Mandelic acid

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Mandelic acid^[1]
	Template:Chembox image sbs cell
Names
	IUPAC name 2-Hydroxy-2-phenylacetic acid
	Other names Mandelic acid; Phenylglycolic acid
Identifiers
CAS Number	90-64-2 ; 611-71-2 (R); 17199-29-0 (S);
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:35825 ;
ChEMBL	ChEMBL1609 ;
ChemSpider	1253 ;
ECHA InfoCard	Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value).
PubChem CID	1292;
UNII	NH496X0UJX ;
	InChI InChI=1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11) Key: IWYDHOAUDWTVEP-UHFFFAOYSA-N ; InChI=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	C8H8O3
Molar mass	152.15 g·mol−1
Hazards
Related compounds
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

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. Since the molecule is chiral, it exists in either of two enantiomers as well as the racemic mixture, known as paramandelic acid.

Isolation and synthesis

Mandelic acid was discovered while heating amygdalin, an extract of bitter almonds, with diluted hydrochloric acid. The name is derived from the German "Mandel" for "almond". Derivatives of mandelic acid are formed as a result of metabolism of adrenaline and noradrenaline by monoamine oxidase and catechol-O-methyl transferase.

Mandelic acid is usually prepared by the acid-catalysed hydrolysis of mandelonitrile,^[3] 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:^[4]

File:Preparation of mandelic acid.png

Alternatively, it arises by base hydrolysis of phenylchloroacetic acid and dibromacetophenone.^[5] It also arises by heating phenylglyoxal with alkalis.

Uses

Mandelic acid has a long history of use in the medical community as an antibacterial, particularly in the treatment of urinary tract infections.^[6] It has also been used as an oral antibiotic, and as a component of "chemical face peels", along with other alpha-hydroxy acids (AHAs).

The drugs cyclandelate and homatropine are esters of mandelic acid.

References

↑ Merck Index, 11th Edition, 5599.
↑ Bjerrum, J., et al. Stability Constants, Chemical Society, London, 1958.
↑ Edwin Ritzer and Rudolf Sundermann "Hydroxycarboxylic Acids, Aromatic" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi: 10.1002/14356007.a13_519
↑ Template:OrgSynth
↑ Template:OrgSynth
↑ Putten, P. L. (1979). "Mandelic acid and urinary tract infections". Antonie van Leeuwenhoek. 45 (4): 622. doi:10.1007/BF00403669.

Template:1911

Template:Other antibacterials

[1] Merck Index, 11th Edition, 5599.

[2] Bjerrum, J., et al. Stability Constants, Chemical Society, London, 1958.

[3] Edwin Ritzer and Rudolf Sundermann "Hydroxycarboxylic Acids, Aromatic" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi: 10.1002/14356007.a13_519

[4] Template:OrgSynth

[5] Template:OrgSynth

[6] Putten, P. L. (1979). "Mandelic acid and urinary tract infections". Antonie van Leeuwenhoek. 45 (4): 622. doi:10.1007/BF00403669.

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Names
Template:Chembox image sbs cell
IUPAC name 2-Hydroxy-2-phenylacetic acid
Other names Mandelic acid Phenylglycolic acid
Identifiers
CAS Number	90-64-2^Y 611-71-2 (R) 17199-29-0 (S)
3D model (JSmol)	Interactive image
ChEBI	CHEBI:35825^Y
ChEMBL	ChEMBL1609^Y
ChemSpider	1253^Y
ECHA InfoCard	Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value).
PubChem CID	1292
UNII	NH496X0UJX^Y
InChI InChI=1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)^Y Key: IWYDHOAUDWTVEP-UHFFFAOYSA-N^Y InChI=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	C₈H₈O₃
Molar mass	152.15 g·mol⁻¹
Hazards
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is ^YN ?)
Infobox references

Mandelic acid

Overview

Isolation and synthesis

Uses

References

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