75078-91-0

Basic information

• Product Name: Temarotene
• Synonyms: Temaroteno [spanish];Temarotenum;Temarotene;AROTINOID;1,2,3,4-Tetrahydro-1,1,4,4-tetramethyl-6-[(E)-1-methyl-2-phenylethenyl]naphthalene;Ro-15-0778;1,2,3,4-Tetrahydro-1,1,4,4-tetramethyl-6-((E)-alpha-methylstyryl)naphthalene;Naphthalene, 1,2,3,4-tetrahydro-1,1,4,4-tetramethyl-6-((1E)-1-methyl-2-phenylethenyl)-
• CAS NO: 75078-91-0
• Molecular Formula: C₂₃H₂₈
• Molecular Weight: 304.47
• Mol File: 75078-91-0.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 403.3°C at 760 mmHg
• Flash Point: 218°C
• Appearance: /
• Density: 0.963g/cm³
• Vapor Pressure: 2.4E-06mmHg at 25°C
• Refractive Index: 1.56
• CAS DataBase Reference: Temarotene(CAS DataBase Reference)
• NIST Chemistry Reference: Temarotene(75078-91-0)
• EPA Substance Registry System: Temarotene(75078-91-0)

Safety Data

• Hazardous Substances Data: 75078-91-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C23H28/c1-17(15-18-9-7-6-8-10-18)19-11-12-20-21(16-19)23(4,5)14-13-22(20,2)3/h6-12,15-16H,13-14H2,1-5H3/b17-15+

Upstream product

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• 27452-17-1 6-bromo-1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalene 
• 110-03-2 2,5-dimethyl-2,5-hexanediol 
• 1398115-53-1 (E)-1-phenylthio-2-[5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthalenyl]-1-propene 
• 38111-44-3 phenylzinc(II) bromide 
• 1398115-51-9 1-thiophenyl-2-[5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthalenyl]ethyne 
• 1398115-52-0 (Z)-1-phenylthio-2-butyltelluro-2-[5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthalenyl]ethene 
• 119362-54-8 6-ethynyl-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene 
• 18826-59-0 1-(4-fluorophenyl)-prop-1-yne 
• 83832-05-7 (E)-1-fluoro-4-(2-phenylprop-1-enyl)benzene 
• 1283231-56-0 (Z)-2-(1-(4-fluorophenyl)prop-1-en-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Relevant articles and documents

Stereospecific Synthesis of Temarotene, Its Structural Isomers, and Mixed Triaryl Alkenes from gem-Borazirconocene Alkenes

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Synthesis of arotinoid acid and temarotene using mixed (Z)-1,2- bis(organylchalcogene)-1-alkene as precursor

An efficient and novel total synthesis of the two bioactive retinoids temarotene and arotinoid acid (TTNPB) is described. The key steps in this process include the regio and stereoselective hydrotelluration of thioacetylene 9 and Te/Li transmetalation of mixed (Z)-1,2-bis(organylchalcogene)-1-alkene (Z)-3. The subsequent reaction involving the β-phenylthio vinyl lithiated intermediate 10 with dimethyl sulfate gave the (E)-vinyl sulfide 11. The Ni +2 cross-coupling of 11 with the corresponding phenylzinc bromide and p-oxazoline phenylzinc bromide 12 afforded the respective temarotene 2 and retinoid-oxazoline substituted 13. Finally, compound 13 was deprotected with HCl to furnish arotinoid acid (TTNPB) 1.

Arotinoids, a new class of highly active retinoids

The synthesis and biological activity of new aromatic retinoids are reported. The most active ones belong to a chemical class of compounds, which we have termed 'arotinoids'. For the compound p-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-propenyl)]-benzoic acid ethyl ester, a therapeutic potency in the antipapilloma test was found which exceeds that of retinoic acid by a factor of 8000, while the concurrently observed toxic hypervitaminosis A effects are only increased by a factor of 800. The structural relationship of the arotinoids with retinoic acid is demonstrated; the arotinoids contain the retinoic acid carbon skeleton in a fixed cisoid geometric conformation.