Glycolic acid
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General
Systematic name	2-Hydroxyethanoic acid
Other names	glycolic acid, hydroxyacetic acid
Molecular formula	C2H4O3
SMILES	O=C(O)CO
Molar mass	76.05 g/mol
Appearance	colorless solid
CAS number	[79-14-1]
Properties
Density and phase	1.27 g/cm3
Solubility in water	0.1 g/mL
Other solvents	alcohols, acetone, acetic acid and ethyl acetate[1]
Melting point	75 °C
Boiling point	decomposes
Acidity (pKa)	3.83
Viscosity	? cP at ? °C
Structure
Crystal structure
Dipole moment	? D
Hazards
MSDS	External MSDS
Main hazards	Corrosive (C)
NFPA 704	IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... In physics, Density is defined as mass m per unit volume V. Mathematically, it is expressed as where, in SI units: ρ (rho) is the density of the substance, measured in kg m-3 m is the mass of the substance, measured in kg v is the volume of the substance... In the physical sciences, a phase is a set of states of a macroscopic physical system that have relatively uniform chemical composition and physical properties (i. ... Solubility refers to the ability for a given substance, the solute, to dissolve in a solvent. ... This article describes water from a scientific and technical perspective. ... Functional group of an alcohol molecule. ... In chemistry, acetone (also known as propanone, dimethyl ketone, 2-propanone, propan-2-one and β-ketopropane) is the simplest representative of the ketones. ... Acetic acid, also known as ethanoic acid, is an organic chemical compound best recognized for giving vinegar its sour taste and pungent smell. ... Ethyl acetate is the organic compound with the formula CH3CH2OC(O)CH3. ... The melting point of a crystalline solid is the temperature at which it changes state from solid to liquid. ... The boiling point of a substance is the temperature at which it can change its state from a liquid to a gas throughout the bulk of the liquid at a given pressure. ... In chemistry and biochemistry, the acid dissociation constant, the acidity constant, or the acid-ionization constant (Ka) is a specific type of equilibrium constant that indicates the extent of dissociation of hydronium ions from an acid. ... The related Category:Units of viscosity has been nominated for deletion, merging, or renaming. ... The poise (P; IPA: ) is the unit of dynamic viscosity in the centimetre gram second system of units. ... Enargite crystals In mineralogy and crystallography, a crystal structure is a unique arrangement of atoms in a crystal. ... The Earths magnetic field, which is approximately a dipole. ... The debye (symbol: D) is a non-SI and non-CGS unit of electrical dipole moment. ... An example MSDS in a US format provides guidance for handling a hazardous substance and information on its composition and properties. ... The examples and perspective in this article or section may not represent a worldwide view. ... NFPA 704 is a standard maintained by the U.S. National Fire Protection Association. ... Image File history File links NFPA_704. ... 1 3 0
Flash point	129 °C [2]
R/S statement	R: R22-R34 S: S26-S36/37/39-S45
RTECS number	MC5250000
Supplementary data page
Structure and properties	n, εr, etc.
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
Related compounds
Related α-hydroxy acids	lactic acid
Related compounds	acetic acid, glycerol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Glycolic acid (or hydroxyacetic acid) is the smallest α-hydroxy acid (AHA). It appears in the form of a colorless, odorless and hydroscopic crystalline solid that is highly soluble in water and related solvents. Glycolic acid is associated with sugar-crops and is isolated from sugarcane, sugar beets, pineapple, and unripe grapes. The flash point of a flammable liquid is the lowest temperature at which it can form an ignitable mixture with air. ... Risk and Safety Statements, also known as R/S statements, R/S numbers, R/S phrases, and R/S sentences, is a system of hazard codes and phrases for labeling dangerous chemicals and compounds. ... R-phrases are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous substances and preparations. ... S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. ... RTECS, also known as Registry of Toxic Effects of Chemical Substances, is a database of toxicity information compiled from the open scientific literature that is available for charge. ... The refractive index (or index of refraction) of a material is the factor by which the phase velocity of electromagnetic radiation is slowed in that material, relative to its velocity in a vacuum. ... The dielectric constant εr (represented as or K in some cases) is defined as the ratio: where εs is the static permittivity of the material in question, and ε0 is the vacuum permittivity. ... Ultraviolet-Visible Spectroscopy or Ultraviolet-Visible Spectrophotometry (UV/ VIS) involves the spectroscopy of photons (spectrophotometry). ... IR spectrum of a thin film of liquid ethanol. ... Nuclear Magnetic Resonance Spectroscopy most commonly known as NMR Spectroscopy is the name given to the technique which exploits the magnetic properties of nuclei. ... Basic schematic of a mass spectrometer Mass spectrometry (also known as mass spectroscopy (deprecated)[1] or in common speech mass-spec) is an analytical technique used to measure the mass-to-charge ratio of ions. ... α-Hydroxy Acids (AHAs) are naturally occurring carboxylic acids which are well-known for their use in the cosmetics industry. ... Lactic acid (IUPAC systematic name: 2-hydroxypropanoic acid), also known as milk acid, is a chemical compound that plays a role in several biochemical processes. ... Acetic acid, also known as ethanoic acid, is an organic chemical compound best recognized for giving vinegar its sour taste and pungent smell. ... Glycerol, also well known as glycerin and glycerine, and less commonly as propane-1,2,3-triol, 1,2,3-propanetriol, 1,2,3-trihydroxypropane, glyceritol, and glycyl alcohol is a colorless, odorless, hygroscopic, and sweet-tasting viscous liquid. ... In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals) and 25 degrees Celsius (298. ... α-Hydroxy Acids (AHAs) are naturally occurring carboxylic acids which are well-known for their use in the cosmetics industry. ... Species Saccharum arundinaceum Saccharum bengalense Saccharum edule Saccharum officinarum Saccharum procerum Saccharum ravennae Saccharum robustum Saccharum sinense Saccharum spontaneum Sugarcane or Sugar cane (Saccharum) is a genus of 6 to 37 species (depending on taxonomic interpretation) of tall grasses (family Poaceae, tribe Andropogoneae), native to warm temperate to tropical regions... Two sugar beets - the one on the left has been cultivated to be smoother than the traditional beet, so that it traps less soil. ... Species Vitis acerifolia Vitis aestivalis Vitis amurensis Vitis arizonica Vitis x bourquina Vitis californica Vitis x champinii Vitis cinerea Vitis x doaniana Vitis girdiana Vitis labrusca Vitis x labruscana Vitis lincecumii Vitis monticola Vitis mustangensis Vitis x novae-angliae Vitis palmata Vitis riparia Vitis rotundifolia Vitis rupestris Vitis shuttleworthii Vitis...

