Glycolic acid


Glycolic acid

Chembox new
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,
hydroxyacetic 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
SolubleOther = alcohols, acetone,
acetic acid and
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
Viscosity =

Section3 = Chembox Structure
CrystalStruct =
Dipole =

Section7 = Chembox Hazards
ExternalMSDS =
MainHazards = Corrosive (C)
NFPA-H = 3
NFPA-F = 1
NFPA-R =
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
OtherFunctn = lactic acid
OtherCpds = 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 hygroscopic 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, canteloupe, and unripe grapes.

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 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.

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.

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.

afety

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.

References

External links

* [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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Look at other dictionaries:

  • Glycolic acid — Glycolic Gly*col ic, a. (Chem.) Pertaining to, or derived from, glycol; as, glycolic ether; glycolic acid. [1913 Webster] {Glycolic acid} (Chem.), an organic acid, found naturally in unripe grapes and in the leaves of the wild grape ({Ampelopsis… …   The Collaborative International Dictionary of English

  • glycolic acid — [glī käl′ik] n. a crystalline acid, CH2OHCOOH, found in sugar cane or prepared by the oxidation of glycol …   English World dictionary

  • glycolic acid — An intermediate in the interconversion of glycine and ethanolamine. SYN: hydroxyacetic acid. * * * glycolic acid also glycollic acid n an alpha hydroxy acid C2H4O3 that is oxidized to glyoxylic acid in photosynthesis, is used as an agent to… …   Medical dictionary

  • glycolic acid — glikolio rūgštis statusas T sritis chemija formulė HOCH₂COOH atitikmenys: angl. glycolic acid rus. гликолевая кислота ryšiai: sinonimas – hidroksietano rūgštis …   Chemijos terminų aiškinamasis žodynas

  • glycolic acid — noun a translucent crystalline compound found in sugar cane and sugar beets and unripe grapes • Syn: ↑glycollic acid, ↑hydroxyacetic acid • Hypernyms: ↑acid …   Useful english dictionary

  • glycolic acid — or glycollic acid noun Etymology: International Scientific Vocabulary glycol + 1 ic Date: 1852 an alpha hydroxy acid C2H4O3 found especially in unripe grapes and sugar beets and used especially in textile and leather processing and in skin care… …   New Collegiate Dictionary

  • glycolic acid — a colorless, crystalline, water soluble powder, C2H4O3, that is a major substrate for photorespiration in plants: used chiefly for textile printing and dyeing and in pesticides. Also, glycollic acid. Also called hydroxyacetic acid. [1850 55] * *… …   Universalium

  • glycolic acid — noun the simplest alpha hydroxy acid, hydroxy acetic acid, found in sugar cane and unripe grapes; used in cosmetics etc See Also: glycolate …   Wiktionary

  • glycolic acid — Hydroxyacetic acid; found in young plants and green fruits. Glycolate is formed from ribulose 1,5 bisphosphate in a seemingly wasteful side reaction of photosynthesis, known as photorespiration …   Dictionary of molecular biology

  • glycolic acid — fruit acid (colorless crystalline compound found in unripe grapes, sugar cane and sugar beet) used in pharmaceuticals (such as topical exfoliation of skin cells) and pesticides …   English contemporary dictionary