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Glycolic acid (hydroxyacetic acid) is the smallest alpha-hydroxy acid (AHA).
Glycolic acid (hydroxyacetic acid) is mainly supplemented to various skin-care products to improve the skin’s appearance and texture.
Glycolic acid (hydroxyacetic acid) can also reduce wrinkles, acne scarring, and hyperpigmentation.
CAS: 79-14-1
MF: C2H4O3
MW: 76.05
EINECS: 201-180-5
Synonyms
Acetic acid, 2-hydroxy-;AKOS BBS-00004277;2-HYDROXYACETIC ACID;GLYCOLIC ACID, HIGH PURITY, 70 WT.% SOLU TION IN WATER;GLYCOLIC ACID REAGENTPLUS(TM) 99%;GLYCOLIC ACID SOLUTION, ~55% IN WATER;GLYCOLIC ACID, TECH., 70 WT. % SOLUTION IN WATER;GLYCOLIC ACID SIGMAULTRA
In textile industry, Glycolic acid (hydroxyacetic acid) can be used as a dyeing and tanning agent.
Glycolic acid (hydroxyacetic acid) can also be used as a flavoring agent in food processing, and as a skin care agent in the pharmaceutical industry.
Glycolic acid (hydroxyacetic acid) can also be added into emulsion polymers, solvents and ink additives to improve flow properties and impart gloss.
Moreover, Glycolic acid (hydroxyacetic acid) is a useful intermediate for organic synthesis including oxidative-reduction, esterification and long chain polymerization.
A 2-hydroxy monocarboxylic acid that is acetic acid where the methyl group has been hydroxylated.
Glycolic acid (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.
Glycolic acid (or hydroxyacetic acid; chemical formula HOCH2CO2H) is a colorless, odorless and hygroscopic crystalline solid that is highly soluble in water.
Glycolic acid (hydroxyacetic acid) is used in various skin-care products. Glycolic acid is widespread in nature.
A glycolate (sometimes spelled "glycollate") is a salt or ester of glycolic acid.
Glycolic acid (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, glycolic acid is often used in skin care products, most often as a chemical peel.
Glycolic acid (hydroxyacetic acid) may reduce wrinkles, acne scarring, and hyperpigmentation and improve many other skin conditions, including actinic keratosis, hyperkeratosis, and seborrheic keratosis.
Once applied, Glycolic acid (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.
Glycolic acid (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.
Glycolic acid (hydroxyacetic acid) delivers a formaldehyde free glycolic acid in a 70% solution (GlyAcid® 70 HP) and 99% crystalline (GlyAcid® 99 HP).
Glycolic acid (hydroxyacetic acid), also known as hydroxyacetic acid (HAA), is a chemical compound used as an exfoliative agent and moisturizer.
When applied alone to the skin, Glycolic acid (hydroxyacetic acid) can cause an irritant effect.
History
The name "Glycolic acid (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 "glycolic acid" (acide glycolique).
Glycolic acid (hydroxyacetic acid) was first prepared in 1851 by German chemist Adolph Strecker and Russian chemist Nikolai Nikolaevich Sokolov.
They produced it by treating hippuric acid with nitric acid and nitrogen dioxide[contradictory] to form an ester of benzoic acid and glycolic acid (C6H5C(=O)OCH2COOH), which they called "benzoglycolic acid" (Benzoglykolsäure; also benzoyl glycolic acid).
They boiled the ester for days with dilute sulfuric acid, thereby obtaining benzoic acid and glycolic acid (Glykolsäure).
Glycolic acid (hydroxyacetic acid) Chemical Properties
Melting point: 75-80 °C (lit.)
Boiling point: 112 °C
Density: 1.25 g/mL at 25 °C
Bulk density: 600kg/m3
Vapor pressure: 10.8 hPa (80 °C)
Refractive index: n20/D 1.424
Fp: 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
Water Solubility: SOLUBLE
Sensitive: Hygroscopic
Merck: 14,4498
BRN1: 209322
Stability: Stable. Incompatible with bases, oxidizing agents and reducing agents.
