Mandelic acid is an aromaticalpha hydroxy acid with the molecular formula C6H5CH(OH)CO2H. It is a white crystalline solid that is soluble in water and polar organic solvents. It is a useful precursor to various drugs. The molecule is chiral. The racemic mixture is known as paramandelic acid.
Mandelic acid was discovered in 1831 by the German pharmacist Ferdinand Ludwig Winckler (1801–1868) while heating amygdalin, an extract of bitter almonds, with diluted hydrochloric acid. The name is derived from the German "Mandel" for "almond".[3]
Alternatively, it can be prepared by base hydrolysis of phenylchloroacetic acid as well as dibromacetophenone.[6] It also arises by heating phenylglyoxal with alkalis.[7][8]
Biosynthesisedit
Mandelic acid is a substrate or product of several biochemical processes called the mandelate pathway. Mandelate racemase interconverts the two enantiomers via a pathway that involves cleavage of the alpha-CH bond. Mandelate dehydrogenase is yet another enzyme on this pathway.[9] Mandelate also arises from trans-cinnamate via phenylacetic acid, which is hydroxylated.[10]Phenylpyruvic acid is another precursor to mandelic acid.
Derivatives of mandelic acid are formed as a result of metabolism of adrenaline and noradrenaline by monoamine oxidase and catechol-O-methyl transferase. The biotechnological production of 4-hydroxy-mandelic acid and mandelic acid on the basis of glucose was demonstrated with a genetically modified yeast Saccharomyces cerevisiae, in which the hydroxymandelate synthase naturally occurring in the bacterium Amycolatopsis was incorporated into a wild-type strain of yeast, partially altered by the exchange of a gene sequence and expressed.[11]
It also arises from the biodegradation of styrene [12] and ethylbenzene, as detected in urine.
Usesedit
Mandelic acid has a long history of use in the medical community as an antibacterial, particularly in the treatment of urinary tract infections.[13] It has also been used as an oral antibiotic, and as a component of chemical face peels analogous to other alpha hydroxy acids.[14]
Winckler, F. L. (1831) "Ueber die Zersetzung des Calomels durch Bittermandelwasser, und einige Beiträge zur genaueren Kenntniss der chemischen Zusammensetzung des Bittermandelwassers" (On the decomposition of calomel [i.e., mercury(I) chloride] 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) "Ueber die chemische Zusammensetzung des Bittermandelwassers; als Fortsetzung der im 37sten Band S. 388 u.s.w. des Repertoriums enthaltenen Mittheilungen" [On the chemical composition of bitter almond water; as a continuation of the report contained in the 37th volume, pp. 388 ff. of the Repertorium], 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) "Ueber einige Bestandtheile der Bittermandeln" (On some components of bitter almonds), Annalen der Chemie und Pharmacie, 4 : 242–247.
Winckler, F. L. (1836) "Ueber die Mandelsäure und einige Salze derselben" (On mandelic acid and some salts of the same), Annalen der Chemie und Pharmacie, 18 (3) : 310–319.
Hermann Schelenz, Geschichte der Pharmazie [The History of Pharmacy] (Berlin, German: Julius Springer, 1904), p. 675.
^Corson, B. B.; Dodge, R. A.; Harris, S. A.; Yeaw, J. S. (1926). "Mandelic Acid". Org. Synth. 6: 58. doi:10.15227/orgsyn.006.0058.
^J. G. Aston; J. D. Newkirk; D. M. Jenkins & Julian Dorsky (1952). "Mandelic Acid". Organic Syntheses; Collected Volumes, vol. 3, p. 538.
^Pechmann, H. von (1887). "Zur Spaltung der Isonitrosoverbindungen". Berichte der Deutschen Chemischen Gesellschaft. 20 (2): 2904–2906. doi:10.1002/cber.188702002156.
^Pechmann, H. von; Muller, Hermann (1889). "Ueber α-Ketoaldehyde". Berichte der Deutschen Chemischen Gesellschaft. 22 (2): 2556–2561. doi:10.1002/cber.188902202145.
^Kenyon, George L.; Gerlt, John A.; Petsko, Gregory A.; Kozarich, John W. (1995). "Mandelate Racemase: Structure-Function Studies of a Pseudosymmetric Enzyme". Accounts of Chemical Research. 28 (4): 178–186. doi:10.1021/ar00052a003.
^Lapadatescu, Carmen; Giniès, Christian; Le QuéRé, Jean-Luc; Bonnarme, Pascal (2000). "Novel Scheme for Biosynthesis of Aryl Metabolites from l-Phenylalanine in the Fungus Bjerkandera adusta". Applied and Environmental Microbiology. 66 (4): 1517–1522. Bibcode:2000ApEnM..66.1517L. doi:10.1128/AEM.66.4.1517-1522.2000. PMC92016. PMID 10742235.
