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DL-Mandelic acid

DL-Mandelic acid structure

CAS No:
611-72-3
Formula:
C8H8O3
Chemical Name:
DL-Mandelic acid
Synonyms:
DL-MANDELSAEURE S;DL-Mandelic acid (AMygdalic acid);(+/-)-alpha-Hydroxyphenylacetic acid;DL-Mandelic acid;DL-MANDELIC ACID 99+%;DL-MANDELICACID,REAGENT;DL-MANDELIC ACID/CYCLANDELATE,PEMOLINE;DL-mandelic acid(mandelic acid)
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

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.

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

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.

DL-Mandelic acid Basic Attributes

Molecular Weight：

152.15

Exact Mass：

152.15

EC Number：

202-007-6

HScode：

29181980

Characteristics

PSA：

57.53000

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.

XLogP3：

0.80460

Appearance：

Wihte crystal or crystal powder

Density：

1.2890

Melting Point：

119-121 °C(lit.)

Boiling Point：

234.6°C (rough estimate)

Flash Point：

162.6ºC

Refractive Index：

1.4945 (estimate)

Water Solubility：

172.5g/L(24 ºC)

Storage Conditions：

Do not store in direct sunlight. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incom

PKA：

3.85(at 25℃)

Safety Information

wgk germany：

hazard class code：

R21/22

safety instructions：

22-24/25

RTECS Number：

OO6300000

Marks：

Precautionary statement(s)：

P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P310, P312, P321, P330, P332+P313, P362, P403+P233, P405, P501

Hazard Statements：

21/22

DL-Mandelic acid Use and Manufacturing

Uses

Present in certain skin care products.

Production

(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.

Material

Benzaldehyde

Chlorine dioxide

Sodium bisulfite

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