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Revision as of 13:50, 15 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 475944501 of page Mandelic_acid for the Chem/Drugbox validation project (updated: '').  Latest revision as of 21:39, 14 November 2024 edit Dough34 (talk | contribs)Extended confirmed users10,249 editsm →Isolation, synthesis, occurrence: remove space, remove duplicate linksTag: Visual edit 
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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
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 411000992 | verifiedrevid = 477003904
| Reference=<ref>'']'', 11th Edition, '''5599'''.</ref> | Reference=<ref>'']'', 11th Edition, '''5599'''.</ref>
| Name = Mandelic acid | Name = Mandelic acid
| ImageFile = kwas_migdałowy.svg | ImageFileL1 = kwas_migdałowy.svg
| ImageSize = 120px | ImageSizeL1 = 120px
| ImageAltL1 = Structural formula of mandelic acid
| ImageName =
| ImageFileR1 = (R)-Mandelic acid molecule ball.png
| IUPACName = 2-Hydroxy-2-phenylacetic acid
| ImageSizeR1 = 120
⚫ | OtherNames = Mandelic acid<br />Phenylglycolic acid
| ImageAltR1 = Ball-and-stick model of the mandelic acid molecule
⚫ | Section1 = {{Chembox Identifiers
| ImageFile2 = Mandlová kyselina.jpg
⚫ | PubChem = 1292
| PIN = Hydroxy(phenyl)acetic acid <!-- The locant '2' for acetic acid is not cited, see rules P-14.3.4.3 and P-14.3.4.6. -->
⚫ | OtherNames = 2-Hydroxy-2-phenylacetic acid<br />Mandelic acid<br />Phenylglycolic acid<br />α-Hydroxyphenylacetic acid
⚫ |Section1={{Chembox Identifiers
⚫ | PubChem = 1292
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = NH496X0UJX | UNII = NH496X0UJX
| UNII1_Ref = {{fdacite|correct|FDA}}
| UNII1 = PPL7YW1M9W
| UNII1_Comment = (''R'')
| UNII2_Ref = {{fdacite|correct|FDA}}
| UNII2 = L0UMW58G3T
| UNII2_Comment = (''S'')

| InChI = 1/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11) | InChI = 1/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)
| InChIKey = IWYDHOAUDWTVEP-UHFFFAOYAD | InChIKey = IWYDHOAUDWTVEP-UHFFFAOYAD
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| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 90-64-2 | CASNo = 90-64-2
| CASNo1_Ref = {{cascite|correct|CAS}}
| CASNo1 = 611-71-2 | CASNo1 = 611-71-2
| CASNo1_Comment = (''R'') | CASNo1_Comment = (''R'')
| CASNo2_Ref = {{cascite|correct|CAS}}
| CASNo2 = 17199-29-0 | CASNo2 = 17199-29-0
| CASNo2_Comment = (''S'') | CASNo2_Comment = (''S'')
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 1253 | ChemSpiderID = 1253
| ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 35825 | ChEBI = 35825
| SMILES = O=C(O)C(O)c1ccccc1 | SMILES = O=C(O)C(O)c1ccccc1
| EINECS = 202-007-6
| RTECS = OO6300000
⚫ }}
|Section2={{Chembox Properties
⚫ | C=8 | H=8 | O=3
⚫ | Appearance = White crystalline powder
⚫ | Density = 1.30 g/cm<sup>3</sup>
| MeltingPtC = 119
| MeltingPt_notes = optically pure: {{convert|132|to|135|C|F K}}
⚫ | BoilingPtC = 321.8
⚫ | Solubility = 15.87 g/100 mL
| SolubleOther = soluble in ], ], ]
⚫ | pKa = 3.41<ref>Bjerrum, J., et al. ''Stability Constants'', Chemical Society, London, 1958.</ref>
| RefractIndex = 1.5204
}}
|Section5={{Chembox Thermochemistry
| DeltaHf = 0.1761 kJ/g
}}
|Section6={{Chembox Pharmacology
| ATCCode_prefix = B05 | ATCCode_prefix = B05
| ATCCode_suffix = CA06 | ATCCode_suffix = CA06
| ATC_Supplemental = {{ATC|J01|XX06}} | ATC_Supplemental = {{ATC|J01|XX06}}
}} }}
| Section2 = {{Chembox Properties |Section7={{Chembox Hazards
| FlashPtC = 162.6
⚫ | C=8|H=8|O=3
⚫ | Appearance = White crystalline powder
⚫ | Density = 1.30 g/cm<sup>3</sup>
| MeltingPt = 119 °C (optically pure: 132 – 135 °C)
⚫ | BoilingPtC =
⚫ | Solubility = 15.87 g per 100 mL
⚫ | pKa = 3.41<ref>Bjerrum, J., et al. ''Stability Constants'', Chemical Society, London, 1958.</ref>
⚫ }}
| Section3 = {{Chembox Hazards
| FlashPt = {{convert|162.6|C|F}}
}} }}
| Section8 = {{Chembox Related |Section8={{Chembox Related
| OtherAnions = | OtherAnions =
| OtherCations = | OtherCations =
| OtherFunctn = | OtherFunction =
| OtherFunction_label =
| Function =
| OtherCpds = ], ], ]}} | OtherCompounds = ], ], ]}}
}} }}

