653152

4-Mercaptophenylacetic acid

97%

• Synonym(s): (4-Carboxymethyl)thiophenol, (4-Sulfanylphenyl)acetic acid, 2-(4-Mercaptophenyl)acetic acid, 2-(4-Sulfanylphenyl)acetic acid, 4-Mercaptobenzeneacetic acid, p-Mercaptophenylacetic acid
• Linear Formula: HSC₆H₄CH₂CO₂H
• CAS Number: 39161-84-7
• Molecular Weight: 168.21
• NACRES: NA.22
• PubChem Substance ID: 24883931
• UNSPSC Code: 12352100
• MDL number: MFCD00797617
• Assay: 97%
• Form: solid

Properties

• Quality Segment: 100
• assay: 97%
• form: solid
• mp: 105-109 °C (lit.)
• functional group: carboxylic acid
• storage temp.: 2-8°C
• SMILES string: OC(=O)Cc1ccc(S)cc1
• InChI: 1S/C8H8O2S/c9-8(10)5-6-1-3-7(11)4-2-6/h1-4,11H,5H2,(H,9,10)
• InChI key: ORXSLDYRYTVAPC-UHFFFAOYSA-N

Description

General description

4-Mercaptophenylacetic acid (MPAA), a thiol additive, is widely used in Native Chemical Ligation (NCL) reactions for selective and efficient ligation of peptide fragments.

Application

4-Mercaptophenylacetic acid has been used in the preparation of small ubiquitin-like modifier peptides from bis(2-sulfanylethyl)amido peptide via sequential native chemical ligation.
It can be used:

• On-resin preparation of peptide-^α thiophenylesters which are used in a chemical ligation process for the chemical synthesis of peptides.
• In one pot deprotection of (acetamido-methyl)cysteine following native chemical ligation and/or desulfurization method for the preparation of peptides.
• Palladium facilitated deprotection of N-terminal cysteine through native chemical ligation method for the preparation of synthetically challenging proteins.

Safety Information

• Pictograms: GHS05,GHS07
• Signal Word: Danger
• Hazard Codes: H315,H318,H335
• Precautionary Statements: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3
• Target Organs: Respiratory system
• Storage Class: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point (°F): Not applicable
• Flash Point (°C): Not applicable
• PPE (personal protective equipment): dust mask type N95 (US), Eyeshields, Gloves