Uses

Due to its excellent capability to penetrate skin, glycolic acid finds applications in skin care products, most often as a chemical peel performed by a dermatologist in concentrations of 20%-80% or at-home kits in lower concentrations of 10%. It is used to improve the skin's appearance and texture. It may reduce wrinkles, acne scarring, hyperpigmentation and improve many other skin conditions. Once applied, glycolic 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, healthier, smoother, brighter-looking skin. It has been suggested that this article or section be merged with Epidermis (skin). ...

Glycolic acid is also a useful intermediate for organic synthesis, in a range of reactions including: oxidation-reduction, esterification and long chain polymerization. It is used as a monomer in the preparation of polyglycolic acid and other biocompatible copolymers (e.g. PLGA). Among other uses this compound finds employment in the textile industry as a dyeing and tanning agent, in food processing as a flavoring agent and as a preservative. Glycolic acid is often included into emulsion polymers, solvents and additives for ink and paint in order to improve flow properties and impart gloss. The most fundamental reactions in chemistry are the redox processes. ... Semi-accurate illustration of a redox reaction Redox reactions include all chemical processes in which atoms have their oxidation number (oxidation state) changed. ... Esterification is the general name for a chemical reaction in which two chemicals (typically an alcohol and an acid) form an ester as the reaction product. ... In chemistry, a monomer (from Greek mono one and meros part) is a small molecule that may become chemically bonded to other monomers to form a polymer. ... Polyglycolide or Polyglycolic acid (PGA) is a biodegradable, thermoplastic polymer and the simplest linear, aliphatic polyester. ... Biocompatible is the adjectival form of biocompatibility and is often used to characterise a biomaterial. ... A heteropolymer, also called a copolymer, is a polymer formed when two (or more) different types of monomer are linked in the same polymer chain, as opposed to a homopolymer where only one monomer is used. ... PLGA or poly(lactic-co-glycolic acid) is an FDA approved polymer which is used in a host of therapeutic devices. ... Yarn drying after being dyed in the early American tradition, at Conner Prairie living history museum. ... Tanning is the process of conversion of putrescible skin into non putrescible leather. ... Flavor or flavour (see spelling differences) is the sensory impression of a food or other substance, and is determined mainly by the chemical senses of taste and smell. ...

Preparation

Glycolic acid is isolated from natural sources and is inexpensively available. It can be prepared by the reaction of chloroacetic acid with sodium hydroxide followed by re-acidification. Monochloroacetic acid, CClH2COOH, (chloroacetic acid, chloracetic acid, chloroethanoic acid or monochloroethanoic acid) is a carboxylic acid which is formed by chlorinating acetic acid. ... Sodium hydroxide (NaOH), also known as lye or caustic soda, is a caustic metallic base. ...

Safety

Glycolic acid is a mild irritant.^[3]

References

1. ^ DuPont Glycolic Acid Technical Information. Retrieved on 2006-07-06.
2. ^ Glycolic Acid MSDS. University of Akron. Retrieved on 2006-09-18.
3. ^ Glycolic Acid MSDS. ICSC:NENG1537 International Chemical Safety Cards (WHO/IPCS/ILO). Retrieved on 2006-06-08.

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External links

• DuPont Glycolic Acid
• Computational Chemistry Wiki
• Links to external chemical sources