Mandelic acid
3140464
222914056
2008-07-01T18:44:22Z
Dr Thermo
4574314
Corrected pK valued based of CRC Hdbk Chemistry and Physics 88th ed.
{{Chembox new
| Reference=<ref>''[[Merck Index]]'', 11th Edition, '''5599'''.</ref>
| Name = Mandelic acid
| ImageFile = Mandelic acid.png
| ImageSize = 120px
| ImageName =
| IUPACName = 2-Hydroxy-2-phenylacetic acid
| OtherNames = Mandelic acid<br />Phenylglycolic acid
| Section1 = {{Chembox Identifiers
| CASNo = 90-64-2
| SMILES = OC(C(O)c1ccccc1)=O
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>8</sub>H<sub>8</sub>O<sub>3</sub>
| MolarMass = 152.14 g/mol
| Density = 1.30 g/cm<sup>3</sup>
| MeltingPt = 119 °C
| BoilingPt =
| Solubility = 1 g per 6.3 mL
| pKa = 3.37
}}
}}
'''Mandelic acid''' is an [[aromatic]] [[alpha hydroxy acid]] with the molecular formula C<sub>8</sub>H<sub>8</sub>O<sub>3</sub>. It is a white crystalline solid that is soluble in water and most common organic [[solvent]]s.
==Discovery and name==
Mandelic acid was discovered while heating [[amygdalin]], an extract of [[bitter almond]]s, with diluted [[hydrochloric acid]]. It was first reported in 1909 by J. W. Walker and V. K. Krieble. The name is derived from the [[German language|German]] "Mandel" for "almond".
==Chemistry==
It is an [[isomer]] of cresotinic acid (2-hydroxy-3-methylbenzoic acid) and oxymethylbenzoic acid (2-methoxybenzoic acid). Derivatives of mandelic acid are formed as a result of metabolism of [[adrenaline]] and [[noradrenaline]] by [[monoamine oxidase]] and [[Transferase|catechol-o-methyl transferase]]. It is also present in certain skin care products, is an intermediate molecule in the production of other biochemicals, may be used as an analytical reagent and is a precursor in the manufacture of dyes.
Since the molecule contains a [[chirality (chemistry)|chiral]] carbon atom, the acid exists in either of two [[optical rotation|optically active]] forms. The [[racemic]] mixture of the two is known as ''paramandelic acid''.
It may be prepared by the action of [[hydrochloric acid]] on the addition compound of [[benzaldehyde]] and [[hydrocyanic acid]], by boiling phenylchloracetic acid with alkalis, by heating benzoyl formaldehyde with alkalis or by the action of dilute alkalis on ω-dibromacetophenone.
==See also==
* [[Phenylacetic acid]]
* [[Vanillylmandelic acid]]
==References==
<references/>
*{{1911}}
{{Other antibacterials}}
[[Category:Hydroxy acids]]
[[Category:Aromatic compounds]]
[[de:Mandelsäure]]
[[es:Ácido mandélico]]
[[fr:Acide mandélique]]
[[nl:Amandelzuur]]
[[ja:マンデル酸]]
[[pl:Kwas migdałowy]]