DL-Mandelic acid Chemical Properties

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)

InChI

InChI=1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)

InChIKey

IWYDHOAUDWTVEP-UHFFFAOYSA-N

SMILES

C1(C=CC=CC=1)C(O)C(=O)O

CAS DataBase Reference

611-72-3(CAS DataBase Reference)

NIST Chemistry Reference

Benzeneacetic acid, «alpha»-hydroxy-, (.+/-.)-(611-72-3)

Safety Information

Risk Statements 

21/22

Safety Statements 

22-24/25

WGK Germany 

3

RTECS 

OO6300000

HS Code 

29181980

MSDS

• Language:English Provider:(+/-)-alpha-Hydroxyphenylacetic acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

DL-Mandelic acid Usage And Synthesis

Description

DL-Mandelic acid is a chemical compound belonging to the family of alpha hydroxy acids (AHAs). It is a racemic mixture containing equal amounts of the D and L enantiomers of Mandelic acid. It is commonly used in skincare products for its exfoliating and antibacterial properties. DL-Mandelic Acid is useful in suppressing pigmentation, treating inflammatory non-cystic acne, and rejuvenating photoaged skin. Moreover, it has proven useful in preparing the skin for laser peeling and helping the skin heal after laser surgery. This product appears as a white crystal substance.

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.

DL-Mandelic acid(611-72-3)Related Product Information

• DL-MANDELIC ACID611-72-3,DL-MANDELIC ACID, FOR GRAVIMETRIC DETERMINATION (OF ZR) 99+%,DL-Mandelic acid,DL-MANDELIC ACID 98%
• Malic acid
• CHLOROPHOSPHONAZO III
• (S)-(+)-Mandelic acid
• α-Lipoic Acid
• Mandelic acid
• Ethyl 2-(Chlorosulfonyl)acetate
• Citric acid
• Hyaluronic acid
• Folic acid
• Glycine
• DL-Malic acid
• Ascoric Acid
• (R)-(+)-alpha-Methoxy-alpha-trifluoromethylphenylacetic acid
• p-Bromo-dl-mandelic acid,4-BROMO-DL-MANDELIC ACID
• (-)-O-ACETYL-D-MANDELIC ACID
• 4-Hydroxy-3-methoxy-DL-mandelic acid, 98%
• 4-CHLORO-DL-MANDELIC ACID,P-CHLORO-DL-MANDELIC ACID