Chemical Properties
colorless low melting solid
Uses
Suberic acid monomethyl ester was used in the synthetic preparation of Prostaglandin E1 (P838600), a primary prostaglandin and a peripheral vasodilator.
Uses
Monomethyl Suberate was used in the synthetic preparation of Prostaglandin E1 (P838600), a primary prostaglandin and a peripheral vasodilator.
General Description
The effects of suberic acid monomethyl ester (monomethyl suberate) on liver lactate metabolism was studied.
Synthesis
General method: 5.1.2 Synthesis of 7-methoxy-7-oxoheptanoic acid (84): a methanolic (150 ml) solution of KOH (5.87 g, 104.65 mmol) was slowly added dropwise to dimethyl heptanedioate (82, 16.94 g, 90 mmol) at 0 °C. The reaction mixture was stirred at room temperature for 4 hours. After completion of the reaction, the solvent was removed under reduced pressure and subsequently extracted by adding ether (100 ml) and water (200 ml). The organic phase was separated and concentrated to give yellow oil 82 (5.08 g, 30% yield). The aqueous phase was acidified to pH 3 with concentrated hydrochloric acid and extracted with ether (100 ml x 3). The combined organic layers were washed with brine (100 ml x 3), dried over magnesium sulfate and the solvent was concentrated under reduced pressure. The product was purified by silica gel column chromatography to give colorless oil 84 (5.96 g, 38% yield). Compound 85 was synthesized using the same method.5.1.2.1 Synthesis of 8-methoxy-8-oxooctanoic acid (85): 44% yield.ESI-MS m/z: 187.4 [M-H]-; 1H NMR (DMSO-d6) δ 1.21-1.32 (m, 4H), 1.43-1.53 (m, 4H), 2.18 (t, J=7.2 Hz, 2H), 2.29 (t, J=7.2Hz, 2H), 3.58 (s, 3H), 11.97 (s, 1H).
References
[1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1993, # 15, p. 1713 - 1714
[2] Synthetic Communications, 1995, vol. 25, # 5, p. 739 - 742
[3] European Journal of Organic Chemistry, 1999, # 10, p. 2655 - 2662
[4] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 16, p. 4253 - 4256
[5] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 21, p. 5766 - 5775
