4-Hydroxy ThalidoMide Chemical Properties

Melting point:

273-275 °C

Boiling point:

568.3±45.0 °C(Predicted)

Density 

1.611±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

DMF: 12 mg/ml; DMSO: 10 mg/ml

form 

A solid

pka

6.82±0.20(Predicted)

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)

InChIKey

XMPJICVFSDYOEG-UHFFFAOYSA-N

SMILES

C1(=O)C2=C(C(O)=CC=C2)C(=O)N1C1CCC(=O)NC1=O

Safety Information

HS Code 

2933998090

4-Hydroxy ThalidoMide Usage And Synthesis

Description

4-Hydroxy-thalidomide is the Thalidomide-based Cereblon ligand used in the recruitment of CRBN protein. It can be connected to the ligand for protein by a linker to form PROTACs.

Uses

2-(2,6-Dioxopiperidin-3-yl)-4-hydroxyisoindoline-1,3-dione is an intermediate for the synthesis of dTAG-13 (D710020), which is a degradation tag which was tested for its efficiency at depleting FKBP12F36V -MELK(sg3R) and was found to have significantly degraded FKBP12F36V -MELK(sg3R) within 4 hours.Used in the study of cancer research.

Biochem/physiol Actions

Thalidomide hydroxylation can occur on glutarimide or phthalimide rings to yield metabolites of 4-hydroxy thalidomide. Interestingly, only metabolites phthaloyl glutamic acid and 4-hydroxy thalidomide have been tested for their anti-angiogenic activities. Hydroxylation of thalidomide on the C4-position of the phthalimide ring (4-hydroxy thalidomide) led to a weakly anti-angiogenic compound. 4-hydroxy thalidomide was not active in the CAM assay but was one of the most active compounds against HUVEC proliferation[1].

References

[1] M. G. Marks. “Effects of putative hydroxylated thalidomide metabolites on blood vessel density in the chorioallantoic membrane (CAM) assay and on tumor and endothelial cell proliferation.” Biological & pharmaceutical bulletin 356 1 (2002): 597–604.

4-Hydroxy ThalidoMide(5054-59-1)Related Product Information

• L-Prolinamide, 3-methyl-L-valyl-4-hydroxy-N-[(1S)-1-[4-(4-methyl-5-thiazolyl)phenyl]ethyl]-, (4R)-
• Pomalidomide-d5
• DL-Glutamine
• 2-(2,6-dioxopiperidin-3-yl)-4-nitroisoindoline-1,3-dione
• (S)-Pomalidomide
• 5-amino-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione
• Thalidomide
• (R)-Pomalidomide
• Pomalidomide Impurity 4
• Pomalidomide Impurity 3
• Pomalidomide Impurity 6
• Pomalidomide
• Pomalidomide Impurity 10
• Pomalidomide Impurity 2
• 3-Nitrophthalic acid
• 3-AMINOPHTHALIC ACID
• 2-(2,6-dioxopiperidin-3-yl)-4-(hydroxyamino)isoindoline-1,3-dione
• 3,4-Diamino-4-oxobutyric acid