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Revision as of 12:36, 15 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 475944556 of page Glycolic_acid for the Chem/Drugbox validation project (updated: '').  Latest revision as of 18:14, 19 May 2024 edit DMacks (talk | contribs)Edit filter managers, Autopatrolled, Administrators186,166 edits poorer writing Undid revision 1224660000 by Ikloblow notchis (talk)Tag: Undo 
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{chembox {{chembox
| Verifiedfields = changed
| verifiedrevid = 443846805
| Watchedfields = changed
| Name = Glycolic acid
| verifiedrevid = 476995142
| ImageFileL1 = glycolic acid.svg
| Name = Glycolic acid
| ImageSizeL1 = 120px
| ImageNameL1 = Chemical structure of glycolic acid | ImageFileL1 = glycolic acid.svg
| ImageNameL1 = Chemical structure of glycolic acid
| ImageFileR1 = Glycolic acid3d.png | ImageFileR1 = Glycolic acid3d.png
| ImageNameR1 = Ball-and-stick model of glycolic acid
| ImageSizeR1 = 140px
| ImageFile2 = Glycolic Acid.jpg
| ImageNameR1 = Ball-and-stick model of glycolic acid
| IUPACName = 2-Hydroxyethanoic acid | ImageName2 = Glycolic acid
| OtherNames = Dicarbonous acid<br /> | PIN = Hydroxyacetic acid
glycolic acid,<br />hydroxyacetic acid | OtherNames = Hydroacetic acid<br />2-Hydroxyethanoic acid
| SystematicName =
| Section1 = {{Chembox Identifiers | Section1 = {{Chembox Identifiers
| CASNo = 79-14-1
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| CASNo_Ref = {{cascite|correct|CAS}}
| DrugBank = DB03085
| ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 17497 | ChEBI = 17497
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| SMILES = C(C(=O)O)O
| ChEMBL = 252557
| UNII_Ref = {{fdacite|correct|FDA}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 737
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB03085
| EC_number = 201-180-5
| SMILES = OC(=O)CO
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 0WT12SX38S | UNII = 0WT12SX38S
| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C03547 | KEGG = C00160
| InChI = 1/C2H4O3/c3-1-2(4)5/h3H,1H2,(H,4,5) | InChI = 1/C2H4O3/c3-1-2(4)5/h3H,1H2,(H,4,5)
| InChIKey = AEMRFAOFKBGASW-UHFFFAOYAR | InChIKey = AEMRFAOFKBGASW-UHFFFAOYAR
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 252557
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C2H4O3/c3-1-2(4)5/h3H,1H2,(H,4,5) | StdInChI = 1S/C2H4O3/c3-1-2(4)5/h3H,1H2,(H,4,5)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = AEMRFAOFKBGASW-UHFFFAOYSA-N | StdInChIKey = AEMRFAOFKBGASW-UHFFFAOYSA-N
| CASNo = 79-14-1 | PubChem = 757
| RTECS = MC5250000
| CASNo_Ref = {{cascite|correct|CAS}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 737
| RTECS = MC5250000
}} }}
| Section2 = {{Chembox Properties | Section2 = {{Chembox Properties
| Formula = C<sub>2</sub>H<sub>4</sub>O<sub>3</sub> | Formula = {{chem2|C2H4O3}}
| MolarMass = 76.05 g/mol | MolarMass = 76.05 g/mol
| Appearance = white, powdery solid | Appearance = White powder or colorless crystals
