- Glycolic acid
Name = Glycolic acid
ImageFileL1 = glycolic acid.svg
ImageSizeL1 = 120px
ImageNameL1 = Chemical structure of glycolic acid
ImageFileR1 = Glycolic acid3d.png
ImageSizeR1 = 140px
ImageNameR1 = Ball-and-stick model of glycolic acid
IUPACName = 2-Hydroxyethanoic acid
OtherNames = glycolic acid,
Section1 = Chembox Identifiers
SMILES = O=C(O)CO
CASNo = 79-14-1
ChemSpiderID = 737
RTECS = MC5250000
Section2 = Chembox Properties
Formula = C2H4O3
MolarMass = 76.05 g/mol
Appearance = colorless solid
Density = 1.27 g/cm3
Solubility = 0.1 g/mL
Solvent = other solvents
acetic acidand ethyl acetatecite web | title=DuPont Glycolic Acid Technical Information | url=http://www.dupont.com/glycolicacid/applications/index.html | accessdate=2006-07-06]
MeltingPt = 75 °C
BoilingPt = decomposes
pKa = 3.83
Section3 = Chembox Structure
Section7 = Chembox Hazards
MainHazards = Corrosive (C)
NFPA-H = 3
NFPA-F = 1
FlashPt = 129 °Ccite web | title=Glycolic Acid MSDS | url=http://ull.chemistry.uakron.edu/erd/chemicals/7/6540.html | publisher = University of Akron | accessdate=2006-09-18]
RPhrases = R22-R34
SPhrases = S26-S36/37/39-S45
Section8 = Chembox Related
Function = α-hydroxy acids
acetic acid, glycerol
Glycolic acid (or hydroxyacetic acid) is the smallest α-hydroxy acid (AHA). It appears in the form of a colorless, odorless and
hygroscopiccrystalline solid that is highly solublein waterand related solvents. Glycolic acid is associated with sugar-crops and is isolated from sugarcane, sugar beets, pineapple, canteloupe, and unripe grapes.
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 dermatologistin 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 skin.
Glycolic acid is also a useful intermediate for organic synthesis, in a range of reactions including:
oxidation-reduction, esterificationand long chain polymerization. It is used as a monomerin the preparation of polyglycolic acid and other biocompatiblecopolymers (e.g. PLGA). Among other uses this compound finds employment in the textile industry as a dyeing and tanningagent, 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.
Glycolic acid is isolated from natural sources and is inexpensively available. It can be prepared by the reaction of
chloroacetic acidwith sodium hydroxidefollowed by re-acidification.
Glycolic acid can also be prepared using an enzymatic biochemical process which produces fewer impurities compared to traditional chemical synthesis, requires less energy in production and produces less co-product. [ [http://www.crosschem.net/crystalline.php GlyAcid EBP Crystalline] at CrossChem.net] This process is used by the specialty chemical company CrossChem.
Glycolic acid is a strong irritant.cite web | title=Glycolic Acid MSDS | work=ICSC:NENG1537 International Chemical Safety Cards (WHO/IPCS/ILO) | CDC/NIOSH | url=http://www.cdc.gov/niosh/ipcsneng/neng1537.html | accessdate=2006-06-08] Like
ethylene glycol, it is metabolized to oxalic acid, which makes it dangerous if ingested.
* [http://www.dupont.com/glycolicacid/ DuPont Glycolic Acid]
* [http://www.crosschem.net/glycolic_acid.php CrossChem GlyAcid EBP (glycolic acid)]
* [http://www.glycolic.org/ Glycolic.org Glycolic Acid]
* [http://www.compchemwiki.org/index.php?title=Glycolic_acid Computational Chemistry Wiki]
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