DL-Mandelic acid

Synonym(s):(±)-α-Hydroxyphenylacetic acid;DL-α-Hydroxyphenylacetic acid, Phenylglycollic acid;DL-Mandelic acid

CAS NO.：611-72-3
Empirical Formula: C8H8O3
Molecular Weight: 152.15
MDL number: MFCD00064250
EINECS: 202-007-6
SAFETY DATA SHEET (SDS)
Update Date: 2024-11-15 19:19:13

What is DL-Mandelic acid?

Chemical properties

Mandelic acid turns brown when exposed to light. It can be esterified easily with alcohols in the presence of hydrogen chloride.

Physical properties

(R,S)-Mandelic acid (a-hydroxyphenylacetic acid, phenylglycolic acid), C6H5CH(OH)COOH, C8H8O3, Mr 152.15, mp 118 – 121℃, is a colorless crystalline powder. It is readily soluble in ethanol and diethyl ether, less soluble in chloroform, and insoluble in petroleum ether. Its water solubility is 15 g per 100 mL of water. In alkaline solution, mandelic acid dissolves to form salts.

Definition

ChEBI: Mandelic acid is a 2-hydroxy monocarboxylic acid that is acetic acid in which two of the methyl hydrogens are substituted by phenyl and hydroxyl groups. It has a role as an antibacterial agent and a human xenobiotic metabolite. It is a 2-hydroxy monocarboxylic acid and a member of benzenes. It is functionally related to an acetic acid. It is a conjugate acid of a mandelate.

Production Methods

(R,S)-mandelic acid is produced by hydrolysis of mandelic acid nitrile [532-28-5] (mp 10℃) with hydrochloric acid. Mandelic acid nitrile is obtained by the conversion of benzaldehyde [100-52-7] and hydrogen cyanide in the nascent state (NaCN + HCl) under refrigeration. Another method of producing mandelic acid is the hydrolysis of a,a-dichloroacetophenone with alkali.

Properties of DL-Mandelic acid

Melting point:	119-121 °C(lit.)
Boiling point:	234.6°C (rough estimate)
Density	1.2890
refractive index	1.4945 (estimate)
pka	3.85(at 25℃)
Water Solubility	172.5g/L(24 ºC)
CAS DataBase Reference	611-72-3(CAS DataBase Reference)
NIST Chemistry Reference	Benzeneacetic acid, «alpha»-hydroxy-, (.+/-.)-(611-72-3)