Mandelic acid

Mandelic acid^[1]
Names
	Preferred IUPAC name Hydroxy(phenyl)acetic acid
	Other names 2-Hydroxy-2-phenylacetic acid; Mandelic acid; Phenylglycolic acid; α-Hydroxyphenylacetic acid
Identifiers
CAS Number	90-64-2 ; (R): 611-71-2 ; (S): 17199-29-0 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	510011
ChEBI	CHEBI:35825 ;
ChEMBL	ChEMBL1609 ;
ChemSpider	1253 ;
DrugBank	DB13218; (R): DB02280; (S): DB03357;
ECHA InfoCard	100.001.825
EC Number	202-007-6;
Gmelin Reference	218213
KEGG	(R): C01983; (S): C01984;
PubChem CID	1292;
RTECS number	OO6300000;
UNII	NH496X0UJX ; (R): PPL7YW1M9W ; (S): L0UMW58G3T ;
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) 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	152.149 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
Refractive index (nD)	1.5204
Thermochemistry
Std enthalpy of; formation (ΔfH⦵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). verify (what is ?) Infobox references

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.

^ Merck Index, 11th Edition, 5599.
^ Bjerrum, J., et al. Stability Constants, Chemical Society, London, 1958.

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

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

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