4-HYDROXYPHENYLRETINAMIDE

4-HYDROXYPHENYLRETINAMIDE
  • CAS No.:65646-68-6
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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
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
pka9.98±0.26(Predicted)
color Yellow
λmax362nm(MeOH)(lit.)
Merck 14,3998
Stability:Light Sensitive - Protect from Light Exposure
InChIKeyAKJHMTWEGVYYSE-FXILSDISSA-N
CAS DataBase Reference65646-68-6(CAS DataBase Reference)
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 Information
ProviderLanguage
SigmaAldrich English
4-HYDROXYPHENYLRETINAMIDE Usage And Synthesis
Chemical Properties4-HYDROXYPHENYLRETINAMIDE is Yellow Powder
Uses4-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
UsesA synthetic analog of Vitamin A.
UsesRetinoic acid receptor ligand
DefinitionChEBI: 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 DescriptionRetinoic acid p-hydroxyanilide is a synthetic analog of retinoid.
Biological ActivitySynthetic 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 ActionsVitamin A acid analogue with antiproliferative activity; induces apoptosis in malignant hemopoietic cell lines.
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.
4-HYDROXYPHENYLRETINAMIDE Preparation Products And Raw materials
Raw materialsRetinoyl chloride-->Retinoic acid-->4-Aminophenol

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