Basic information Safety Supplier Related

4-HYDROXYPHENYLRETINAMIDE

Basic information Safety Supplier Related

4-HYDROXYPHENYLRETINAMIDE Basic information

Product Name:
4-HYDROXYPHENYLRETINAMIDE
Synonyms:
  • 4-HYDROXYPHENYLRETINAMIDE
  • 4HPR
  • FENRETINIDE
  • p-Hydroxyphenylretinamide
  • 4-HPR, Fenretinide, N-(4-Hydroxyphenyl)retinamide
  • (2E,4E,6E,8E)-N-(4-Hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenamide
  • Fenretinimide
  • Fenretinide(4-HPR)
CAS:
65646-68-6
MF:
C26H33NO2
MW:
391.55
EINECS:
200-256-5
Product Categories:
  • Intracellular receptor
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Retinoids
  • Drug Analogues
  • Inhibitors
Mol File:
65646-68-6.mol
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4-HYDROXYPHENYLRETINAMIDE Chemical Properties

Melting point:
162-163°C
Boiling point:
597.6±42.0 °C(Predicted)
Density 
1.081±0.06 g/cm3(Predicted)
storage temp. 
-20°C
solubility 
Chloroform (Slightly), Methanol (Slightly)
form 
Orange solid
pka
9.98±0.26(Predicted)
color 
Yellow
λmax
362nm(MeOH)(lit.)
Merck 
14,3998
Stability:
Light Sensitive - Protect from Light Exposure
InChIKey
AKJHMTWEGVYYSE-FXILSDISSA-N
CAS DataBase Reference
65646-68-6(CAS DataBase Reference)
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Safety Information

Hazard Codes 
T
Risk Statements 
60-61-20/21/22-36/37/38
Safety Statements 
53-26-36/37/39-45-52
WGK Germany 
3
RTECS 
VH6420000
HS Code 
2924297099

MSDS

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4-HYDROXYPHENYLRETINAMIDE Usage And Synthesis

Chemical Properties

4-HYDROXYPHENYLRETINAMIDE is Yellow Powder

Uses

4-HYDROXYPHENYLRETINAMIDE is an effective agent for the chemoprevention and growth modulation of oncogene-induced prostate cancer in the mouse prostate reconstitution model system and may be effective for the chemoprevention of human prostate cancer

Uses

A synthetic analog of Vitamin A.

Uses

Retinoic acid receptor ligand

Definition

ChEBI: A retinoid obtained by formal condensation of the carboxy group of all-trans retinoic acid and the anilino group of 4-hydroxyaniline. Synthetic retinoid agonist. Antiproliferative, antioxidant and anticancer agent with a long half-life in ivo. Apoptotic effects appear to be mediated by a mechanism distinct from that of 'classical' retinoids.

General Description

Retinoic acid p-hydroxyanilide is a synthetic analog of retinoid.

Biological Activity

Synthetic retinoid agonist. Antiproliferative, antioxidant and anticancer agent with a long half-life in vivo . Apoptotic effects appear to be mediated by a mechanism distinct from that of 'classical' retinoids.

Biochem/physiol Actions

Vitamin A acid analogue with antiproliferative activity; induces apoptosis in malignant hemopoietic cell lines.

storage

Store at -20°C

References

[1] roberto benelli, stefano monteghirfo, roberta venè, francesca tosettiand nicoletta ferrari.the chemopreventive retinoid 4hpr impairs prostate cancer cell migration and invasion by interfering with fak/akt/gsk3β pathway andβ-catenin stability. molecular cancer.2010, 9:142-154.
[2] anita l. sabichi, denver t. hendricks, mary a. bober, michael j. birrer. retinoic acid receptorβexpression and growthinhibition of gynecologic cancer cells by thesynthetic retinoidn-(4-hydroxyphenyl) retinamide. journal of the national cancer institute. 1998, 90(8): 597-605.
[3] shi-yong sun, ping yue, and reuben lotan. induction of apoptosis by n-(4-hydroxyphenyl)retinamide andits association with reactive oxygen species, nuclearretinoic acid receptors, and apoptosis-related genes in human prostate carcinoma cells.molecular pharmacology. 1999, 55:403–410.

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