75858-21-8

Basic information

• Product Name: (13cis)-15-{[4-(propanoyloxy)phenyl]amino}retinal
• CAS NO: 75858-21-8
• Molecular Formula: C₂₉H₃₇NO₃
• Molecular Weight: 447.609
• Mol File: 75858-21-8.mol

Chemical Properties

• Boiling Point: 616.5°C at 760 mmHg
• Flash Point: 326.6°C
• Density: 1.071g/cm³
• Vapor Pressure: 3.95E-15mmHg at 25°C
• Refractive Index: 1.58
• CAS DataBase Reference: (13cis)-15-{[4-(propanoyloxy)phenyl]amino}retinal(CAS DataBase Reference)
• NIST Chemistry Reference: (13cis)-15-{[4-(propanoyloxy)phenyl]amino}retinal(75858-21-8)
• EPA Substance Registry System: (13cis)-15-{[4-(propanoyloxy)phenyl]amino}retinal(75858-21-8)

Safety Data

• Hazardous Substances Data: 75858-21-8(Hazardous Substances Data)

Upstream product

• 802294-64-0 propionic acid 
• 65646-68-6 N-(4-hydroxyphenyl)-all-trans-retinamide 

Relevant articles and documents

Potent cytotoxic effects of novel retinamide derivatives in ovarian cancer cells

4-(N-Hydroxyphenyl)retinamide (also known as 4-HPR or fenretinide), a synthetic amide of all-trans retinoic acid (RA), has been implicated as a promising anticancer agent associated with reducing the toxicity related to RA. However, the low plasma levels of 4-HPR in patients limited clinical trials, leading to a search for derivatives with better efficacy. In this study, we synthesized a series of 4-HPR derivatives in good yields by introducing acetate (compound 1), propionate (2), pyruvate (3), butyrate (4), or stearate (5) to the 4-hydroxylphenyl moiety of 4-HPR. In our initial proliferation assays, we identified compound 3 as the most cytotoxic of the series against four ovarian cancer cell lines (OVCAR-3, PA-1, 2774, and SKOV-3). Dose-response curves yielded IC50 values of 3.75 - 7.75 μM for AtRA, 2.80 - 5.50 μM for 9-cis RA, 0.65-4.05 μM for 4-HPR, and 0.25 - 0.75 μM for compound 3, depending on the cell type treated. Nuclear staining with 4′,6-diamidino- 2-phenylindole (DAPI) and DNA fragmentation assays clearly indicated that the antiproliferative effect of compound 3 was mediated by apoptosis. In contrast to natural retinoids, both 4-HPR and compound 3 activated two (RARβ and RARγ) of the three retinoic acid receptor (RAR) subtypes tested, but did not activate any of the three retinoid X receptors (RXRs), as determined by transcription assays in OVCAR-3 cells. However, like natural retinoids, 4-HPR and compound 3 actively suppressed c-Jun transcriptional activity. Thus, compound 3 not only showed more potent antiproliferative activity than any other retinoid derivatives tested, but also effectively inhibited the c-Jun activity that has been implicated in tumor promotion and invasion. These results, together with compound 3's selectivity for RAR subtypes, suggest that compound 3 could be an effective anticancer drug for ovarian cancer, with less toxicity than RA.

Novel retinoids and their use in preventing carcinogenesis

Novel N-(4-acyloxyphenyl)-all-trans-retinamide compounds are useful in preventing epithelial cancer in mammals.