| Density = 1.49 g/cm<sup>3</sup><ref name=HSDB>United States National Library of Medicine "Hydroxyacetic Acid" in TOXNET Hazardous Substances Data Bank (HSDB), citing Gerhartz, W. (exec ed.), Ullmann's Encyclopedia of Industrial Chemistry. 5th ed.Vol A1: Deerfield Beach, FL: VCH Publishers, 1985 to Present., p. VA13 509.</ref>
| Density = 1.27 g/cm<sup>3</sup>
| Solubility = 70% solution | Solubility = 70% solution
| Solvent = other solvents | Solvent = other solvents
| SolubleOther = ]s, ],<br /> ] and<br />]<ref name="dupont">{{cite web | title=DuPont Glycolic Acid Technical Information | url=http://www.dupont.com/glycolicacid/applications/index.html | accessdate=2006-07-06}}</ref> | SolubleOther = ]s, ],<br /> ] and<br />]<ref name="dupont">{{cite web | title=DuPont Glycolic Acid Technical Information | url=http://www.dupont.com/glycolicacid/applications/index.html | access-date=2006-07-06 | archive-url=https://web.archive.org/web/20060714181421/http://www.dupont.com/glycolicacid/applications/index.html | archive-date=2006-07-14 | url-status=dead }}</ref>
| MeltingPt = 75 °C | MeltingPtC = 75
| BoilingPtC = 100
| BoilingPt = decomposes
| BoilingPt_notes = Decomposes above 100 °C
| pKa = 3.83
| Viscosity = | pKa = 3.83
| Viscosity =
| VaporPressure = 1.051 kPa (80&nbsp;°C)
| LogP = −1.05<ref name="chemsrc">{{Cite web|url=https://www.chemsrc.com/en/cas/79-14-1_509829.html|title=Glycolic acid|website=www.chemsrc.com|access-date=2018-05-16|archive-date=2020-07-27|archive-url=https://web.archive.org/web/20200727162847/https://www.chemsrc.com/en/cas/79-14-1_509829.html|url-status=live}}</ref>
}} }}
| Section3 = {{Chembox Structure | Section3 = {{Chembox Structure
| CrystalStruct = | CrystalStruct =
| Dipole = | Dipole =
}} }}
| Section4 =
| Section5 =
| Section6 =
| Section7 = {{Chembox Hazards | Section7 = {{Chembox Hazards
| ExternalMSDS = | ExternalSDS =
| MainHazards = Corrosive ('''C''') | MainHazards = Corrosive
| NFPA-H = 3 | NFPA-H = 3
| NFPA-F = 1 | NFPA-F = 1
| NFPA-R = | NFPA-R = 1
| FlashPtC = 300
| FlashPt = 129 °C<ref name="Akron">{{cite web | title=Glycolic Acid MSDS | url=http://ull.chemistry.uakron.edu/erd/chemicals/7/6540.html | publisher = University of Akron | accessdate=2006-09-18}}</ref>
| FlashPt_ref = <ref name="Akron">{{cite web | title=Glycolic Acid MSDS | url=http://ull.chemistry.uakron.edu/erd/chemicals/7/6540.html | publisher=University of Akron | access-date=2006-09-18 }}{{dead link|date=October 2017 |bot=InternetArchiveBot |fix-attempted=yes }}</ref>
| RPhrases = {{R22}}-{{R34}}
| SPhrases = {{S26}}-{{S36/37/39}}-{{S45}} | GHSPictograms = {{GHS05}}{{GHS07}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|302|314|332}}
| PPhrases = {{P-phrases|260|261|264|270|271|280|301+312|301+330+331|303+361+353|304+312|304+340|305+351+338|310|312|321|330|363|405|501}}
| LD50 = 1950 mg/kg (rat, oral)<br>2040 mg/kg (rat, oral)
| LC50 = 7.7 ppm (rat, 4h)<br>3.6 ppm (rat, 4h)
}} }}
| Section8 = {{Chembox Related | Section8 = {{Chembox Related
| Function = ]s | OtherFunction_label = ]s
| OtherFunctn = ] | OtherFunction = ]
| OtherCpds = ],<br />] | OtherCompounds = ]<br />]<br />]
}} }}
}} }}

