)
Boiling point: Decomposes
Solubility in water: 70% solution
Solubility in other solvents: Alcohols, acetone, acetic acid and ethyl acetate
log P: −1.05
Acidity (pKa): 3.83
Quality Level: 200
product line: ReagentPlus®
Assay: 99%
form: solid
mp: 75-80 °C (lit.)
solubility: H2O: 50 mg/mL, clear, colorless
SMILES string: OCC(O)=O
InChI: 1S/C2H4O3/c3-1-2(4)5/h3H,1H2,(H,4,5)
InChI key: AEMRFAOFKBGASW-UHFFFAOYSA-N
Melting point: 75-80 °C (lit.)
Boiling point: 112 °C
Density: 1.25 g/mL at 25 °C
vapor pressure: 10.8 hPa (80 °C)
refractive index: n20/D 1.424
Flash point: 112°C
storage temp.: Store below +30°C.
solubility: H2O: 0.1 g/mL, clear
pka: 3.83(at 25℃)
form: Solution
color: White to off-white
PH: 2 (50g/l, H2O, 20℃)
Odor: at 100.00 %. odorless very mild buttery
Odor Type: buttery
Viscosity: 6.149mm2/s
Water Solubility: SOLUBLE
Sensitive: Hygroscopic
Merck: 14,4498
BRN: 1209322
Stability: Stable. Incompatible with bases, oxidizing agents and reducing agents.
InChIKey: AEMRFAOFKBGASW-UHFFFAOYSA-N
LogP: -1.07 at 20℃
Indirect Additives used in Food Contact Substances: Hydroxyacetic acid
FDA 21 CFR: 175.105
Specifications of Hydroxyacetic Acid:
Color according to color reference solution Ph.Eur.: colorless liquid
Assay (acidimetric): 69.0 - 74.0 %
Density (d 20 °C/ 4 °C): 1.260 - 1.280
Heavy metals (as Pb): ≤ 3 ppm
Refractive index (n 20°/D): 1.410 - 1.415
pH-value: 0.0 - 1.0
Related compounds of Hydroxyacetic Acid:
Glycolaldehyde
Acetic acid
Glycerol
Related α-hydroxy acids:
Lactic acid
Names of Hydroxyacetic Acid:
Preferred IUPAC name:
Hydroxyacetic acid
Other names:
Hydroacetic acid
2-Hydroxyethanoic acid
