An active metabolite of thalidomide and a PROTAC synthetic intermediate
Related Products
Parent Compound(s)
14967(–)-Thalidomide 14610(±)-Thalidomide
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E3 Ligase Ligand 2

Item No. 36664

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-(2,6-dioxo-3-piperidinyl)-4-hydroxy-1H-isoindole-1,3(2H)-dione
CAS Number
5054-59-1
Synonyms
  • 4-hydroxy Thalidomide
Molecular Formula
C13H10N2O5
Formula Weight
274.2
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 12 mg/mlDMSO: 10 mg/ml
λmax
220 nm
SMILES
O=C1C2=C(C(N1C3C(NC(CC3)=O)=O)=O)C(O)=CC=C2
InChi Code
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)
InChi Key
XMPJICVFSDYOEG-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

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    1 g

    $33

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    5 g

    $123

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    Cayman Chemical
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    Product Description

    E3 ligase ligand 2 is an active metabolite of thalidomide (Item No. 14610) and an intermediate in the synthesis of proteolysis-targeting chimeras (PROTACs) containing thalidomide, a ligand for the E3 ubiquitin ligase cereblon (CRBN), used in targeted protein degradation.1,2 E3 ligase ligand 2 is formed from thalidomide via hydroxylation. It decreases the production of TNF-α induced by 12-O-tetradecanoylphorbol 13-acetate (TPA; Item No. 10008014) in THP-1 cells when used at a concentration of 30 µM.3 E3 ligase ligand 2 (333 µM) completely inhibits the proliferation of human umbilical vein endothelial cells (HUVECs). It inhibits VEGF- and FGF2-induced angiogenesis by 14% in a chicken chorioallantoic membrane (CAM) assay in utero when administered at a dose of 100 µg/embryo.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Marks, M.G., Shi, J., Fry, M.O., et al. Effects of putative hydroxylated thalidomide metabolites on blood vessel density in the chorioallantoic membrane (CAM) assay and on tumor and endothelial cell proliferation. Biol. Pharm. Bull. 25(5), 597-604 (2002).

    2. Robb, C.M., Contreras, J.I., Kour, S., et al. Chemically induced degradation of CDK9 by a proteolysis targeting chimera (PROTAC). Chem. Commun. (Camb.) 53(54), 7577-7580 (2017).

    3. Nakamura, T., Noguchi, T., Kobayashi, H., et al. Mono- and dihydroxylated metabolites of thalidomide: Synthesis and TNF-α production-inhibitory activity. Chem. Pharm. Bull. (Tokyo) 54(12), 1709-1714 (2006).