Benzoic acid, 4-[1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl]-, methyl ester Chemical Properties

Melting point:

160-161 °C(Solv: ethyl acetate (141-78-6); methanol (67-56-1))

Boiling point:

472.3±44.0 °C(Predicted)

Density 

1.007±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform, Methanol (Slightly)

form 

Solid

color 

White to Light Beige

Benzoic acid, 4-[1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl]-, methyl ester Usage And Synthesis

Uses

Methyl Bexarotenate is a related compound of Bexarotene (B336750), which is an antineoplastic agent and a selective retinoid X receptor (RXR) agonist.

Synthesis

Methyl 4-(1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-carbonyl)benzoate was synthesized by Wittig reaction using methyltriphenylphosphonium bromide and methyl 4-(1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)vinyl)benzoate as starting materials. During the synthesis, crystals of compound 35 were found to be suitable for X-ray diffraction analysis. To complete the synthesis of bexarotene, compound 35 was first subjected to Friedel-Crafts acylation using crude monomethyl terephthaloyl chloride (36) to give ketone 37. Subsequently, ketone 37 was converted to olefinic ester 38 by Wittig reaction. finally, olefinic ester 38 was subjected to saponification in the presence of potassium hydroxide followed by acidification with aqueous hydrochloric acid. to obtain the target product bexarotene (39) (Scheme 2).

References

[1] Journal of Medicinal Chemistry, 2009, vol. 52, # 19, p. 5950 - 5966
[2] Patent: WO2011/103321, 2011, A1. Location in patent: Page/Page column 19
[3] Journal of Medicinal Chemistry, 1994, vol. 37, # 18, p. 2930 - 2941
[4] Journal of Labelled Compounds and Radiopharmaceuticals, 1995, vol. 36, # 7, p. 701 - 712
[5] Journal of Medicinal Chemistry, 1995, vol. 38, # 17, p. 3368 - 3383

Benzoic acid, 4-[1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl]-, methyl ester(153559-48-9)Related Product Information

• Bexarotene Impurity 8
• Bexarotene Impurity 3
• Bexarotene Impurity 7
• Bexarotene
• Bexarotene Impurity 2
• Methyl 4-[(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl]benzoate
• Bexarotene Impurity 10
• Bexarotene Impurity 1
• Bexarotene Impurity 9
• Bexarotene Impurity 4
• Bexarotene Acyl-β-D-glucuronide
• METHANE