SUBERIC ACID MONOMETHYL ESTER Chemical Properties

Melting point:

17-19 °C (lit.)

Boiling point:

185-186 °C/18 mmHg (lit.)

Density 

1.047 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.444(lit.)

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO, Methanol

form 

Solid

pka

4.76±0.10(Predicted)

color 

Colourless

InChI

InChI=1S/C9H16O4/c1-13-9(12)7-5-3-2-4-6-8(10)11/h2-7H2,1H3,(H,10,11)

InChIKey

KOVPXZDUVJGGFU-UHFFFAOYSA-N

SMILES

C(OC)(=O)CCCCCCC(O)=O

CAS DataBase Reference

3946-32-5

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

HS Code 

29171900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

SUBERIC ACID MONOMETHYL ESTER Usage And Synthesis

Chemical Properties

colorless low melting solid

Uses

Monomethyl Suberate was used in the synthetic preparation of Prostaglandin E1 (P838600), a primary prostaglandin and a peripheral vasodilator.

Uses

Suberic acid monomethyl ester 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

SUBERIC ACID MONOMETHYL ESTER(3946-32-5)Related Product Information

• Dimethyl suberate
• DIETHYL SUBERATE
• Suberic acid
• Methyl vanillate
• 2-Ethylhexyl nitrate
• Ethyl caprylate
• (PYRIDINE-3-CARBONYL)-AMINO-ACETIC ACID ETHYL ESTER
• DISUCCINIMIDYL SUBERATE
• octanedial
• 1-Octanol
• STYRENE MALEIC ANHYDRIDE COPOLYMER
• POLY(ETHYLENE-ALT-MALEIC ANHYDRIDE)
• 1,2-Cyclohexanedicarboxylic acid diethyl ester
• DIMETHYL DODECAFLUOROSUBERATE
• 5-(2,5-DIOXOTETRAHYDROFURYL)-3-METHYL-3-CYCLOHEXENE-1,2-DICARBOXYLIC ANHYDRIDE
• Dimethyl cyclohexane-1,2-dicarboxylate
• CORFREE(R) M1
• METHYL VINYL ETHER-MONOETHYL MALEATE COPOLYMER