65646-68-6

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 NO: 65646-68-6
• Molecular Formula: C₂₆H₃₃NO₂
• Molecular Weight: 391.55
• EINECS: 200-256-5
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Retinoids;Intracellular receptor;Drug Analogues;Inhibitors
• Mol File: 65646-68-6.mol
• Article Data: 6

Chemical Properties

• Melting Point: 162-163°C
• Boiling Point: 597.6 ºC at 760 mmHg
• Flash Point: 315.2 ºC
• Appearance: Yellow Powder
• Density: 1.081 g/cm³
• Vapor Pressure: 7.07E-15mmHg at 25°C
• Refractive Index: 1.607
• Storage Temp.: −20°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 9.98±0.26(Predicted)
• Stability: Light Sensitive - Protect from Light Exposure
• Merck: 14,3998
• CAS DataBase Reference: 4-HYDROXYPHENYLRETINAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-HYDROXYPHENYLRETINAMIDE(65646-68-6)
• EPA Substance Registry System: 4-HYDROXYPHENYLRETINAMIDE(65646-68-6)

Safety Data

• Hazard Codes: T
• Statements: 60-61-20/21/22-36/37/38
• Safety Statements: 53-26-36/37/39-45-52
• WGK Germany: 3
• RTECS: VH6420000
• Hazardous Substances Data: 65646-68-6(Hazardous Substances Data)

Usage

Chemical Properties

4-HYDROXYPHENYLRETINAMIDE is Yellow Powder

Uses

Different sources of media describe the Uses of 65646-68-6 differently. You can refer to the following data:
1. 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
2. A synthetic analog of Vitamin A.
3. 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.

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.

InChI:InChI=1/C26H33NO2/c1-19(11-16-24-21(3)10-7-17-26(24,4)5)8-6-9-20(2)18-25(29)27-22-12-14-23(28)15-13-22/h6,8-9,11-16,18,28H,7,10,17H2,1-5H3,(H,27,29)/b9-6+,16-11+,19-8+,20-18+

Upstream product

• 53839-60-4 retinoyl chloride 
• 123-30-8 4-amino-phenol 
• 302-79-4 all-trans-retinoic-acid 

Downstream Products

• 79965-10-9 4-Methoxyfenretinide 
• 1276090-87-9 4'-hydroxy 4-HPR 
• 75858-21-8 4-{(2E,4E,6E,8E)-[3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoylamino]}-phenyl propionate 
• 75664-77-6 all-trans-N-<4-(Pivaloyloxy)phenyl>retinamide 

Relevant articles and documents

Fenretinide derivatives act as disrupters of interactions of serum retinol binding protein (sRBP) with transthyretin and the sRBP receptor

Serum retinol binding protein (sRBP) is released from the liver as a complex with transthyretin (TTR), a process under the control of dietary retinol. Elevated levels of sRBP may be involved in inhibiting cellular responses to insulin and in generating first insulin resistance and then type 2 diabetes, offering a new target for therapeutic attack for these conditions. A series of retinoid analogues were synthesized and examined for their binding to sRBP and their ability to disrupt the sRBP-TTR and sRBP-sRBP receptor interactions. A number inhibit the sRBP-TTR and sRBP-sRBP receptor interactions as well as or better than Fenretinide (FEN), presenting a potential novel dual mechanism of action and perhaps offering a new therapeutic intervention against type 2 diabetes and its development. Shortening the chain length of the FEN derivative substantially abolished binding to sRBP, indicating that the strength of the interaction lies in the polyene chain region. Differences in potency against the sRBP-TTR and sRBP-sRBP receptor interactions suggest variant effects of the compounds on the two loops of sRBP guarding the entrance of the binding pocket that are responsible for these two protein-protein interactions.

Solid phase-assisted synthesis and screening of a small library of N-(4-hydroxyphenyl)retinamide (4-HPR) analogs

Using solid phase-assisted synthesis and purification, a 49 member library of analogs of the mammary tumor chemopreventive retinoid N-(4-hydroxyphenyl)retinamide (4-HPR) has been prepared. After prescreening for growth inhibitory activity in human mammary tumor cells (MCF-7) in culture, most of those analogs which showed activity (12 of them) were assayed for apoptosis-inducing activity in the MCF-7 cells. At least 3 of the analogs (13, 24, and 28) showed activity approaching that of 4-HPR.

A simple, general and efficient method for O and N-retinoylation. Application to the synthesis of 2-retinoyl-lecithin

The synthesis of the new 1-stearoyl-2-retinoyl-glycero-3- phosphorylcholine by coupling of retinoic acid and lysolecithin with DCC- DMAP (1.2 eq.) is reported. This method is applied to O and N-retinoylation of uncharged organic substrates such as aliphatic alcohols, free hydroxyl anomeric sugars, aromatic amines and C-protected α-aminoacids.