53839-65-9

Basic information

• Product Name: (2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoic acid octadecylamide
• CAS NO: 53839-65-9
• Molecular Weight: 551.94
• Mol File: 53839-65-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoic acid octadecylamide(CAS DataBase Reference)
• NIST Chemistry Reference: (2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoic acid octadecylamide(53839-65-9)
• EPA Substance Registry System: (2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoic acid octadecylamide(53839-65-9)

Safety Data

• Hazardous Substances Data: 53839-65-9(Hazardous Substances Data)

Upstream product

• 65646-64-2 N-(all-trans-Retinoyloxy)-succinimide 
• 124-30-1 1-aminooctadecane 

Relevant articles and documents

Synthesis of octadecylamine-retinoic acid conjugate for enhanced cytotoxic effects of 5-FU using LDL targeted nanostructured lipid carriers

The aim of the present study was to reduce 5-FU side effects by targeted nanostructured lipid carriers (NLCs) to LDL receptors that are over expressed in colorectal carcinoma and also use of a new synthesized conjugate of retinoic acid as a cytotoxic agent. Fatty acyl amide derivative of retinoic acid was synthesized by its conjugation to octadecylamine with the expectation to improve its loading capacity in NLCs of 5-FU. The NLCs were prepared by an emulsification-solvent evaporation method using cholesterol and cholesteryl stearate. Physical properties and drug release were studied in NLCs. The cytotoxicity of NLCs loaded with 5-FU and retinoic acid conjugate was studied on colon cancer cells (HT29) using MTT assay. To confirm that drug targeting has been done through LDL receptors, APO-E was omitted from the cell culture and the MTT assay was repeated. FTIR and 1H NMR spectra confirmed successful production of the conjugate. Results showed the IC50 of free 5-FU was about 7.6 μM while in comparable concentration, the cytotoxicity of 5-FU loaded in NLCs containing the retinoic acid conjugate was nearly 2 fold of NLCs just loaded with 5-FU and more than 5 fold of free 5-FU. The retinoic acid conjugate loaded NLCs prepared by cholesterol can target LDL receptors of HT29 cells and seems promising in reducing 5-FU dose in colorectal cancer.