'''Glycolic acid''' (or '''hydroxyacetic acid'''; chemical formula {{chem2|HOCH2CO2H}}) is a colorless, odorless and ] ], highly ] in water. It is used in various ] products. Glycolic acid is widespread in nature. A '''glycolate''' (sometimes spelled "glycollate") is a ] or ] of glycolic acid.

== History ==
The name "glycolic acid" was coined in 1848 by French chemist ] (1807–1853). He proposed that the ] ]—which was then called ''glycocolle''—might be the ] of a hypothetical acid, which he called "glycolic acid" (''acide glycolique'').<ref>Laurent, Auguste (1848). {{Webarchive|url=https://web.archive.org/web/20200727162914/https://babel.hathitrust.org/cgi/pt?id=hvd.hx3dy2&view=1up&seq=114 |date=2020-07-27 }} ("On aminated acids and the sugar of gelatine "), ''Annales de Chimie et de Physique'', 3rd series, '''23''': 110–123. From p. 112: "''Appelons ce dernier ''acide glycolique'' ... ''" ("Let us call the latter 'glycolic acid' ...")</ref>

Glycolic acid was first prepared in 1851 by German chemist ] (1822–1871) and Russian chemist Nikolai Nikolaevich Sokolov (1826–1877). They produced it by treating ] with ] and ] to form an ] of ] and glycolic acid ({{chem2|C6H5C(\dO)OCH2COOH}}), which they called "benzoglycolic acid" (''Benzoglykolsäure''; also benzoyl glycolic acid). They boiled the ester for days with dilute ], thereby obtaining benzoic acid and glycolic acid (''Glykolsäure'').<ref>Socoloff, Nicolaus and Strecker, Adolph (1851) {{Webarchive|url=https://web.archive.org/web/20200727162846/https://babel.hathitrust.org/cgi/pt?id=njp.32101044011185&view=1up&seq=409 |date=2020-07-27 }} ("Investigation of some products that arise from hippuric acid"), ''Annalen der Chemie und Pharmacie'', '''80''': 17–43. For their production of glycolic acid, see pp. 34–37. Note: Strecker and Sokolov's empirical formula for glycolic acid (viz, {{chem2|C4H4O6}}) was incorrect, because like many chemists at that time, they used the wrong atomic masses for carbon (6 instead of 12) and for oxygen (8 instead of 16).</ref><ref>(Socoloff and Strecker, 1851), p. 37. In recognition of Laurent's correct surmise, Strecker and Sokolov named glycolic acid: ''"Die in dem Barytsalz enthaltene Säure {{chem2|C4H3O5}} oder als Säurehydrat gedacht {{chem2|C4H4O6}} kommt mit der Säure überein, als deren Amidverbindung man das Glycocoll betrachten kann, und welche daher von Laurent den Namen ''Glycolsäure'' erhalten hat."'' (The acid {{chem2|C4H3O5}} contained in the barium salt — or considered as the acid hydrate {{chem2|C4H4O6}} — is consistent with the acid whose amide can be regarded as glycocoll and which therefore obtained from Laurent the name "glycolic acid".)</ref>

== Preparation ==
Glycolic acid can be synthesized in various ways. The predominant approaches use a catalyzed reaction of ] with ] (] of formaldehyde), for its low cost.<ref name="carbonylation">D.J. Loder, {{US Patent| 2152852}} (1939).</ref>

It is also prepared by the reaction of ] with ] followed by re-acidification.

Other methods, not noticeably in use, include ] of ], and ] of the ] derived from ].<ref name=Ullmann/> Some of today's glycolic acids are ]-free. Glycolic acid can be isolated from natural sources, such as ], ]s, ], ] and unripe ]s.<ref>{{Cite web|url=http://www.3dchem.com/glycolic-acid.asp|title=Glycolic acid, What is Glycolic acid? About its Science, Chemistry and Structure|website=www.3dchem.com|language=en|access-date=2018-04-11|archive-date=2018-04-12|archive-url=https://web.archive.org/web/20180412001217/http://www.3dchem.com/glycolic-acid.asp|url-status=live}}</ref>

Glycolic acid can also be prepared using an enzymatic biochemical process that may require less energy.<ref>{{Cite web|url=http://thaipolychemicals.weebly.com/glycolic-acid.html|title=Glycolic acid|website=thaipolychemicals.weebly.com|access-date=2017-05-02|archive-date=2017-08-25|archive-url=https://web.archive.org/web/20170825204815/http://thaipolychemicals.weebly.com/glycolic-acid.html|url-status=live}}</ref>

==Properties==
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 Pb<sup>2+</sup> and Cu<sup>2+</sup> 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.<ref>{{cite book|last1=Sigel |first1=Astrid| last2=Operschall| first2=Bert P.|last3=Sigel |first3=Helmut
|chapter= Chapter 11. Complex Formation of Lead(II) with Nucleotides and Their Constituents|pages= 319–402
|publisher= de Gruyter|date= 2017|series= Metal Ions in Life Sciences|volume=17|title=Lead: Its Effects on Environment and Health|editor1-last=Astrid|editor1-first= S.|editor2-last=Helmut|editor2-first=S.|editor3-last=Sigel |editor3-first= R. K. O.|doi=10.1515/9783110434330-011|pmid=28731304}}</ref>

