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ChemicalBook--->CAS DataBase List--->5054-59-1

5054-59-1

5054-59-1 Structure

5054-59-1 Structure
IdentificationBack Directory
[Name]

4-Hydroxy ThalidoMide
[CAS]

5054-59-1
[Synonyms]

186942
E3 ligase Ligand 2
4-Hydroxy ThalidoMide
Thalidomide Impurity 1
Pomalidomide Impurity 15
Thalidomide 4-Hydroxy Impurity
2-(2,6-Dioxo-3-piperidinyl)-4-hydroxyisoindoline-1,3-dione
2-(2,6-dioxopiperidin-3-yl)-4-hydroxyisoindoline-1,3-dione
2-(2,6-Dioxo-piperidin-3-yl)-4-hydroxy-isoindole-1,3-dione
4-hydroxy-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione
2-(2,6-dioxo-piperidine-3-yl)-4-hydroxy-isoindole-1,3-dione
1H-Isoindole-1,3(2H)-dione, 2-(2,6-dioxo-3-piperidinyl)-4-hydroxy-
2-(2,6-dioxopiperidin-3-yl)-4-hydroxy-2,3-dihydro-1H-isoindole-1,3-dione
[Molecular Formula]

C13H10N2O5
[MDL Number]

MFCD03699892
[MOL File]

5054-59-1.mol
[Molecular Weight]

274.23
Chemical PropertiesBack Directory
[Melting point ]

273-275 °C
[Boiling point ]

568.3±45.0 °C(Predicted)
[density ]

1.611±0.06 g/cm3(Predicted)
[storage temp. ]

Inert atmosphere,2-8°C
[solubility ]

DMF: 12 mg/ml; DMSO: 10 mg/ml
[form ]

A solid
[pka]

6.82±0.20(Predicted)
[color ]

White to gray
[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 DataBack Directory
[Symbol(GHS) ]


GHS07,GHS08
[Signal word ]

Warning
[Hazard statements ]

H302-H361
[Precautionary statements ]

P264-P270-P301+P312-P330-P501-P201-P202-P281-P308+P313-P405-P501
[HS Code ]

2933998090
Hazard InformationBack Directory
[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.
Spectrum DetailBack Directory
[Spectrum Detail]

4-Hydroxy ThalidoMide(5054-59-1)1HNMR
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