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90-64-2

Basic Information
CAS No.: 90-64-2
Name: DL-Mandelic acid
Article Data: 268
Molecular Structure:
Molecular Structure of 90-64-2 (DL-Mandelic acid)
Formula: C8H8O3
Molecular Weight: 152.15
Synonyms: Mandelicacid (7CI,8CI);(RS)-2-Hydroxy-2-phenylacetic acid;(RS)-Mandelic acid;2-Hydroxy-2-phenylaceticacid;2-Phenyl-2-hydroxyacetic acid;2-Phenylglycolic acid;Almond acid;Amygdalic acid;DL-Amygdalic acid;DL-Hydroxy(phenyl)acetic acid;DL-Mandelicacid;NSC 7925;Paramandelic acid;Phenylglycolic acid;Phenylhydroxyaceticacid;Uromaline;dl-Mandelic acid;a-Hydroxy-a-toluicacid;a-Hydroxybenzeneacetic acid;a-Hydroxyphenylacetic acid;Mandelic acid;
EINECS: 202-007-6
Density: 1.30 g/cm3
Melting Point: 119-121 °C(lit.)
Boiling Point: 321.8 °C at 760 mmHg
Flash Point: 162.6 °C
Solubility: 150 g/L (20 °C) in water
Appearance: White crystallized powder
Hazard Symbols: HarmfulXn, IrritantXi
Risk Codes: 36/37/38-22
Safety: 22-24/25-37/39-26
PSA: 57.53000
LogP: 0.80460
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History

Mandelic acid ( 90-64-2) was discovered ,while heating amygdalin, an extract of bitter almonds, with diluted hydrochloric acid. It was first reported in 1909 by J. W. Walker and V. K. Krieble. The name is derived from the German "Mandel" for "almond".

Specification

The Mandelic acid, with the CAS registry number 90-64-2, is also known as alpha-Hydroxybenzeneacetic acid. It belongs to the product categories of C8; Carbonyl Compounds; Carboxylic Acids. Its EINECS registry number is 202-007-6. This chemical's molecular formula is C8H8O3 and molecular weight is 152.14732. Its IUPAC name is called 2-hydroxy-2-phenylacetic acid. Mandelic acid is a useful precursor to various drugs. Since the molecule is chiral, it exists in either of two enantiomers as well as the racemic mixture, known as paramandelic acid.

Physical properties of Mandelic acid: (1)ACD/LogP: 0.92; (2)ACD/LogD (pH 5.5): -1.6; (3)ACD/LogD (pH 7.4): -2.75; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 3; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 3; (11)Index of Refraction: 1.59; (12)Molar Refractivity: 38.9 cm3; (13)Molar Volume: 115.1 cm3; (14)Surface Tension: 60.4 dyne/cm; (15)Density: 1.321 g/cm3; (16)Flash Point: 162.6 °C; (17)Enthalpy of Vaporization: 59.5 kJ/mol; (18)Boiling Point: 321.8 °C at 760 mmHg; (19)Vapour Pressure: 0.00012 mmHg at 25°C.

Preparation of Mandelic acid: It is usually prepared by the acid-catalysed hydrolysis of mandelonitrile, which is the cyanohydrin of benzaldehyde. Mandelonitrile can also be prepared by reacting benzaldehyde with sodium bisulfite to give the corresponding adduct, forming mandelonitrile with sodium cyanide, which is hydrolyzed:

Mandelic acid is usually prepared by the acid-catalysed hydrolysis

Uses: Mandelic acid has a long history of use in the medical community as an antibacterial, particularly in the treatment of urinary tract infections. It has also been used as an oral antibiotic. In skin care, it is also an alternative to glycolic acid in skin care products. Mandelic acid products have been used as an alternative treatment for rosacea sufferers, as it reduces inflammation and redness. Mandelic acid is also recommended for pre- and post-laser treatment, reducing the amount of redness and irritation caused by laser resurfacing.

When you are using this chemical, please be cautious about it as the following:
This chemical may cause inflammation to the skin or other mucous membranes. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing, gloves and eye/face protection.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1=CC=C(C=C1)C(C(=O)O)O
(2)InChI: InChI=1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)
(3)InChIKey: IWYDHOAUDWTVEP-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rabbit LDLo oral 2gm/kg (2000mg/kg) GASTROINTESTINAL: GASTRITIS

GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH

LIVER: OTHER CHANGES
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 64, Pg. 79, 1940.
rat LD50 intramuscular > 300mg/kg (300mg/kg)   Experimental Medicine and Surgery. Vol. 4, Pg. 223, 1946.
rat LD50 intraperitoneal 4100mg/kg (4100mg/kg)   Bollettino Chimico Farmaceutico. Vol. 112, Pg. 53, 1973.
rat LDLo oral 3gm/kg (3000mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 64, Pg. 79, 1940.