7322-88-5

Basic information

• Product Name: (S)-(+)-O-Acetyl-L-mandelic acid
• Synonyms: (S)-(+)-O-ACETYLMANDELIC ACID;(S)-(+)-ALPHA-ACETOXYPHENYLACETIC ACID;(S)-ALPHA-ACETOXYPHENYLACETIC ACID;(+)-O-ACETYL-L-MANDELIC ACID;O-ACETYL MANDELIC ACID;A-(ACETYLOXY)BENZENEACETIC ACID;(S)-A-ACETOXYPHENYLACETIC ACID;S- 0 - ACETYLMANDELIC ACID
• CAS NO: 7322-88-5
• Molecular Formula: C₁₀H₁₀O₄
• Molecular Weight: 194.18
• Product Categories: chiral;for Resolution of Alcohols & Thiols;for Resolution of Bases;Optical Resolution;Synthetic Organic Chemistry;Chiral Compound;Aromatics;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 7322-88-5.mol
• Article Data: 33

Chemical Properties

• Melting Point: 98-101 °C
• Boiling Point: 317.8 °C at 760 mmHg
• Flash Point: 125 °C
• Appearance: white to light yellow crystal powder
• Density: 1.259 g/cm³
• Vapor Pressure: 3.08E-07mmHg at 25°C
• Refractive Index: 153 ° (C=2, Acetone)
• Storage Temp.: Refrigerator
• Solubility: Acetone, Chloroform
• PKA: 2.76±0.10(Predicted)
• BRN: 2694109
• CAS DataBase Reference: (S)-(+)-O-Acetyl-L-mandelic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-O-Acetyl-L-mandelic acid(7322-88-5)
• EPA Substance Registry System: (S)-(+)-O-Acetyl-L-mandelic acid(7322-88-5)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 7322-88-5(Hazardous Substances Data)

Usage

Description

(S)-(+)-O-Acetyl-L-mandelic acid is a chiral organic compound derived from L-mandelic acid, featuring an acetyl group attached to the chiral center. It exhibits optical activity and is characterized by its specific stereochemistry, with the S configuration at the chiral carbon.
Used in Pharmaceutical Industry:
(S)-(+)-O-Acetyl-L-mandelic acid is used as an antibacterial agent for the treatment of urinary tract infections. Its chiral nature and specific configuration allow for targeted action against bacteria, potentially reducing side effects and enhancing therapeutic efficacy in treating such infections.

Purification Methods

Recrystallise it from *benzene/hexane or toluene, and it has characteristic NMR and IR spectra. [Pracejus Justus Liebig

InChI:InChI=1/C10H10O4/c1-6(11)7-4-2-3-5-8(7)9(12)10(13)14/h2-5,9,12H,1H3,(H,13,14)/t9-/m0/s1

Upstream product

• 29071-09-8 2-acetoxy-2-phenylacetic acid 
• 108-05-4 vinyl acetate 
• 611-71-2 MANDELIC ACID 
• 98-86-2 acetophenone 
• 611-73-4 Benzoylformic acid 
• 17199-29-0 (S)-Mandelic acid 
• 75-36-5 acetyl chloride 
• 1100171-65-0 C₁₉H₁₇NO₅ 
• 33149-64-3 (S)-(4-nitro-phenyl)-phenyl-methanol 
• 101402-02-2 (S)-(4-aminophenyl)(phenyl)methanol 
• 119718-88-6 O-acetyl (S)-mandelonitrile 
• 108-24-7 acetic anhydride 
• 101402-03-3 (S)-(-)-p-acetamidobenzhydryl acetate 

Downstream Products

• 133008-60-3 (4'S)-<4'-2H1>-3,5'-O-dibenzylpyridox-4'-yl (S)-(+)-O-acetylmandelate 
• 133008-59-0 (4'R)-<4'-2H1>-3,5'-O-dibenzylpyridox-4'-yl (S)-(+)-O-acetylmandelate 
• 112497-03-7 (S)-Acetoxy-phenyl-acetic acid (R)-1-[(2S,5R)-5-((S)-1-hydroxy-4-methoxymethoxy-1-methyl-butyl)-2-methyl-tetrahydro-furan-2-yl]-ethyl ester 
• 112572-14-2 (S)-Acetoxy-phenyl-acetic acid (S)-1-[(2R,5S)-5-((R)-1-hydroxy-4-methoxymethoxy-1-methyl-butyl)-2-methyl-tetrahydro-furan-2-yl]-ethyl ester 
• 117229-40-0 2(S)-exo-hydroxy-1(R),4(S)-cineole (S)-(+)-O-acetylmandelate 
• 117306-76-0 2(R)-exo-hydroxy-1(S),4(R)-cineole (S)-(+)-O-acetylmandelate 
• 29071-09-8 2-acetoxy-2-phenylacetic acid 
• 359887-05-1 (1R,6R,8S)-8-[(1R)-1-[(2S)-2-acetoxy-2-phenylacetoxy]-3-methylbutyl]-3-methyl-7-methylene-9-oxabicyclo[4.3.0]non-2-ene 
• 359887-06-2 (1S,6S,8R)-8-[(1S)-1-[(2S)-2-acetoxy-2-phenylacetoxy]-3-methylbutyl]-3-methyl-7-methylene-9-oxabicyclo[4.3.0]non-2-ene 
• 369633-44-3 (S)-1-[O-(acetyl)mandelyl]pyrrolidine 
• 469874-40-6 (S)-1-[O-(acetyl)mandelyl]morpholine 

Relevant articles and documents

Deracemization of (±)-mandelic acid using a lipase-mandelate racemase two-enzyme system

Deracemization of (±)-mandelic acid was achieved by using a novel two- enzyme process consisting of: (i) Pseudomonas sp. lipase catalyzed O- acylation of (±)-mandelic acid in diisopropyl ether; followed by (ii) mandelate racemase catalyzed racemization of the remaining unreacted (R)- mandelic acid in aqueous buffer. When this one-pot sequence was repeated four times, (S)-O-acetylmandelic acid was obtained in 80% isolated yield and >98% ee as the sole product.

METHODS AND COMPOSITIONS FOR PREVENTING OPIOID ABUSE

Abuse-resistant opioid compounds, drug delivery systems, pharmaceutical compositions comprising an opioid covalently bound to a chemical moiety are provided. Methods of delivering an active ingredient to a subject and methods of preventing opioid abuse are also provided.

An efficient enzymatic aminolysis for kinetic resolution of aromatic α-hydroxyl acid in non-aqueous media

A new and highly efficient enzymatic aminolysis approach for kinetic resolution of aromatic α-hydroxy acid in non-aqueous media has been developed. The corresponding α-hydroxyl acid ester was employed as the substrate, and commercially available Candida antarctica lipase B is used as the biocatalyst, anhydrous ammonia is the resolving agent. Reactions can be proceeded smoothly in organic solvent at ambient temperatures. High concentration of substrate is allowed due to the application of organic media and the products are obtained in yields of up to 49% with ee values of up to 99%, and with E value of >300, representing an appealing and promising protocol for large-scale preparations.