'''Mandelic acid''' is an ] ] with the molecular formula C<sub>6</sub>H<sub>5</sub>CH(OH)CO<sub>2</sub>H. It is a white crystalline solid that is soluble in water and polar organic ]s. It is a useful precursor to various drugs. The molecule is ]. The ] mixture is known as ''paramandelic acid''.

==Isolation, synthesis, occurrence==
Mandelic acid was discovered in 1831 by the German pharmacist Ferdinand Ludwig Winckler (1801–1868) while heating ], an extract of ]s, with diluted ]. The name is derived from the ] "Mandel" for "almond".<ref>See:
* Winckler, F. L. (1831) (On the decomposition of calomel by bitter almond water, and some contributions to a more precise knowledge of the chemical composition of bitter almond water), ''Repertorium für die Pharmacie'', '''37''' : 388–418; mandelic acid is named on p. 415.
* Winckler, F. L. (1831) , ''Repertorium für die Pharmacie'', '''38''' : 169–196. On p. 193, Winckler describes the preparation of mandelic acid from bitter almond water and hydrochloric acid (''Salzsäure'').
* (Editor) (1832) (On some components of bitter almonds), ''Annalen der Chemie und Pharmacie'', '''4''' : 242–247.
* Winckler, F. L. (1836) (On mandelic acid and some salts of the same), ''Annalen der Chemie und Pharmacie'', '''18''' (3) : 310–319.
* Hermann Schelenz, ''Geschichte der Pharmazie'' (Berlin, German: Julius Springer, 1904), </ref>

Mandelic acid is usually prepared by the acid-catalysed hydrolysis of ],<ref>{{Ullmann| doi=10.1002/14356007.a13_519| chapter=Hydroxycarboxylic Acids, Aromatic|year=2000| last1=Ritzer| first1=Edwin| last2=Sundermann| first2=Rudolf| isbn=3527306730}}</ref> which is the ] of ]. Mandelonitrile can also be prepared by reacting benzaldehyde with ] to give the corresponding adduct, forming mandelonitrile with ], which is ]:<ref>{{cite journal| author = Corson, B. B.| author2 = Dodge, R. A.| author3 = Harris, S. A.| author4 = Yeaw, J. S. |journal=Org. Synth.| title = Mandelic Acid | volume= 6 | page = 58| year = 1926| doi=10.15227/orgsyn.006.0058}}</ref>
:]
Alternatively, it can be prepared by base hydrolysis of phenylchloroacetic acid as well as dibromacetophenone.<ref>{{OrgSynth | author = J. G. Aston | author2 = J. D. Newkirk | author3 = D. M. Jenkins | author4 = Julian Dorsky | name-list-style=amp | title = Mandelic Acid | collvol = 3 | collvolpages = 538 | year = 1952 | prep = cv3p0538}}</ref> It also arises by heating ] with alkalis.<ref>{{cite journal|last1=Pechmann|first1=H. von|title=Zur Spaltung der Isonitrosoverbindungen|journal=Berichte der Deutschen Chemischen Gesellschaft|date=1887|volume=20|issue=2|pages=2904–2906|doi=10.1002/cber.188702002156|url=https://zenodo.org/record/1425483}}</ref><ref>{{cite journal|last1=Pechmann|first1=H. von|last2=Muller|first2=Hermann|title=Ueber α-Ketoaldehyde|journal=Berichte der Deutschen Chemischen Gesellschaft|date=1889|volume=22|issue=2|pages=2556–2561|doi=10.1002/cber.188902202145|url=https://zenodo.org/record/1425555}}</ref>

