54350-48-0

Basic information

• Product Name: Etretinate
• Synonyms: 2,4,6,8-nonanetetraenoicacid,9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl;3,7-dimethyl-9-(4-methoxy-2,3,6-trimethylphenyl)-2,4,6,8-nonanetetraenoicaci;all-trans-ethylester;ethylall-trans-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nona;ethyletrinoate;ro10-9359;tetraenoate;TIGASON
• CAS NO: 54350-48-0
• Molecular Formula: C₂₃H₃₀O₃
• Molecular Weight: 354.48
• EINECS: 259-119-3
• Product Categories: Aromatics Compounds;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;Retinoids;API
• Mol File: 54350-48-0.mol
• Article Data: 8

Chemical Properties

• Melting Point: 104-1050C
• Boiling Point: 447.69°C (rough estimate)
• Flash Point: 219.4 °C
• Appearance: Crystalline solid
• Density: 1.0304 (rough estimate)
• Vapor Pressure: 2.22E-10mmHg at 25°C
• Refractive Index: 1.5480 (estimate)
• Storage Temp.: Amber Vial, -20°C Freezer
• Solubility: Chloroform (Slightly), DMSO (Slightly, Sonicated), Ethyl Acetate (Slightly), Met
• Stability: Light Sensitive
• CAS DataBase Reference: Etretinate(CAS DataBase Reference)
• NIST Chemistry Reference: Etretinate(54350-48-0)
• EPA Substance Registry System: Etretinate(54350-48-0)

Safety Data

• Hazardous Substances Data: 54350-48-0(Hazardous Substances Data)

Usage

Chemical Properties

Crystalline Solid

Originator

Tigason,Roche,UK,1981

Uses

Different sources of media describe the Uses of 54350-48-0 differently. You can refer to the following data:
1. Aromatic analog of Retinoic Acid. Immunomodulator. Antipsoriatic.
2. Aromatic analog of Retinoic Acid. Immunomodulator. Antipsoriatic

Manufacturing Process

228 g of 5-(4-methoxy-2,3,6-trimethylphenyl)-3-methyl-penta-2,4-diene-1- triphenylphosphonium bromide are introduced under nitrogen gassing into 910 ml of dimethylformamide and treated with cooling at 5°C to 10°C within 20 minutes with 17.5 g of a suspension of sodium hydride (about 50% by weight) in mineral oil. The mixture is stirred for 1 hour at about 10°C, then treated at 5°C to 8°C dropwise with 61.8 g of 3-formylcrotonic acid butyl ester, heating for 2 hours at 65°C, subsequently introduced into 8 liters of ice water, and, after the addition of 300 g of sodium chloride, thoroughly extracted with a total of 18 liters of hexane. The extract is washed 5 times with 1 liter of methanol/water (6:4 parts by volume) each time and 2 times with 1.5 liter of water each time, dried over sodium sulfate and evaporated under reduced pressure to leave 9-(4-methoxy-2,3,6-trimethylphenyl)-3,7- dimethyl-nona-2,4,6,8-tetraen-1-oic acid butyl ester, MP 80°C to 81°C as the residue.125.8 g of 9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-nona-2,4,6,8- tetraen-1-oic acid butyl ester are introduced into 2,000 ml of abs. ethanol and treated with a solution of 125.8 g of potassium hydroxide in 195 ml of water. The mixture is heated to boiling under nitrogen gassing for 30 minutes, then cooled, introduced into 10 liters of ice water and, after the addition of about 240 ml of concentrated hydrochloric acid (PH 2-4), thoroughly extracted with a total of 9 liters of methylene chloride. The extract is washed with about 6 liters of water to neutrality, dried over calcium chloride and evaporated under reduced pressure. The residue is taken up in 700 ml of hexane. The precipitated 9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-nona-2,4,6,8- tetraen-1-oic acid melts at 228°C to 230°C.60 g of 9-(4-methoxy -2,3,6-trimethylphenyl )-3,7-dimethyl-nona-2,4,6 8- tetraen-1-oic acid are dissolved in 1,000 ml of acetone. After the addition of 128 g of ethyl iodide and 128 g of potassium carbonate, the solution is stirred under nitrogen gassing for 16 hours at 55°C to 60°C and subsequentlyevaporated under reduced pressure. The residue is dissolved in 1,300 ml of petroleum ether (BP 80°C to 105°C). The 9-(4-methoxy-2,3,6- trimethylphenyl)-3,7-dimethyl-nona-2,4,6,8-tetraen-1-oic acid ethyl ester crystallizing out at -20°C, melts at 104°C to 105°C.

Brand name

Tegison (Roche);Ro 10-9359;Tigasan.

Therapeutic Function

Antipsoriatic, Antitumor

World Health Organization (WHO)

Etretinate, a retinol derivative, was introduced in 1981 for the treatment of psoriasis. Its use in pregnant women has resulted in major foetal abnormalities. The manufacturer's information emphasizes that the drug is teratogenic and must not be given to women who are pregnant, and that contraceptive measures must be maintained for at least two years after discontinuation of treatment. In some countries, blood banks are advised not to accept as donors persons who have taken etretinate within the previous year.