^Mara Reifenrath, Eckhard Boles: 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.
^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.
^Putten, P. L. (1979). "Mandelic acid and urinary tract infections". Antonie van Leeuwenhoek. 45 (4): 622–623. doi:10.1007/BF00403669. S2CID 28467515.
^Taylor, MB. (1999). "Summary of mandelic acid for the improvement of skin conditions". Cosmetic Dermatology. 21: 26–28.
This article incorporates text from a publication now in the public domain: Chisholm, Hugh, ed. (1911). "Mandelic Acid". Encyclopædia Britannica. Vol. 17 (11th ed.). Cambridge University Press. p. 559.
January 01, 1970
mandelic, acid, aromatic, alpha, hydroxy, acid, with, molecular, formula, c6h5ch, co2h, white, crystalline, solid, that, soluble, water, polar, organic, solvents, useful, precursor, various, drugs, molecule, chiral, racemic, mixture, known, paramandelic, acid,. Mandelic acid is an aromatic alpha hydroxy acid with the molecular formula C6H5CH OH CO2H It is a white crystalline solid that is soluble in water and polar organic solvents It is a useful precursor to various drugs The molecule is chiral The racemic mixture is known as paramandelic acid Mandelic acid 1 Names Preferred IUPAC name Hydroxy phenyl acetic acid Other names 2 Hydroxy 2 phenylacetic acidMandelic acidPhenylglycolic acida Hydroxyphenylacetic acid Identifiers CAS Number 90 64 2 Y611 71 2 R Y17199 29 0 S Y 3D model JSmol Interactive image ChEBI CHEBI 35825 Y ChEMBL ChEMBL1609 Y ChemSpider 1253 Y ECHA InfoCard 100 001 825 EC Number 202 007 6 PubChem CID 1292 RTECS number OO6300000 UNII NH496X0UJX YPPL7YW1M9W R YL0UMW58G3T S Y CompTox Dashboard EPA DTXSID6023234 InChI InChI 1S C8H8O3 c9 7 8 10 11 6 4 2 1 3 5 6 h1 5 7 9H H 10 11 YKey IWYDHOAUDWTVEP UHFFFAOYSA N YInChI 1 C8H8O3 c9 7 8 10 11 6 4 2 1 3 5 6 h1 5 7 9H H 10 11 Key IWYDHOAUDWTVEP UHFFFAOYAD SMILES O C O C O c1ccccc1 Properties Chemical formula C 8H 8O 3 Molar mass 152 149 g mol 1 Appearance White crystalline powder Density 1 30 g cm3 Melting point 119 C 246 F 392 K optically pure 132 to 135 C 270 to 275 F 405 to 408 K Boiling point 321 8 C 611 2 F 595 0 K Solubility in water 15 87 g 100 mL Solubility soluble in diethyl ether ethanol isopropanol Acidity pKa 3 41 2 Refractive index nD 1 5204 Thermochemistry Std enthalpy offormation DfH 298 0 1761 kJ g Pharmacology ATC code B05CA06 WHO J01XX06 WHO Hazards Flash point 162 6 C 324 7 F 435 8 K Related compounds Related compounds mandelonitrile phenylacetic acid vanillylmandelic acid Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references Contents 1 Isolation synthesis occurrence 1 1 Biosynthesis 2 Uses 3 ReferencesIsolation synthesis occurrence editMandelic acid was discovered in 1831 by the German pharmacist Ferdinand Ludwig Winckler 1801 1868 while heating amygdalin an extract of bitter almonds with diluted hydrochloric acid The name is derived from the German Mandel for almond 3 Mandelic acid is usually prepared by the acid catalysed hydrolysis of mandelonitrile 4 which is the cyanohydrin of benzaldehyde Mandelonitrile can also be prepared by reacting benzaldehyde with sodium bisulfite to give the corresponding adduct forming mandelonitrile with sodium cyanide which is hydrolyzed 5 nbsp Alternatively it can be prepared by base hydrolysis of phenylchloroacetic acid as well as dibromacetophenone 6 It also arises by heating phenylglyoxal with alkalis 7 8 Biosynthesis edit Mandelic acid is a substrate or product of several biochemical processes called the mandelate pathway Mandelate racemase interconverts the two enantiomers via a pathway that involves cleavage of the alpha CH bond Mandelate dehydrogenase is yet another enzyme on this pathway 9 Mandelate also arises from trans cinnamate via phenylacetic acid which is hydroxylated 10 Phenylpyruvic acid is another precursor to mandelic acid Derivatives of mandelic acid are formed as a result of metabolism of adrenaline and noradrenaline by monoamine oxidase and catechol O methyl transferase The biotechnological production of 4 hydroxy mandelic acid and mandelic acid on