3-PHENOXYMANDELIC ACID

• CAS: 66637-86-3
• Catalog Number: ACM66637863
• Category: Main Products
• Molecular Weight: 244.24
• Molecular Formula: C14H12O4
• Synonyms: RARECHEM AL BO 1082
• Appearance: White solid

Case Study

3-Phenoxymandelic Acid Participates In The Study Of Synthetic Pyrethroid Immunoassays

Lee, Nanju, David P. McAdam, and John H. Skerritt. Journal of agricultural and food chemistry 46.2 (1998): 520-534.

The esterification of 3-phenoxymandelic acid with pyrethroid acid chlorides produces pyrethroid analogs containing carboxylic acid instead of cyano substituents, thereby forming amide derivatives with tert-butyl-β-alanine. Three different pyrethric acids were used here: bromopermethrinic acid, dichloropermethrinic acid, and trifluoropermethrinic acid to obtain structurally different haptens on the cyclopropane moiety. The esterification produced a number of isomers (according to NMR data), and the combined isomers were used in subsequent steps without any attempt to identify the stereochemistry of these isomers.
((±)-1-Carboxy(3'-phenoxyphenyl)methyl 3-(2',2'-dibromovinyl)-2,2-methylcyclopropanecarboxylic acid. 3-Phenoxymandelic acid was prepared by treating the acid (0.86 g, 3.0 mmol) with thionyl chloride (SOCl, 5 mL), stirring at reflux for 1 h, concentrating the solution under reduced pressure to remove excess SOCl, and purifying the resulting yellow liquid by bulb-to-bulb distillation. 3-Phenoxybenzaldehyde cyanohydrin was treated with concentrated HCl. 3-Phenoxymandelic acid (104 mg, 0.43 mmol) was added to a flask containing 1 mL of the acid chloride 8 and stirred for 6 days, then 1,4. Dioxane (1 mL) and saturated aqueous NaHCO3 (2 mL) were added and stirred for 1 h. The solution was acidified to pH 1 with concentrated HCl (caution) and extracted 3 times with ethyl acetate.
After drying and concentration with MgSO4 , the residue was chromatographed on silica [chloroform/acetic acid (99.5:0.5)] to give a white solid (109 mg, 49%)

Custom Q&A

What is the molecular formula of 3-Phenoxymandelic acid?

The molecular formula of 3-Phenoxymandelic acid is C14H12O4.

What are the synonyms for 3-Phenoxymandelic acid?

The synonyms for 3-Phenoxymandelic acid are 66637-86-3, 2-hydroxy-2-(3-phenoxyphenyl)acetic acid, and MFCD03789126.

What is the molecular weight of 3-Phenoxymandelic acid?

The molecular weight of 3-Phenoxymandelic acid is 244.24 g/mol.

When was 3-Phenoxymandelic acid created?

3-Phenoxymandelic acid was created on July 19, 2005.

When was 3-Phenoxymandelic acid last modified?

3-Phenoxymandelic acid was last modified on October 21, 2023.

What is the IUPAC name of 3-Phenoxymandelic acid?

The IUPAC name of 3-Phenoxymandelic acid is 2-hydroxy-2-(3-phenoxyphenyl)acetic acid.

What is the InChI of 3-Phenoxymandelic acid?

The InChI of 3-Phenoxymandelic acid is InChI=1S/C14H12O4/c15-13(14(16)17)10-5-4-8-12(9-10)18-11-6-2-1-3-7-11/h1-9,13,15H,(H,16,17).

What is the InChIKey of 3-Phenoxymandelic acid?

The InChIKey of 3-Phenoxymandelic acid is FPUCYPXKIFVDSD-UHFFFAOYSA-N.

What is the canonical SMILES of 3-Phenoxymandelic acid?

The canonical SMILES of 3-Phenoxymandelic acid is C1=CC=C(C=C1)OC2=CC=CC(=C2)C(C(=O)O)O.

What is the hydrogen bond acceptor count of 3-Phenoxymandelic acid?

The hydrogen bond acceptor count of 3-Phenoxymandelic acid is 4.