InChI:InChI=1/C23H30O3/c1-8-26-23(24)14-17(3)11-9-10-16(2)12-13-21-18(4)15-22(25-7)20(6)19(21)5/h9-15H,8H2,1-7H3/b11-9+,13-12+,16-10+,17-14+

Upstream product

• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 62924-31-6 1-(2,5,6-trimethyl-4-methoxyphenyl)-but-1-en-3-one 
• 54344-92-2 2,3,6-trimethyl-4-methoxy-benzaldehyde 
• 51318-62-8 ethyl (E)-4-bromo-3-methyl-2-butenoate 
• 65527-85-7 ethyl (E)-4-hydroxy-3-methyl-2-butenoate 
• 697-82-5 2,3,5-trimethylphenol 
• 41891-54-7 diethyl 3-(ethoxycarbonyl)-3-methylprop-2-en-yl phosphate 
• 69877-38-9 5-(4-methoxy-2,3,6-trimethylphenyl)-3-methyl-2(E),4(E)-pentadien-1-al 
• 63650-98-6 5-(4-methoxy-2,3,6-trimethylphenyl)-3-methylpenta-2,4-dien-1-ol 
• 1269259-99-5 (2E,4E)-ethyl 5-(-4-methoxy-2,3,6-trimethylphenyl)-3-methylpenta-2,4-dienoate 
• 124743-95-9 Ethyl-4-hydroxy-9-(4-methoxy-2,3,6-trimethylphenyl)-5,7-dimethylnona-2,7-dien-5-inoat 
• 124743-94-8 2,3,5-Trimethyl-4-(3-methylpent-2-en-4-inyl)anisol 
• 20469-61-8 2,3,5-trimethylanisole 
• 3230-69-1 3-methyl-1-penten-4-yn-3-ol 

Downstream Products

• 113432-38-5 ethyl 5-<3α-(ethoxycarbonyl)>-2α-<(E)-4-methoxy-1,2,6-trimethylstyryl>-4β-<(all-E)-6-(4-methoxy-2,3,6-trimethylphenyl)-4-methyl-1,3,5-hexatrienyl>-2,4-dimethyl-1β-cyclobutyl-3-methyl-2,4-pentadieonate 
• 120591-51-7 diethyl-6α-<(all-E)-6-(4-methoxy-2,3,6-trimethylphenyl)-4-methyl-1,3,5-hexatriene-yl>-5α-<(all-E)-4-(4-methoxy-2,3,6-trimethylphenyl)-2-methyl-1,3-butadienyl>-3,6-dimethyl-3-cyclohexene-1β,2α-dicarboxylate 
• 120591-51-7 diethyl-6α-<(all-E)-6-(4-methoxy-2,3,6-trimethylphenyl)-4-methyl-1,3,5-hexatriene-yl>-5α-<(all-E)-4-(4-methoxy-2,3,6-trimethylphenyl)-2-methyl-1,3-butadienyl>-3,6-dimethyl-3-cyclohexene-1α,2α-dicarboxylate 
• 120591-51-7 diethyl-6β-<(1E,3E,5Z)-6-(4-methoxy-2,3,6-trimethylphenyl)-4-methyl-1,3,5-hexatrienyl>-5α-<(all-E)-4-(4-methoxy-2,3,6-trimethylphenyl)-2-methyl-1,3-butadienyl>-3,6-dimethyl-3-cyclohexene-1α,2α-dicarboxamide 
• 120591-51-7 diethyl-6α-<(1E,3E,5Z)-6-(4-methoxy-2,3,6-trimethylphenyl)-4-methyl-1,3,5-hexatrienyl>-5α-<(all-E)-4-(4-methoxy-2,3,6-trimethylphenyl)-2-methyl-1,3-butadienyl>-3,6-dimethyl-3-cyclohexene-1β,2β-dicarboxamide 
• 61630-49-7 (2E,4E,6E,8E)-9-(4-methoxyl-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraen-1-ol 
• 58508-38-6 (2E,4E,6E,8E)-9-(4-methoxyl-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenal 
• 1621284-01-2 4,4’-((1E,3E,5E,7E,9E,11E,13E)-3,7,12-trimethyltetradeca-1,3,5,7,9,11,13-heptaene-1,14-diyl)bis(1-methoxy-2,3,5-trimethylbenzene) 
• 1621283-97-3 4,4’-((1E,3E,5E,7E,9E,11E,13E)-3,7,12-trimethyltetradeca-1,3,5,7,9,11,13-heptaene-1,14-diyl)bis(1-methoxy-2,3,5-trimethylphenol) 
• 54757-46-9 acitretin 

Relevant articles and documents

Dual Nickel/Ruthenium Strategy for Photoinduced Decarboxylative Cross-Coupling of α,β-Unsaturated Carboxylic Acids with Cycloketone Oxime Esters

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Method for treating psoriasis using selected phosphorylase kinase inhibitor and additional compounds

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