Mandelic Acid

Base Information

• Chemical Name: Mandelic Acid
• CAS No.: 611-72-3
• Deprecated CAS: 15769-78-5,611-72-3,71036-61-8,611-72-3
• Molecular Formula: C₈H₈O₃
• Molecular Weight: 152.15
• Hs Code.: 29181980
• European Community (EC) Number: 202-007-6,210-277-1
• NSC Number: 7925
• UNII: NH496X0UJX
• DSSTox Substance ID: DTXSID6023234
• Nikkaji Number: J2.433.033H,J2.433.034F,J3.918G
• Wikipedia: Mandelic_acid
• Wikidata: Q412293
• NCI Thesaurus Code: C61822
• RXCUI: 29256
• Metabolomics Workbench ID: 143609
• ChEMBL ID: CHEMBL1609
• Mol file: 611-72-3.mol

Synonyms:mandelic acid;mandelic acid, (+-)-isomer;mandelic acid, (11)C-labeled;mandelic acid, (R)-isomer;mandelic acid, (S)-isomer;mandelic acid, calcium (2:1) salt;mandelic acid, monoammonium salt;mandelic acid, monocalcium salt;mandelic acid, monolithium salt;mandelic acid, monosodium salt;mandelic acid, monosodium salt, (R)-isomer;mandelic acid, monosodium salt, (S)-isomer

Chemical Property of Mandelic Acid

Chemical Property:

• Appearance/Colour: Wihte crystal or crystal powder
• Melting Point: 119-121 °C(lit.)
• Refractive Index: 1.4945 (estimate)
• Boiling Point: 321.827 °C at 760 mmHg
• PKA: 3.85(at 25℃)
• Flash Point: 162.649 °C
• PSA: 57.53000
• Density: 1.322 g/cm³
• LogP: 0.80460
• Water Solubility.: 150 g/L (20℃)
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 152.047344113
• Heavy Atom Count: 11
• Complexity: 138

Purity/Quality:

99% ^*data from raw suppliers

DL-Mandelic acid 99+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R21/22:
• Hazard Codes: Xn:Harmful
• Statements: 21/22
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: C1=CC=C(C=C1)C(C(=O)O)O

Technology Process of Mandelic Acid

There total 258 articles about Mandelic 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: 75.0%

[bis(acetoxy)iodo]benzene (3240-34-4) + Ethyl 2-phenylethanoate (101-97-3) → MANDELIC ACID (611-71-2,611-72-3,17199-29-0,90-64-2)

Guidance literature:

With potassium hydroxide; In water; benzene;

DOI:10.1016/S0040-4039(01)90541-6

Reference yield: 75.0%

C17H18N2O5S (85515-89-5) → MANDELIC ACID (611-71-2,611-72-3,17199-29-0,90-64-2)

Guidance literature:

With copper dichloride; In methanol; water; for 20h; Heating;

Reference yield: 50.0%

[bis(acetoxy)iodo]benzene (3240-34-4) + benzeneacetic acid methyl ester (101-41-7) → MANDELIC ACID (611-71-2,611-72-3,17199-29-0,90-64-2)

Guidance literature:

With potassium hydroxide; In water; benzene;

DOI:10.1016/S0040-4039(01)90541-6

upstream raw materials:

2-(morpholin-4-yl)ethanethiol

2,2-dihydroxy-1-phenyl-ethanone

tetrachloromethane

1-Phenyl-2-propen-1-ol

Downstream raw materials:

2-methyl-5-phenyl-[1,3]dioxolan-4-one

mandelic acid-tetrahydrofurfuryl ester

4,7-dimethyl-3-phenyl-3H-benzofuran-2-one

5,6-dimethyl-3-phenyl-3H-benzofuran-2-one

Refernces

The mandelic acid keto-enol system in aqueous solution. Generation of the enol by hydration of phenylhydroxyketene and phenylcarboxycarbene

10.1021/ja971774r

Y. Chiang, A. J. Kresge, V. V. Popik, and N. P. Schepp investigate the enolization and ketonization processes of mandelic acid in aqueous solution through flash photolysis. The study identifies the transient species generated from the photolysis of phenyldiazoacetic acid and benzoylformic acid esters as the enol of mandelic acid. The enol is formed via different pathways depending on the substrate: from phenylhydroxyketene when benzoylformate esters are used, and from phenylcarboxycarbene when phenyldiazoacetic acid is used. The researchers measured the rates of enolization and ketonization, determining the keto-enol equilibrium constant (pKE = 16.19) and the acidity constant of the enol (pQaE = 6.39). They also compared these findings to other keto-enol systems and discussed the implications for the enzymatic racemization of mandelic acid, providing insights into the thermodynamic barriers that mandelate racemase must overcome.