InChIKey: AEMRFAOFKBGASW-UHFFFAOYSA-N
LogP: -1.07 at 20℃
CAS DataBase Reference: 79-14-1(CAS DataBase Reference)
NIST Chemistry Reference: Acetic acid, hydroxy-(79-14-1)
EPA Substance Registry System: Glycolic acid (hydroxyacetic acid) (79-14-1)
Glycolic acid (hydroxyacetic acid) ,CH20HCOOH, also known as hydroxyacetic acid, is composed of colorless deliquescent leaflets that decompose at approximately 78° C (172 OF).
Glycolic acid (hydroxyacetic acid) is soluble in water,alcohol,and ether.
Glycolic acid is used in dyeing, tanning, electropolishing,and in foodstuffs.
Glycolic acid (hydroxyacetic acid) is produced by oxidizing glycol with dilute nitric acid.
Glycolic 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 its proton.
Uses
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.
Glycolic 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.
Glycolic acid (hydroxyacetic acid) acts by dissolving the internal cellular cement responsible for abnormal keratinization, facilitating the sloughing of dead skin cells.
Glycolic acid (hydroxyacetic acid) also improves skin hydration by enhancing moisture uptake as well as increasing the skin’s ability to bind water.
This occurs in the cellular cement through an activation of Glycolic acid (hydroxyacetic acid) and the skin’s own hyaluronic acid content.
Glycolic acid (hydroxyacetic acid) is known to retain an impressive amount of moisture and this capacity is enhanced by glycolic acid.
As a result, the skin’s own ability to raise its moisture content is increased.
Glycolic acid (hydroxyacetic acid) is the simplest alpha hydroxyacid (AHA).
Glycolic acid (hydroxyacetic acid) is also the AHA that scientists and formulators believe has greater penetration potential largely due to its smaller molecular weight.
Glycolic acid (hydroxyacetic acid) is mildly irritating to the skin and mucous membranes if the formulation contains a high glycolic acid concentration and/ or a low pH.
Glycolic acid (hydroxyacetic acid) proves beneficial for acne-prone skin as it helps keep pores clear of excess keratinocytes.
Glycolic acid (hydroxyacetic acid) is also used for diminishing the signs of age spots, as well as actinic keratosis.
However, Glycolic acid (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.
Regardless of the G skin type, Glycolic acid (hydroxyacetic acid) use is associated with softer, smoother, healthier, and younger looking skin.
Glycolic acid (hydroxyacetic acid) is naturally found in sugarcane but synthetic versions are most often used in cosmetic formulations.
Glycolic acid is used in the textile industry as a dyeing and tanning agent.
Organic synthesis
Glycolic acid (hydroxyacetic acid) is a useful intermediate for organic synthesis, in a range of reactions including: oxidation-reduction, esterification and long chain polymerization.
Glycolic acid (hydroxyacetic acid) is used as a monomer in the preparation of polyglycolic acid and other biocompatible copolymers (e.g. PLGA). Commercially, important derivatives include the methyl (CAS# 96-35-5) 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 Glycolic acid (hydroxyacetic acid) is nonvolatile and has good dissolving properties.
Glycolic acid (hydroxyacetic acid)is the cyclic dimer, a bislactone, which is used in some of the polymerization processes.
Preparation
There are different preparation methods to synthesize glycolic acid.
However, the most common method is the catalyzed reaction of formaldehyde with synthesis gas, which costs less.
Glycolic acid (hydroxyacetic acid) can be prepared when chloroacetic acid reacts with sodium hydroxide and undergoes re-acidification.
Electrolytic reduction of oxalic acid also could synthesize this compound.
Glycolic acid (hydroxyacetic acid) can be separated from natural sources like sugarcane, sugar beets, pineapple, cantaloupe, and unripe grapes.
Glycolic acid (hydroxyacetic acid) can be prepared by hydrolyzing the cyanohydrin that is derived from formaldehyde.
Preparation
Glycolic 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 its low cost.
Glycolic acid (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 glycolic acids are formic acid-free.
Glycolic acid (hydroxyacetic acid) can be isolated from natural sources, such as sugarcane, sugar beets, pineapple, cantaloupe and unripe grapes.
Glycolic acid (hydroxyacetic acid) can also be prepared using an enzymatic biochemical process that may require less energy.
Side effects
Common side effects of Glycolic acid (hydroxyacetic acid) include dry skin, erythema (skin redness), burning sensation, itching, skin irritation, and skin rash.
Glycolic acid (hydroxyacetic acid) can make the skin more sensitive in the sunlight, hence always use sunscreen and protective clothing before you step outdoors.
