(S)-2-Acetoxy-2-phenylacetic Acid

Base Information

• Chemical Name: (S)-2-Acetoxy-2-phenylacetic Acid
• CAS No.: 7322-88-5
• Molecular Formula: C10H10O4
• Molecular Weight: 194.187
• Hs Code.: 29181990
• European Community (EC) Number: 672-773-8
• UNII: 0N6KT18K98
• DSSTox Substance ID: DTXSID50872032
• Nikkaji Number: J74.072A
• Wikidata: Q27236985
• Mol file: 7322-88-5.mol

Synonyms:7322-88-5;(S)-2-Acetoxy-2-phenylacetic Acid;(+)-O-Acetyl-L-mandelic Acid;(S)-(+)-O-Acetyl-L-mandelic acid;(S)-(+)-O-Acetylmandelic acid;(2S)-2-acetyloxy-2-phenylacetic acid;acetyl mandelic acid;S-Acetylmandelic Acid;Acetylmandelic acid, (+)-;(+)-acetylmandelic acid;(+)-o-acetylmandelic acid;(S)-O-Acetylmandelic Acid;L-(+)-O-Acetylmandelic Acid;(S)-alpha-Acetoxyphenylacetic acid;(S)-(+)-alpha-Acetoxyphenylacetic acid;Mandelic acid, acetate, L-;Acetyl mandelic acid [INCI];MFCD00064215;UNII-0N6KT18K98;0N6KT18K98;Benzeneacetic acid, alpha-(acetyloxy)-, (alphaS)-;(2S)-2-(acetyloxy)-2-phenylacetic acid;Benzeneacetic acid, alpha-(acetyloxy)-, (S)-;(2S)-2-Acetoxy-2-phenyl-acetic acid;(S)-Acetoxyphenylacetic acid;SCHEMBL1286155;OBCUSTCTKLTMBX-VIFPVBQESA-;DTXSID50872032;OBCUSTCTKLTMBX-VIFPVBQESA-N;CS-D1447;(S)-2-acetyloxy-2-phenylacetic acid;AKOS017342896;GS-3391;(AS)-A-(Acetyloxy)-benzeneacetic acid;(S)-(+)-O-Acetylmandelic acid, 99%;AM20060715;EN300-316469;(S)-(+)-.ALPHA.-ACETOXYPHENYLACETIC ACID;Q27236985;BENZENEACETIC ACID, .ALPHA.-(ACETYLOXY)-, (S)-;BENZENEACETIC ACID, .ALPHA.-(ACETYLOXY)-, (.ALPHA.S)-;InChI=1/C10H10O4/c1-7(11)14-9(10(12)13)8-5-3-2-4-6-8/h2-6,9H,1H3,(H,12,13)/t9-/m0/s1

Chemical Property of (S)-2-Acetoxy-2-phenylacetic Acid

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 3.08E-07mmHg at 25°C
• Melting Point: 98-101 °C
• Refractive Index: 153 ° (C=2, Acetone)
• Boiling Point: 317.8 °C at 760 mmHg
• PKA: 2.76±0.10(Predicted)
• Flash Point: 125 °C
• PSA: 74.60000
• Density: 1.259 g/cm³
• LogP: 1.00720
• Storage Temp.: Refrigerator
• Solubility.: Acetone, Chloroform
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 194.05790880
• Heavy Atom Count: 14
• Complexity: 218

Purity/Quality:

99% ^*data from raw suppliers

(S)-(+)-O-Acetylmandelic acid ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC(C1=CC=CC=C1)C(=O)O
• Isomeric SMILES: CC(=O)O[C@@H](C1=CC=CC=C1)C(=O)O
• Uses: (S)-(+)-O-Acetyl-L-mandelic acid is an antibacterial used particularly in the treatment of urinary tract infections.

Technology Process of (S)-2-Acetoxy-2-phenylacetic Acid

There total 18 articles about (S)-2-Acetoxy-2-phenylacetic Acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

(S)-Mandelic acid (17199-29-0) + acetyl chloride (75-36-5) → (S)-acetylmandelic acid (7322-88-5)

Guidance literature:

at 20 ℃; for 12h;

DOI:10.1016/S0040-4020(03)01236-5

Reference yield: 92.0%

vinyl acetate (108-05-4,9003-20-7) + MANDELIC ACID (611-71-2,611-72-3,17199-29-0,90-64-2) → (R)-Mandelic Acid (611-71-2) + (S)-acetylmandelic acid (7322-88-5)

Guidance literature:

In acetone; toluene; at 37 ℃; for 24h; Pseudomonas sp. lipase;

DOI:10.1002/prac.19923340614

Reference yield: 91.0%

(S)-Mandelic acid (17199-29-0) + acetic anhydride (108-24-7) → (S)-acetylmandelic acid (7322-88-5)

Guidance literature:

With pyridine; dmap; In diethyl ether; at 20 ℃;

DOI:10.1016/S0957-4166(99)00387-0

upstream raw materials:

vinyl acetate

MANDELIC ACID

(S)-(-)-p-acetamidobenzhydryl acetate

(S)-Mandelic acid

Downstream raw materials:

(+)-methyl (S)-α-acetoxyphenylacetate

(R)-PhCH(OAc)C(O)OCH₂Et

(S)-2-acetoxy-2-phenylacetic acid ethyl ester

(S)-Acetoxy-phenyl-acetic acid 1,3,3-trimethyl-2-oxo-butyl ester

Refernces

Facile total syntheses of idarubicinone-7-β-D-glucuronide: Convenient preparations of AB-ring synthon using some carboxylic acid derivatives

10.1081/SCC-120030758

The study presents a facile total synthesis of idarubicinone-7-β-D-glucuronide, an anthracycline antibiotic analog, using a series of carboxylic acid derivatives as key intermediates. The researchers employed polyphosphoric acid (PPA) and AlCl3 as catalysts to cyclize dimethoxybenzene with various carboxylic acid derivatives, yielding naphthalenones, which were further transformed into (+)-idarubicinone 3b. Esterification with (S)-(+)-O-acetylmandelic acid and subsequent separation and deprotection steps led to the isolation of (+)-3b and (2)-3b. These compounds were then glycosylated with acetobromo-α-D-glucuronic acid methyl ester, using ZnBr2 as a catalyst, to produce two kinds of idarubicinone-7-β-D-glucuronide (20 and 21). The synthesized compounds were intended to enhance drug efficacy, potentially improving the pharmacological profile of idarubicinone by attaching glucuronic acid moieties. The study also detailed the synthetic method for an AB-ring synthon necessary for the synthesis of the aglycone and provided a comprehensive analysis of the synthesized compounds using various analytical techniques.

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