Name: 2-(2,6-Dioxo-3-piperidinyl)-4-hydroxyisoindoline-1,3-dione
Brand: BOC Sciences
Rating: 5 (1 reviews)

Size

Price

Stock

Quantity

$--

In stock

Purity

> 95 %

Solubility

DMSO : ≥ 36.5 mg/mL

Appearance

White to off-white solid

Storage

4 °C, stored under nitrogen<br/>*In solvent : -80 °C, 6 months; -20 °C, 1 month (stored under nitrogen)

Shipping

Room temperature in continental US; may vary elsewhere

IUPACName

2-(2,6-dioxopiperidin-3-yl)-4-hydroxyisoindole-1,3-dione

Synonyms

4-Hydroxy thalidomide; E3 ligase Ligand 2; Thalidomide-4-OH; 4-Hydroxy thalidomide, (+/-)-; 3-Hydroxythalidomide; 4-Hydroxy-thalidomide; α-(3-Hydroxy-phthalimido)-glutarimid; 2-(2,6-dioxopiperidin-3-yl)-4-hydroxyisoindoline-1,3-dione; 2-(2,6-dioxo-3-piperidinyl)-4-hydroxy-1H-isoindole-1,3(2H)-dione

Boiling Point

568.3±45.0 °C (Predicted)

Melting Point

273-282 °C

Density

1.611±0.06 g/cm<sup>3</sup> (Predicted)

InChI Key

XMPJICVFSDYOEG-UHFFFAOYSA-N

InChI

InChI=1S/C13H10N2O5/c16-8-3-1-2-6-10(8)13(20)15(12(6)19)7-4-5-9(17)14-11(7)18/h1-3,7,16H,4-5H2,(H,14,17,18)

Canonical SMILES

C1CC(=O)NC(=O)C1N2C(=O)C3=C(C2=O)C(=CC=C3)O

Background Introduction

2-(2,6-Dioxo-3-piperidinyl)-4-hydroxyisoindoline-1,3-dione is a structural analog of thalidomide, belonging to the family of IMiDs (immunomodulatory imide drugs). This compound contains a reactive hydroxy group at position 4 of the isoindoline core, representing a valuable scaffold for the design of Cereblon (CRBN)-recruiting E3 ligase ligands for targeted protein degradation strategies such as PROTACs (Proteolysis Targeting Chimeras) and molecular glues.

Mechanism

As a CRBN E3 ligase ligand, 2-(2,6-Dioxo-3-piperidinyl)-4-hydroxyisoindoline-1,3-dione selectively binds the Cereblon protein, a key substrate receptor within the CUL4-CRBN E3 ubiquitin ligase complex. When included in a bifunctional PROTAC molecule, it mediates the recruitment of the target protein—via a conjugated ligand—to the CRBN E3 ligase. This spatial proximity triggers ubiquitination of the target, marking it for selective degradation by the ubiquitin-proteasome system.

Applications

2-(2,6-Dioxo-3-piperidinyl)-4-hydroxyisoindoline-1,3-dione is a highly useful intermediate for constructing CRBN-based PROTACs and molecular glues. Its 4-hydroxy functional group allows facile chemical modification and linker attachment, supporting the development of custom degrader molecules. Common application areas include:

• Synthesis of CRBN E3 ligase-binding motifs for next-generation PROTACs
• Structure-activity relationship (SAR) studies to optimize degrader efficacy in drug discovery
• Developing tool compounds for mechanistic studies of protein degradation
• Enabling academic and biotech research in targeted degradation platforms

• High-purity compound verified by HPLC, NMR, and LC-MS
• Consistent batch-to-batch reproducibility with complete QC documentation
• Supplied with COA, MSDS, and analytical data for traceability
• Reliable global shipping with stability-guaranteed packaging
• Dedicated technical support and optional custom synthesis service
• Demonstrates strong binding affinity to CRBN, VHL, or other E3 ligases
• Enables stable E3 ligase recruitment for targeted protein degradation
• High-affinity ligand for the CRBN E3 ligase ensures efficient target protein degradation in PROTAC development.
• Optimized chemical structure enables versatile conjugation, facilitating diverse PROTAC design and rapid SAR studies.

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* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C₁V₁ = C₂V₂