===Biosynthesis===
Mandelic acid is a substrate or product of several biochemical processes called the mandelate pathway. ] interconverts the two enantiomers via a pathway that involves cleavage of the alpha-CH bond. Mandelate dehydrogenase is yet another enzyme on this pathway.<ref>{{cite journal |doi=10.1021/ar00052a003|title=Mandelate Racemase: Structure-Function Studies of a Pseudosymmetric Enzyme|year=1995|last1=Kenyon|first1=George L.|last2=Gerlt|first2=John A.|last3=Petsko|first3=Gregory A.|last4=Kozarich|first4=John W.|journal=Accounts of Chemical Research|volume=28|issue=4|pages=178–186}}</ref> Mandelate also arises from trans-] via ], which is ]d.<ref>{{cite journal |doi=10.1128/AEM.66.4.1517-1522.2000|title=Novel Scheme for Biosynthesis of Aryl Metabolites from l-Phenylalanine in the Fungus ''Bjerkandera'' adusta|year=2000|last1=Lapadatescu|first1=Carmen|last2=Giniès|first2=Christian|last3=Le QuéRé|first3=Jean-Luc|last4=Bonnarme|first4=Pascal|journal=Applied and Environmental Microbiology|volume=66|issue=4|pages=1517–1522|pmid=10742235|pmc=92016|bibcode=2000ApEnM..66.1517L }}</ref> ] is another precursor to mandelic acid.

Derivatives of mandelic acid are formed as a result of metabolism of ] and ] by ] and ]. The ] production of 4-hydroxy-mandelic acid and mandelic acid on the basis of ] was demonstrated with a genetically modified yeast '']'', in which the hydroxymandelate synthase naturally occurring in the bacterium '']'' was incorporated into a wild-type strain of yeast, partially altered by the exchange of a gene sequence and expressed.<ref name="Reifenrath & Boles 2018">Mara Reifenrath, ]: ''Engineering of hydroxymandelate synthases and the aromatic amino acid pathway enables de novo biosynthesis of mandelic and 4-hydroxymandelic acid with Saccharomyces cerevisiae.'' Metabolic Engineering 45, Januar 2018; S. 246-254. {{doi|10.1016/j.ymben.2018.01.001}}.</ref>

It also arises from the biodegradation of ]<ref>Engström K, Härkönen H, Kalliokoski P, Rantanen J. "Urinary mandelic acid concentration after occupational exposure to styrene and its use as a biological exposure test" Scand. J. Work Environ. Health. 1976, volume 2, pp. 21-6.</ref> and ], as detected in urine.

==Uses==
Mandelic acid has a long history of use in the medical community as an antibacterial, particularly in the treatment of urinary tract infections.<ref>{{cite journal | doi = 10.1007/BF00403669 | title = Mandelic acid and urinary tract infections | year = 1979 | author = Putten, P. L. | journal = Antonie van Leeuwenhoek | volume = 45 | pages = 622–623 | issue = 4| s2cid = 28467515 }}</ref> It has also been used as an oral antibiotic, and as a component of chemical face peels analogous to other ]s.<ref>{{cite journal | author = Taylor, MB. | year = 1999 | title = Summary of mandelic acid for the improvement of skin conditions | journal = ] | volume = 21 | pages = 26–28}}</ref>

The drugs ] and ] are ]s of mandelic acid.

==References==
{{Reflist|30em}}

*{{EB1911|wstitle=Mandelic Acid|volume=17|page=559}}

{{Other antibacterials}}

{{Authority control}}

]
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