Etarotene

Base Information

• Chemical Name: Etarotene
• CAS No.: 87719-32-2
• Molecular Formula: C25H32O2S
• Molecular Weight: 396.59
• UNII: PD3817FE9N
• ChEMBL ID: CHEMBL549872
• DSSTox Substance ID: DTXSID101318671
• NCI Thesaurus Code: C96705
• Nikkaji Number: J364.131G
• Wikidata: Q27286488
• Mol file: 87719-32-2.mol

Synonyms:arotinoid ethylsulfone;ethyl 4-(2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)propenyl)phenylsulfone;Ro 15-1570;Ro-15-1570

Chemical Property of Etarotene

Chemical Property:

• Vapor Pressure: 7.04E-11mmHg at 25°C
• Boiling Point: 532.4°C at 760 mmHg
• Flash Point: 309°C
• PSA: 42.52000
• Density: 1.059g/cm³
• LogP: 7.47050
• XLogP3: 7.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 396.21230143
• Heavy Atom Count: 28
• Complexity: 672

Purity/Quality:

ETAROTENE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCS(=O)(=O)C1=CC=C(C=C1)C=C(C)C2=CC3=C(C=C2)C(CCC3(C)C)(C)C
• Isomeric SMILES: CCS(=O)(=O)C1=CC=C(C=C1)/C=C(\C)/C2=CC3=C(C=C2)C(CCC3(C)C)(C)C

Technology Process of Etarotene

There total 7 articles about Etarotene 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: 75.0%

sodium p-<(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)propenyl>benzenesulfinate (87719-33-3) → Etarotene (87719-32-2,127463-75-6)

Guidance literature:

With ethyl iodide; In N,N-dimethyl-formamide; for 4h; Ambient temperature;

Reference yield: 75.0%

ethyl p-<(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)propenyl>phenylsulfide (89471-17-0) → Etarotene (87719-32-2,127463-75-6)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid;

Reference yield:

[1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-ethyl]-triphenylphosphonium bromide (69251-24-7) → Etarotene (87719-32-2,127463-75-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 31.5 percent / toluene; not given / 48 h / Heating

2: 75 percent / m-chloroperbenzoic acid

With 3-chloro-benzenecarboperoxoic acid; In toluene;

upstream raw materials:

4-(ethanesulfonyl)benzaldehyde

[1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-ethyl]-triphenylphosphonium bromide

ethyl p-<(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)propenyl>phenylsulfide

sodium p-<(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)propenyl>benzenesulfinate