==Applications==
Glycolic acid is used in the textile industry as a ] and ] agent.<ref>{{Cite web |url=http://www2.dupont.com/Glycolic_Acid/en_US/uses_apps/industrial/ind_pgs/leather_tanning.html |title=DuPont Glycolic Acid Leather Dyeing & Tanning Applications |access-date=2013-04-11 |archive-date=2013-05-22 |archive-url=https://web.archive.org/web/20130522024848/http://www2.dupont.com/Glycolic_Acid/en_US/uses_apps/industrial/ind_pgs/leather_tanning.html |url-status=dead }}</ref>

=== Organic synthesis ===
Glycolic acid is a useful intermediate for organic synthesis, in a range of reactions including: ]-], ] and long chain ]. It is used as a ] in the preparation of ] and other ] ]s (e.g. ]). Commercially, important derivatives include the methyl (CAS# 96-35-5) and ethyl (CAS# 623-50-7) esters which are readily distillable (boiling points 147–149&nbsp;°C and 158–159&nbsp;°C, respectively), unlike the parent acid. The butyl ester (b.p.&nbsp;178–186&nbsp;°C) is a component of some ]es, being desirable because it is nonvolatile and has good dissolving properties.<ref name="Ullmann">{{Ullmann|author=Karlheinz Miltenberger|title=Hydroxycarboxylic Acids, Aliphatic|year=2005|doi=10.1002/14356007.a13_507}}</ref>

== Occurrence ==
Plants produce glycolic acid during ]. It is recycled by conversion to glycine within the peroxisomes and to ] within the chloroplasts.<ref>{{Cite web |first1=T. |last1=Kisaki |first2=N. E. |last2=Tolbert |title=Glycolate and glyoxylate metabolism by isolated peroxisomes or chloroplasts |url=https://academic.oup.com/plphys/article/44/2/242-250/6093788 |access-date=2023-08-24 |journal=Plant Physiology |volume=44 |issue=2 |pages= 242–250 |doi=10.1104/pp.44.2.242 |pmc=396069 |pmid=16657053}}</ref>

Because photorespiration is a wasteful side reaction in regard to ], much effort has been devoted to suppressing its formation. One process converts glycolate into ] without using the conventional BASS6 and PLGG1 route; see ].<ref>{{Cite news|url=http://www.zmescience.com/science/plant-respiration-carbon-dioxide-03042017|title=New protein can increase yields, save farmers millions every year|last=Gerea|first=Alexandra|date=2017-04-03|work=ZME Science|access-date=2017-04-06|language=en-US|archive-date=2017-04-07|archive-url=https://web.archive.org/web/20170407055659/http://www.zmescience.com/science/plant-respiration-carbon-dioxide-03042017/|url-status=live}}</ref><ref>{{Cite journal|last1=South|first1=Paul F.|last2=Walker|first2=Berkley J.|last3=Cavanagh|first3=Amanda P.|last4=Rolland|first4=Vivien|last5=Badger|first5=Murray|last6=Ort|first6=Donald R.|date=2017-03-28|title=Bile Acid Sodium Symporter BASS6 Can Transport Glycolate and Is Involved in Photorespiratory Metabolism in Arabidopsis thaliana|journal=The Plant Cell|language=en|pages=808–823|doi=10.1105/tpc.16.00775|issn=1532-298X|pmid=28351992|volume=29|issue=4|pmc=5435425}}</ref>

==Safety==
Glycolic acid is an irritant to the skin.<ref name="NIOSH">{{cite web | title=Glycolic Acid MSDS | work=ICSC:NENG1537 International Chemical Safety Cards (WHO/IPCS/ILO) | publisher=CDC/NIOSH | url=https://www.cdc.gov/niosh/ipcsneng/neng1537.html | access-date=2006-06-08 | archive-date=2005-09-21 | archive-url=https://web.archive.org/web/20050921220728/http://www.cdc.gov/niosh/ipcsneng/neng1537.html | url-status=live }}</ref> It occurs in all green plants.<ref name="Ullmann"/>

==References==
{{Reflist}}

==External links==
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{{DEFAULTSORT:Glycolic Acid}}
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