Fenretinide

Base Information

• Chemical Name: Fenretinide
• CAS No.: 65646-68-6
• Molecular Formula: C26H33NO2
• Molecular Weight: 391.554
• Hs Code.: 2924297099
• European Community (EC) Number: 636-255-5
• NSC Number: 760419,374551
• UNII: 187EJ7QEXL
• DSSTox Substance ID: DTXSID2032005
• Nikkaji Number: J2.845.877K,J23.263G
• Wikipedia: Fenretinide
• Wikidata: Q5443576
• NCI Thesaurus Code: C1098
• Pharos Ligand ID: NMY5THLZ9P6V
• Metabolomics Workbench ID: 56466
• ChEMBL ID: CHEMBL7301
• Mol file: 65646-68-6.mol

Synonyms:13-cis-Isomer Fenretinide;4 Hydroxyphenylretinamide;4-HPR;4-Hydroxyphenylretinamide;Fenretinide;Fenretinide, 13 cis Isomer;Fenretinide, 13-cis-Isomer;Fenretinimide;MCN R 1967;MCN-R-1967;MCNR1967;N-(4-Hydroxyphenyl)-trans-Retinamide;N-(4-Hydroxyphenyl)retinamide

Chemical Property of Fenretinide

Chemical Property:

• Appearance/Colour: Yellow Powder
• Vapor Pressure: 7.07E-15mmHg at 25°C
• Melting Point: 162-163°C
• Refractive Index: 1.607
• Boiling Point: 597.6 ºC at 760 mmHg
• PKA: 9.98±0.26(Predicted)
• Flash Point: 315.2 ºC
• PSA: 49.33000
• Density: 1.081 g/cm³
• LogP: 6.93530
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 7.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 391.251129295
• Heavy Atom Count: 29
• Complexity: 726

Purity/Quality:

99% ^*data from raw suppliers

HPR ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 60-61-20/21/22-36/37/38
• Safety Statements: 53-26-36/37/39-45-52

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CC(=O)NC2=CC=C(C=C2)O)C)C
• Isomeric SMILES: CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C/C(=O)NC2=CC=C(C=C2)O)/C)/C
• Recent ClinicalTrials: N2004-03: Intravenous Fenretinide in Treating Young Patients With Recurrent or Resistant Neuroblastoma
• Recent EU Clinical Trials: A randomized double blind placebo controlled study on the effects of fenretinide Lym-X-Sorb on insulin sensitivity in obese insulin resistant subjects
• 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 A synthetic analog of Vitamin A. Retinoic acid receptor ligand

Technology Process of Fenretinide

There total 6 articles about Fenretinide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

all-trans-retinoic-acid (302-79-4) + 4-amino-phenol (123-30-8) → N-(4-hydroxyphenyl)-all-trans-retinamide (65646-68-6)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; N,N-dimethyl-formamide; for 1h; Ambient temperature;

DOI:10.1080/00397919808004874

Reference yield:

retinoic acid, t-butyl mixed anhydride + 4-amino-phenol (123-30-8) → N-(4-hydroxyphenyl)-all-trans-retinamide (65646-68-6)

Guidance literature:

With pyridine; In ethyl acetate; at 3 - 5 ℃; for 2.5h; Product distribution / selectivity;

Reference yield:

retinoic acid, isobutyl mixed carbonate + 4-amino-phenol (123-30-8) → N-(4-hydroxyphenyl)-all-trans-retinamide (65646-68-6)

Guidance literature:

retinoic acid, isobutyl mixed carbonate; 4-amino-phenol; In tert-butyl methyl ether; N,N-dimethyl-formamide; at 10 ℃; for 2.16667h;

With hydrogenchloride; In tert-butyl methyl ether; water; N,N-dimethyl-formamide; at 10 ℃; Product distribution / selectivity;

upstream raw materials:

retinoyl chloride

4-amino-phenol

all-trans-retinoic-acid

Downstream raw materials:

all-trans-N-<4-(Pivaloyloxy)phenyl>retinamide

4-{(2E,4E,6E,8E)-[3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoylamino]}-phenyl propionate

4-Methoxyfenretinide

4'-hydroxy 4-HPR

Refernces

• 1、 -. "Preparation of amides of retinoic acid via mixed anhydride and mixed carbonate intermediates". Page/Page column 5-6. . Retrieved 2008/06/13.
• 2、 Um, Soo-Jong,Kwon, Youn-Ja,Han, Hye-Sook,Park, Si-Ho,Park, Myoung-Soon,Rho, Young-Soy,Sin, Hong-Sig. "Synthesis and biological activity of novel retinamide and retinoate derivatives". . p. 501 - 506. Retrieved 2007/10/03.