DL-Mandelic acid

CAS NO.：90-64-2
Empirical Formula: C8H8O3
Molecular Weight: 152.15
MDL number: MFCD00064250
EINECS: 202-007-6
SAFETY DATA SHEET (SDS)
Update Date: 2024-08-21 22:41:43

What is DL-Mandelic acid ?

Chemical properties

White rhomboidal crystals, decompose when exposed to light. Soluble in ether and isopropanol, soluble in ethanol and water; R-form melting point is 133°C, [α]-159.73° (ethanol), gradually racemic at 160°C. S-form melting point is 133.8°C, [α]+156.57° (water).

The Uses of DL-Mandelic acid

DL-Mandelic acid may be used as an analytical reference standard for the determination of DL-mandelic acid in:
Human urine samples by high performance liquid chromatography (HPLC) equipped with ultraviolet (UV) detector.
Rat urine samples by gas chromatography-mass spectrometry (GC-MS) with selected ion monitoring (SIM) detection.

The Uses of DL-Mandelic acid

Organic synthesis, medicine (urinary antiseptic).

Background

Mandelic acid is an approved aromatic, alpha hydroxy acid . Mandelic acid is used as an ingredient in cosmetics and drug products applied topically.

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 derives from an acetic acid. It is a conjugate acid of a mandelate. Exists in stereoisomeric forms. The properties are those of the dl-form.

Preparation

Mandelic acid can be prepared by the hydrolysis of amygdalin with sulfuric acid or of mandelonitrile with hydrochloric acid. The mandelonitrile can be prepared by the action of hydrocyanic acid on benzaldehyde, and by the action of sodium or potassium cyanide on the sodium bisulfite addition product of benzaldehyde. The procedure described differs from earlier methods in that the sodium bisulfite addition compound of benzaldehyde is prepared in the presence of sodium cyanide and the nitrile is formed immediately.
synthesis of mandelic acid

General Description

DL-Mandelic acid is an aromatic hydrocarbon metabolite of styrene.

Hazard

Toxic by ingestion.

Flammability and Explosibility

Not classified

Safety Profile

Poison by intramuscular route. Moderately toxic by ingestion. Continued absorption can cause kidney irritation. When heated to decomposition it emits acrid smoke and irritating fumes.

Preparation

DL-Mandelic acid stands as an aromatic alpha hydroxy acid (AHA) resulting from the hydrolysis of mandelonitrile.

Metabolism

Not Available

Properties of DL-Mandelic acid

Melting point:	119-121 °C (lit.)
Boiling point:	214.6°C (rough estimate)
alpha	[α]D20 -0.5～+0.5° (c=2, H2O)
Density	1.30
vapor pressure	0.01 Pa (50 °C)
refractive index	1.4810 (estimate)
storage temp.	Store below +30°C.
solubility	139g/l
form	Crystals or Crystalline Powder
pka	3.85(at 25℃)
color	White
PH	2.3 (10g/l, H2O)
Odor	faint odor
optical activity	[α]/D 0±1°, c = 5 in H2O
Water Solubility	150 g/L (20 ºC)
Sensitive	Light Sensitive
Merck	14,5717
BRN	510011
CAS DataBase Reference	90-64-2(CAS DataBase Reference)
NIST Chemistry Reference	Benzeneacetic acid, «alpha»-hydroxy-(90-64-2)
EPA Substance Registry System	Mandelic acid (90-64-2)

Safety information for DL-Mandelic acid

Signal word	Danger
Pictogram(s)	Corrosion Corrosives GHS05
GHS Hazard Statements	H318:Serious eye damage/eye irritation
Precautionary Statement Codes	P280:Wear protective gloves/protective clothing/eye protection/face protection. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.