the basis of glucose was demonstrated with a genetically modified yeast Saccharomyces cerevisiae in which the hydroxymandelate synthase naturally occurring in the bacterium Amycolatopsis was incorporated into a wild type strain of yeast partially altered by the exchange of a gene sequence and expressed 11 It also arises from the biodegradation of styrene 12 and ethylbenzene as detected in urine Uses editMandelic acid has a long history of use in the medical community as an antibacterial particularly in the treatment of urinary tract infections 13 It has also been used as an oral antibiotic and as a component of chemical face peels analogous to other alpha hydroxy acids 14 The drugs cyclandelate and homatropine are esters of mandelic acid References edit Merck Index 11th Edition 5599 Bjerrum J et al Stability Constants Chemical Society London 1958 See Winckler F L 1831 Ueber die Zersetzung des Calomels durch Bittermandelwasser und einige Beitrage zur genaueren Kenntniss der chemischen Zusammensetzung des Bittermandelwassers On the decomposition of calomel i e mercury I chloride by bitter almond water and some contributions to a more precise knowledge of the chemical composition of bitter almond water Repertorium fur die Pharmacie 37 388 418 mandelic acid is named on p 415 Winckler F L 1831 Ueber die chemische Zusammensetzung des Bittermandelwassers als Fortsetzung der im 37sten Band S 388 u s w des Repertoriums enthaltenen Mittheilungen On the chemical composition of bitter almond water as a continuation of the report contained in the 37th volume pp 388 ff of the Repertorium Repertorium fur die Pharmacie 38 169 196 On p 193 Winckler describes the preparation of mandelic acid from bitter almond water and hydrochloric acid Salzsaure Editor 1832 Ueber einige Bestandtheile der Bittermandeln On some components of bitter almonds Annalen der Chemie und Pharmacie 4 242 247 Winckler F L 1836 Ueber die Mandelsaure und einige Salze derselben On mandelic acid and some salts of the same Annalen der Chemie und Pharmacie 18 3 310 319 Hermann Schelenz Geschichte der Pharmazie The History of Pharmacy Berlin German Julius Springer 1904 p 675 Ritzer Edwin Sundermann Rudolf 2000 Ullmann s Encyclopedia of Industrial Chemistry Weinheim Wiley VCH doi 10 1002 14356007 a13 519 ISBN 978 3527306732 Corson B B Dodge R A Harris S A Yeaw J S 1926 Mandelic Acid Org Synth 6 58 doi 10 15227 orgsyn 006 0058 J G Aston J D Newkirk D M Jenkins amp Julian Dorsky 1952 Mandelic Acid Organic Syntheses Collected Volumes vol 3 p 538 Pechmann H von 1887 Zur Spaltung der Isonitrosoverbindungen Berichte der Deutschen Chemischen Gesellschaft 20 2 2904 2906 doi 10 1002 cber 188702002156 Pechmann H von Muller Hermann 1889 Ueber a Ketoaldehyde Berichte der Deutschen Chemischen Gesellschaft 22 2 2556 2561 doi 10 1002 cber 188902202145 Kenyon George L Gerlt John A Petsko Gregory A Kozarich John W 1995 Mandelate Racemase Structure Function Studies of a Pseudosymmetric Enzyme Accounts of Chemical Research 28 4 178 186 doi 10 1021 ar00052a003 Lapadatescu Carmen Ginies Christian Le QueRe Jean Luc Bonnarme Pascal 2000 Novel Scheme for Biosynthesis of Aryl Metabolites from l Phenylalanine in the Fungus Bjerkandera adusta Applied and Environmental Microbiology 66 4 1517 1522 Bibcode 2000ApEnM 66 1517L doi 10 1128 AEM 66 4 1517 1522 2000 PMC 92016 PMID 10742235 Mara Reifenrath Eckhard Boles 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 Engstrom K Harkonen 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 Putten P L 1979 Mandelic acid and urinary tract infections Antonie van Leeuwenhoek 45 4 622 623 doi 10 1007 BF00403669 S2CID 28467515 Taylor MB 1999 Summary of mandelic acid for the improvement of skin conditions Cosmetic Dermatology 21 26 28 nbsp This article incorporates text from a publication now in the public domain Chisholm Hugh ed 1911 Mandelic Acid Encyclopaedia Britannica Vol 17 11th ed Cambridge University Press p 559 Retrieved from https en wikipedia org w index php title Mandelic acid amp oldid 1194487428, wikipedia, wiki, book, books, library,
