ChemicalBook > CAS DataBase List > 4-Hydroxy ThalidoMide

4-Hydroxy ThalidoMide

Product Name
4-Hydroxy ThalidoMide
CAS No.
5054-59-1
Chemical Name
4-Hydroxy ThalidoMide
Synonyms
2-(2,6-dioxopiperidin-3-yl)-4-hydroxyisoindoline-1,3-dione;Thalidomide-4-OH;2-(2,6-Dioxo-3-piperidinyl)-4-hydroxyisoindoline-1,3-dione;186942;Cereblon ligand 2;E3 ligase Ligand 2;4-Hydroxy ThalidoMide;Thalidomide Impurity 1;Pomalidomide Impurity 15;Thalidomide 4-Hydroxy Impurity
CBNumber
CB92706477
Molecular Formula
C13H10N2O5
Formula Weight
274.23
MOL File
5054-59-1.mol
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4-Hydroxy ThalidoMide Property

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
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Safety

HS Code 
2933998090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H361Suspected of damaging fertility or the unborn child

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P281Use personal protective equipment as required.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P308+P313IF exposed or concerned: Get medical advice/attention.

P330Rinse mouth.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

AK Scientific
Product number
4854BB
Product name
4-Hydroxythalidomide
Packaging
100mg
Price
$99
Updated
2021/12/16
ApexBio Technology
Product number
C6597
Product name
Thalidomide-4-OH
Packaging
500mg
Price
$250
Updated
2021/12/16
Biorbyt Ltd
Product number
orb611275
Product name
E3 Ligase Ligand 2
Purity
>98%
Packaging
1g
Price
$1060.8
Updated
2021/12/16
BroadPharm
Product number
BP-24437
Product name
4-Hydroxy-thalidomide
Purity
98%
Packaging
5G
Price
$330
Updated
2021/12/16
Biorbyt Ltd
Product number
orb611275
Product name
E3 Ligase Ligand 2
Purity
>98%
Packaging
5G
Price
$2691.1
Updated
2021/12/16
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4-Hydroxy ThalidoMide Chemical Properties,Usage,Production

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 Preparation Products And Raw materials

Raw materials

Preparation Products

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4-Hydroxy ThalidoMide Suppliers

China 134 United States 10 Global 144
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View Lastest Price from 4-Hydroxy ThalidoMide manufacturers

LY Global chemicals co.,ltd .
Product
4-Hydroxy ThalidoMide 5054-59-1
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
98%Min
Supply Ability
1000kg
Release date
2023-03-14
LY Global chemicals co.,ltd .
Product
2-(2,6-dioxo-piperidin-3-yl)-4-hydroxy-isoindole-1,3-dione; 5054-59-1
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
98%Min
Supply Ability
1000kg
Release date
2023-03-14
Henan Aochuang Chemical Co.,Ltd.
Product
4-Hydroxy ThalidoMide 5054-59-1
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
98%
Supply Ability
1ton
Release date
2022-09-23

5054-59-1, 4-Hydroxy ThalidoMideRelated Search:

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

  • 4-Hydroxy ThalidoMide
  • 2-(2,6-dioxopiperidin-3-yl)-4-hydroxyisoindoline-1,3-dione
  • 2-(2,6-Dioxo-piperidin-3-yl)-4-hydroxy-isoindole-1,3-dione
  • 2-(2,6-dioxopiperidin-3-yl)-4-hydroxy-2,3-dihydro-1H-isoindole-1,3-dione
  • E3 ligase Ligand 2
  • Pomalidomide Impurity 15
  • 2-(2,6-Dioxo-3-piperidinyl)-4-hydroxyisoindoline-1,3-dione
  • Thalidomide Impurity 1
  • 186942
  • Thalidomide 4-Hydroxy Impurity
  • 1H-Isoindole-1,3(2H)-dione, 2-(2,6-dioxo-3-piperidinyl)-4-hydroxy-
  • 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
  • Thalidomide-4-OH
  • Cereblon ligand 2
  • 2-(2,6-dioxo-3-piperidyl)-4-hydroxy-isoindoline-1,3-dione
  • 5054-59-1
  • 260939
  • 2614/6/4